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Tryptophan
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"Tryptan" redirects here. For the type of anti-migraine drug, see Triptan. For the hydrocarbon, see Triptane.
L-Tryptophan
Names
IUPAC name
Tryptophan or (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid
Other names
2-Amino-3-(1H-indol-3-yl)propanoic acid
Identifiers
CAS Number
73-22-3 Y
3D model (JSmol)
Interactive image
ChEBI
CHEBI:16828
ChEMBL
ChEMBL54976 Y
ChemSpider
6066 Y
DrugBank
DB00150 Y
ECHA InfoCard 100.000.723
IUPHAR/BPS
717
KEGG
D00020 Y
PubChem CID
6305
UNII
8DUH1N11BX Y
InChI[show]
InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1 Y
Key: QIVBCDIJIAJPQS-VIFPVBQESA-N Y
InChI=1/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1
Key: QIVBCDIJIAJPQS-VIFPVBQEBP
SMILES[show]
c1ccc2c(c1)c(c[nH]2)C[C@@H](C(=O)O)N
Properties
Chemical formula
C11H12N2O2
Molar mass 204.23 g·mol−1
Solubility in water
Soluble: 0.23 g/L at 0 °C,
11.4 g/L at 25 °C,
17.1 g/L at 50 °C,
27.95 g/L at 75 °C
Solubility Soluble in hot alcohol, alkali hydroxides; insoluble in chloroform.
Acidity (pKa) 2.38 (carboxyl), 9.39 (amino)[1]
Magnetic susceptibility (χ)
-132.0·10−6 cm3/mol
Pharmacology
ATC code
N06AX02 (WHO)
Supplementary data page
Structure and
properties
Refractive index (n),
Dielectric constant (εr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
Spectral data
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is Y ?)
Infobox references
Tryptophan (symbol Trp or W)[2] is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a non-polar aromatic amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Tryptophan is also a precursor to the neurotransmitter serotonin and the hormone melatonin.[3] It is encoded by the codon UGG.
Like other amino acids, tryptophan is a zwitterion at physiological pH where the amino group is protonated (–NH3+; pKa = 9.39) and the carboxylic acid is deprotonated ( –COO−; pKa = 2.38).[4]
Contents
[hide]
1 Function
2 Recommended dietary allowance
2.1 Dietary sources
3 Use as a dietary supplement
4 Side effects
5 Interactions
6 Isolation
7 Biosynthesis and industrial production
8 Society and culture
8.1 Eosinophilia–myalgia syndrome
8.2 Turkey meat and drowsiness
9 Research
9.1 Fluorescence
10 See also
11 References
12 Further reading
13 External links
Function[edit]
Metabolism of L-tryptophan into serotonin and melatonin (left) and niacin (right). Transformed functional groups after each chemical reaction are highlighted in red.
Amino acids, including tryptophan, are used as building blocks in protein biosynthesis, and proteins are required to sustain life. Many animals (including humans) cannot synthesize tryptophan: they need to obtain it through their diet, making it an essential amino acid. Tryptophan is among the less common amino acids found in proteins, but it plays important structural or functional roles whenever it occurs. For instance, tryptophan and tyrosine residues play special roles in "anchoring" membrane proteins within the cell membrane. In addition, tryptophan functions as a biochemical precursor for the following compounds (see also figure to the right):
Serotonin (a neurotransmitter), synthesized by tryptophan hydroxylase.[5][6]
Melatonin (a neurohormone) is in turn synthesized from serotonin, via N-acetyltransferase and 5-hydroxyindole-O-methyltransferase enzymes.[7]
Niacin, also known as vitamin B3, is synthesized from tryptophan via kynurenine and quinolinic acids.[8]
Auxins (a class of phytohormones) are synthesized from tryptophan.[9]
The disorder fructose malabsorption causes improper absorption of tryptophan in the intestine, reduced levels of tryptophan in the blood,[10] and depression.[11]
In bacteria that synthesize tryptophan, high cellular levels of this amino acid activate a repressor protein, which binds to the trp operon.[12] Binding of this repressor to the tryptophan operon prevents transcription of downstream DNA that codes for the enzymes involved in the biosynthesis of tryptophan. So high levels of tryptophan prevent tryptophan synthesis through a negative feedback loop, and when the cell's tryptophan levels go down again, transcription from the trp operon resumes. This permits tightly regulated and rapid responses to changes in the cell's internal and external tryptophan levels.
Tryptophan metabolism by human gastrointestinal microbiota (
v
t
e
)
Tryptophan
Clostridium
sporogenes
Lacto-
bacilli
Tryptophanase-
expressing
bacteria
IPA
I3A
Indole
Liver
Brain
IPA
I3A
Indole
Indoxyl
sulfate
AST-120
AhR
Intestinal
immune
cells
Intestinal
epithelium
PXR
Mucosal homeostasis:
↓TNF-α
↑Junction protein-
coding mRNAs
L cell
GLP-1
T J
Neuroprotectant:
↓Activation of glial cells and astrocytes
↓4-Hydroxy-2-nonenal levels
↓DNA damage
–Antioxidant
–Inhibits β-amyloid fibril formation
Maintains mucosal reactivity:
↑IL-22 production
Associated with vascular disease:
↑Oxidative stress
↑Smooth muscle cell proliferation
↑Aortic wall thickness and calcification
Associated with chronic kidney disease:
↑Renal dysfunction
–Uremic toxin
Kidneys
This diagram shows the biosynthesis of bioactive compounds (indole and certain other derivatives) from tryptophan by bacteria in the gut.[13] Indole is produced from tryptophan by bacteria that express tryptophanase.[13] Clostridium sporogenes metabolizes tryptophan into indole and subsequently 3-indolepropionic acid (IPA),[14] a highly potent neuroprotective antioxidant that scavenges hydroxyl radicals.[13][15][16] IPA binds to the pregnane X receptor (PXR) in intestinal cells, thereby facilitating mucosal homeostasis and barrier function.[13] Following absorption from the intestine and distribution to the brain, IPA confers a neuroprotective effect against cerebral ischemia and Alzheimer’s disease.[13] Lactobacillus species metabolize tryptophan into indole-3-aldehyde (I3A) which acts on the aryl hydrocarbon receptor (AhR) in intestinal immune cells, in turn increasing interleukin-22 (IL-22) production.[13] Indole itself triggers the secretion of glucagon-like peptide-1 (GLP-1) in intestinal L cells and acts as a ligand for AhR.[13] Indole can also be metabolized by the liver into indoxyl sulfate, a compound that is toxic in high concentrations and associated with vascular disease and renal dysfunction.[13] AST-120 (activated charcoal), an intestinal sorbent that is taken by mouth, adsorbs indole, in turn decreasing the concentration of indoxyl sulfate in blood plasma.[13]
Recommended dietary allowance[edit]
In 2002, the U.S. Institute of Medicine set a Recommended Dietary Allowance (RDA) of 5 mg/kg body weight/day of Tryptophan for adults 19 years and over.[17]
Dietary sources[edit]
Tryptophan is present in most protein-based foods or dietary proteins. It is particularly plentiful in chocolate, oats, dried dates, milk, yogurt, cottage cheese, red meat, eggs, fish, poultry, sesame, chickpeas, almonds, sunflower seeds, pumpkin seeds, buckwheat, spirulina, and peanuts. Contrary to the popular belief[18][19][20] that turkey contains an abundance of tryptophan, the tryptophan content in turkey is typical of poultry.[21]
Tryptophan (Trp) Content of Various Foods[21][22]
Food
Tryptophan
[g/100 g of food]
Protein
[g/100 g of food]
Tryptophan/Protein [%]
Egg white, dried 1.00 81.10 1.23
spirulina, dried 0.92 57.47 1.62
cod, atlantic, dried 0.70 62.82 1.11
Soybeans, raw 0.59 36.49 1.62
Cheese, Parmesan 0.56 37.90 1.47
Sesame seed 0.37 17.00 2.17
Cheese, cheddar 0.32 24.90 1.29
Sunflower seed 0.30 17.20 1.74
Pork, chop 0.25 19.27 1.27
Turkey 0.24 21.89 1.11
Chicken 0.24 20.85 1.14
Beef 0.23 20.13 1.12
Oats 0.23 16.89 1.39
Salmon 0.22 19.84 1.12
Lamb, chop 0.21 18.33 1.17
Perch, Atlantic 0.21 18.62 1.12
Chickpeas, raw 0.19 19.30 0.96
Egg 0.17 12.58 1.33
Wheat flour, white 0.13 10.33 1.23
Baking chocolate, unsweetened 0.13 12.9 1.23
Milk 0.08 3.22 2.34
Rice, white, medium-grain, cooked 0.028 2.38 1.18
Quinoa, uncooked 0.167 14.12 1.2
Quinoa, cooked 0.052 4.40 1.1
Potatoes, russet 0.02 2.14 0.84
Tamarind 0.018 2.80 0.64
Banana 0.01 1.03 0.87
Use as a dietary supplement[edit]
Because tryptophan is converted into 5-hydroxytryptophan (5-HTP) which is then converted into the neurotransmitter serotonin, it has been proposed that consumption of tryptophan or 5-HTP may improve depression symptoms by increasing the level of serotonin in the brain. Tryptophan is sold over the counter in the United States (after being banned to varying extents between 1989 and 2005) and the United Kingdom as a dietary supplement for use as an antidepressant, anxiolytic, and sleep aid. It is also marketed as a prescription drug in some European countries for the treatment of major depression. There is evidence that blood tryptophan levels are unlikely to be altered by changing the diet,[23][24] but consuming purified tryptophan increases the serotonin level in the brain, whereas eating foods containing tryptophan does not.[25] This is because the transport system that brings tryptophan across the blood–brain barrier also transports other amino acids which are contained in protein food sources.[26] High blood plasma levels of other large neutral amino acids prevent the plasma concentration of tryptophan from increasing brain concentration levels.[26]
In 2001 a Cochrane review of the effect of 5-HTP and tryptophan on depression was published. The authors included only studies of a high rigor and included both 5-HTP and tryptophan in their review because of the limited data on either. Of 108 studies of 5-HTP and tryptophan on depression published between 1966 and 2000, only two met the authors' quality standards for inclusion, totaling 64 study participants. The substances were more effective than placebo in the two studies included but the authors state that "the evidence was of insufficient quality to be conclusive" and note that "because alternative antidepressants exist which have been proven to be effective and safe, the clinical usefulness of 5-HTP and tryptophan is limited at present".[27] The use of tryptophan as an adjunctive therapy in addition to standard treatment for mood and anxiety disorders is not supported by the scientific evidence.[28][27][28]
Side effects[edit]
Potential side effects of tryptophan supplementation include nausea, diarrhea, drowsiness, lightheadedness, headache, dry mouth, blurred vision, sedation, euphoria, and nystagmus (involuntary eye movements).[29][30]
Interactions[edit]
Tryptophan taken as a dietary supplement (such as in tablet form) has the potential to cause serotonin syndrome when combined with antidepressants of the MAOI or SSRI class or other strongly serotonergic drugs.[30] Because tryptophan supplementation has not been thoroughly studied in a clinical setting, its interactions with other drugs are not well known.[27]
Isolation[edit]
The isolation of tryptophan was first reported by Frederick Hopkins in 1901.[31] Hopkins recovered tryptophan from hydrolysed casein, recovering 4-8 g of tryptophan from 600 g of crude casein.[32]
Biosynthesis and industrial production[edit]
As an essential amino acid, tryptophan is not synthesized from simpler substances in humans and other animals, so it needs to be present in the diet in the form of tryptophan-containing proteins. Plants and microorganisms commonly synthesize tryptophan from shikimic acid or anthranilate:[33] anthranilate condenses with phosphoribosylpyrophosphate (PRPP), generating pyrophosphate as a by-product. The ring of the ribose moiety is opened and subjected to reductive decarboxylation, producing indole-3-glycerol phosphate; this, in turn, is transformed into indole. In the last step, tryptophan synthase catalyzes the formation of tryptophan from indole and the amino acid serine.
The industrial production of tryptophan is also biosynthetic and is based on the fermentation of serine and indole using either wild-type or genetically modified bacteria such as B. amyloliquefaciens, B. subtilis, C. glutamicum or E. coli. These strains carry mutations that prevent the reuptake of aromatic amino acids or multiple/overexpressed trp operons. The conversion is catalyzed by the enzyme tryptophan synthase.[34][35][36]
Society and culture[edit]
Eosinophilia–myalgia syndrome[edit]
There was a large outbreak of eosinophilia-myalgia syndrome (EMS) in the U.S. in 1989, with more than 1,500 cases reported to the CDC and at least 37 deaths.[37] After preliminary investigation revealed that the outbreak was linked to intake of tryptophan, the U.S. Food and Drug Administration (FDA) recalled tryptophan supplements in 1989 and banned most public sales in 1990,[38][39][40] with other countries following suit.[41][42]
Subsequent studies suggested that EMS was linked to specific batches of L-tryptophan supplied by a single large Japanese manufacturer, Showa Denko.[38][43][44][45] It eventually became clear that recent batches of Showa Denko's L-tryptophan were contaminated by trace impurities, which were subsequently thought to be responsible for the 1989 EMS outbreak.[38][46][47] However, other evidence suggests that tryptophan itself may be a potentially major contributory factor in EMS.[48]
The FDA loosened its restrictions on sales and marketing of tryptophan in February 2001,[38] but continued to limit the importation of tryptophan not intended for an exempted use until 2005.[49]
The fact that the Showa Denko facility used genetically engineered bacteria to produce the contaminated batches of L-tryptophan later found to have caused the outbreak of eosinophilia-myalgia syndrome has been cited as evidence of a need for "close monitoring of the chemical purity of biotechnology-derived products".[50] Those calling for purity monitoring have, in turn, been criticized as anti-GMO activists who overlook possible non-GMO causes of contamination and threaten the development of biotech.[51]
Turkey meat and drowsiness[edit]
See also: Postprandial somnolence § Turkey and tryptophan
A common assertion in the US is that heavy consumption of turkey meat results in drowsiness, due to high levels of tryptophan contained in turkey.[18][20] However, the amount of tryptophan in turkey is comparable to that contained in other meats.[19][21] Drowsiness after eating may be caused by other foods eaten with the turkey, particularly carbohydrates.[52] Ingestion of a meal rich in carbohydrates triggers the release of insulin.[53][54][55][56] Insulin in turn stimulates the uptake of large neutral branched-chain amino acids (BCAA), but not tryptophan, into muscle, increasing the ratio of tryptophan to BCAA in the blood stream. The resulting increased tryptophan ratio reduces competition at the large neutral amino acid transporter (which transports both BCAA and aromatic amino acids), resulting in more uptake of tryptophan across the blood–brain barrier into the cerebrospinal fluid (CSF).[57][58][56] Once in the CSF, tryptophan is converted into serotonin in the raphe nuclei by the normal enzymatic pathway.[59][54] The resultant serotonin is further metabolised into melatonin by the pineal gland.[7] Hence, these data suggest that "feast-induced drowsiness"—or postprandial somnolence—may be the result of a heavy meal rich in carbohydrates, which indirectly increases the production of melatonin in the brain, and thereby promotes sleep.[59][53][54][55]
Research[edit]
In 1912 Felix Ehrlich demonstrated that yeast attacks the natural amino acids essentially by splitting off carbon dioxide and replacing the amino group with hydroxyl. By this reaction, tryptophan gives rise to tryptophol.[60]
Tryptophan affects brain serotonin synthesis when given orally in a purified form and is used to modify serotonin levels for research.[25] Low brain serotonin level is induced by administration of tryptophan-poor protein in a technique called "acute tryptophan depletion".[61] Studies using this method have evaluated the effect of serotonin on mood and social behavior, finding that serotonin reduces aggression and increases agreeableness.[62]
Fluorescence[edit]
Main article: Fluorescence spectroscopy § Tryptophan fluorescence
Tryptophan is an important intrinsic fluorescent probe (amino acid), which can be used to estimate the nature of the microenvironment around the tryptophan residue. Most of the intrinsic fluorescence emissions of a folded protein are due to excitation of tryptophan residues.
See also[edit]
5-HTP
Acree-Rosenheim reaction
Adamkiewicz reaction
attenuator (genetics)
dimethyltryptamine
Hopkins Cole reaction
serotonin
tryptamine
References[edit]
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Table 2: Microbial metabolites: their synthesis, mechanisms of action, and effects on health and disease
Figure 1: Molecular mechanisms of action of indole and its metabolites on host physiology and disease
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IPA metabolism diagram
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Origin: • Endogenous • Microbial
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Jump up ^ Kilbourne EM, Philen RM, Kamb ML, Falk H (October 1996). "Tryptophan produced by Showa Denko and epidemic eosinophilia-myalgia syndrome". The Journal of Rheumatology. Supplement. 46: 81–8; discussion 89–91. PMID 8895184.
Jump up ^ Mayeno AN, Lin F, Foote CS, Loegering DA, Ames MM, Hedberg CW, Gleich GJ (December 1990). "Characterization of "peak E," a novel amino acid associated with eosinophilia-myalgia syndrome". Science. 250 (4988): 1707–8. doi:10.1126/science.2270484. PMID 2270484.
Jump up ^ Ito J, Hosaki Y, Torigoe Y, Sakimoto K (January 1992). "Identification of substances formed by decomposition of peak E substance in tryptophan". Food and Chemical Toxicology. 30 (1): 71–81. doi:10.1016/0278-6915(92)90139-C. PMID 1544609.
Jump up ^ Smith MJ, Garrett RH (November 2005). "A heretofore undisclosed crux of eosinophilia-myalgia syndrome: compromised histamine degradation". Inflammation Research. 54 (11): 435–50. doi:10.1007/s00011-005-1380-7. PMID 16307217.
Jump up ^ Allen, JA; Peterson, A; Sufit, R; Hinchcliff, ME; Mahoney, JM; Wood, TA; Miller, FW; Whitfield, ML; Varga, J (November 2011). "Post-epidemic eosinophilia-myalgia syndrome associated with L-tryptophan". Arthritis and Rheumatism. 63 (11): 3633–9. doi:10.1002/art.30514. PMC 3848710  . PMID 21702023.
Jump up ^ Mayeno AN, Gleich GJ (September 1994). "Eosinophilia-myalgia syndrome and tryptophan production: a cautionary tale". Trends in Biotechnology. 12 (9): 346–52. doi:10.1016/0167-7799(94)90035-3. PMID 7765187.
Jump up ^ Raphals P (November 1990). "Does medical mystery threaten biotech?". Science. 250 (4981): 619. doi:10.1126/science.2237411. PMID 2237411.
Jump up ^ "Food & mood. (neuroscience professor Richard Wurtman) (Interview)". Nutrition Action Healthletter. HighBeam Research. September 1992.
^ Jump up to: a b Lyons PM, Truswell AS (March 1988). "Serotonin precursor influenced by type of carbohydrate meal in healthy adults" (PDF). The American Journal of Clinical Nutrition. 47 (3): 433–9. PMID 3279747.
^ Jump up to: a b c Wurtman RJ, Wurtman JJ, Regan MM, McDermott JM, Tsay RH, Breu JJ (January 2003). "Effects of normal meals rich in carbohydrates or proteins on plasma tryptophan and tyrosine ratios". The American Journal of Clinical Nutrition. 77 (1): 128–32. PMID 12499331.
^ Jump up to: a b Afaghi A, O'Connor H, Chow CM (February 2007). "High-glycemic-index carbohydrate meals shorten sleep onset". The American Journal of Clinical Nutrition. 85 (2): 426–30. PMID 17284739.
^ Jump up to: a b Banks WA, Owen JB, Erickson MA (2012). "Insulin in the Brain: There and Back Again". Pharmacology & Therapeutics. 136 (1): 82–93. doi:10.1016/j.pharmthera.2012.07.006. ISSN 0163-7258. PMC 4134675  . PMID 22820012.
Jump up ^ Pardridge WM, Oldendorf WH (August 1975). "Kinetic analysis of blood-brain barrier transport of amino acids". Biochimica et Biophysica Acta. 401 (1): 128–36. doi:10.1016/0005-2736(75)90347-8. PMID 1148286.
Jump up ^ Maher TJ, Glaeser BS, Wurtman RJ (May 1984). "Diurnal variations in plasma concentrations of basic and neutral amino acids and in red cell concentrations of aspartate and glutamate: effects of dietary protein intake". The American Journal of Clinical Nutrition. 39 (5): 722–9. PMID 6538743.
^ Jump up to: a b Fernstrom JD, Wurtman RJ (1971). "Brain serotonin content: increase following ingestion of carbohydrate diet". Science. 174 (4013): 1023–5. doi:10.1126/science.174.4013.1023. PMID 5120086.
Jump up ^ Jackson RW (1930). "A synthesis of tryptophol" (PDF). Journal of Biological Chemistry. 88 (3): 659–662.
Jump up ^ Young SN (September 2013). "Acute tryptophan depletion in humans: a review of theoretical, practical and ethical aspects". Journal of Psychiatry & Neuroscience. 38 (5): 294–305. doi:10.1503/jpn.120209. PMC 3756112  . PMID 23428157.
Jump up ^ Young SN (2013). "The effect of raising and lowering tryptophan levels on human mood and social behaviour". Philosophical Transactions of the Royal Society of London. Series B, Biological Sciences. 368 (1615): 20110375. doi:10.1098/rstb.2011.0375. PMC 3638380  . PMID 23440461.
Further reading[edit]
Wood RM, Rilling JK, Sanfey AG, Bhagwagar Z, Rogers RD (May 2006). "Effects of tryptophan depletion on the performance of an iterated Prisoner's Dilemma game in healthy adults". Neuropsychopharmacology. 31 (5): 1075–84. doi:10.1038/sj.npp.1300932. PMID 16407905.
Sturtz R (2009). "what is the difference between L-Tryptophan and 5-HTP?". The Lidtke letter: 1.
External links[edit]
"KEGG PATHWAY: Tryptophan metabolism - Homo sapiens". KEGG: Kyoto Encyclopedia of Genes and Genomes. 2006-08-23. Retrieved 2008-04-20.
G. P. Moss. "Tryptophan Catabolism (early stages)". Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Retrieved 2008-04-20.
G. P. Moss. "Tryptophan Catabolism (later stages)". Nomenclature Committee of the International Union of Biochemistry and Molecular Biology (NC-IUBMB). Retrieved 2008-04-20.
B. Mikkelson; D. P. Mikkelson (2007-11-22). "Turkey Causes Sleepiness". Urban Legends Reference Pages. Snopes.com. Retrieved 2008-04-20.
show
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Encoded (proteinogenic) amino acids
General topics
Protein
Peptide
Genetic code
By properties
Aliphatic
Branched-chain amino acids (Valine
Isoleucine
Leucine)
Methionine
Alanine
Proline
Glycine
Aromatic
Phenylalanine
Tyrosine
Tryptophan
Histidine
Polar, uncharged
Asparagine
Glutamine
Serine
Threonine
Positive charge (pKa)
Lysine (≈10.8)
Arginine (≈12.5)
Histidine (≈6.1)
Negative charge (pKa)
Aspartic acid (≈3.9)
Glutamic acid (≈4.1)
Cysteine (≈8.3)
Tyrosine (≈10.1)
Amino acids types: Encoded (proteins)
Essential
Non-proteinogenic
Ketogenic
Glucogenic
Imino acids
D-amino acids
Dehydroamino acids
hide
v
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e
Amino acid metabolism metabolic intermediates
K→acetyl-CoA
lysine→
Saccharopine
Allysine
α-Aminoadipic acid
α-Ketoadipate
Glutaryl-CoA
Glutaconyl-CoA
Crotonyl-CoA
β-Hydroxybutyryl-CoA
leucine→
β-Hydroxy β-methylbutyric acid
β-Hydroxy β-methylbutyryl-CoA
Isovaleryl-CoA
α-Ketoisocaproic acid
β-Ketoisocaproic acid
β-Ketoisocaproyl-CoA
β-Leucine
β-Methylcrotonyl-CoA
β-Methylglutaconyl-CoA
β-Hydroxy β-methylglutaryl-CoA
tryptophan→alanine→
N'-Formylkynurenine
Kynurenine
Anthranilic acid
3-Hydroxykynurenine
3-Hydroxyanthranilic acid
2-Amino-3-carboxymuconic semialdehyde
2-Aminomuconic semialdehyde
2-Aminomuconic acid
Glutaryl-CoA
G
G→pyruvate→citrate
glycine→serine→
3-Phosphoglyceric acid
glycine→creatine: Glycocyamine
Phosphocreatine
Creatinine
G→glutamate→
α-ketoglutarate
histidine→
Urocanic acid
Imidazol-4-one-5-propionic acid
Formiminoglutamic acid
Glutamate-1-semialdehyde
proline→
1-Pyrroline-5-carboxylic acid
arginine→
Agmatine
Ornithine
Citrulline
Cadaverine
Putrescine
other
cysteine+glutamate→glutathione: γ-Glutamylcysteine
G→propionyl-CoA→
succinyl-CoA
valine→
α-Ketoisovaleric acid
Isobutyryl-CoA
Methacrylyl-CoA
3-Hydroxyisobutyryl-CoA
3-Hydroxyisobutyric acid
2-Methyl-3-oxopropanoic acid
isoleucine→
2,3-Dihydroxy-3-methylpentanoic acid
2-Methylbutyryl-CoA
Tiglyl-CoA
2-Methylacetoacetyl-CoA
methionine→
generation of homocysteine: S-Adenosyl methionine
S-Adenosyl-L-homocysteine
Homocysteine
conversion to cysteine: Cystathionine
alpha-Ketobutyric acid+Cysteine
threonine→
α-Ketobutyric acid
propionyl-CoA→
Methylmalonyl-CoA
G→fumarate
phenylalanine→tyrosine→
4-Hydroxyphenylpyruvic acid
Homogentisic acid
4-Maleylacetoacetic acid
G→oxaloacetate
see urea cycle
Other
Cysteine metabolism
Cysteine sulfinic acid
show
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Neurotransmitter metabolic intermediates
catecholamines
Anabolism
(tyrosine→epinephrine)
Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine
Catabolism/
metabolites
dopamine:
DOPAL
DOPAC
MOPET
Hydroxytyrosol
3-Methoxytyramine
Homovanillic acid
norepinephrine:
3,4-Dihydroxymandelic acid
Normetanephrine
Vanillylmandelic acid
3-Methoxy-4-hydroxyphenylglycol
Dihydroxyphenylethylene glycol
epinephrine:
Metanephrine
tryptophan→serotonin
anabolism:
5-Hydroxytryptophan
catabolism:
5-Hydroxyindoleacetic acid
serotonin→melatonin
Normelatonin
show
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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
Arazasetron
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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Tryptamines
1-Methylpsilocin
2-Methyl-5-HT
4,5-DHP-DMT
4,5-MDO-DMT
4,5-MDO-DiPT
4-AcO-DALT
4-AcO-DET
4-AcO-DMT
4-AcO-DiPT
4-AcO-NMT
4-AcO-MET
4-AcO-DPT
4-AcO-MiPT
4-HO-DALT
4-HO-DET
4-HO-DiPT
4-HO-DSBT
4-HO-MET
4-HO-MiPT
4-HO-NMT
4-HO-αMT
4-Me-αET
4-Me-αMT
4-MeO-DiPT
4-MeO-DMT
5-BT
5-Bromo-DMT
5-CT
5-Chloro-αMT
5-Ethoxy-αMT
5-Fluoro-αMT
5-HO-αMT
5-HO-DiPT
5-HTP
5-Ethoxy-DMT
5-Ethyl-DMT
5-Fluoro-DMT
5-Methyl-DMT
5-Methoxytryptamine
5-MeO-7,N,N-TMT
5-Methyl-αET
5-MeO-αET
5-MeO-αMT
5-MeO-DALT
5-MeO-DET
5-MeO-DiPT
5-MeO-DMT
5-MeO-DPT
5-MeO-EiPT
5-MeO-EPT
5-MeO-MALT
5-MeO-MiPT
5-MeO-NBpBrT
5,7-Dihydroxytryptamine
5-(Nonyloxy)tryptamine
6-Fluoro-αMT
6-Hydroxymelatonin
7-Methyl-αET
7-Methyl-DMT
Acetryptine
Aeruginascin
αET
AL-37350A
αMT
BW-723C86
Baeocystin
Bufotenidine
Bufotenin (5-HO-DMT)
Convolutindole A
DALT
Desformylflustrabromine
DET
DiPT
DMT
DPT
Ethocybin
EiPT
EMDT
EPT
FGIN-127
FGIN-143
HIOC
Ibogaine
Indorenate
Iprocin
Lespedamine
Luzindole
MET
MiPT
MPT
Miprocin
Melatonin
MS-245
NAS
N-Feruloylserotonin
NMT
Norbaeocystin
Normelatonin
O-4310
Oxypertine
Plakohypaphorine
PiPT
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Rizatriptan
Serotonin
ST-1936
Sumatriptan
Tryptamine
Tryptophan
Yohimbine
Yuremamine
Zolmitriptan
Authority control
NDL: 00573319
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tryptophan&oldid=848875278"
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Aromatic amino acids
Essential amino acids
Tryptamine alkaloids
Dietary supplements
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values: Template:Tryptophan metabolism by human microbiota

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text:
List of highest scoring NFL games
From Wikipedia, the free encyclopedia
This is the latest accepted revision, reviewed on 11 February 2018.
Jump to: navigation, search
The highest score in a National Football League (NFL) game occurred on November 27, 1966, when the Washington Redskins and New York Giants combined for 113 points in a 72–41 victory for the Redskins. Only four games in NFL history have eclipsed 100 total points, with the most recent being a 101-point game in 2015 between the Giants and New Orleans Saints. The highest score in a playoff game occurred in the 2009–10 NFL playoffs, a 96-point game in which the Arizona Cardinals defeated the Green Bay Packers 51–45 in overtime. The most points scored in a Super Bowl was 75, in Super Bowl XXIX, which the San Francisco 49ers won 49–26 over the San Diego Chargers.
Contents
[hide]
1 List
1.1 Regular season
1.2 Playoffs
1.3 Super Bowl
2 Game notes
2.1 Regular season
2.1.1 113 points (New York Giants vs. Washington Redskins, 1966)
2.1.2 106 points (Cincinnati Bengals vs. Cleveland Browns, 2004)
2.1.3 101 points (Oakland Raiders vs. Houston Oilers, 1963)
2.1.4 101 points (New York Giants vs. New Orleans Saints, 2015)
2.1.5 99 points (Seattle Seahawks vs. Kansas City Chiefs, 1983)
2.1.6 99 points (Denver Broncos vs. Dallas Cowboys, 2013)
2.1.7 98 points (Pittsburgh Steelers vs. San Diego Chargers, 1985)
2.1.8 96 points (Cincinnati Bengals vs. Cleveland Browns, 2007)
2.1.9 96 points (Miami Dolphins vs. New York Jets, 1986)
2.1.10 95 points (Washington Redskins vs. Green Bay Packers, 1983)
2.2 Playoffs
2.2.1 96 points (Green Bay Packers vs. Arizona Cardinals, 2009 playoffs)
2.2.2 95 points (Detroit Lions vs. Philadelphia Eagles, 1995 playoffs)
2.2.3 89 points (Indianapolis Colts vs. Kansas City Chiefs, 2013 playoffs)
2.3 Super Bowl
2.3.1 75 points (Super Bowl XXIX: San Diego Chargers vs. San Francisco 49ers)
3 Notes
4 References
List[edit]
Regular season[edit]
Points scored
Score
Winning team
Losing team
Date
Ref
113
72–41 Washington Redskins New York Giants November 27, 1966 [1]
106
58–48 Cincinnati Bengals Cleveland Browns November 28, 2004 [2]
101
52–49 Oakland Raiders Houston Oilers December 22, 1963 [3]
101
52–49 New Orleans Saints New York Giants November 1, 2015 [4]
99
51–48 (OT) Seattle Seahawks Kansas City Chiefs November 27, 1983 [5]
99
51–48 Denver Broncos Dallas Cowboys October 6, 2013 [6]
98
54–44 San Diego Chargers Pittsburgh Steelers December 8, 1985 [7]
96
51–45 Cleveland Browns Cincinnati Bengals September 16, 2007 [8]
96
51–45 (OT) New York Jets Miami Dolphins September 21, 1986 [9]
95
48–47 Green Bay Packers Washington Redskins October 17, 1983 [10]
90
52–38 New Orleans Saints Detroit Lions October 15, 2017 [11]
89
48–41 New Orleans Saints Arizona Cardinals December 18, 2016 [12]
85
51–34 Pittsburgh Steelers Indianapolis Colts October 26, 2014 [13]
Playoffs[edit]
Points scored
Score
Winning team
Losing team
Date
Ref
96
51–45 (OT) Arizona Cardinals Green Bay Packers January 10, 2010 [14]
95
58–37 Philadelphia Eagles Detroit Lions December 30, 1995 [15]
89
45–44 Indianapolis Colts Kansas City Chiefs January 4, 2014 [16]
87
45–42 Jacksonville Jaguars Pittsburgh Steelers January 14, 2018 [17]
Super Bowl[edit]
Points scored
Score
Winning team
Losing team
Date
Ref
75
49–26 San Francisco 49ers San Diego Chargers January 29, 1995 [18]
74
41–33 Philadelphia Eagles New England Patriots February 4, 2018 [19]
69
52–17 Dallas Cowboys Buffalo Bills January 31, 1993 [20]
69
48–21 Tampa Bay Buccaneers Oakland Raiders January 26, 2003 [21]
Game notes[edit]
Regular season[edit]
113 points (New York Giants vs. Washington Redskins, 1966)[edit]
The Washington Redskins and the New York Giants combined for a total of 113 points in one game on November 27, 1966, in Washington, D.C.. The Redskins outscored the Giants 72–41. There were a total of 16 touchdowns: 10 by the Redskins and 6 by the Giants, plus a field goal by Washington's kicker Charlie Gogolak[22] with only 7 seconds left. The game was played before the introduction of nets behind the goal post causing the loss of fourteen footballs to the stands. Thirteen of the footballs were lost due to extra points, and one was lost by Brig Owens who threw the ball into the crowd after he returned a fumble 69 yards for a touchdown.[23]
106 points (Cincinnati Bengals vs. Cleveland Browns, 2004)[edit]
On November 28, 2004, Cincinnati Bengals quarterback Carson Palmer threw for 4 touchdowns and Rudi Johnson ran for 2 more along with a career-high 202 rushing yards as the Bengals survived 413 passing yards and 5 touchdowns by Kelly Holcomb to defeat the Cleveland Browns 58–48, in the second-highest scoring game in NFL history. Deltha O'Neal returned an interception 69 yards for a touchdown in the final 2 minutes to end the Browns' comeback hopes and to cap the scoring.
101 points (Oakland Raiders vs. Houston Oilers, 1963)[edit]
Played on December 22, 1963, the game took place in the American Football League (AFL), but it was absorbed into official NFL records after the NFL–AFL merger. The Oakland Raiders defeated the Houston Oilers 52–49, combining for a total of 101 points. It was Oakland's eighth win in a row.
Oakland placekicker Mike Mercer kicked a field goal with 4:37 left in the fourth quarter, breaking the 49–49 tie and giving Oakland the win. Raiders quarterback Tom Flores threw for 407 yards and 6 touchdowns. The Oilers quarterback and future Hall of Famer George Blanda passed for 342 yards and 5 touchdowns.[24] Oakland's wide receiver Art Powell caught 10 passes for a total of 247 yards and 4 touchdowns. Houston had their own offensive threat in Willard Dewveall who had seven catches adding up to a total amount of 137 yards and four touchdowns.[25]
101 points (New York Giants vs. New Orleans Saints, 2015)[edit]
On November 1, 2015, the New York Giants and New Orleans Saints scored a combined 101 points.[26] The Saints won 52–49. Notably, Saints quarterback Drew Brees tied an NFL record by throwing seven touchdown passes, and Giants quarterback Eli Manning threw six touchdown passes. The 13 touchdown passes between the two quarterbacks set an NFL record.[27] The only field goal was scored on the final play of the game, when the Saints' Kai Forbath successfully kicked a 50-yard field goal to win the game, the longest kick of his career at the time.
99 points (Seattle Seahawks vs. Kansas City Chiefs, 1983)[edit]
On November 27, 1983, the Seattle Seahawks defeated the visiting Kansas City Chiefs 51–48 in overtime. The 99 points scored is tied for fifth-highest scoring game in NFL history. Seahawks running back Curt Warner rushed for 207 yards on 32 carries. Chiefs receiver Carlos Carson had seven catches for 149 yards and one touchdown. The game ended when placekicker Norm Johnson converted a 42-yard field goal with 1:46 left in overtime.[25]
99 points (Denver Broncos vs. Dallas Cowboys, 2013)[edit]
On October 6, 2013, the Dallas Cowboys hosted the Denver Broncos for a game in which 99 total points were scored, tied for fifth-highest in NFL history. Near the end of the fourth quarter the game was tied, 48-48. Cowboys quarterback Tony Romo (who achieved more than 500 passing yards for the first time in franchise history) threw a critical interception to Broncos linebacker Danny Trevathan at his own 24-yard line with 2 minutes remaining in the game. Denver placekicker Matt Prater kicked a 28-yard field goal as time expired to give the Broncos a 51-48 win.
Broncos quarterback Peyton Manning completed 33 of 42 passes for 414 yards, throwing 4 touchdown passes and 1 interception in a winning effort. This performance prompted KCNC-TV to report, "After 5 games and 5 big wins, the Broncos are on pace to become the first team in the history of the NFL to exceed 600, maybe even 700 points, in a season. It is the most remarkable five-game stretch in the history of professional football. The numbers don't lie. What Manning has done in his first five games — his "assault" on the record books — is simply unprecedented."[28]
98 points (Pittsburgh Steelers vs. San Diego Chargers, 1985)[edit]
On December 8, 1985, the San Diego Chargers and Pittsburgh Steelers combined for 98 points in a 54–44 Chargers victory.
96 points (Cincinnati Bengals vs. Cleveland Browns, 2007)[edit]
On September 16, 2007, Ohio intrastate rivals Cleveland and Cincinnati battled to combine for 96 points, with the Browns defeating the Bengals 51–45.
96 points (Miami Dolphins vs. New York Jets, 1986)[edit]
In a September 21, 1986, AFC East showdown at Giants Stadium in East Rutherford, New Jersey, the New York Jets hosted the Miami Dolphins, combining for 96 points, with the Jets defeating the Dolphins in overtime, 51–45.
The contest featured 1,066 yards of combined offense, 59 first downs and 93 total pass attempts. Dolphins quarterback Dan Marino had 448 yards through the air and a personal best six touchdown passes, while Jets signal-caller Ken O'Brien threw for 479 yards and 4 touchdown passes. The shootout came to an end when Jets wide receiver Wesley Walker caught a 43-yard bomb touchdown from O'Brien in overtime, his fourth of the game. Walker finished with 6 catches for 179 yards. The Dolphins receiving corps was led by the "Marks Brothers", Mark Duper and Mark Clayton, combining for 328 yards receiving and 3 touchdown receptions.
95 points (Washington Redskins vs. Green Bay Packers, 1983)[edit]
On October 17, 1983, the Redskins and Packers played on a Monday night with the Packers winning 48–47, a combined 95-point total. Redskins kicker Mark Moseley missed a field goal in the final seconds, securing the win for the Packers.
Playoffs[edit]
96 points (Green Bay Packers vs. Arizona Cardinals, 2009 playoffs)[edit]
In the 2009–10 playoffs, the Cardinals and Packers combined for 96 points in a 51–45 overtime Arizona win.
95 points (Detroit Lions vs. Philadelphia Eagles, 1995 playoffs)[edit]
In a December 30, 1995 Wild Card playoff game, the Philadelphia Eagles and Detroit Lions combined for 95 points in what was the NFL's highest scoring postseason game until the 2009–10 playoffs.
The Eagles dominated the game on seven Detroit turnovers, winning 58–37. The Eagles scored 31 points in the second quarter alone, and led 38–7 at halftime. They extended their lead to 51–7 with nine minutes left in the third quarter. After that, Detroit scored four touchdowns while the Eagles added another.
89 points (Indianapolis Colts vs. Kansas City Chiefs, 2013 playoffs)[edit]
On January 4, 2014, the Colts and the Chiefs played in a Saturday evening 2014 NFL Wild Card playoff game. The teams combined for 89 points, with the Colts winning 45-44. Following an early second half Chiefs touchdown, the Colts rallied back for a 28-point comeback, the second largest comeback in NFL playoff history.[a][29]
Super Bowl[edit]
75 points (Super Bowl XXIX: San Diego Chargers vs. San Francisco 49ers)[edit]
The highest-scoring Super Bowl was Super Bowl XXIX on January 29, 1995, in which the NFC champion San Francisco 49ers defeated the AFC champion San Diego Chargers 49–26 for a combined 75 points.[30]
Notes[edit]
Jump up ^ Behind only "The Comeback"
References[edit]
Jump up ^ "New York Giants at Washington Redskins – November 27th, 1966". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Cleveland Browns at Cincinnati Bengals – November 28th, 2004". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Houston Oilers at Oakland Raiders – December 22nd, 1963". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "New York Giants at New Orleans Saints – November 1st, 2015". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Kansas City Chiefs at Seattle Seahawks – November 27th, 1983". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Denver Broncos at Dallas Cowboys – October 6th, 2013". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Pittsburgh Steelers at San Diego Chargers – December 8th, 1985". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Cincinnati Bengals at Cleveland Browns – September 16th, 2007". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Miami Dolphins at New York Jets – September 21st, 1986". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Washington Redskins at Green Bay Packers – October 17th, 1983". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Detroit Lions at New Orleans Saints – October 15th, 2017". Pro-Football-Reference.com. Sports Reference. Retrieved January 22, 2018.
Jump up ^ "New Orleans Saints at Arizona Cardinals – December 18th, 2016". Pro-Football-Reference.com. Sports Reference. Retrieved January 22, 2018.
Jump up ^ "Indianapolis Colts at Pittsburgh Steelers – October 26th, 2014". Pro-Football-Reference.com. Sports Reference. Retrieved January 22, 2018.
Jump up ^ "Wild Card – Green Bay Packers at Arizona Cardinals – January 10th, 2010". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Wild Card – Detroit Lions at Philadelphia Eagles – December 30th, 1995". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Wild Card – Kansas City Chiefs at Indianapolis Colts – January 4th, 2014". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Division – Jacksonville Jaguars at Pittsburgh Steelers – January 14th, 2018". Pro-Football-Reference.com. Sports Reference. Retrieved January 22, 2018.
Jump up ^ "Super Bowl XXIX – San Francisco 49ers vs. San Diego Chargers – January 29th, 1995". Pro-Football-Reference.com. Sports Reference. Retrieved October 6, 2017.
Jump up ^ "Super Bowl LII – Philadelphia Eagles vs. New England Patriots – February 4th, 2018". Pro-Football-Reference.com. Sports Reference. Retrieved February 4, 2018.
Jump up ^ "Super Bowl XXVII – Dallas Cowboys vs. Buffalo Bills – January 31st, 1993". Pro-Football-Reference.com. Sports Reference. Retrieved January 22, 2018.
Jump up ^ "Super Bowl XXXVII – Tampa Bay Buccaneers vs. Oakland Raiders – January 26th, 2003". Pro-Football-Reference.com. Sports Reference. Retrieved January 22, 2018.
Jump up ^ "Highest Scoring NFL Game". Retrieved 25 October 2011.
Jump up ^ "Inside the Numbers" (PDF). Retrieved 25 October 2011.
Jump up ^ "The Half of It". Archived from the original on 2 October 2013. Retrieved 3 November 2011.
^ Jump up to: a b "NFL Shootouts". Retrieved 29 November 2011.
Jump up ^ Duncan, Jeff (November 1, 2015). "Saints, Giants combine for 101 points: Where does it rank in NFL history?". The Times-Picayune. Retrieved October 6, 2017.
Jump up ^ Greenberg, Neil (November 1, 2015). "Drew Brees threw for 511 yards and 7 TDs. Best game ever by a QB? Nope". The Washington Post. Retrieved May 9, 2016.
Jump up ^ "Super Bowl Or Bust: If NFL-Leading Broncos Don't Win It All, Will Season Be 'Utter Failure?'". KCNC-TV. Archived from the original on 11 October 2013. Retrieved 13 October 2013.
Jump up ^ http://www.cbssports.com/nfl/gametracker/recap/NFL_20140104_KC@IND/luck-rallies-colts-to-wildcard-win-over-chiefs
Jump up ^ "Super Bowl Records: Team". NFL. Retrieved 2017-05-26.
Retrieved from "https://en.wikipedia.org/w/index.php?title=List_of_highest_scoring_NFL_games&oldid=825022682"
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