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MDMA
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Not to be confused with MDA, EDMA or 2,3-MDMA.
MDMA
INN: Midomafetamine[1]
Clinical data
Pronunciation
methylenedioxymethamphetamine:
/ˈmɛ.θɪ.liːn.daɪ.ˈɒk.si./
/ˌmɛθæmˈfɛtəmiːn/
Synonyms
3,4-MDMA; Ecstasy (E, X, XTC); Molly; Mandy;[8][9]
AHFS/Drugs.com
MDMA
Dependence
liability
Physical: not typical[2]
Psychological: moderate
Addiction
liability
Low–moderate[3][4][5]
Routes of
administration
Common: by mouth[6]
Uncommon: snorting,[6] inhalation (vaporization),[6] injection,[6][7] rectal
Drug class
empathogen–entactogen
stimulant
ATC code
none
Legal status
Legal status
AU: S9 (Prohibited)
BR: Class F (Prohibited substances)
CA: Schedule I
DE: Anlage I (Authorized scientific use only)
NZ: Class B
UK: Class A
US: Schedule I
UN: Psychotropic Schedule I
Pharmacokinetic data
Metabolism
Liver, CYP450 extensively involved, including CYP2D6
Metabolites
MDA, HMMA, HMA, DHA, MDP2P, MDOH[10]
Onset of action
30–45 minutes (by mouth)[11]
Biological half-life
(R)-MDMA: 5.8 ± 2.2 hours (variable)[12]
(S)-MDMA: 3.6 ± 0.9 hours (variable)[12]
Duration of action
4–6 hours[4][11]
Excretion
Kidney
Identifiers
IUPAC name[show]
(RS)-1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
CAS Number
42542-10-9 Y[TOXNET]
PubChem CID
1615
IUPHAR/BPS
4574
DrugBank
DB01454 Y
ChemSpider
1556 Y
UNII
KE1SEN21RM
KEGG
C07577 Y
ChEBI
CHEBI:1391 Y
ChEMBL
CHEMBL43048 Y
PDB ligand
B41 (PDBe, RCSB PDB)
Chemical and physical data
Formula
C11H15NO2
Molar mass
193.25 g·mol−1
3D model (JSmol)
Interactive image
Chirality
Racemic mixture
Boiling point
105 °C (221 °F) at 0.4 mmHg (experimental)
SMILES[show]
CC(NC)CC1=CC=C(OCO2)C2=C1
InChI[show]
InChI=1S/C11H15NO2/c1-8(12-2)5-9-3-4-10-11(6-9)14-7-13-10/h3-4,6,8,12H,5,7H2,1-2H3 Y
Key:SHXWCVYOXRDMCX-UHFFFAOYSA-N Y
(verify)
3,4-Methylenedioxymethamphetamine (MDMA),[note 1] commonly known as ecstasy (E), is a psychoactive drug used primarily as a recreational drug. The desired recreational effects include increased empathy, euphoria, and heightened sensations.[13][14][15] When taken by mouth, effects begin after 30–45 minutes and last 3–6 hours.[11][16] As of 2017[update], MDMA has no accepted medical uses.[6]
Adverse effects of MDMA use include addiction, memory problems, paranoia, difficulty sleeping, teeth grinding, blurred vision, sweating, and a rapid heartbeat.[15] Use may also lead to depression and fatigue.[15] Deaths have been reported due to increased body temperature and dehydration.[15] MDMA increases the release and slows the reuptake of the neurotransmitters serotonin, dopamine, and norepinephrine in parts of the brain. It has stimulant and psychedelic effects.[2][17] The initial increase is followed by a short-term decrease in the neurotransmitters.[15][16] MDMA belongs to the substituted methylenedioxyphenethylamine and substituted amphetamine classes of drugs.
MDMA was first made in 1912.[15] It was used to improve psychotherapy beginning in the 1970s and became popular as a street drug in the 1980s.[15][16][18] MDMA is commonly associated with dance parties, raves, and electronic dance music.[19] It is often sold mixed with other substances such as ephedrine, amphetamine, and methamphetamine.[15] In 2014, between 9 and 29 million people between the ages of 15 and 64 used ecstasy (0.2% to 0.6% of the world population).[20] This was broadly similar to the percentage of people who use cocaine, amphetamines, and opioids, but fewer than for cannabis.[20] In the United States, about 0.9 million people used ecstasy in 2010.[15]
MDMA is generally illegal in most countries.[15][21] Limited exceptions are sometimes made for research.[16] Researchers are investigating whether a few low doses of MDMA may assist in treating severe, treatment-resistant posttraumatic stress disorder (PTSD).[22] In November 2016, phase 3 clinical trials for PTSD were approved by the United States Food and Drug Administration (FDA) to assess effectiveness and safety.[23] The FDA granted MDMA a breakthrough therapy designation[note 2] for the treatment of PTSD in August 2017.[27]
Contents
[hide]
1 Effects
2 Use
2.1 Recreational
2.2 Medical
2.3 Other
2.4 Forms
3 Adverse effects
3.1 Short-term
3.2 Long-term
3.3 During pregnancy
3.4 Reinforcement disorders
3.5 Harm assessment
4 Overdose
5 Interactions
6 Pharmacology
6.1 Pharmacodynamics
6.2 Pharmacokinetics
7 Chemistry
7.1 Synthesis
7.2 Detection in body fluids
8 History
8.1 Early research and use
8.2 Shulgin's research and early use in therapy
8.3 Rising recreational use
8.4 Media attention and scheduling
8.4.1 United States
8.4.2 United Nations
8.5 Post-scheduling
9 Society and culture
9.1 Legal status
9.1.1 Australia
9.1.2 United Kingdom
9.1.3 United States
9.1.4 Netherlands
9.1.5 Canada
9.2 Demographics
9.3 Economics
9.3.1 Europe
9.3.2 North America
9.3.3 Australia
9.3.4 Corporate logos on pills
10 Research
11 Notes
12 References
13 External links
Effects
In general, MDMA users report feeling the onset of subjective effects within 30–60 minutes of MDMA consumption and reaching the peak effect at 75–120 minutes, which then plateaus for about 3.5 hours.[28] The desired short-term psychoactive effects of MDMA have been reported to include:
Euphoria – a sense of general well-being and happiness[13][14]
Increased self-confidence, sociability and feelings of communication being easy or simple[4][13][14]
Entactogenic effects – increased empathy or feelings of closeness with others[13][14] and oneself[4]
Relaxation and reduced anxiety[4]
Increased emotionality[4]
A sense of inner peace[14]
Mild hallucination[14]
Enhanced sensation, perception, or sexuality[4][13][14]
Altered sense of time[16]
The experience elicited by MDMA depends on the dose, setting, and user.[4] The variability of the induced altered state by MDMA is lower compared to other psychedelics. For example, MDMA used at parties is associated with high motor activity, reduced sense of self-identity as well as poor awareness of the background surroundings. Use of MDMA individually or in a small groups in a quiet environment and when concentrating, is associated with increased lucidity, capability of concentration, sensitivity of aesthetic aspects of the background and emotions, as well as greater capability of communication with others.[10][29] In psychotherapeutic settings MDMA effects have been described by infantile ideas, alternating phases of mood, sometimes memories and moods connected with childhood experiences.[29][30]
Sometimes MDMA is labelled as an “empathogenic” drug, because of its empathy-producing effects.[31][32] Results of different studies show its effects of powerful empathy with others.[31] When testing the MDMA for medium and high dosage ranges it showed increase on hedonic as well as arousal continuum.[33][34] The effect of MDMA increasing sociability is consistent, however effects on empathy have been more mixed.[35]
Use
Recreational
MDMA is often considered the drug of choice within the rave culture and is also used at clubs, festivals and house parties.[10] In the rave environment, the sensory effects from the music and lighting are often highly synergistic with the drug. The psychedelic amphetamine quality of MDMA offers multiple reasons for its appeal to users in the rave setting. Some users enjoy the feeling of mass communion from the inhibition-reducing effects of the drug, while others use it as party fuel because of the drug's stimulatory effects.[36] MDMA is used less frequently than other stimulants, typically less than once per week.[37]
MDMA is sometimes taken in conjunction with other psychoactive drugs known as such as LSD, psilocybin mushrooms, and ketamine, an act called "candy-flipping".[38]
Medical
See also: MDMA § Research
As of 2017[update], MDMA has no accepted medical indications.[6][39][40] Before it was widely banned, it saw limited use in therapy.[4][6][41]
Other
A small number of therapists continue to use MDMA in therapy despite its illegal status.[42][43]
Small doses of MDMA are used as an entheogen to enhance prayer or meditation by some religious practitioners.[44] MDMA has been used as an adjunct to New Age spiritual practices.[45]
Forms
MDMA has become widely known as ecstasy (shortened "E", "X", or "XTC"), usually referring to its tablet form, although this term may also include the presence of possible adulterants or dilutants. The UK term "mandy" and the US term "molly" colloquially refer to MDMA in a crystalline powder form that is thought to be free of adulterants.[8][9][46] MDMA is also sold in the form of the hydrochloride salt, either as loose crystals or in gelcaps.[47][48]
In part due to the global supply shortage of sassafras oil, substances that are sold as molly frequently contain no MDMA and instead contain methylone, ethylone, MDPV, mephedrone, or any other of the group of compounds commonly known as bath salts.[9][46][47][48] Powdered MDMA ranges from pure MDMA to crushed tablets with 30–40% purity.[6] MDMA tablets typically have low purity due to bulking agents that are added to dilute the drug and increase profits (e.g., lactose) and binding agents.[6] Tablets sold as ecstasy sometimes contain 3,4-methylenedioxyamphetamine (MDA), 3,4-methylenedioxyethylamphetamine (MDEA), other amphetamine derivatives, caffeine, opiates, or painkillers.[4] Some tablets contain little or no MDMA.[4][6][12] The proportion of seized ecstasy tablets with MDMA-like impurities has varied annually and by country.[6] The average content of MDMA in a preparation is 70 to 120 mg with the purity having increased since the 1990s.[4]
MDMA is usually consumed by mouth. It is also sometimes snorted.[15]
Ecstasy tablets which may contain MDMA
A salt of MDMA (typically white) with impurities, resulting in a tan discoloration
Crushed MDMA (1 gram) crystals
High purity MDMA in capsules
Adverse effects
Short-term
The most serious short-term physical health risks of MDMA are hyperthermia and dehydration.[14][49] Cases of life-threatening or fatal hyponatremia (excessively low sodium concentration in the blood) have developed in MDMA users attempting to prevent dehydration by consuming excessive amounts of water without replenishing electrolytes.[14][49][50]
The immediate adverse effects of MDMA use can include:
Dehydration[10][14][49]
Hyperthermia[4][10][49]
Bruxism (grinding and clenching of the teeth)[4][10][13]
Increased wakefulness or insomnia[4][14]
Increased perspiration and sweating[14][49]
Increased heart rate and blood pressure[4][10][49]
Increased psychomotor activity[4]
Loss of appetite[4][12]
Nausea and vomiting[13]
Diarrhea[14]
Erectile dysfunction[4][51]
Visual and auditory hallucinations (rarely)[4]
Mydriasis[4]
The adverse effects that last up to a week[13][52] following cessation of moderate MDMA use include:
Physiological
Trismus[13]
Loss of appetite[52]
Insomnia[52]
Tiredness or lethargy[53][54]
Psychological
Anxiety or paranoia[52]
Depression[13][52]
Irritability[52]
Impulsiveness[52]
Restlessness[52]
Memory impairment[13]
Anhedonia[52]
Long-term
As of 2015[update], the long-term effects of MDMA on human brain structure and function have not been fully determined.[55] However, there is consistent evidence of structural and functional deficits in MDMA users with a high lifetime exposure.[55][56] In contrast, there is no evidence of structural or functional changes in MDMA users with only a moderate (<50 doses used and <100 tablets consumed) lifetime exposure.[56] MDMA use at high doses has been shown to produce brain lesions, a form of brain damage, in the serotonergic neural pathways of humans and animals.[3][12] It is unclear if typical MDMA users may develop neurotoxic brain lesions.[57] Long-term exposure to MDMA in humans has been shown to produce marked neurodegeneration in striatal, hippocampal, prefrontal, and occipital serotonergic axon terminals.[55][58] Neurotoxic damage to serotonergic axon terminals has been shown to persist for more than two years.[58] Elevations in brain temperature from MDMA use are positively correlated with MDMA-induced neurotoxicity.[10][55] Adverse neuroplastic changes to brain microvasculature and white matter also occur in humans using low doses of MDMA.[10][55] Reduced gray matter density in certain brain structures has also been noted in human MDMA users.[10][55] Global reductions in gray matter volume, thinning of the parietal and orbitofrontal cortices, and decreased hippocampal activity have been observed in long term users.[4] The effects established so far for recreational use of ecstasy lie in the range of moderate to large effects for SERT reduction.[59]
Impairments in multiple aspects of cognition, including attention, learning, memory, visual processing, and sleep have been found in regular MDMA users.[4][13][60][55] The magnitude of these impairments is correlated with lifetime MDMA usage[13][60][55] and are partially reversible with abstinence.[4] Several forms of memory are impaired by chronic ecstasy use;[13][60] however, the effect sizes for memory impairments in ecstasy users are generally small overall.[61][62] MDMA use is also associated with increased impulsivity and depression.[4]
Serotonin depletion following MDMA use can cause depression in subsequent days. In some cases depressive symptoms persist for longer.[4] Some studies indicate repeated recreational users of ecstasy have increased rates of depression and anxiety, even after quitting the drug.[63] Depression is one of the main factors for cessation of use.[4]
At high doses, MDMA induces a neuroimmune response which, through several mechanisms, increases the permeability of the blood-brain barrier, thereby making the brain more susceptible to environmental toxins and pathogens.[64][65][page needed] In addition, MDMA has immunosuppressive effects in the peripheral nervous system and pro-inflammatory effects in the central nervous system.[66]
During pregnancy
Addiction experts in psychiatry, chemistry, pharmacology, forensic science, epidemiology, and the police and legal services engaged in delphic analysis regarding 20 popular recreational drugs. Ecstasy was ranked 16th in dependence, physical harm, and social harm.[67]
MDMA is a moderately teratogenic drug (i.e., it is toxic to the fetus).[68][69] In utero exposure to MDMA is associated with a neuro- and cardiotoxicity[69] and impaired motor functioning. Motor delays may be temporary during infancy or long-term. The severity of these developmental delays increases with heavier MDMA use.[60][70]
Reinforcement disorders
Approximately 60% of MDMA users experience withdrawal symptoms when they stop taking MDMA.[12] Some of these symptoms include fatigue, loss of appetite, depression, and trouble concentrating.[12] Tolerance to some of the desired and adverse effects of MDMA is expected to occur with consistent MDMA use.[12] A 2007 analysis estimated MDMA to have a psychological dependence and physical dependence potential roughly three fourths and four fifths that of cannabis.[67]
MDMA has been shown to induce ΔFosB in the nucleus accumbens.[71] Because MDMA releases dopamine in the striatum, the mechanisms by which it induces ΔFosB in the nucleus accumbens are analogous to other dopaminergic psychostimulants.[71][72] Therefore, chronic use of MDMA at high doses can result in altered brain structure and drug addiction, which occur as a consequence of ΔFosB overexpression in the nucleus accumbens.[72] MDMA is less addictive than other stimulants such as methamphetamine and cocaine.[73][74] Compared with amphetamine, MDMA and its metabolite MDA are less reinforcing.[75]
One study found approximately 15% of chronic MDMA users met the DSM-IV diagnostic criteria for substance dependence.[76] However, there is little evidence for a specific diagnosable MDMA dependence syndrome because MDMA is typically used relatively infrequently.[37]
There are currently no medications to treat MDMA addiction.[77]
Harm assessment
A 2007 UK study ranked MDMA 18th in harmfulness out of 20 recreational drugs. Rankings for each drug were based on the risk for acute physical harm, the propensity for physical and psychological dependency on the drug, and the negative familial and societal impacts of the drug. The authors did not evaluate or rate the negative impact of ecstasy on the cognitive health of ecstasy users (e.g. impaired memory and concentration).[67]
Overdose
MDMA overdose symptoms vary widely due to the involvement of multiple organ systems. Some of the more overt overdose symptoms are listed in the table below. The number of instances of fatal MDMA intoxication is low relative to its usage rates. In most fatalities MDMA was not the only drug involved. Acute toxicity is mainly caused by serotonin syndrome and sympathomimetic effects.[76] MDMA's toxicity in overdose may be exacerbated by caffeine, with which it is frequently cut (mixed with to increase volume).[78] A scheme for management of acute MDMA toxicity has been published focusing on treatment of hyperthermia, hyponatraemia, seratonin syndrome, and multiple organ failure.[79]
Symptoms of overdose
System
Minor or moderate overdose[80]
Severe overdose[80]
Cardiovascular
Disseminated intravascular coagulation[14]
Intracranial hemorrhage[14]
Severe hypertension[14][81] or hypotension[14]
Hypotensive bleeding[4]
Central nervous
system
Abnormally fast reflexes[82]
Agitation[14][81]
Mental confusion[14]
Paranoia[14][81]
Stimulant psychosis[4][10]
Cognitive and memory impairment[14] potentially to the point of retrograde or anterograde amnesia[83]
Coma[10][81]
Convulsions[14][81]
Hallucinations[14][81]
Loss of consciousness[10]
Serotonin syndrome[10][14][50]
Musculoskeletal
Muscle rigidity[14]
Rhabdomyolysis (i.e., rapid muscle breakdown)[14][50]
Respiratory
Acute respiratory distress syndrome[14]
Urinary
Acute kidney injury[14][84]
Other
Cerebral edema[10]
Hepatitis[14][50]
Hyperpyrexia (a life-threatening elevation of body temperature)[14][50]
Hyponatremia (Syndrome of inappropriate antidiuretic hormone)[14][49][50]
Interactions
A number of drug interactions can occur between MDMA and other drugs, including serotonergic drugs.[12][85] MDMA also interacts with drugs which inhibit CYP450 enzymes, like ritonavir (Norvir), particularly CYP2D6 inhibitors.[12] Concurrent use of MDMA high dosages with another serotonergic drug can result in a life-threatening condition called serotonin syndrome.[4][12] Severe overdose resulting in death has also been reported in people who took MDMA in combination with certain monoamine oxidase inhibitors,[4][12] such as phenelzine (Nardil), tranylcypromine (Parnate), or moclobemide (Aurorix, Manerix).[86]
Pharmacology
Pharmacodynamics
MDMA binds to serotonin transporters.
MDMA acts primarily as a presynaptic releasing agent of serotonin, norepinephrine, and dopamine, which arises from its activity at trace amine-associated receptor 1 (TAAR1) and vesicular monoamine transporter 2 (VMAT2).[12][87][88] MDMA is a monoamine transporter substrate (i.e., a substrate for DAT, NET, and SERT), so it enters monoamine neurons via these neuronal membrane transport proteins;[87] by acting as a monoamine transporter substrate, MDMA produces competitive reuptake inhibition at the neuronal membrane transporters (i.e., it competes with endogenous monoamines for reuptake).[87][89] MDMA inhibits both vesicular monoamine transporters (VMATs), the second of which (VMAT2) is highly expressed within monoamine neurons at vesicular membranes.[88] Once inside a monoamine neuron, MDMA acts as a VMAT2 inhibitor and a TAAR1 agonist.[87][88]
Inhibition of VMAT2 by MDMA results in increased concentrations of the associated neurotransmitter (serotonin, norepinephrine, or dopamine) in the cytosol of a monoamine neuron.[88][90] Activation of TAAR1 by MDMA triggers protein kinase A and protein kinase C signaling events which then phosphorylates the associated monoamine transporters – DAT, NET, or SERT – of the neuron.[87] In turn, these phosphorylated monoamine transporters either reverse transport direction – i.e., move neurotransmitters from the cytosol to the synaptic cleft – or withdraw into the neuron, respectively producing neurotransmitter efflux and noncompetitive reuptake inhibition at the neuronal membrane transporters.[87] MDMA has ten times more affinity for uptake at serotonin transporters compared to dopamine and norepinephrine transporters and consequently has mainly serotonergic effects.[91]:1080
In summary, MDMA enters monoamine neurons by acting as a monoamine transporter substrate.[87] MDMA activity at VMAT2 moves neurotransmitters out from synaptic vesicles and into the cytosol;[88] MDMA activity at TAAR1 moves neurotransmitters out of the cytosol and into the synaptic cleft.[87]
MDMA also has weak agonist activity at postsynaptic serotonin receptors 5-HT1 and 5-HT2 receptors, and its more efficacious metabolite MDA likely augments this action.[92][93][94][95] Cortisol, prolactin, and oxytocin quantities in serum are increased by MDMA.[4] A placebo-controlled study in 15 human volunteers found 100 mg MDMA increased blood levels of oxytocin, and the amount of oxytocin increase was correlated with the subjective prosocial effects of MDMA.[96](S)-MDMA is more effective in eliciting 5-HT, NE, and DA release, while (D)-MDMA is overall less effective, and more selective for 5-HT and NE release (having only a very faint efficacy on DA release).[97]
MDMA is a ligand at both sigma receptor subtypes, though its efficacies at the receptors have not yet been elucidated.[98]
Pharmacokinetics
Diagram showing the sequence of MDMA metabolization.
MDMA reaches maximal concentrations in the blood stream between 1.5 and 3 hours after ingestion.[99] It is then slowly metabolized and excreted, with levels of MDMA and its metabolites decreasing to half their peak concentration over the next several hours.[100] The duration of action of MDMA is usually four to six hours, after which serotonin levels in the brain are depleted.[4] Serotonin levels typically return to normal within 24–48 hours.[4]
Metabolites of MDMA that have been identified in humans include 3,4-methylenedioxyamphetamine (MDA), 4-hydroxy-3-methoxymethamphetamine (HMMA), 4-hydroxy-3-methoxyamphetamine (HMA), 3,4-dihydroxyamphetamine (DHA) (also called alpha-methyldopamine (α-Me-DA)), 3,4-methylenedioxyphenylacetone (MDP2P), and 3,4-Methylenedioxy-N-hydroxyamphetamine (MDOH). The contributions of these metabolites to the psychoactive and toxic effects of MDMA are an area of active research. 80% of MDMA is metabolised in the liver, and about 20% is excreted unchanged in the urine.[10]
MDMA is known to be metabolized by two main metabolic pathways: (1) O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine.[80] The metabolism may be primarily by cytochrome P450 (CYP450) enzymes CYP2D6 and CYP3A4 and COMT. Complex, nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8, resulting in zeroth order kinetics at higher doses. It is thought that this can result in sustained and higher concentrations of MDMA if the user takes consecutive doses of the drug.[101][non-primary source needed]
MDMA and metabolites are primarily excreted as conjugates, such as sulfates and glucuronides.[102] MDMA is a chiral compound and has been almost exclusively administered as a racemate. However, the two enantiomers have been shown to exhibit different kinetics. The disposition of MDMA may also be stereoselective, with the S-enantiomer having a shorter elimination half-life and greater excretion than the R-enantiomer. Evidence suggests[103] that the area under the blood plasma concentration versus time curve (AUC) was two to four times higher for the (R)-enantiomer than the (S)-enantiomer after a 40 mg oral dose in human volunteers. Likewise, the plasma half-life of (R)-MDMA was significantly longer than that of the (S)-enantiomer (5.8 ± 2.2 hours vs 3.6 ± 0.9 hours).[12] However, because MDMA excretion and metabolism have nonlinear kinetics,[104] the half-lives would be higher at more typical doses (100 mg is sometimes considered a typical dose[99]).
Chemistry
(R)-MDMA
(S)-MDMA
MDMA is a racemic mixture and exists as two enantiomers: (R)- and (S)-MDMA.
A powdered salt of MDMA
Reactors used to synthesize MDMA on an industrial scale in a clandestine chemical factory in Cikande, Indonesia
MDMA is in the substituted methylenedioxyphenethylamine and substituted amphetamine classes of chemicals. As a free base, MDMA is a colorless oil insoluble in water.[6] The most common salt of MDMA is the hydrochloride salt;[6] pure MDMA hydrochloride is water-soluble and appears as a white or off-white powder or crystal.[6]
Synthesis
There are numerous methods available to synthesize MDMA via different intermediates.[105][106][107][108] The original MDMA synthesis described in Merck's patent involves brominating safrole to 1-(3,4-methylenedioxyphenyl)-2-bromopropane and then reacting this adduct with methylamine.[109][110] Most illicit MDMA is synthesized using MDP2P (3,4-methylenedioxyphenyl-2-propanone) as a precursor. MDP2P in turn is generally synthesized from piperonal, safrole or isosafrole.[111] One method is to isomerize safrole to isosafrole in the presence of a strong base, and then oxidize isosafrole to MDP2P. Another method uses the Wacker process to oxidize safrole directly to the MDP2P intermediate with a palladium catalyst. Once the MDP2P intermediate has been prepared, a reductive amination leads to racemic MDMA (an equal parts mixture of (R)-MDMA and (S)-MDMA).[citation needed] Relatively small quantities of essential oil are required to make large amounts of MDMA. The essential oil of Ocotea cymbarum, for example, typically contains between 80 and 94% safrole. This allows 500 ml of the oil to produce between 150 and 340 grams of MDMA.[112]
Synthesis of MDMA from piperonal
Synthesis of MDMA and related analogs from safrole
Detection in body fluids
MDMA and MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDMA or its major metabolites, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.[113][114][115]
History
Early research and use
German patents for MDMA synthesis and the subsequent methylhydrastinine synthesis filed by Merck on 24 December 1912 and issued in 1914.
MDMA was first synthesized in 1912 by Merck chemist Anton Köllisch. At the time, Merck was interested in developing substances that stopped abnormal bleeding. Merck wanted to avoid an existing patent held by Bayer for one such compound: hydrastinine. Köllisch developed a preparation of a hydrastinine analogue, methylhydrastinine, at the request of fellow lab members, Walther Beckh and Otto Wolfes. MDMA (called methylsafrylamin, safrylmethylamin or N-Methyl-a-Methylhomopiperonylamin in Merck laboratory reports) was an intermediate compound in the synthesis of methylhydrastinine. Merck was not interested in MDMA itself at the time.[116] On 24 December 1912, Merck filed two patent applications that described the synthesis and some chemical properties of MDMA[117] and its subsequent conversion to methylhydrastinine.[118]
Merck records indicate its researchers returned to the compound sporadically. A 1920 Merck patent describes a chemical modification to MDMA.[119] In 1927, Max Oberlin studied the pharmacology of MDMA while searching for substances with effects similar to adrenaline or ephedrine, the latter being structurally similar to MDMA. Compared to ephedrine, Oberlin observed that it had similar effects on vascular smooth muscle tissue, stronger effects at the uterus, and no "local effect at the eye". MDMA was also found to have effects on blood sugar levels comparable to high doses of ephedrine. Oberlin concluded that the effects of MDMA were not limited to the sympathetic nervous system. Research was stopped "particularly due to a strong price increase of safrylmethylamine", which was still used as an intermediate in methylhydrastinine synthesis. Albert van Schoor performed simple toxicological tests with the drug in 1952, most likely while researching new stimulants or circulatory medications. After pharmacological studies, research on MDMA was not continued. In 1959, Wolfgang Fruhstorfer synthesized MDMA for pharmacological testing while researching stimulants. It is unclear if Fruhstorfer investigated the effects of MDMA in humans.[116]
Outside of Merck, other researchers began to investigate MDMA. In 1953 and 1954, the United States Army commissioned a study of toxicity and behavioral effects in animals injected with mescaline and several analogues, including MDMA. Conducted at the University of Michigan in Ann Arbor, these investigations were declassified in October 1969 and published in 1973.[120][121] A 1960 Polish paper by Biniecki and Krajewski describing the synthesis of MDMA as an intermediate was the first published scientific paper on the substance.[116][121][122]
MDMA may have been in non-medical use in the western United States in 1968.[123] An August 1970 report at a meeting of crime laboratory chemists indicates MDMA was being used recreationally in the Chicago area by 1970.[121][124] MDMA likely emerged as a substitute for its analog methylenedioxyamphetamine (MDA),[125] a drug at the time popular among users of psychedelics[126] which was made a Schedule 1 substance in the United States in 1970.[127][128]
Shulgin's research and early use in therapy
Alexander and Ann Shulgin in December 2011
American chemist and psychopharmacologist Alexander Shulgin reported he synthesized MDMA in 1965 while researching methylenedioxy compounds at Dow Chemical Company, but did not test the psychoactivity of the compound at this time. Around 1970, Shulgin sent instructions for N-methylated MDA (MDMA) synthesis to the founder of a Los Angeles chemical company who had requested them. This individual later provided these instructions to a client in the Midwest. Shulgin may have suspected he played a role in the emergence of MDMA in Chicago.[121]
Shulgin first heard of the psychoactive effects of N-methylated MDA around 1975 from a young student who reported "amphetamine-like content".[121] Around 30 May 1976, Shulgin again heard about the effects of N-methylated MDA,[121] this time from a graduate student in a medicinal chemistry group he advised at San Francisco State University[126][129] who directed him to the University of Michigan study.[130] She and two close friends had consumed 100 mg of MDMA and reported positive emotional experiences.[121] Following the self-trials of a colleague at the University of San Francisco, Shulgin synthesized MDMA and tried it himself in September and October 1976.[121][126] Shulgin first reported on MDMA in a presentation at a conference in Bethesda, Maryland in December 1976.[121] In 1978, he and David E. Nichols published a report on the drug's psychoactive effect in humans. They described MDMA as inducing "an easily controlled altered state of consciousness with emotional and sensual overtones" comparable "to marijuana, to psilocybin devoid of the hallucinatory component, or to low levels of MDA".[131]
While not finding his own experiences with MDMA particularly powerful,[130][132] Shulgin was impressed with the drug's disinhibiting effects and thought it could be useful in therapy.[132] Believing MDMA allowed users to strip away habits and perceive the world clearly, Shulgin called the drug "window".[130][133] Shulgin occasionally used MDMA for relaxation, referring to it as "my low-calorie martini", and gave the drug to friends, researchers, and others who he thought could benefit from it.[130] One such person was Leo Zeff, a psychotherapist who had been known to use psychedelic substances in his practice. When he tried the drug in 1977, Zeff was impressed with the effects of MDMA and came out of his semi-retirement to promote its use in therapy. Over the following years, Zeff traveled around the US and occasionally to Europe, eventually training an estimated four thousand psychotherapists in the therapeutic use of MDMA.[132][134] Zeff named the drug "Adam", believing it put users in a state of primordial innocence.[126]
Psychotherapists who used MDMA believed the drug eliminated the typical fear response and increased communication. Sessions were usually held in the home of the patient or the therapist. The role therapist was minimized in favor of patient self-discovery accompanied by MDMA induced feelings of empathy. Depression, substance abuse, relationship problems, premenstrual syndrome, and autism were among several psychiatric disorders MDMA assisted therapy was reported to treat.[128] According to psychiatrist George Greer, therapists who used MDMA in their practice were impressed by the results. Anecdotally, MDMA was said to greatly accelerate therapy.[132]
Rising recreational use
In the late 1970s and early 1980s, "Adam" spread through personal networks of psychotherapists, psychiatrists, users of psychedelics, and yuppies. Hoping MDMA could avoid criminalization like LSD and mescaline, psychotherapists and experimenters attempted to limit the spread of MDMA and information about it while conducting informal research.[128][135] Early MDMA distributors were deterred from large scale operations by the threat of possible legislation.[136] Between the 1970s and the mid-1980s, this network of MDMA users consumed an estimated 500,000 doses.[13][137]
A small recreational market for MDMA developed by the late 1970s,[138] consuming perhaps 10,000 doses in 1976.[127] By the early 1980s MDMA was being used in Boston and New York City nightclubs such as Studio 54 and Paradise Garage.[139][140] Into the early 1980s, as the recreational market slowly expanded, production of MDMA was dominated by a small group of therapeutically minded Boston chemists. Having commenced production in 1976, this "Boston Group" did not keep up with growing demand and shortages frequently occurred.[136]
Perceiving a business opportunity, Michael Clegg, the Southwest distributor for the Boston Group, started his own "Texas Group" backed financially by Texas friends.[136][141] In 1981,[136] Clegg had coined "Ecstasy" as a slang term for MDMA to increase its marketability.[133][135] Starting in 1983,[136] the Texas Group mass-produced MDMA in a Texas lab[135] or imported it from California[133] and marketed tablets using pyramid sales structures and toll-free numbers.[137] MDMA could be purchased via credit card and taxes were paid on sales.[136] Under the brand name "Sassyfras", MDMA tablets were sold in brown bottles.[135] The Texas Group advertised "Ecstasy parties" at bars and discos, describing MDMA as a "fun drug" and "good to dance to".[136] MDMA was openly distributed in Austin and Dallas-Fort Worth area bars and nightclubs, becoming popular with yuppies, college students, and gays.[125][136][137]
Recreational use also increased after several cocaine dealers switched to distributing MDMA following experiences with the drug.[137] A California laboratory that analyzed confidentially submitted drug samples first detected MDMA in 1975. Over the following years the number of MDMA samples increased, eventually exceeding the number of MDA samples in the early 1980s.[142][143] By the mid-1980s, MDMA use had spread to colleges around the United States.[136]:33
Media attention and scheduling
United States
27 July 1984 Federal Register notice of the proposed MDMA scheduling
In an early media report on MDMA published in 1982, a Drug Enforcement Administration (DEA) spokesman stated the agency would ban the drug if enough evidence for abuse could be found.[136] By mid-1984, MDMA use was becoming more noticed. Bill Mandel reported on "Adam" in a 10 June San Francisco Chronicle article, but misidentified the drug as methyloxymethylenedioxyamphetamine (MMDA). In the next month, the World Health Organization identified MDMA as the only substance out of twenty phenethylamines to be seized a significant number of times.[135]
After a year of planning and data collection, MDMA was proposed for scheduling by the DEA on 27 July 1984 with a request for comments and objections.[135][144] The DEA was surprised when a number of psychiatrists, psychotherapists, and researchers objected to the proposed scheduling and requested a hearing.[128] In a Newsweek article published the next year, a DEA pharmacologist stated that the agency had been unaware of its use among psychiatrists.[145] An initial hearing was held on 1 February 1985 at the DEA offices in Washington, D.C. with administrative law judge Francis L. Young presiding.[135] It was decided there to hold three more hearings that year: Los Angeles on 10 June, Kansas City, Missouri on 10–11 July, and Washington, D.C. on 8–11 October.[128][135]
Sensational media attention was given to the proposed criminalization and the reaction of MDMA proponents, effectively advertising the drug.[128] In response to the proposed scheduling, the Texas Group increased production from 1985 estimates of 30,000 tablets a month to as many as 8,000 per day, potentially making two million ecstasy tablets in the months before MDMA was made illegal.[146] By some estimates the Texas Group distributed 500,000 tablets per month in Dallas alone.[133] According to one participant in an ethnographic study, the Texas Group produced more MDMA in eighteen months than all other distribution networks combined across their entire histories.[136] By May 1985, MDMA use was widespread in California, Texas, southern Florida, and the northeastern United States.[123][147] According to the DEA there was evidence of use in twenty-eight states[148] and Canada.[123] Urged by Senator Lloyd Bentsen, the DEA announced an emergency Schedule I classification of MDMA on 31 May 1985. The agency cited increased distribution in Texas, escalating street use, and new evidence of MDA (an analog of MDMA) neurotoxicity as reasons for the emergency measure.[147][149][150] The ban took effect one month later on 1 July 1985[146] in the midst of Nancy Reagan's "Just Say No" campaign.[151][152]
As a result of several expert witnesses testifying that MDMA had an accepted medical usage, the administrative law judge presiding over the hearings recommended that MDMA be classified as a Schedule III substance. Despite this, DEA administrator John C. Lawn overruled and classified the drug as Schedule I.[128][153] Later Harvard psychiatrist Lester Grinspoon sued the DEA, claiming that the DEA had ignored the medical uses of MDMA, and the federal court sided with Grinspoon, calling Lawn's argument "strained" and "unpersuasive", and vacated MDMA's Schedule I status. Despite this, less than a month later Lawn reviewed the evidence and reclassified MDMA as Schedule I again, claiming that the expert testimony of several psychiatrists claiming over 200 cases where MDMA had been used in a therapeutic context with positive results could be dismissed because they weren't published in medical journals.[128][citation needed] No double blind studies had yet been conducted as to the efficacy of MDMA for therapy.[citation needed]
United Nations
While engaged in scheduling debates in the United States, the DEA also pushed for international scheduling.[146] In 1985 the World Health Organization's Expert Committee on Drug Dependence recommended that MDMA be placed in Schedule I of the 1971 United Nations Convention on Psychotropic Substances. The committee made this recommendation on the basis of the pharmacological similarity of MDMA to previously scheduled drugs, reports of illicit trafficking in Canada, drug seizures in the United States, and lack of well-defined therapeutic use. While intrigued by reports of psychotherapeutic uses for the drug, the committee viewed the studies as lacking appropriate methodological design and encouraged further research. Committee chairman Paul Grof dissented, believing international control was not warranted at the time and a recommendation should await further therapeutic data.[154] The Commission on Narcotic Drugs added MDMA to Schedule I of the convention on 11 February 1986.[155]
Post-scheduling
A 1995 Vibe Tribe rave in Erskineville, New South Wales, Australia being broken up by police. MDMA use spread globally along with rave culture.
Play media
A 2000 United States Air Force video dramatizing the dangers of MDMA abuse.
The use of MDMA in Texas clubs declined rapidly after criminalization, although by 1991 the drug remained popular among young middle-class whites and in nightclubs.[136]:46 In 1985, MDMA use became associated with Acid House on the Spanish island of Ibiza.[136]:50[156] Thereafter in the late 1980s, the drug spread alongside rave culture to the UK and then to other European and American cities.[136]:50 Illicit MDMA use became increasingly widespread among young adults in universities and later, in high schools. Since the mid-1990s, MDMA has become the most widely used amphetamine-type drug by college students and teenagers.[91]:1080 MDMA became one of the four most widely used illicit drugs in the US, along with cocaine, heroin, and cannabis.[133] According to some estimates as of 2004, only marijuana attracts more first time users in the US.[133]
After MDMA was criminalized, most medical use stopped, although some therapists continued to prescribe the drug illegally. Later,[when?] Charles Grob initiated an ascending-dose safety study in healthy volunteers. Subsequent legally-approved MDMA studies in humans have taken place in the US. in Detroit (Wayne State University), Chicago (University of Chicago), San Francisco (UCSF and California Pacific Medical Center), Baltimore (NIDA–NIH Intramural Program), and South Carolina, as well as in Switzerland (University Hospital of Psychiatry, Zürich), the Netherlands (Maastricht University), and Spain (Universitat Autònoma de Barcelona).[157]
"Molly", short for 'molecule', was recognized as a slang term for crystalline or powder MDMA in the 2000s.[158][159]
In 2010, the BBC reported that use of MDMA had decreased in the UK in previous years. This may be due to increased seizures during use and decreased production of the precursor chemicals used to manufacture MDMA. Unwitting substitution with other drugs, such as mephedrone and methamphetamine,[160] as well as legal alternatives to MDMA, such as BZP, MDPV, and methylone, are also thought to have contributed to its decrease in popularity.[161]
Society and culture
Global estimates of illegal drug users in 2014
(in millions of users)[162]
Substance
Best
estimate
Low
estimate
High
estimate
Amphetamine-
type stimulants 35.65 15.34 55.90
Cannabis 182.50 127.54 233.65
Cocaine 18.26 14.88 22.08
Ecstasy 19.40 9.89 29.01
Opiates 17.44 13.74 21.59
Opioids 33.12 28.57 38.52
Legal status
MDMA is legally controlled in most of the world under the UN Convention on Psychotropic Substances and other international agreements, although exceptions exist for research and limited medical use. In general, the unlicensed use, sale or manufacture of MDMA are all criminal offences.
Australia
In Australia, MDMA was declared an illegal substance in 1986 because of its harmful effects and potential for abuse. It is classed as a Schedule 9 Prohibited Substance in the country, meaning it is available for scientific research purposes only. Any other type of sale, use or manufacture is strictly prohibited by law. Permits for research uses on humans must be approved by a recognized ethics committee on human research.
In Western Australia under the Misuse of Drugs Act 1981 4.0g of MDMA is the amount required determining a court of trial, 2.0g is considered a presumption with intent to sell or supply and 28.0g is considered trafficking under Australian law.[163]
United Kingdom
In the United Kingdom, MDMA was made illegal in 1977 by a modification order to the existing Misuse of Drugs Act 1971. Although MDMA was not named explicitly in this legislation, the order extended the definition of Class A drugs to include various ring-substituted phenethylamines.[164][165] The drug is therefore illegal to sell, buy, or possess the drug without a licence in the UK. Penalties include a maximum of seven years and/or unlimited fine for possession; life and/or unlimited fine for production or trafficking.
Some researchers such as David Nutt have criticized the current scheduling of MDMA, what he determined to be a relatively harmless drug.[166][167] An editorial he wrote in the Journal of Psychopharmacology, where he compared the risk of harm for horse riding (1 adverse event in 350) to that of ecstasy (1 in 10,000) resulted in his dismissal as well as the resignation of his colleagues from the ACMD.[168]
United States
In the United States, MDMA is currently placed in Schedule I of the Controlled Substances Act.[169] In a 2011 federal court hearing the American Civil Liberties Union successfully argued that the sentencing guideline for MDMA/ecstasy is based on outdated science, leading to excessive prison sentences.[170] Other courts have upheld the sentencing guidelines. The United States District Court for the Eastern District of Tennessee explained its ruling by noting that "an individual federal district court judge simply cannot marshal resources akin to those available to the Commission for tackling the manifold issues involved with determining a proper drug equivalency."[171]
Netherlands
In the Netherlands, the Expert Committee on the List (Expertcommissie Lijstensystematiek Opiumwet) issued a report in June 2011 which discussed the evidence for harm and the legal status of MDMA, arguing in favor of maintaining it on List I.[171][172][173]
Canada
In Canada, MDMA is listed as a Schedule 1[174] as it is an analogue of amphetamine.[175] The CDSA was updated as a result of the Safe Streets Act changing amphetamines from Schedule III to Schedule I in March 2012.
Demographics
UNODC map showing the use of ecstasy by country in 2014 for the global population aged 15–64.
In 2014, 3.5% of 18 to 25 year-olds had used MDMA in the United States.[4] In Europe, an estimated 37% of regular club-goers aged 14 to 35 used MDMA in the past year according to the 2015 European Drug report.[4] The highest one-year prevalence of MDMA use in Germany in 2012 was 1.7% among people aged 25 to 29 compared with a population average of 0.4%.[4] Among adolescent users in the United States between 1999 and 2008, girls were more likely to use MDMA than boys.[176]
Economics
Europe
In 2008 the European Monitoring Centre for Drugs and Drug Addiction noted that although there were some reports of tablets being sold for as little as €1, most countries in Europe then reported typical retail prices in the range of €3 to €9 per tablet, typically containing 25–65 mg of MDMA.[177] By 2014 the EMCDDA reported that the range was more usually between €5 and €10 per tablet, typically containing 57–102 mg of MDMA, although MDMA in powder form was becoming more common.[178]
North America
The United Nations Office on Drugs and Crime stated in its 2014 World Drug Report that US ecstasy retail prices range from US$1 to $70 per pill, or from $15,000 to $32,000 per kilogram.[179] A new research area named Drug Intelligence aims to automatically monitor distribution networks based on image processing and machine learning techniques, in which an Ecstasy pill picture is analyzed to detect correlations among different production batches.[180] These novel techniques allow police scientists to facilitate the monitoring of illicit distribution networks.
As of October 2015[update], most of the MDMA in the United States is produced in British Columbia, Canada and imported by Canada-based Asian transnational criminal organizations.[46] The market for MDMA in the United States is relatively small compared to methamphetamine, cocaine, and heroin.[46] In the United States, about 0.9 million people used ecstasy in 2010.[15]
Australia
MDMA is particularly expensive in Australia, costing A$15–A$30 per tablet. In terms of purity data for Australian MDMA, the average is around 34%, ranging from less than 1% to about 85%. The majority of tablets contain 70–85 mg of MDMA. Most MDMA enters Australia from the Netherlands, the UK, Asia, and the US.[181]
Corporate logos on pills
A number of ecstasy manufacturers brand their pills with a logo, often being a corporate logo,[182] to help distinguish between suppliers; one of the most notable logos that appears on pills is the Mitsubishi logo.[183] Some pills depict logos of products or shows popular with children, such as Shaun the Sheep.[184]
Research
See also: List of investigational anxiolytics
The Multidisciplinary Association for Psychedelic Studies (MAPS) is funding pilot studies and clinical trials investigating the use of MDMA in psychotherapy to treat posttraumatic stress disorder (PTSD),[43] social anxiety in autistic adults,[4][185][186][187][188] and anxiety in terminal illness.[189][190] In November 2016, the United States Food and Drug Administration (FDA) approved large-scale phase 3 clinical trials involving the use of MDMA for the treatment of PTSD in individuals who do not respond to traditional prescription drugs or psychotherapy.[23] MDMA has also been proposed as an adjunct to substance abuse treatment.[5] In 2017, doctors in the UK began the first clinical study of MDMA in alcohol addiction.[191]
The potential for MDMA to be used as a rapid-acting antidepressant has been studied in clinical trials, but as of 2017 the evidence on efficacy and safety were insufficient to reach a conclusion.[192] A 2014 review of the safety and efficacy of MDMA as a treatment for various disorders, particularly PTSD, indicated that MDMA has therapeutic efficacy in some patients;[60] however, it emphasized that issues regarding the control-ability of MDMA-induced experiences and neurochemical recovery must be addressed.[60] The author noted that oxytocin and D-cycloserine are potentially safer co-drugs in PTSD treatment, albeit with limited evidence of efficacy.[60] This review and a second corroborating review by a different author both concluded that, because of MDMA's demonstrated potential to cause lasting harm in humans (e.g., serotonergic neurotoxicity and persistent memory impairment), "considerably more research must be performed" on its efficacy in PTSD treatment to determine if the potential treatment benefits outweigh its potential to harm to a patient.[13][60]
Notes
Jump up ^ The term MDMA is a contraction of 3,4-methylenedioxy-methamphetamine; it is also known as ecstasy (shortened to "E", "X", or "XTC"), mandy, and molly.[8][9] The international nonproprietary name is midomafetamine.[1]
Jump up ^ The FDA's "breakthrough therapy" designation is not intended to imply that a drug is actually a "breakthrough" or that there is high-quality evidence of treatment efficacy for a particular condition;[24][25] rather, it allows the FDA to grant priority review to drug candidates if preliminary clinical trials indicate that the therapy may offer substantial treatment advantages over existing options for patients with serious or life-threatening diseases.[25][26]
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Jump up ^ Sylvan, Robin (2005). "A Brief History of the Rave Scene". Trance Formation: The Spiritual and Religious Dimensions of Global Rave Culture. New York, NY: Routledge. pp. 21–22. ISBN 0415970903.
Jump up ^ Parrott, A. C. (1 May 2004). "Is ecstasy MDMA? A review of the proportion of ecstasy tablets containing MDMA, their dosage levels, and the changing perceptions of purity" (PDF). Psychopharmacology. 173 (3–4): 234–241. PMID 15007594. doi:10.1007/s00213-003-1712-7. Retrieved 7 August 2015.
Jump up ^ Renfroe, Charles L. (October 1986). "MDMA on the Street: Analysis Anonymous®". Journal of Psychoactive Drugs. 18 (4): 363–369. doi:10.1080/02791072.1986.10472371. Retrieved 7 August 2015.
Jump up ^ "Schedules of Controlled Substances Proposed Placement of 3,4-Methylenedioxymethamphetamine in Schedule I" (PDF). Federal Register. 49 (146): 30210. 27 July 1984. Retrieved 15 January 2015.
Jump up ^ Adler, Jerry; Abramson, Pamela; Katz, Susan; Hager, Mary (15 April 1985). "Getting High on 'Ecstasy'" (PDF). Newsweek. Life/Style: Newsweek Magazine. p. 96. Retrieved 1 February 2015.
^ Jump up to: a b c Holland, Julie (2001). "The History of MDMA". In Holland, Julie. Ecstasy: the complete guide; a comprehensive look at the risks and benefits of MDMA. Rochester, VT: Park Street Press. ISBN 0892818573.
^ Jump up to: a b "U.S. will ban 'ecstasy,' a hallucinogenic drug". The New York Times. The Associated Press. 1 June 1985. Retrieved 29 April 2015.
Jump up ^ "MDMA – FDA REPORT, 1985". Erowid. Food and Drug Administration. 1985. Retrieved 11 August 2015.
Jump up ^ Baker, Kathryn (30 May 1985). "DEA To Ban "Ecstasy" – The Drug MDMA". The Associated Press. Retrieved 7 August 2015.
Jump up ^ Corwin, Miles (31 May 1985). "U.S. to Ban Use of Drug MDMA : Street Abuse Cited; Used by Psychiatrists". Los Angeles Times. Retrieved 11 August 2015.
Jump up ^ Weber, Bruce (7 June 2014). "Alexander Shulgin, Psychedelia Researcher, Dies at 88". The New York Times. The New York Times Company. Retrieved 28 August 2015.
Jump up ^ Vastag, Brian (3 June 2014). "Chemist Alexander Shulgin, popularizer of the drug Ecstasy, dies at 88". The Washington Post. WP Company LLC. Retrieved 28 August 2015.
Jump up ^ "Ecstasy has its pros and cons". Kokomo Tribune. Kokomo, Indiana. Harper's Bazaar. 23 November 1985. p. 6 – via newspaperarchive.com.
Jump up ^ WHO Expert Committee on Drug Dependence: Twenty-second Report. (PDF). Geneva: World Health Organization. 1985. pp. 24–25. ISBN 9241207299. Archived from the original (PDF) on 19 October 2014. Retrieved 29 August 2012.
Jump up ^ "Decision to place MDMA into Schedule I" (PDF). UNODC. Commission on Narcotic Drugs. 11 February 1986. Retrieved 9 May 2015.
Jump up ^ McKinley, Jr., James C. (12 September 2013). "Overdoses of ‘Molly’ Led to Electric Zoo Deaths". The New York Times. Retrieved 9 December 2013.
Jump up ^ Bibliography of Psychedelic Research Studies. collected by the Multidisciplinary Association for Psychedelic Studies Archived 3 December 2013 at the Wayback Machine.
Jump up ^ Susan Donaldson James (23 February 2015). "What Is Molly and Why Is It Dangerous?". NBCNews.com. Retrieved 23 February 2015. Why is it called Molly? That's short for "molecule." "You can put a ribbon and bow on it and call it a cute name like 'Molly' and people are all in," said Paul Doering, professor emeritus of pharmacology at the University of Florida.
Jump up ^ Aleksander, Irina (21 June 2013). "Molly: Pure, but Not So Simple". The New York Times. The New York Times Company. Retrieved 24 February 2015.
Jump up ^ "Mephedrone (4-Methylmethcathinone) appearing in "Ecstasy" in the Netherlands". 19 September 2010. Retrieved 31 December 2012.
Jump up ^ "Why ecstasy is 'vanishing' from UK nightclubs". BBC News. 19 January 2010. Retrieved 14 February 2010.
Jump up ^ "Statistical tables". World Drug Report 2016 (pdf). Vienna, Austria: United Nations Office on Drugs and Crime. 2016. ISBN 9789210578622. Retrieved 1 August 2016.
Jump up ^ "Misuse of Drugs Act 1981". The Government of Western Australia. Department of the Premier and Cabinet. 23 October 1981.
Jump up ^ Power, Mike (2013). Drugs 2.0 : the web revolution that's changing how the world gets high (epub file). London: Portobello. ISBN 9781846274596.
Jump up ^ Misuse of Drugs Act 1971. Statutelaw.gov.uk (5 January 1998). Retrieved on 11 June 2011.
Jump up ^ "Ecstasy 'no more dangerous than horse riding'". Telegraph.co.uk. Retrieved 4 December 2015.
Jump up ^ Nutt, D. (21 January 2009). "Equasy – An overlooked addiction with implications for the current debate on drug harms". Journal of Psychopharmacology. 23 (1): 3–5. PMID 19158127. doi:10.1177/0269881108099672.
Jump up ^ Johnson, Alan (2 November 2009). "Why Professor David Nutt was shown the door". London: The Guardian. Retrieved 3 November 2009.
Jump up ^ Schedules of Controlled Substances; Scheduling of 3,4-Methylenedioxymethamphetamine (MDMA) Into Schedule I of the Controlled Substances Act; Remand, 53 Fed. Reg. 5,156 (DEA 22 February 1988).
Jump up ^ Court Rejects Harsh Federal Drug Sentencing Guideline as Scientifically Unjustified | American Civil Liberties Union. Aclu.org (15 July 2011). Retrieved on 29 August 2012.
^ Jump up to: a b "An Examination of Federal Sentencing Guidelines' Treatment of MDMA ('Ecstasy') by Alyssa C. Hennig :: SSRN". SSRN 2481227  . Missing or empty |url= (help)
Jump up ^ Rapport Drugs in Lijsten | Rapport. Rijksoverheid.nl (27 June 2011). Retrieved on 29 August 2012.
Jump up ^ "Committee: the current system of the Opium Act does not have to be changed". government.nl. 24 June 2011. Retrieved 29 August 2012.
Jump up ^ "Schedule I". Controlled Drugs and Substances Act. Isomer Design. Retrieved 9 December 2013.
Jump up ^ "Definitions and interpretations". Controlled Drugs and Substances Act. Isomer Design. Retrieved 9 December 2013.
Jump up ^ Wu, Ping; Liu, Xinhua; Pham, Trang Hoang; Jin, Jue; Fan, Bin; Jin, Zhezhen (1 November 2010). "Ecstasy use among US adolescents from 1999 to 2008". Drug and Alcohol Dependence. 112 (1–2): 33–38. PMC 2967577  . PMID 20570447. doi:10.1016/j.drugalcdep.2010.05.006. Retrieved 7 October 2015.
Jump up ^ European Monitoring Centre for Drugs and Drug Addiction (2008). Annual report: the state of the drugs problem in Europe (PDF). Luxembourg: Office for Official Publications of the European Communities. p. 49. ISBN 978-92-9168-324-6.
Jump up ^ "European Drug Report 2014, page 26" (PDF).
Jump up ^ "Ecstasy-type substances Retail and wholesale prices* and purity levels, by drug, region and country or territory". United Nations Office on Drugs and Crime. Archived from the original on 8 December 2015. Retrieved 2 January 2015.
Jump up ^ Camargo J, Esseiva P, González F, Wist J, Patiny L (30 November 2012). "Monitoring of illicit pill distribution networks using an image collection exploration framework". Forensic Science International. 223 (1): 298–305. PMID 23107059. doi:10.1016/j.forsciint.2012.10.004. Retrieved 9 December 2013.
Jump up ^ Drugtext – 10 years of ecstasy and other party drug use in Australia: What have we done and what is there left to do?. Drugtext.org. Retrieved on 11 June 2011. Archived 9 February 2012 at the Wayback Machine.
Jump up ^ "Erowid MDMA Vault : Images". Retrieved 3 March 2016.
Jump up ^ Steven B. Karch. (2011). "A Historical Review of MDMA" (PDF). The Open Forensic Science Journal. 4: 20–24. doi:10.2174/1874402801104010020. Archived from the original (PDF) on 7 April 2016.
Jump up ^ "Now sick dealers peddle Shaun the Sheep Ecstasy tablets". Western Daily Press. Retrieved 3 March 2016.
Jump up ^ Danforth, Alicia L.; Struble, Christopher M.; Yazar-Klosinski, Berra; Grob, Charles S. (March 2015). "MDMA-assisted therapy: A new treatment model for social anxiety in autistic adults". Progress in Neuro-Psychopharmacology and Biological Psychiatry. 64: 237–249. doi:10.1016/j.pnpbp.2015.03.011. Retrieved 17 April 2015.
Jump up ^ Maxmen, Amy. "Psychedelic Compound in Ecstasy Moves Closer to Approval to Treat PTSD". Scientific American. Retrieved 18 May 2017.
Jump up ^ Maxmen, Amy. "Psychedelic compound in ecstasy moves closer to approval to treat PTSD". Nature. doi:10.1038/nature.2017.21917. Retrieved 18 May 2017.
Jump up ^ Waldman, Ayelet (2017-01-10). A Really Good Day: How Microdosing Made a Mega Difference in My Mood, My Marriage, and My Life. Knopf Doubleday Publishing Group. ISBN 9780451494108. Retrieved 18 May 2017.
Jump up ^ Lattin, Don (19 March 2015). "Patients in ecstasy clinical trial find drug beneficial". San Francisco Chronicle. Hearst Corporation. Archived from the original on 24 April 2016. Retrieved 28 April 2016.
Jump up ^ Mithoefer, Michael C.; Grob, Charles S.; Brewerton, Timothy D. (2016). "Novel psychopharmacological therapies for psychiatric disorders: psilocybin and MDMA". The Lancet. Psychiatry. 3 (5): 481–8. ISSN 2215-0374. PMID 27067625. doi:10.1016/S2215-0366(15)00576-3.
Jump up ^ Hannah Devlin (30 June 2017). "World's first trials of MDMA to treat alcohol addiction set to begin". The Guardian.
Jump up ^ Patel, Rachel; Titheradge, Daniel (11 January 2017). "MDMA for the treatment of mood disorder: all talk no substance?". Therapeutic Advances in Psychopharmacology. 5 (3): 179–188. ISSN 2045-1253. PMC 4502590  . PMID 26199721. doi:10.1177/2045125315583786.
External links
Find more aboutMDMAat Wikipedia's sister projects
Definitions from Wiktionary
Media from Commons
News from Wikinews
Data from Wikidata
MDMA Facts and Statistics National Institute on Drug Abuse
Methylenedioxymethamphetamine (MDMA or 'Ecstasy') drug profile European Monitoring Centre for Drugs and Drug Addiction
MDMA-Assisted Psychotherapy Multidisciplinary Association for Psychedelic Studies
[show]
Recreational uses
[show]
v
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Recreational drug use
Major
recreational
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[show]
v
t
e
Empathogens/entactogens
Phenylalkyl-
amines
(other than
cathinones)
Unfused benzene ring: 4-CAB
4-FA
4-FMA
4-MTA
4,4'-DMAR
Ariadne
Metaescaline
MMA
PMA
PMEA
PMMA
Benzodioxine: EDMA
Benzodioxoles: Phenethylamine: { Lophophine }
Amphetamines: { 2-Methyl-MDA
2,3-MDA
3,4-MDA (tenamfetamine)
5-Methyl-MDA
6-Methyl-MDA
DiFMDA
DMMDA
DMMDA-2
EIDA
MDEA
MDMA (midomafetamine)
MDMOH
MDOH
MMDA
MMDA-2
MMDMA }
1-Phenylbutan-2-amines: { BDB
EBDB
MBDB }
Phentermines: { MDMP
MDPH }
Benzofurans and dihidrobenzofurans: 5-APB
5-APDB
5-EAPB
5-MAPB
5-MAPDB
5-MBPB
6-APB
6-APDB
6-EAPB
6-MAPB
6-MAPDB
Indanes: 5-APDI
5-MAPDI
Indole: 6-API
Naphtalenes: Methamnetamine
Naphthylaminopropane
Tetralin: 6-APT
Cyclized phenyl-
alkylamines
Aminoindanes: 5-IAI
AMMI
ETAI
MDAI
MDMAI
MMAI
NM-2-AI
TAI
Aminotetralins: 6-CAT
MDAT
MDMAT
Cathinones
3-MMC
4-EMC
Brephedrone
Butylone
Ethylone
Eutylone
Flephedrone
Mephedrone
Methedrone
Methylone
Pentylone
Tryptamines
4-Methyl-αET
αET
αMT
Chemical classes
Substituted amphetamine
Sub. benzofuran
Sub. cathinone
Sub. MDPEA
Sub. PEA
Sub. tryptamine
[show]
v
t
e
Euphoriants
μ-Opioid receptor agonists (opioids) (e.g., morphine, heroin, hydrocodone, oxycodone, opium, kratom)
α2δ subunit-containing voltage-dependent calcium channels blockers (gabapentinoids) (e.g., gabapentin, pregabalin, phenibut)
AMPA receptor antagonists (e.g., perampanel)
CB1 receptor agonists (cannabinoids) (e.g., THC, cannabis)
Dopamine receptor agonists (e.g., levodopa)
Dopamine releasing agents (e.g., amphetamine, methamphetamine, MDMA, mephedrone)
Dopamine reuptake inhibitors (e.g., cocaine, methylphenidate)
GABAA receptor positive allosteric modulators (e.g., barbiturates, benzodiazepines, carbamates, ethanol (alcohol) (alcoholic drink), inhalants, nonbenzodiazepines, quinazolinones)
GHB (sodium oxybate) and analogues
Glucocorticoids (corticosteroids) (e.g., dexamethasone, prednisone)
nACh receptor agonists (e.g., nicotine, tobacco, arecoline, areca nut)
Nitric oxide prodrugs (e.g., alkyl nitrites (poppers))
NMDA receptor antagonists (e.g., DXM, ketamine, methoxetamine, nitrous oxide, phencyclidine, inhalants)
Orexin receptor antagonists (e.g., suvorexant)
See also: Recreational drug use
[show]
v
t
e
Hallucinogens
Psychedelics
(5-HT2A
agonists)
Benzofurans
2C-B-FLY
2CBFly-NBOMe
5-MeO-BFE
5-MeO-DiBF
Bromo-DragonFLY
F-2
F-22
TFMFly
Lyserg‐
amides
1P-ETH-LAD
1P-LSD
2-Butyllysergamide
3-Pentyllysergamide
AL-LAD
ALD-52
BU-LAD
Diallyllysergamide
Dimethyllysergamide
Ergometrine
ETH-LAD
IP-LAD
LAE-32
LPD-824
LSA
LSD
LSD-Pip
LSH
LSM-775
LSZ
Methylergometrine
Methylisopropyllysergamide
Methysergide
MLD-41
PARGY-LAD
PRO-LAD
Phenethyl‐
amines
2C-x
2C-B
2C-B-AN
2C-Bn
2C-Bu
2C-C
2C-CN
2C-CP
2C-D
2C-E
2C-EF
2C-F
2C-G
2C-G-1
2C-G-2
2C-G-3
2C-G-4
2C-G-5
2C-G-6
2C-G-N
2C-H
2C-I
2C-iP
2C-N
2C-NH2
2C-O
2C-O-4
2C-P
2C-Ph
2C-SE
2C-T
2C-T-2
2C-T-3
2C-T-4
2C-T-5
2C-T-6
2C-T-7
2C-T-8
2C-T-9
2C-T-10
2C-T-11
2C-T-12
2C-T-13
2C-T-14
2C-T-15
2C-T-16
2C-T-17
2C-T-18
2C-T-19
2C-T-20
2C-T-21
2C-T-22
2C-T-22.5
2C-T-23
2C-T-24
2C-T-25
2C-T-27
2C-T-28
2C-T-30
2C-T-31
2C-T-32
2C-T-33
2C-TFE
2C-TFM
2C-YN
2C-V
25x-NBx
25x-NB3OMe
25B-NB3OMe
25C-NB3OMe
25D-NB3OMe
25E-NB3OMe
25H-NB3OMe
25I-NB3OMe
25N-NB3OMe
25P-NB3OMe
25T2-NB3OMe
25T4-NB3OMe
25T7-NB3OMe
25TFM-NB3OMe
25x-NB4OMe
25B-NB4OMe
25C-NB4OMe
25D-NB4OMe
25E-NB4OMe
25H-NB4OMe
25I-NB4OMe
25N-NB4OMe
25P-NB4OMe
25T2-NB4OMe
25T4-NB4OMe
25T7-NB4OMe
25TFM-NB4OMe
25x-NBF
25B-NBF
25C-NBF
25D-NBF
25E-NBF
25H-NBF
25I-NBF
25P-NBF
25T2-NBF
25T7-NBF
25TFM-NBF
25x-NBMD
25B-NBMD
25C-NBMD
25D-NBMD
25E-NBMD
25F-NBMD
25H-NBMD
25I-NBMD
25P-NBMD
25T2-NBMD
25T7-NBMD
25TFM-NBMD
25x-NBOH
25B-NBOH
25C-NBOH
25CN-NBOH
25D-NBOH
25E-NBOH
25F-NBOH
25H-NBOH
25I-NBOH
25P-NBOH
25T2-NBOH
25T7-NBOH
25TFM-NBOH
25x-NBOMe
25B-NBOMe
25C-NBOMe
25CN-NBOMe
25D-NBOMe
25E-NBOMe
25F-NBOMe
25G-NBOMe
25H-NBOMe
25I-NBOMe
25iP-NBOMe
25N-NBOMe
25P-NBOMe
25T2-NBOMe
25T4-NBOMe
25T7-NBOMe
25TFM-NBOMe
Atypical structures
25I-NB34MD
2CBCB-NBOMe
2CBFly-NBOMe
NBOMe-mescaline
3C-x
3C-AL
3C-BZ
3C-DFE
3C-E
3C-P
4C-x
4C-B
4C-D
4C-T-2
DOx
DOT
DOB
DOC
DOEF
DOET
DOF
DOI
DOiPR
DOM
DON
DOPR
DOTFM
MEM
HOT-x
HOT-2
HOT-7
HOT-17
MDxx
DMMDA
DMMDA-2
Lophophine
MDA
MMDA
MMDA-2
MMDA-3a
MMDMA
Mescaline (subst.)
2-Bromomescaline
3-TE
4-TE
3-TM
4-TM
Allylescaline
Asymbescaline
Buscaline
Cyclopropylmescaline
Difluoromescaline
Difluoroescaline
Escaline
Fluoroproscaline
Isobuscaline
Isoproscaline
Jimscaline
Mescaline
Metaescaline
Methallylescaline
Proscaline
Thioproscaline
Trifluoroescaline
Trifluoromescaline
TMAs
TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6
Others
2C-B-BUTTERFLY
2C-B-DragonFLY
2CB-5-hemifly
2-TOM
5-TOET
5-TOM
2CB-Ind
2CD-5EtO
BOB
BOD
βk-2C-B
βk-2C-I
DESOXY
DMCPA
DMBMPP
DOB-FLY
Fenfluramine
Ganesha
Macromerine
MMA
TCB-2
TOMSO
Piperazines
BZP
pFPP
Tryptamines
alpha-alkyltryptamines
4,5-DHP-α-MT
5-MeO-α-ET
5-MeO-α-MT
α-ET
α-MT
x-DALT
(Daltocin) 4-HO-DALT
(Daltacetin) 4-AcO-DALT
5-MeO-DALT
DALT
x-DET
(Ethacetin) 4-AcO-DET
(Ethocin) 4-HO-DET
5-MeO-DET
(T-9) DET
(Ethocybin) 4-PO-DET
x-DiPT
1-Me-5-MeO-DiPT
(Ipracetin) 4-AcO-DiPT
(Iprocin) 4-HO-DiPT
(Foxy Methoxy) 5-MeO-DiPT
DiPT
x-DMT
4,5-DHP-DMT
2,N,N-TMT
4-AcO-DMT
4-HO-5-MeO-DMT
4,N,N-TMT
4-Propionyloxy-DMT
5,6-diBr-DMT
5-AcO-DMT
5-Bromo-DMT
5-MeO-2,N,N-TMT
5-MeO-4,N,N-TMT
5-MeO-α,N,N-TMT
5-MeO-DMT
5-N,N-TMT
7,N,N-TMT
α,N,N-TMT
(Bufotenin) 5-HO-DMT
DMT
Norbaeocystin
(Psilocin) 4-HO-DMT
(Psilocybin) 4-PO-DMT
x-DPT
(Depracetin) 4-AcO-DPT
(Deprocin) 4-HO-DPT
5-MeO-DPT
(The Light) DPT
Ibogaine-related
18-MAC
18-MC
Coronaridine
Ibogaine
Ibogamine
ME-18-MC
Noribogaine
Tabernanthine
Voacangine
x-MET
(Metocin) 4-HO-MET
(Metocetin) 4-AcO-MET
5-MeO-MET
MET
x-MiPT
(Mipracetin) 4-AcO-MiPT
(Miprocin) 4-HO-MiPT
5-Me-MiPT
(Moxy) 5-MeO-MiPT
MiPT
Others
4-HO-DBT
4-HO-EPT
4-HO-McPT
(Lucigenol) 4-HO-MPMI
(Meprocin) 4-HO-MPT
5-MeO-EiPT
5-MeO-MALT
5-MeO-MPMI
Aeruginascin
Baeocystin
DBT
DCPT
EiPT
EPT
MPT
PiPT
Others
5-MeO-DiBF
AL-38022A
ALPHA
Dimemebfe
Efavirenz
Lorcaserin
M-ALPHA
RH-34
Also empathogens in general (e. g.: 5-APB, 5-MAPB, 6-APB and other substituted benzofurans, MDAI, MDMA).
Dissociatives
(NMDAR
antagonists)
Arylcyclo‐
hexylamines
Ketamine-related
2-Fluorodeschloroketamine
Arketamine ((R)-ketamine)
Deschloroketamine
Ethketamine (N-Ethylnorketamine)
Esketamine ((S)-ketamine)
Ketamine
Methoxetamine
Methoxmetamine
Methoxyketamine
Norketamine
Tiletamine
PCP-related
3'-HO-PCP
3'-MeO-PCE
3'-MeO-PCMo
3'-MeO-PCP
BDPC
Dieticyclidine (PCDE)
Eticyclidine (PCE)
Methoxydine (4'-MeO-PCP)
PCPr
Phencyclidine (PCP)
Rolicyclidine (PCPy)
Tenocyclidine (TCP)
Others
BTCP
Gacyclidine
PRE-084
Diarylethylamines
Diphenidine
Ephenidine
Fluorolintane
Methoxphenidine
Morphinans
Dextrallorphan
Dextromethorphan
Dextrorphan
Racemethorphan
Racemorphan
Others
2-EMSB
2-MDP
8A-PDHQ
Aptiganel
Budipine
Delucemine
Dexoxadrol
Dizocilpine
Etoxadrol
Herkinorin
Ibogaine
Midafotel
NEFA
Neramexane
Nitrous oxide
Noribogaine
Perzinfotel
RB-64
Remacemide
Salvinorin A
Selfotel
Xenon
Deliriants
(mAChR
antagonists)
Atropine
Benactyzine
Benzatropine
Benzydamine
Biperiden
BRN-1484501
Brompheniramine
BZ
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Chloropyramine
Chlorphenamine
Clemastine
CS-27349
Cyclizine
Cyproheptadine
Dicycloverine
Dimenhydrinate
Diphenhydramine
Ditran
Doxylamine
EA-3167
EA-3443
EA-3580
EA-3834
Elemicin
Flavoxate
Hyoscyamine
JB-318
JB-336
Meclozine
Mepyramine
Myristicin
Orphenadrine
Oxybutynin
Pheniramine
Phenyltoloxamine
Procyclidine
Promethazine
Scopolamine
Tolterodine
Trihexyphenidyl
Tripelennamine
Triprolidine
WIN-2299
Others
Cannabinoids
(CB1 agonists)
Natural
THC (Dronabinol)
THCV
Synthetic
AM-x
AM-087
AM-251
AM-279
AM-281
AM-356
AM-374
AM-381
AM-404
AM-411
AM-630
AM-661
AM-678
AM-679
AM-694
AM-735
AM-855
AM-881
AM-883
AM-905
AM-906
AM-919
AM-926
AM-938
AM-1116
AM-1172
AM-1220
AM-1221
AM-1235
AM-1241
AM-1248
AM-1710
AM-1714
AM-1902
AM-2201
AM-2212
AM-2213
AM-2232
AM-2233
AM-2389
AM-3102
AM-4030
AM-4054
AM-4056
AM-4113
AM-6545
CP x
CP 47,497
CP 55,244
CP 55,940
(±)-CP 55,940
(+)-CP 55,940
(-)-CP 55,940
HU-x
HU-210
HU-211
HU-239
HU-243
HU-308
HU-320
HU-331
HU-336
HU-345
JWH-x
JWH-007
JWH-015
JWH-018
JWH-019
JWH-030
JWH-047
JWH-048
JWH-051
JWH-057
JWH-073
JWH-081
JWH-098
JWH-116
JWH-120
JWH-122
JWH-133
JWH-139
JWH-147
JWH-148
JWH-149
JWH-149
JWH-161
JWH-164
JWH-166
JWH-167
JWH-171
JWH-175
JWH-176
JWH-181
JWH-182
JWH-184
JWH-185
JWH-192
JWH-193
JWH-193
JWH-194
JWH-195
JWH-196
JWH-197
JWH-198
JWH-199
JWH-200
JWH-203
JWH-205
JWH-210
JWH-210
JWH-213
JWH-220
JWH-229
JWH-234
JWH-249
JWH-250
JWH-251
JWH-253
JWH-258
JWH-300
JWH-302
JWH-307
JWH-336
JWH-350
JWH-359
JWH-387
JWH-398
JWH-424
Misc. designer cannabinoids
4-HTMPIPO
5F-AB-FUPPYCA
5F-AB-PINACA
5F-ADB
5F-ADB-PINACA
5F-ADBICA
5F-AMB
5F-APINACA
5F-CUMYL-PINACA
5F-NNE1
5F-PB-22
5F-SDB-006
A-796,260
A-836,339
AB-001
AB-005
AB-CHFUPYCA
AB-CHMINACA
AB-FUBINACA
AB-PINACA
ADAMANTYL-THPINACA
ADB-CHMINACA
ADB-FUBINACA
ADB-PINACA
ADBICA
ADSB-FUB-187
AMB-FUBINACA
APICA
APINACA
APP-FUBINACA
CB-13
CUMYL-PICA
CUMYL-PINACA
CUMYL-THPINACA
DMHP
EAM-2201
FAB-144
FDU-PB-22
FUB-144
FUB-APINACA
FUB-JWH-018
FUB-PB-22
FUBIMINA
JTE 7-31
JTE-907
Levonantradol
MDMB-CHMICA
MDMB-CHMINACA
MDMB-FUBINACA
MEPIRAPIM
MAM-2201
MDA-19
MN-18
MN-25
NESS-0327
NESS-040C5
Nabilone
Nabitan
NM-2201
NNE1
Org 28611
Parahexyl
PTI-1
PTI-2
PX-1
PX-2
PX-3
QUCHIC
QUPIC
RCS-4
RCS-8
SDB-005
SDB-006
STS-135
THC-O-acetate
THC-O-phosphate
THJ-018
THJ-2201
UR-144
WIN 55,212-2
XLR-11
D2 agonists
Apomorphine
Aporphine
Bromocriptine
Cabergoline
Lisuride
Memantine
Nuciferine
Pergolide
Phenethylamine
Piribedil
Pramipexole
Ropinirole
Rotigotine
Salvinorin A
Also indirect D2 agonists, such as dopamine reuptake inhibitors (cocaine, methylphenidate), releasing agents (amphetamine, methamphetamine), and precursors (levodopa).
GABAA
enhancers
CI-966
Eszopiclone
Ibotenic acid
Muscimol (Amanita muscaria)
Zaleplon
Zolpidem
Zopiclone
Inhalants
(Mixed MOA)
Aliphatic hydrocarbons
Butane
Gasoline
Kerosene
Propane
Aromatic hydrocarbons
Toluene
Ethers
Diethyl ether
Enflurane
Haloalkanes
Chlorofluorocarbons
Chloroform
κOR agonists
2-EMSB
Alazocine
Bremazocine
Butorphan
Butorphanol
Cyclazocine
Cyclorphan
Cyprenorphine
Diprenorphine
Enadoline
Herkinorin
Heroin
HZ-2
Ibogaine
Ketazocine
Levallorphan
Levomethorphan
Levorphanol
LPK-26
Metazocine
Morphine
Nalbuphine
Nalmefene
Nalorphine
Noribogaine
Oxilorphan
Pentazocine
Phenazocine
Proxorphan
Racemethorphan
Racemorphan
Salvinorin A
Spiradoline
Tifluadom
U-50488
U-69,593
Xorphanol
Others
Glaucine
Isoaminile
Noscapine
Pukateine
[show]
v
t
e
Stimulants
Adamantanes
Adapromine
Amantadine
Bromantane
Memantine
Rimantadine
Adenosine antagonists
8-Chlorotheophylline
8-Cyclopentyltheophylline
8-Phenyltheophylline
Aminophylline
Caffeine
CGS-15943
Dimethazan
Paraxanthine
SCH-58261
Theobromine
Theophylline
Alkylamines
Cyclopentamine
Cypenamine
Cyprodenate
Heptaminol
Isometheptene
Levopropylhexedrine
Methylhexaneamine
Octodrine
Propylhexedrine
Tuaminoheptane
Ampakines
CX-516
CX-546
CX-614
CX-691
CX-717
IDRA-21
LY-404,187
LY-503,430
Nooglutyl
Org 26576
PEPA
S-18986
Sunifiram
Unifiram
Arylcyclohexylamines
Benocyclidine
Dieticyclidine
Esketamine
Eticyclidine
Gacyclidine
Ketamine
Phencyclamine
Phencyclidine
Rolicyclidine
Tenocyclidine
Tiletamine
Benzazepines
6-Br-APB
SKF-77434
SKF-81297
SKF-82958
Cholinergics
A-84,543
A-366,833
ABT-202
ABT-418
AR-R17779
Altinicline
Anabasine
Arecoline
Bradanicline
Cotinine
Cytisine
Dianicline
Epibatidine
Epiboxidine
GTS-21
Ispronicline
Nicotine
PHA-543,613
PNU-120,596
PNU-282,987
Pozanicline
Rivanicline
Sazetidine A
SIB-1553A
SSR-180,711
TC-1698
TC-1827
TC-2216
Tebanicline
UB-165
Varenicline
WAY-317,538
Convulsants
Anatoxin-a
Bicuculline
DMCM
Flurothyl
Gabazine
Pentetrazol
Picrotoxin
Strychnine
Thujone
Eugeroics
Adrafinil
Armodafinil
CRL-40,940
CRL-40,941
Fluorenol
JZ-IV-10
Modafinil
Oxazolines
4-Methylaminorex
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone
Phenethylamines
1-(4-Methylphenyl)-2-aminobutane
1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
2-Fuoroamphetamine
2-Fuoromethamphetamine
2-OH-PEA
2-Phenyl-3-aminobutane
2,3-MDA
3-Fuoroamphetamine
3-Fluoroethamphetamine
3-Fluoromethcathinone
3-Methoxyamphetamine
3-Methylamphetamine
3,4-DMMC
4-BMC
4-CMC
4-Ethylamphetamine
4-Fluoroamphetamine
4-Fluoromethamphetamine
4-MA
4-Methylbuphedrone
4-Methylcathinone
4-MMA
4-Methylpentedrone
4-MTA
6-FNE
AL-1095
Alfetamine
a-Ethylphenethylamine
Amfecloral
Amfepentorex
Amfepramone
Amidephrine
2-Amino-1,2-dihydronaphthalene
2-Aminoindane
5-(2-Aminopropyl)indole
2-Aminotetralin
Acridorex
Amphetamine (Dextroamphetamine, Levoamphetamine)
Amphetaminil
Arbutamine
β-Methylphenethylamine
β-Phenylmethamphetamine
Benfluorex
Benzedrone
Benzphetamine
BDB
BOH
3-Benzhydrylmorpholine
BPAP
Buphedrone
Bupropion
Butylone
Camfetamine
Cathine
Cathinone
Chlorphentermine
Cilobamine
Cinnamedrine
Clenbuterol
Clobenzorex
Cloforex
Clortermine
Cypenamine
D-Deprenyl
Denopamine
Dimethoxyamphetamine
Dimethylamphetamine
Dimethylcathinone
Dobutamine
DOPA (Dextrodopa, Levodopa)
Dopamine
Dopexamine
Droxidopa
EBDB
Ephedrine
Epinephrine
Epinine
Etafedrine
Ethcathinone
Ethylnorepinephrine
Ethylone
Etilamfetamine
Etilefrine
Famprofazone
Fencamfamin
Fencamine
Fenethylline
Fenfluramine (Dexfenfluramine, Levofenfluramine)
Fenproporex
Feprosidnine
Flephedrone
Fludorex
Formetorex
Furfenorex
Gepefrine
Hexapradol
Hexedrone
HMMA
Hordenine
4-Hydroxyamphetamine
5-Iodo-2-aminoindane
Ibopamine
IMP
Indanylamphetamine
Iofetamine
Isoetarine
Isoethcathinone
Isoprenaline
L-Deprenyl (Selegiline)
Lefetamine
Lisdexamfetamine
Lophophine
MBDB
MDA (tenamfetamine)
MDBU
MDEA
MDMA (midomafetamine)
MDMPEA
MDOH
MDPR
MDPEA
Mefenorex
Mephedrone
Mephentermine
Metanephrine
Metaraminol
Mesocarb
Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
Methoxamine
Methoxyphenamine
MMA
Methcathinone
Methedrone
Methoxyphenamine
Methylenedioxycathinone
Methylone
Mexedrone
MMDA
MMDMA
MMMA
Morforex
N,alpha-Diethylphenylethylamine
N-Ethylbuphedrone
N-Ethylhexedrone
N,N-Dimethylphenethylamine
Naphthylamphetamine
Nisoxetine
Norepinephrine
Norfenefrine
Norfenfluramine
Normetanephrine
L-Norpseudoephedrine
Octopamine (drug)
Orciprenaline
Ortetamine
Oxifentorex
Oxilofrine
PBA
PCA
PCMA
PHA
Pentorex
Pentedrone
Pentylone
Phenatine
Phenpromethamine
Phentermine
Phenylalanine
Phenylephrine
Phenylpropanolamine
Pholedrine
PIA
PMA
PMEA
PMMA
PPAP
Phthalimidopropiophenone
Prenylamine
Propylamphetamine
Pseudoephedrine
Ropinirole
Salbutamol (Levosalbutamol)
Sibutramine
Solriamfetol
Synephrine
Theodrenaline
Tiflorex
Tranylcypromine
Tyramine
Tyrosine
Xylopropamine
Zylofuramine
Phenylmorpholines
3-Fluorophenmetrazine
Fenbutrazate
Fenmetramide
G-130
Manifaxine
Morazone
Morforex
Oxaflozane
PD-128,907
Phendimetrazine
Phenmetrazine
2-Phenyl-3,6-dimethylmorpholine
Pseudophenmetrazine
Radafaxine
Piperazines
2C-B-BZP
3C-PEP
BZP
CM156
DBL-583
GBR-12783
GBR-12935
GBR-13069
GBR-13098
GBR-13119
MeOPP
MBZP
oMPP
Vanoxerine
Piperidines
1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine
2-Benzylpiperidine
2-Methyl-3-phenylpiperidine
3,4-Dichloromethylphenidate
4-Benzylpiperidine
4-Fluoromethylphenidate
4-Methylmethylphenidate
Desoxypipradrol
Difemetorex
Diphenylpyraline
Ethylnaphthidate
Ethylphenidate
Methylnaphthidate
Isopropylphenidate
Methylphenidate (Dexmethylphenidate)
Nocaine
Phacetoperane
Pipradrol
Propylphenidate
SCH-5472
Pyrrolidines
2-Diphenylmethylpyrrolidine
5-DBFPV
α-PPP
α-PBP
α-PHP
α-PVP
α-PVT
Diphenylprolinol
DMPVP
FPOP
FPVP
MDPPP
MDPBP
MPBP
MPHP
MPPP
MOPVP
MOPPP
Indapyrophenidone
MDPV
Naphyrone
PEP
Picilorex
Prolintane
Pyrovalerone
Racetams
Oxiracetam
Phenylpiracetam
Phenylpiracetam hydrazide
Tropanes
4-fluorotropacocaine
4'-Fluorococaine
Altropane (IACFT)
Brasofensine
CFT (WIN 35,428)
β-CIT (RTI-55)
Cocaethylene
Cocaine
Dichloropane (RTI-111)
Difluoropine
FE-β-CPPIT
FP-β-CPPIT
Ioflupane (123I)
Norcocaine
PIT
PTT
RTI-31
RTI-32
RTI-51
RTI-112
RTI-113
RTI-120
RTI-121 (IPCIT)
RTI-126
RTI-150
RTI-177
RTI-229
RTI-336
RTI-354
RTI-371
RTI-386
Salicylmethylecgonine
Tesofensine
Troparil (β-CPT, WIN 35,065-2)
Tropoxane
WF-23
WF-33
Tryptamines
4-HO-αMT
4-Methyl-αET
4-Methyl-αMT
5-Chloro-αMT
5-Fluoro-αMT
5-MeO-αET
5-MeO-αMT
5-MeO-DIPT
6-Fluoro-αMT
7-Methyl-αET
αET
αMT
Others
2-MDP
3,3-Diphenylcyclobutanamine
Amfonelic acid
Amineptine
Amiphenazole
Atipamezole
Atomoxetine
Bemegride
Benzydamine
BTQ
BTS 74,398
Centanafadine
Ciclazindol
Clofenciclan
Cropropamide
Crotetamide
D-161
Desipramine
Diclofensine
Dimethocaine
Efaroxan
Etamivan
Fenisorex
Fenpentadiol
Gamfexine
Gilutensin
GSK1360707F
GYKI-52895
Hexacyclonate
Idazoxan
Indanorex
Indatraline
JNJ-7925476
Lazabemide
Leptacline
Lomevactone
LR-5182
Mazindol
Meclofenoxate
Medifoxamine
Mefexamide
Methamnetamine
Methastyridone
Methiopropamine
Naphthylaminopropane
Nefopam
Nikethamide
Nomifensine
O-2172
Oxaprotiline
PNU-99,194
PRC200-SS
Rasagiline
Rauwolscine
Rubidium chloride
Setazindol
Tametraline
Tandamine
Thiopropamine
Thiothinone
Trazium
UH-232
Yohimbine
ATC code: N06B
[show]
Pharmacodynamics
[show]
v
t
e
Monoamine neurotoxins
Adrenergic
DSP-4
Oxidopamine (6-OHDA)
Dopaminergic
Fenpropathrin
Methamphetamine
MPP+
MPTP
Norsalsolinol
Oxidopamine (6-OHDA)
Rotenone
Serotonergic
3-CA
4-CAB
5,7-DHT
α-Me-DA (3,4-DHA)
αET
αMT
DCA
MDA (tenamfetamine)
MDMA (midomafetamine)
PBA
PCA
PIA
See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine metabolism modulators
[show]
v
t
e
Monoamine releasing agents
DRAs
Morpholines: Fenbutrazate
Fenmetramide
Morazone
Morforex
Phendimetrazine
Phenmetrazine
Pseudophenmetrazine
Oxazolines: 4-MAR
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone
Phenethylamines: 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine (Dextroamphetamine
Levoamphetamine)
Amphetaminil
β-Me-PEA
BDB
BOH
Benzphetamine
Buphedrone
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
D-Deprenyl
DMA
DMMA
Dimethylamphetamine
Ephedrine
Ethcathinone
EBDB
Ethylone
Etilamfetamine
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
4-Hydroxyamphetamine
Iofetamine (123I)
Lophophine
Mefenorex
Mephedrone
Metamfepramone
Methamphetamine
Dextromethamphetamine
Levomethamphetamine
Methcathinone
Methedrone
MMDA
MMDMA
MBDB
MDA (tenamfetamine)
MDEA
MDMA (midomafetamine)
MDMPEA
MDOH
MDPEA
Methylone
Morforex
Ortetamine
pBA
pCA
pIA
Pholedrine
Phenethylamine
Pholedrine
Phenpromethamine
Prenylamine
Propylamphetamine
Pseudoephedrine
Tiflorex
Tyramine
Xylopropamine
Zylofuramine
Piperazines: 2C-B-BZP
BZP
MBZP
MDBZP
MeOPP
oMPP
Others: 2-ADN
2-AI
2-AT
4-BP
5-APDI
5-IAI
Amineptine
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
Indanorex
Isometheptene
Methylhexanamine
Naphthylaminopropane
Octodrine
Phthalimidopropiophenone
Phenylbiguanide
Propylhexedrine
Levopropylhexedrine
NRAs
Morpholines: Fenbutrazate
Fenmetramide
Morazone
Morforex
Phendimetrazine
Phenmetrazine
Pseudophenmetrazine
Oxazolines: 4-MAR
Aminorex
Clominorex
Cyclazodone
Fenozolone
Fluminorex
Pemoline
Thozalinone
Phenethylamines: 2-OH-PEA
4-CAB
4-FA
4-FMA
4-MA
4-MMA
Alfetamine
Amfecloral
Amfepentorex
Amfepramone
Amphetamine
Dextroamphetamine
Levoamphetamine
Amphetaminil
β-Me-PEA
BDB
Benzphetamine
BOH
Buphedrone
Butylone
Cathine
Cathinone
Clobenzorex
Clortermine
Dimethylamphetamine
DMA
DMMA
EBDB
Ephedrine
Ethcathinone
Ethylone
Etilamfetamine
Famprofazone
Fenethylline
Fenproporex
Flephedrone
Fludorex
Furfenorex
Hordenine
4-Hydroxyamphetamine
5-APDI (IAP)
5-MAPDI (IMP)
Iofetamine (123I)
Lisdexamfetamine
Lophophine
MBDB
MDA (tenamfetamine)
MDEA
MDMA (midomafetamine)
Metamfepramone
MDMPEA
MDOH
MDPEA
Mefenorex
Mephedrone
Mephentermine
Methamphetamine
Dextromethamphetamine
Levomethamphetamine
Methcathinone
Methedrone
Methylone
Morforex
Naphthylaminopropane
Ortetamine
pBA
pCA
Pentorex
Phenethylamine
Pholedrine
Phenpromethamine
Phentermine
Phenylpropanolamine
pIA
Prenylamine
Propylamphetamine
Pseudoephedrine
Selegiline (also D-Deprenyl)
Tiflorex
Tyramine
Xylopropamine
Zylofuramine
Piperazines: 2C-B-BZP
BZP
MBZP
mCPP
MDBZP
MeOPP
oMPP
pFPP
Others: 2-ADN
2-AI
2-AT
2-BP
4-BP
5-IAI
Clofenciclan
Cyclopentamine
Cypenamine
Cyprodenate
Feprosidnine
Gilutensin
Heptaminol
Hexacyclonate
Indanorex
Isometheptene
Methylhexanamine
Octodrine
Phthalimidopropiophenone
Propylhexedrine (Levopropylhexedrine)
Tuaminoheptane
SRAs
Aminoindanes: 5-IAI
AMMI
ETAI
MDAI
MDMAI
MMAI
TAI
Aminotetralins: 6-CAT
8-OH-DPAT
MDAT
MDMAT
Oxazolines: 4-Methylaminorex
Aminorex
Clominorex
Fluminorex
Phenethylamines: 2-Methyl-MDA
4-CAB
4-FA
4-FMA
4-HA
4-MTA
5-APDB
5-Methyl-MDA
6-APDB
6-Methyl-MDA
AEMMA
Amiflamine
BDB
BOH
Brephedrone
Butylone
Chlorphentermine
Cloforex
Amfepramone
Metamfepramone
DCA
Dexfenfluramine
DFMDA
DMA
DMMA
EBDB
EDMA
Ethylone
Etolorex
Fenfluramine
Flephedrone
Flucetorex
IAP
IMP
Iofetamine
Levofenfluramine
Lophophine
MBDB
MDA (tenamfetamine)
MDEA
MDHMA
MDMA (midomafetamine)
MDMPEA
MDOH
MDPEA
Mephedrone
Methedrone
Methylone
MMA
MMDA
MMDMA
MMMA
NAP
Norfenfluramine
4-TFMA
pBA
pCA
pIA
PMA
PMEA
PMMA
TAP
Piperazines: 2C-B-BZP
3-MeOPP
BZP
DCPP
MBZP
mCPP
MDBZP
MeOPP
Mepiprazole
oMPP
pCPP
pFPP
pTFMPP
TFMPP
Tryptamines: 4-Methyl-αET
4-Methyl-αMT
5-CT
5-MeO-αET
5-MeO-αMT
5-MT
αET
αMT
DMT
Tryptamine
Others: Indeloxazine
Viqualine
Others
Monoamine activity enhancers: BPAP
PPAP
DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041
Adrenergic release blockers: Bethanidine
Bretylium
Guanadrel
Guanazodine
Guanethidine
Guanoxan
See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins
[show]
v
t
e
Serotonin receptor modulators
5-HT1
5-HT1A
Agonists: 8-OH-DPAT
Adatanserin
Amphetamine
Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine)
Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone)
Azapirones (e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone)
Bay R 1531
Befiradol
BMY-14802
Cannabidiol
Dimemebfe
Dopamine
Ebalzotan
Eltoprazine
Enciprazine
Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide)
F-11461
F-12826
F-13714
F-14679
F-15063
F-15599
Flesinoxan
Flibanserin
Flumexadol
Lesopitron
LY-293284
LY-301317
mCPP
MKC-242
Naluzotan
NBUMP
Osemozotan
Oxaflozane
Pardoprunox
Piclozotan
Rauwolscine
Repinotan
Roxindole
RU-24969
S-14506
S-14671
S-15535
Sarizotan
Serotonin (5-HT)
SSR-181507
Sunepitron
Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin)
TGBA01AD
U-92016A
Urapidil
Vilazodone
Xaliproden
Yohimbine
Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole)
AV965
Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol)
BMY-7378
CSP-2503
Dotarizine
Ergolines (e.g., metergoline)
Flopropione
GR-46611
Isamoltane
Lecozotan
Mefway
Metitepine (methiothepin)
MIN-117 (WF-516)
MPPF
NAN-190
Robalzotan
S-15535
SB-649915
SDZ 216-525
Spiperone
Spiramide
Spiroxatrine
UH-301
WAY-100135
WAY-100635
Xylamidine
Unknown/unsorted: Acetryptine
Ergolines (e.g., ergometrine (ergonovine))
5-HT1B
Agonists: CGS-12066A
CP-93129
CP-94253
CP-122,288
CP-135807
Eltoprazine
Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide)
mCPP
RU-24969
Serotonin (5-HT)
Triptans (e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan)
TFMPP
Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT)
Vortioxetine
Antagonists: AR-A000002
Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol)
Elzasonan
Ergolines (e.g., metergoline)
GR-127935
Isamoltane
LY-393558
Metitepine (methiothepin)
SB-216641
SB-224289
SB-236057
Yohimbine
Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)
5-HT1D
Agonists: CP-122,288
CP-135807
CP-286601
Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide)
GR-46611
L-694247
L-772405
mCPP
PNU-109291
PNU-142633
Serotonin (5-HT)
TGBA01AD
Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan)
Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT)
Antagonists: Alniditan
BRL-15572
Elzasonan
Ergolines (e.g., metergoline)
GR-127935
Ketanserin
LY-310762
LY-367642
LY-393558
LY-456219
LY-456220
Metitepine (methiothepin)
Mianserin
Ritanserin
Yohimbine
Ziprasidone
Unknown/unsorted: Acetryptine
Ergolines (e.g., lisuride, lysergol, pergolide)
5-HT1E
Agonists: BRL-54443
Ergolines (e.g., methysergide)
Serotonin (5-HT)
Triptans (e.g., eletriptan)
Tryptamines (e.g., tryptamine)
Antagonists: Metitepine (methiothepin)
Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine)
5-HT1F
Agonists: BRL-54443
CP-122,288
Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide)
Lasmiditan
LY-334370
Serotonin (5-HT)
Triptans (e.g., eletriptan, naratriptan, sumatriptan)
Tryptamines (e.g., 5-MT)
Antagonists: Mianserin
Metitepine (methiothepin)
5-HT2
5-HT2A
Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe)
2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21)
2C-B-FLY
2CB-Ind
5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT)
α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT)
AL-34662
AL-37350A
Bromo-DragonFLY
Dimemebfe
DMBMPP
DOx (e.g., DOB, DOC, DOI, DOM)
Efavirenz
Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergometrine (ergonovine), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide)
Flumexadol
Jimscaline
Lorcaserin
MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA)
O-4310
Oxaflozane
PHA-57378
PNU-22394
PNU-181731
RH-34
Phenethylamines (e.g., lophophine, mescaline)
Piperazines (e.g., BZP, quipazine, TFMPP)
Serotonin (5-HT)
TCB-2
TFMFly
Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)
Antagonists: 5-I-R91150
5-MeO-NBpBrT
AC-90179
Adatanserin
Altanserin
Antihistamines (e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine)
AMDA
Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine)
Cinanserin
CSP-2503
Deramciclane
Dotarizine
Eplivanserin
Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole)
Fananserin
Flibanserin
Glemanserin
Irindalone
Ketanserin
KML-010
Landipirdine
LY-393558
mCPP
Medifoxamine
Metitepine (methiothepin)
MIN-101
MIN-117 (WF-516)
Naftidrofuryl
Nantenine
Nelotanserin
Opiranserin (VVZ-149)
Pelanserin
Phenoxybenzamine
Pimavanserin
Pirenperone
Pizotifen
Pruvanserin
Rauwolscine
Ritanserin
S-14671
Sarpogrelate
Serotonin antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone)
SR-46349B
TGBA01AD
Teniloxazine
Temanogrel
Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine)
Tricyclic antidepressants (e.g., amitriptyline)
Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine)
Volinanserin
Xylamidine
Yohimbine
Unknown/unsorted: Ergolines (e.g., dihydroergotamine, nicergoline)
5-HT2B
Agonists: 4-Methylaminorex
Aminorex
Amphetamines (e.g., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine)
BW-723C86
DOx (e.g., DOB, DOC, DOI, DOM)
Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide)
Lorcaserin
MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, [MMDA (drug)
Antagonists: Agomelatine
Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N-desalkylquetiapine (norquetiapine), N-desmethylclozapine (norclozapine), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone)
Cyproheptadine
EGIS-7625
Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine)
Ketanserin
LY-393558
mCPP
Metadoxine
Metitepine (methiothepin)
Pirenperone
Pizotifen
Propranolol
PRX-08066
Rauwolscine
Ritanserin
RS-127445
Sarpogrelate
SB-200646
SB-204741
SB-206553
SB-215505
SB-221284
SB-228357
SDZ SER-082
Tegaserod
Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine)
Trazodone
Typical antipsychotics (e.g., chlorpromazine)
TIK-301
Yohimbine
Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))
5-HT2C
Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21)
5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT)
α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT)
A-372159
AL-38022A
Alstonine
CP-809101
Dimemebfe
DOx (e.g., DOB, DOC, DOI, DOM)
Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide)
Flumexadol
Lorcaserin
MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA)
MK-212
Org 12962
Org 37684
Oxaflozane
PHA-57378
Phenethylamines (e.g., lophophine, mescaline)
Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP)
PNU-22394
PNU-181731
Ro60-0175
Ro60-0213
Serotonin (5-HT)
Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine)
Vabicaserin
WAY-629
WAY-161503
YM-348
Antagonists: Adatanserin
Agomelatine
Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine)
Captodiame
CEPC
Cinanserin
Cyproheptadine
Deramciclane
Desmetramadol
Dotarizine
Eltoprazine
Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole)
Etoperidone
Fluoxetine
FR-260010
Irindalone
Ketanserin
Ketotifen
Latrepirdine (dimebolin)
Medifoxamine
Metitepine (methiothepin)
Nefazodone
Pirenperone
Pizotifen
Propranolol
Ritanserin
RS-102221
S-14671
SB-200646
SB-206553
SB-221284
SB-228357
SB-242084
SB-243213
SDZ SER-082
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine)
TIK-301
Tramadol
Trazodone
Tricyclic antidepressants (e.g., amitriptyline, nortriptyline)
Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine)
Xylamidine
Unknown/unsorted: Efavirenz
Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))
5-HT3–7
5-HT3
Agonists: Alcohols (e.g., butanol, ethanol (alcohol), trichloroethanol)
m-CPBG
Phenylbiguanide
Piperazines (e.g., BZP, mCPP, quipazine)
RS-56812
Serotonin (5-HT)
SR-57227
SR-57227A
Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ))
Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane)
YM-31636
Antagonists: Alosetron
AS-8112
Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine)
Azasetron
Batanopride
Bemesetron (MDL-72222)
Bupropion
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
Hydroxybupropion
ICS-205930
Lerisetron
Memantine
Ondansetron
Palonosetron
Ramosetron
Renzapride
Ricasetron
Tedatioxetine
Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine)
Thujone
Tropanserin
Tropisetron
Typical antipsychotics (e.g., loxapine)
Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon)
Vortioxetine
Zacopride
Zatosetron
Unknown/unsorted: LY-53857
Piperazines (e.g., naphthylpiperazine)
5-HT4
Agonists: 5-MT
BIMU8
Capeserod
Cinitapride
Cisapride
CJ-033466
Dazopride
Metoclopramide
Minesapride
Mosapride
Prucalopride
PRX-03140
Renzapride
RS-67333
RS-67506
Serotonin (5-HT)
Tegaserod
Velusetrag
Zacopride
Antagonists: GR-113808
GR-125487
L-Lysine
Piboserod
RS-39604
RS-67532
SB-203186
SB-204070
5-HT5A
Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD)
Serotonin (5-HT)
Tryptamines (e.g., 5-CT)
Valerenic Acid
Antagonists: Asenapine
Latrepirdine (dimebolin)
Metitepine (methiothepin)
Ritanserin
SB-699551
Unknown/unsorted: Ergolines (e.g., metergoline, methysergide)
Piperazines (e.g., naphthylpiperazine)
5-HT6
Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide)
Serotonin (5-HT)
Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, tryptamine)
WAY-181187
WAY-208466
Antagonists: ABT-354
Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone)
AVN-101
AVN-211
AVN-322
AVN-397
BGC20-760
BVT-5182
BVT-74316
Cerlapirdine
EGIS-12233
GW-742457
Idalopirdine
Ketanserin
Landipirdine
Latrepirdine (dimebolin)
Metitepine (methiothepin)
MS-245
PRX-07034
Ritanserin
Ro 04-6790
Ro 63-0563
SB-258585
SB-271046
SB-357134
SB-399885
SB-742457
Tetracyclic antidepressants (e.g., amoxapine, mianserin)
Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline)
Typical antipsychotics (e.g., chlorpromazine, loxapine)
Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide)
Piperazines (e.g., naphthylpiperazine)
5-HT7
Agonists: 8-OH-DPAT
AS-19
Bifeprunox
E-55888
Ergolines (e.g., LSD)
LP-12
LP-44
RU-24969
Sarizotan
Serotonin (5-HT)
Triptans (e.g., frovatriptan)
Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT)
Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine)
Butaclamol
DR-4485
EGIS-12233
Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole)
JNJ-18038683
Ketanserin
LY-215840
Metitepine (methiothepin)
Ritanserin
SB-258719
SB-258741
SB-269970
SB-656104
SB-656104A
SB-691673
SLV-313
SLV-314
Spiperone
SSR-181507
Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine)
Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine)
Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide)
Vortioxetine
Unknown/unsorted: Ergolines (e.g., lisuride, pergolide)
Piperazines (e.g., naphthylpiperazine)
See also: Receptor/signaling modulators
Adrenergics
Dopaminergics
Melatonergics
Monoamine reuptake inhibitors and releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins
[show]
v
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Sigma receptor modulators
σ1
Agonists: 3-PPP
4-PPBP
5-MeO-DMT
Alazocine (SKF-10047)
Amantadine
ANAVEX2-73
Arketamine
BD-737
BD-1052
Captodiame
Citalopram
CGRP
Cloperastine
Cocaine
Cutamesine (SA-4503)
Cyclazocine
Dehydroepiandrosterone (DHEA) (prasterone)
Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate)
Dextrallorphan
Dextromethorphan (DXM)
Dextrorphan (DXO)
Dimemorfan
Dimethyltryptamine (DMT)
Ditolylguanidine (DTG)
Donepezil
Eliprodil
Escitalopram
Fabomotizole (afobazole)
Fluoxetine
Fluvoxamine
Ifenprodil
Igmesine (JO-1784)
IPAB
Ketamine
L-687384
MDMA (midomafetamine)
Memantine
Methamphetamine
Methoxetamine
Methylphenidate
Nepinalone
Neuropeptide Y
Noscapine
OPC-14523
Opipramol
Pentazocine
Pentoxyverine (carbetapentane)
PRE-084
Pregnenolone
Pregnenolone sulfate
Pridopidine
Racemethorphan (methorphan)
Racemorphan (morphanol)
UMB-23
UMB-82
Antagonists: 3-PPP
AC-927
BD-1008
BD-1031
BD-1047
BD-1060
BD-1063
BD-1067
BMY-14802 (BMS-181100)
CM-156
Dup-734
E-5842
E-52862 (S1RA)
Haloperidol
LR-132
LR-172
MS-377
NE-100
NPC-16377
Panamesine (EMD-57455)
PD-144418
Pentazocine
Progesterone
Rimcazole (BW-234U)
Sertraline
SR-31742A
Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam
SOMCL-668
Unknown/unsorted: 3-Methoxydextrallorphan
3-MeO-PCP
4C-T-2
4-IBP
4-IPBS
4-MeO-PCP
5-MeO-DALT
5-MeO-DiPT
Amitriptyline
Azidopamil
Chlorpromazine
Clemastine
Clomipramine
Clorgiline
D-Deprenyl
DiPT
DPT
Ibogaine
Imipramine
KCR-12-83.1
Nemonapride
Noribogaine
RHL-033
RS-67,333
RTI-55
Saffron
Safinamide
Selegiline
Spipethiane
Trifluoperazine
W-18
YKP10A
σ2
Agonists: 3-PPP
Arketamine
BD-1047
BD1063
Ditolylguanidine (DTG)
DKR-1005
DKR-1051
Haloperidol
Ifenprodil
Ketamine
MDMA (midomafetamine)
Methamphetamine
OPC-14523
Opipramol
PB-28
Phencyclidine
Siramesine (Lu 28-179)
UKH-1114
Antagonists: AC-927
BD-1008
BD-1067
CM-156
CT-1812
LR-172
MIN-101
Panamesine (EMD-57455)
SAS-0132
Unknown/unsorted: 3-Methoxydextrallorphan
3-MeO-PCE
4-MeO-PCP
5-MeO-DALT
5-MeO-DiPT
Clemastine
DiPT
DPT
Ibogaine
Nemonapride
Nepinalone
Noribogaine
Pentazocine
RS-67,333
Safinamide
TMA
UMB-23
UMB-82
W-18
Unsorted
Agonists: Berberine
Ethylketazocine
Fourphit
Metaphit
Nalbuphine
Naluzotan
Tapentadol
Tenocyclidine
Antagonists: AHD1
AZ66
Lamotrigine
Naloxone
SM-21
UMB-100
UMB-101
UMB-103
UMB-116
YZ-011
YZ-069
YZ-185
Allosteric modulators: SKF-83959
Unknown/unsorted: 18-Methoxycoronaridine
BMY-13980
Butaclamol
Caramiphen
Carvotroline
Chlorphenamine (chlorpheniramine)
Chlorpromazine
Cinnarizine
Cinuperone
Clocapramine
Dezocine
EMD-59983
Hypericin (St. John's wort)
Fluphenazine
Gevotroline (WY-47384)
Mepyramine (pyrilamine)
Molindone
Perphenazine
Pimozide
Proadifen
Promethazine
Propranolol
Quinidine
Remoxipride
SL 82.0715
SR-31747A
Tiospirone (BMY-13859)
Venlafaxine
See also: Receptor/signaling modulators
[show]
v
t
e
Human trace amine-associated receptor ligands
TAAR1
Agonists
Endogenous†
Classical monoamine neurotransmitters
Dopamine
Histamine
Norepinephrine
Serotonin
Trace amines
3-Iodothyronamine
3-Methoxytyramine
N-Methylphenethylamine
N-Methyltyramine
m-Octopamine
p-Octopamine
Phenethylamine
Phenylethanolamine
Synephrine
Tryptamine
m-Tyramine
p-Tyramine
Synthetic‡
Amphetamine
DOB
DOET
4-Hydroxyamphetamine
Isoprenaline
MDA (tenamfetamine)
MDMA (midomafetamine)
2-Methylphenethylamine
3-Methylphenethylamine
4-Methylphenethylamine
β-Methylphenethylamine
Methamphetamine
3-MMA
Norfenfluramine
Phentermine
o-PIT
Propylhexedrine
RO5166017
N,N-Dimethylphenethylamine
Neutral antagonists
Inverse agonists
EPPTB (RO5212773)
TAAR2
Agonists‡
3-Iodothyronamine
Phenethylamine
Tyramine
Neutral antagonists
TAAR5
Agonists‡
Dimethylethylamine
Trimethylamine
Neutral antagonists
Inverse agonists‡
3-Iodothyronamine
†References for all endogenous human TAAR1 ligands are provided at List of trace amines

‡References for synthetic TAAR1 agonists can be found at TAAR1 or in the associated compound articles. For TAAR2 and TAAR5 agonists and inverse agonists, see TAAR for references.

See also: Receptor/signaling modulators
[show]
v
t
e
Phenethylamines
Phenethylamines
Psychedelics: 25B-NBOMe
25C-NBOMe
25D-NBOMe
25I-NBOMe
25N-NBOMe
2C-B
2C-B-AN
2C-Bn
2C-Bu
2C-C
2C-CN
2C-CP
2C-D
2C-E
2C-EF
2C-F
2C-G
2C-G-1
2C-G-2
2C-G-3
2C-G-4
2C-G-5
2C-G-6
2C-G-N
2C-H
2C-I
2C-iP
2C-N
2C-NH2
2C-O
2C-O-4
2C-P
2C-Ph
2C-SE
2C-T
2C-T-2
2C-T-3
2C-T-4
2C-T-5
2C-T-6
2C-T-7
2C-T-8
2C-T-9
2C-T-10
2C-T-11
2C-T-12
2C-T-13
2C-T-14
2C-T-15
2C-T-16
2C-T-17
2C-T-18
2C-T-19
2C-T-20
2C-T-21
2C-T-22
2C-T-22.5
2C-T-23
2C-T-24
2C-T-25
2C-T-27
2C-T-28
2C-T-30
2C-T-31
2C-T-32
2C-T-33
2C-TFE
2C-TFM
2C-YN
2C-V
Allylescaline
DESOXY
Escaline
Isoproscaline
Jimscaline
Macromerine
MEPEA
Mescaline
Metaescaline
Methallylescaline
Proscaline
Psi-2C-T-4
TCB-2
Stimulants: Phenylethanolamine
Hordenine
Phenethylamine
α-Methylphenethylamine (amphetamine)
β-Methylphenethylamine
m-Methylphenethylamine
N-Methylphenethylamine
o-Methylphenethylamine
p-Methylphenethylamine
Entactogens: Lophophine
MDPEA
MDMPEA
Others: BOH
DMPEA
Amphetamines
Psychedelics: 3C-BZ
3C-E
3C-P
Aleph
Beatrice
Bromo-DragonFLY
D-Deprenyl
DMA
DMCPA
DMMDA
DOB
DOC
DOEF
DOET
DOI
DOM
DON
DOPR
DOTFM
Ganesha
MMDA
MMDA-2
Psi-DOM
TMA
TeMA
Stimulants: 2-FA
2-FMA
3-FA
3-FMA
Acridorex
Alfetamine
Amfecloral
Amfepentorex
Amphetamine (Dextroamphetamine, Levoamphetamine)
Amphetaminil
Benfluorex
Benzphetamine
Cathine
Clobenzorex
Dimethylamphetamine
Ephedrine
Etilamfetamine
Fencamfamin
Fencamine
Fenethylline
Fenfluramine (Dexfenfluramine, Levofenfluramine)
Fenproporex
Flucetorex
Fludorex
Formetorex
Furfenorex
Gepefrine
4-Hydroxyamphetamine
Iofetamine
Isopropylamphetamine
Lefetamine
Lisdexamfetamine
Mefenorex
Metaraminol
Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
Methoxyphenamine
MMA
Morforex
Norfenfluramine
L -Norpseudoephedrine
N,alpha-Diethylphenylethylamine
Oxifentorex
Oxilofrine
Ortetamine
PBA
PCA
Phenpromethamine
PFA
PFMA
PIA
PMA
PMEA
PMMA
Phenylpropanolamine
Pholedrine
Prenylamine
Propylamphetamine
Pseudoephedrine
Sibutramine
Tiflorex
Tranylcypromine
Xylopropamine
Zylofuramine
Entactogens: 4-FA
4-FMA
4-MA
4-MMA
4-MTA
5-APB
5-APDB
5-EAPB
5-IT
5-MAPB
5-MAPDB
6-APB
6-APDB
6-Chloro-MDMA
6-EAPB
6-IT
6-MAPB
6-MAPDB
EDA
IAP
2,3-MDA
3,4-MDA (tenamfetamine)
MDEA
MDHMA
MDMA (midomafetamine)
MDOH
Methamnetamine
MMDMA
Naphthylaminopropane
TAP
Others: 3,4-DCA
Amiflamine
DiFMDA
Selegiline (also D -Deprenyl)
Phentermines
Stimulants: Chlorphentermine
Cloforex
Clortermine
Etolorex
Mephentermine
Pentorex
Phentermine
Entactogens: MDPH
MDMPH
Others: Cericlamine
Cathinones
Stimulants: 3-FMC
4-MC
4-BMC
4-CMC
4-EMC
4-FMC
4-MEC
4-MeMABP
4-MPD
Amfepramone
Benzedrone
Brephedrone
Buphedrone
Bupropion
Cathinone
Dimethylcathinone
Ethcathinone
Eutylone
Hydroxybupropion
Methcathinone
Methedrone
NEB
Pentedrone
Pentylone
Radafaxine
Entactogens: 3,4-DMMC
3-MMC
Butylone
Ethylone
Methylone
Methylenedioxycathinone
Mephedrone
Phenylisobutylamines
Entactogens: 4-CAB
4-MAB
Ariadne
BDB
Butylone
EBDB
Eutylone
MBDB
Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines
Stimulants: α-PBP
α-PHP
α-PPP
α-PVP
MDPBP
MDPPP
MDPV
4-MePBP
4-MePHP
4-MePPP
MOPPP
MOPVP
MPBP
MPHP
MPPP
Naphyrone
PEP
Prolintane
Pyrovalerone
Catecholamines
(and close relatives)
6-FNE
6-OHDA
a-Me-DA
a-Me-TRA
Adrenochrome
Ciladopa
D -DOPA (Dextrodopa)
Dimetofrine
Dopamine
Epinephrine
Epinine
Etilefrine
Ethylnorepinephrine
Fenclonine
Ibopamine
Isoprenaline
Isoetarine
L -DOPA (Levodopa)
L -DOPS (Droxidopa)
L -Phenylalanine
L -Tyrosine
m-Tyramine
Metanephrine
Metaraminol
Metaterol
Metirosine
Methyldopa
N,N-Dimethyldopamine
Nordefrin (Levonordefrin)
Norepinephrine
Norfenefrine (m-Octopamine)
Normetanephrine
Orciprenaline
p-Octopamine
p-Tyramine
Phenylephrine
Synephrine
Miscellaneous
AL-LAD
Amidephrine
Arbutamine
Cafedrine
Denopamine
Desvenlafaxine
Diphenidine
Dizocilpine
Dobutamine
Dopexamine
Ephenidine
Etafedrine
ETH-LAD
Famprofazone
Fluorolintane
Hexapradol
IP-LAD
Lysergic acid amide
Lysergic acid 2-butyl amide
Lysergic acid 2,4-dimethylazetidide
Lysergic acid diethylamide
Methoxamine
Methoxphenidine
MT-45
PARGY-LAD
Phenibut
PRO-LAD
Pronethalol
Salbutamol (Levosalbutamol)
Solriamfetol
Theodrenaline
Thiamphenicol
UWA-101
[show]
v
t
e
Drugs from PiHKAL
AEM
AL
Aleph
Aleph-2
Aleph-4
Aleph-6
Aleph-7
Ariadne
Asymbescaline
Buscaline
Beatrice
Bis-TOM
BOB
BOD
BOH
BOHD
BOM
4-Bromo-3,5-dimethoxyamphetamine
2-Bromo-4,5-methylenedioxyamphetamine
2C-B
3C-BZ
2C-C
2C-D
2C-E
3C-E
2C-F
2C-G
2C-G-3
2C-G-4
2C-G-5
2C-G-N
2C-H
2C-I
2C-N
2C-O
2C-O-4
2C-P
CPM
2C-SE
2C-T
2C-T-2
2C-T-4
psi-2C-T-4
2C-T-7
2C-T-8
2C-T-9
2C-T-13
2C-T-15
2C-T-16
2C-T-17
2C-T-19
2C-T-21
4-D
beta-D
DESOXY
2,4-DMA
2,5-DMA
3,4-DMA
DMCPA
DME
DMMDA
DMMDA-2
DMPEA
DOAM
DOB
DOBU
DOC
DOEF
DOET
DOI
DOM
psi-DOM
DON
DOPR
Escaline
EEE
EEM
EME
EMM
Ethyl-J (EBDB)
Ethyl-K
F-2
F-22
Flea
G-3
G-4
G-5
G-N
Ganesha
HOT-2
HOT-7
HOT-17
IDNNA
Isomescaline
Isoproscaline
Iris
J (BDB)
Lophophine
PMA
Mescaline
Madam-6
Methallylescaline
MDA
MDAL
MDBU
MDBZ
MDCPM
MDDM
MDE
MDHOET
MDIP
MDMA
MDMC (EDMA)
MDMEO
MDMEOET
MDMP
MDOH
MDPEA
MDPH
MDPL
MDPR
Metaescaline
MEDA
MEE
MEM
MEPEA
Meta-DOB
Meta-DOT
Methyl-DMA
Methyl-DOB
Methyl-J (MBDB)
Methyl-K
Methyl-MA (PMMA)
Methyl-MMDA-2
MMDA
MMDA-2
MMDA-3a
MMDA-3b
MME
Metaproscaline
MPM
Ortho-DOT
Proscaline
Phenescaline
Phenethylamine
Propynyl
Symbescaline
2,3,4,5-Tetramethoxyamphetamine
3-TASB
4-TASB
5-TASB
Thiobuscaline
3-TE
4-TE
3-TIM
4-TIM
5-TIM
3-TM
4-TM
TMA
TMA-2
TMA-3
TMA-4
TMA-5
TMA-6
3-TME
4-TME
5-TME
2T-MMDA-3a
4T-MMDA-2
2-TOET
5-TOET
2-TOM
5-TOM
TOMSO
Thioproscaline
Trisescaline
3-TSB
4-TSB
3-T-Trisescaline
4-T-Trisescaline
Retrieved from "https://en.wikipedia.org/w/index.php?title=MDMA&oldid=807119712"
Categories:
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5-HT2B agonists
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Substituted amphetamines
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Entactogens and empathogens
Entheogens
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Serotonin receptor agonists
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MDMA structure

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Loss of consciousness

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Releasing agent

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Reuptake inhibition

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TAAR1 agonist

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