text:
The House on Mango Street
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The House on Mango Street
1984 edition
Author
Sandra Cisneros
Cover artist
illustration: Nivia Gonzalez
design: Lorraine Louie
lettering: Henry Sene Yee
Country
United States
Language
English
Genre
Coming-of-age story, novella, a book of vignettes
Published
1984 (Arte Público Press)
Media type
Print (Hardcover, Paperback, & library binding), audio cassette, and audio CD
Pages
110 (2nd edition, paperback)
ISBN
0-679-73477-5 (2nd edition, paperback)
OCLC
81009584
Dewey Decimal
813/.54 20
LC Class
PS3553.I78 H6 1991
The House on Mango Street is a 1984 coming-of-age novel by Mexican-American writer Sandra Cisneros. It deals with Esperanza Cordero, a young Latina girl, and her life growing up in Chicago with Chicanos and Puerto Ricans. Esperanza is determined to "say goodbye"[1] to her impoverished Latino neighborhood by turning to a life on the streets. Major themes include her quest for a better life and the importance of her promise to come back for "the ones [she] left behind".[1] The novel has been critically acclaimed, and has also become a New York Times Bestseller. It has also been adapted into a stage play by Tanya Saracho.
Contents
[hide]
1 Plot
2 Genre
3 Autobiographical elements
4 Critical reception
5 Publication history
6 See also
7 References
Plot[edit]
The story begins with Esperanza, the protagonist, describing how her family arrived at the house on Mango Street. Before the family settled in their new house, they moved around frequently. The reader develops a sense of Esperanza’s observant and descriptive nature as she begins the novel with descriptions of minute behaviors and observations about her family members. Though Esperanza's age is never revealed to the reader, it is implied that she is about thirteen. She begins to write as a way of expressing herself and as a way to escape the suffocating effect of the neighborhood. The novel also includes the stories of many of Esperanza’s neighbors, providing a picture of the neighborhood and offering examples of the many influences surrounding her. Esperanza quickly befriends Lucy and Rachel Guerrero, two Texan girls who live across the street. Lucy, Rachel, Esperanza, and Esperanza’s little sister, Nenny, have many adventures in the small space of their neighborhood. As the vignettes progress, the novel depicts Esperanza's budding personal maturity and developing world outlook.
Esperanza later slips into puberty and likes it when a boy watches her dance at a baptism party. Esperanza's newfound views lead her to become friends with Sally, a girl her age who wears black nylon stockings, makeup, high heels, and short skirts, and uses boys as an escape from her abusive father. Sally, a beautiful girl according to her father, can get into trouble with being as beautiful as she is. Esperanza is not completely comfortable with Sally’s sexuality. Their friendship is compromised when Sally ditches Esperanza for a boy at a carnival. As a result, Esperanza is sexually assaulted by a man at the carnival. Earlier at her first job, an elderly man tricked her into kissing him on the lips. Esperanza’s traumatic experiences and observations of the women in her neighborhood cement her desire to escape Mango Street. She later realizes that she will never fully be able to leave Mango Street behind. She vows that after she leaves she will return to help the people she has left behind. Esperanza exclaims that Mango Street does not hold her in both arms; instead, it sets her free.
Genre[edit]
The House on Mango Street is made up of vignettes that are not quite poems and not quite full stories. Not wanting to write directly about herself, Cisneros constructs the book in a combination of genres pulling mantles of poetry, autobiography, and fiction. Certain parts of the book directly reflect Cisneros’ life, while others stray. Esperanza narrates these vignettes in first-person present tense, focusing on her day-to-day activities but sometimes narrating sections that are a series of observations. The vignettes can be as short as two or three paragraphs long and sometimes contain internal rhymes. In "The Family of Little Feet" for example, Esperanza says:
"Their arms were little, and their hands were little, and their height was not tall, and their feet very small."[2] Each vignette can stand as an independent story. These vignettes don't follow a complete or chronological narrative, although they often mention characters introduced in earlier sections. The conflicts and problems in these short stories are never fully resolved, just as the futures of people in the neighborhood are often uncertain. The overall tone of the novel is earnest and intimate, with very little distance between the reader and the narrator. The tone varies from pessimistic to hopeful, as Esperanza herself sometimes expresses her jaded views on life:
"I knew then I had to have a house. A real house. One I could point to. But this isn't it. The house on Mango Street isn't it. For the time being, Mama says. Temporary, says Papa. But I know how those things go."[3]
The set of vignettes charts her life as Esperanza Cordero grows during the year: both physically and emotionally.
Cisneros asserts that the goal of The House on Mango Street was to make the novel accessible to everyone. She wrote the book initially as a catharsis, not realizing that it would eventually represent a voice for Latinos and become enveloped in the works of great Latino literature. She wanted it to be lyrical enough to be appreciated by poetry enthusiasts, but also accessible enough that laymen could read and enjoy the novel. She desired the book to resonate with children, adults, and ages in between, and in totality chose to keep the novel short so that even the busiest of parents and adults who worked long shifts like her father always had, could still find time to read it.
Autobiographical elements[edit]
Sandra Cisneros' early life was a subject she would later draw on as a writer in books like The House on Mango Street. She was the only daughter among seven children in her family. Cisneros’ family and father specifically did not initially support her writing. Her father never wanted her to be an author. When she was growing up, the only famous Latinas were those on TV, and in the seventies they were seen most often on television as weather girls. Cisneros and her father envisioned her as a newscaster for that reason.[4] Despite a lacking support system, Cisneros continued to pursue writing, and used her life to inspire her early works. The House on Mango Street includes information inspired by her life. The story also is about the subject of migration, and about the struggles of her life during it, which included poverty, as well as misogyny. Cisneros first began writing about the protagonist, Esperanza, when she had just finished graduate school. Cisneros created Esperanza from personal feelings of displacement she had while writing. She had recently graduated from the University of Iowa and had felt marginalized as a person of color, a woman, and an individual of lower socioeconomic status.[4] The House on Mango Street became a way for her to solidify her identities through reflection in writing. Esperanza is one of four children, with a younger sister and two younger brothers. In reality, Cisneros was the middle child and only girl with six brothers, two older and four younger. While writing, Cisneros explains that because she was new to fiction, she initially craved simplicity, which resulted in Esperanza’s family being smaller than her actual family had been. She believed it would be easier to write about fewer family members.[4]
Critical reception[edit]
Acclaimed by critics, The House on Mango Street has been translated into various languages and has been taught in schools across the United States and Canada. The book received highly positive reception upon release and has been re-issued in a 25th Anniversary Edition.[5] The novel has especially earned high praise from the Latino/Latina community. Oscar Hijuelos, the first Hispanic writer to win a Pulitzer Prize for Fiction, said that the novel has "conveyed the Southwestern Latino experience with verve, charm, and passion."[6] The book won her the American Book Award from the Before Columbus Foundation (1985).[7]
After the initial release, the response to The House on Mango Street by the public and various academics was varied. Much of the critical reception surrounding the novel stems from the sexual content present throughout multiple scenes. During the “Red Clowns” chapter of the novel, Esperanza is raped by a male who repeatedly defines her as a “Spanish girl”[8] whom he loves. Critics argued that the suspected audience of the book was perceived to be too young for this content.[9]
Protesters are seen in June 2011 in support of the Tucson Unified School District's Mexican-American studies program. A new state law effectively ended the program saying it was divisive.
Despite its high praise in the realm of Latino literature, The House on Mango Street has also received criticism and has been banned from come school curriculums.
In response to these criticisms as well as the removal of the MAS program from TUSD schools, teachers, authors, and activists headed by Tony Diaz, a teacher from the MAS program formed a caravan in spring of 2012 that moved across the southwest conducting workshops in major cities. The caravan, called the Librotraficante Project, originated at the Alamo and ended in Tucson orchestrating workshops distributing books that had been removed with the curriculum, and informing attendees of H.B. 2281.[10] Though The House on Mango Street was never removed from TUSD's curriculum and continued to be taught in middle and high school English classes within TUSD, Cisneros traveled with the caravan reading The House on Mango Street and ran workshops about Chicano literature. She brought numerous copies of the book with her, distributed them, and discussed thematic implications of her novel as well as talked about the book’s autobiographical elements.[11]
Parents and education boards in other areas have found the content to be too graphic/real for children of a young age.[9] In response to this categorization as a children’s novel, Cisernos replies that even though it’s marketed as a young people’s book, the range of readers stems all the way to college level students.[12] Cisernos’ novel has one general theme: to promote individuality and drive within individuals which will conversely promote a distaste for conformity and cultural labeling.[8] Much of the critical reception surrounding the book today recants this theme due to its suspected negative effects on individuals challenging superior powers such as the government and educational institutions.[13]
Publication history[edit]
1984, The United States, Arte Público Press ISBN 0-934770-20-4, Pub date 1 January 1984, paperback
1991, The United States, Vintage Contemporaries ISBN 0-679-73477-5, Pub date 3 April 1991, paperback
See also[edit]
Chicago literature
Chicano literature
References[edit]
^ Jump up to: a b Cisneros, Sandra (1991). The House on Mango Street. Vintage Contemporaries. ISBN 0-679-73477-5.
Jump up ^ Cisneros, The House on Mango Street, p.39
Jump up ^ Cisneros, The House on Mango Street, p. 5
^ Jump up to: a b c Cisneros, Sandra (2009-04-09). "House on Mango Street Celebrates 25 Years". National Public Radio. Retrieved 2016-11-13.
Jump up ^ https://www.amazon.com/dp/0679734775
Jump up ^ Hijuelos, Oscar. "José Rubén De León Takes a Stab At 'The House on Mango Street". San Antonio Current. Retrieved 7 November 2016.
Jump up ^ American Booksellers Association (2013). "The American Book Awards / Before Columbus Foundation [1980–2012]". BookWeb. Archived from the original on March 13, 2013. Retrieved September 25, 2013. 1985 [...] The House on Mango Street, Sandra Cisneros
^ Jump up to: a b Petty, Leslie. "Literature Resource Center - Document - Re-Envisioning Chicano Cultural Archetypes: The 'Dual'-ing Images of la Malinche and la Virgen de Guadalupe in Sandra Cisneros's The House on Mango Street". go.galegroup.com. Retrieved 2016-12-01.
^ Jump up to: a b Cisneros, Sandra. "Spiritual Sustenance: Interview with Sandra Cisneros". go.galegroup.com. Susquehanna University Press. Retrieved 2016-12-01.
Jump up ^ Hoinski, Michael (2012-03-08). "GTT, The Papers Trail, San Antonio". New York Times. Retrieved 2016-11-13.
Jump up ^ Fernandez, Valeria (2012-03-15). "Librotraficantes Bring Banned Books into Arizona". New America Media. Retrieved 2016-11-13.
Jump up ^ Satz, Martha. "Returning to One's House: An Interview with Sandra Cisneros". go.galegroup.com. Gale Cengage Learning. Retrieved 2016-12-01.
Jump up ^ Matchie, Thomas. "Literary Continuity in Sandra Cisneros's The House on Mango Street". go.galegroup.com. Gale. Retrieved 2016-12-01.
[hide]
v
t
e
Sandra Cisneros
Works
Bad Boys (1980)
The House on Mango Street (1984)
My Wicked, Wicked Ways (1987)
Woman Hollering Creek and Other Stories (1991)
Hairs = Pelitos (1994)
Loose woman: Poems (1994)
Caramelo, or, Pure Cuento: A Novel (2002)
Vintage Cisneros (2004)
Contributed to
Days and Nights of Love and War (2000)
Family Pictures/ Cuadros de Familia (2005)
Emergency Tacos: Seven Poets Con Picante (2007)
List of works
Retrieved from "https://en.wikipedia.org/w/index.php?title=The_House_on_Mango_Street&oldid=813601940"
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Novels by Sandra Cisneros
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text:
Methoxyflurane
From Wikipedia, the free encyclopedia
Jump to: navigation, search
Methoxyflurane
Clinical data
Synonyms
2,2-dichloro-1,1-difluoroethyl methyl ether
Pregnancy
category
AU: C
US: C (Risk not ruled out)
Routes of
administration
Inhalation
ATC code
N02BG09 (WHO)
Legal status
Legal status
AU: S4 (Prescription only)
Pharmacokinetic data
Metabolism
70%
Identifiers
IUPAC name[show]
2,2-dichloro-1,1-difluoro-1-methoxyethane
CAS Number
76-38-0 Y
PubChem CID
4116
DrugBank
DB01028 Y
ChemSpider
3973 Y
UNII
30905R8O7B
KEGG
D00544 Y
ChEBI
CHEBI:6843 N
ChEMBL
CHEMBL1341 Y
ECHA InfoCard
100.000.870
Chemical and physical data
Formula
C3H4Cl2F2O
Molar mass
164.966 g/mol
3D model (JSmol)
Interactive image
SMILES[show]
ClC(Cl)C(F)(F)OC
InChI[show]
InChI=1S/C3H4Cl2F2O/c1-8-3(6,7)2(4)5/h2H,1H3 Y
Key:RFKMCNOHBTXSMU-UHFFFAOYSA-N Y
N Y (what is this?) (verify)
Methoxyflurane (INN), formerly marketed as Penthrane by Abbott Laboratories, is a halogenated ether that was in clinical use as a volatile inhalational anesthetic from its introduction by Joseph F. Artusio et al in 1960 until the late 1970s. It was first synthesized in the late 1940s by William T. Miller and his team of chemists following their involvement in the Manhattan Project.[1]
Methoxyflurane is an extremely potent and highly lipid-soluble anesthetic agent, characterized by very slow induction (onset of action) and emergence (offset or dissipation) times. It is non-flammable, has relatively mild hemodynamic effects, and it does not predispose the heart to rhythm disturbances. It is, however, a significant respiratory depressant. Methoxyflurane has powerful analgesic (pain-relieving) properties at well below full anesthetic doses. It was utilized in self-administration devices for obstetric analgesia, in a manner that foreshadowed the patient-controlled analgesia infusion pumps of today.
The biodegradation of methoxyflurane produces inorganic fluoride and dichloroacetic acid (DCAA). The combined effects of these two compounds may be responsible for the toxicity of methoxyflurane to some of the major organs of the human body. Methoxyflurane was determined to be nephrotoxic (damaging to the kidneys) in a dose-dependent response and hepatotoxic (damaging to the liver) at anesthetic doses in 1973, and the drug was abandoned as a general anesthetic in the late 1970s.[2] In 1999, the manufacturer discontinued distribution of methoxyflurane in the United States and Canada, and on September 6, 2005, the Food and Drug Administration determined that it should be withdrawn from the market for safety concerns.[2] It is however still used in Australia as an emergency analgesic for the initial management of pain due to acute trauma, as well as for brief painful procedures such as changing of wound dressings or for transport of injured people.
Contents
[hide]
1 Medical use
2 Chemical and physical properties
3 Pharmacokinetics
4 Pharmacodynamics
5 Biodegradation and toxicity
6 History
7 Notes
8 References
9 Further reading
10 External links
Medical use[edit]
Methoxyflurane has been extensively used since the 1970s in Australia as an emergency analgesic for short-term use, mostly by the Australian and New Zealand Defence Forces,[3] and the Australian ambulance services.[4][5][6] The drug is currently only available from one manufacturer (Medical Developments International, Melbourne, Victoria, Australia). It is self-administered to children and adults using the Penthrox inhaler, a hand-held inhaler device, known as "the green whistle".[3][4][7][8] A non-opioid alternative to morphine, it is also easier to use than nitrous oxide.[9] As of 2010, methoxyflurane was listed under the Pharmaceutical Benefits Scheme for the initial management of pain due to acute trauma, as well as for brief painful procedures such as changing of wound dressings or for patient transport.[9] A portable, disposable, single-use inhaler device (the Penthrox inhaler), along with a single 3 milliliter brown glass vial of methoxyflurane is provided in doctor's kits that allows conscious hemodynamically stable patients (including children over the age of 5 years) to self-administer the drug, under supervision.[9]
Each 3 milliliter dose lasts approximately 30 minutes.[10] Pain relief begins after 6–8 breaths and continues for several minutes after stopping inhalation.[11] The maximum recommended dose is 6 milliliters per day or 15 milliliters per week because of the risk of cumulative dose-related nephrotoxicity, and it should not be used on consecutive days.[9] Despite the potential for renal impairment when used at anesthetic doses, no significant adverse effects have been reported in the literature when it is used at the lower doses (up to 6 milliliters) used for producing analgesia and sedation.[4][8][12] Due to the risk of organ (especially renal) toxicity, methoxyflurane is contraindicated in patients with pre-existing kidney disease or diabetes mellitus, and is not recommended to be administered in conjunction with tetracyclines or other potentially nephrotoxic or enzyme-inducing drugs.[8]
Chemical and physical properties[edit]
Further information: Organofluorine
Space-filling model (three-dimensional molecular structure) of methoxyflurane
With a molecular formula of C3H4Cl2F2O and a condensed structural formula of CHCl2CF2OCH3, the International Union of Pure and Applied Chemistry (IUPAC) name for methoxyflurane is 2,2-dichloro-1,1-difluoro-1-methoxyethane. It is a halogenated ether in form of a clear, colorless liquid, and its vapor has a strong fruity aroma. It is miscible with ethanol, acetone, chloroform, diethyl ether, and fixed oils. It is soluble in rubber.[10]
With a minimum alveolar concentration (MAC) of 0.16%,[13] methoxyflurane is an extremely potent anesthetic agent. It is a powerful analgesic agent at well below full anesthetic concentrations.[7][14][15][16][17] Because of its low volatility and very high boiling point (104.8 °C at 1 atmosphere), methoxyflurane has a low vapor pressure at ambient temperature and atmospheric pressure. It is therefore quite difficult to vaporize methoxyflurane using conventional anesthetic vaporizers.
Property
Value[10][18][19]
Boiling point (at 1 atmosphere) 104.8 °C
Minimum alveolar concentration (MAC) 0.16%[13]
Vapor pressure (mmHg at 20 °C) 22.5
Partition coefficient (Blood:Gas) 12
Partition coefficient (Oil:Gas) 950
Partition coefficient (Oil:Water) 400
Specific gravity at 25 °C 1.42
Flash point 63 °C
Molecular weight (g mol−1) 164.97
Vapor-liquid equilibrium (mL) 208
Flammability limits 7% in air
Chemical stabilizer necessary Yes
The carbon–fluorine bond, a component of all organofluorine compounds, is the strongest chemical bond in organic chemistry.[20] Furthermore, this bond becomes shorter and stronger as more fluorine atoms are added to the same carbon on a given molecule. Because of this, fluoroalkanes are some of the most chemically stable organic compounds.
Pharmacokinetics[edit]
Methoxyflurane has a very high lipid solubility (oil:gas partition coefficient of around 950), which gives it very slow pharmacokinetics (induction and emergence characteristics); this being undesirable for routine application in the clinical setting. Initial studies performed in 1961 revealed that in unpremedicated healthy individuals, induction of general anesthesia with methoxyflurane-oxygen alone or with nitrous oxide was difficult or even impossible using the vaporizers available at that time. It was found to be necessary to administer an intravenous anesthetic agent such as sodium thiopental to ensure a smooth and rapid induction. It was further found that after thiopental induction, it was necessary to administer nitrous oxide for at least ten minutes before a sufficient amount of methoxyflurane could accumulate in the bloodstream to ensure an adequate level of anesthesia. This was despite using high flow (liters/minute) of nitrous oxide and oxygen, and with the vaporizers delivering the maximum possible concentration of methoxyflurane.[18]
Similar to its induction pharmacokinetics, methoxyflurane has very slow and somewhat unpredictable emergence characteristics. During initial clinical studies in 1961, the average time to emergence after discontinuation of methoxyflurane was 59 minutes after administration of methoxyflurane for an average duration of 87 minutes. The longest time to emergence was 285 minutes, after 165 minutes of methoxyflurane administration.[18]
Pharmacodynamics[edit]
Cardiovascular effects
The effects of methoxyflurane on the circulatory system resemble those of diethyl ether.[21] In dogs, methoxyflurane anesthesia causes a moderate decrease in blood pressure with minimal changes in heart rate, and no significant effect on blood sugar, epinephrine, or norepinephrine. Bleeding and increased arterial partial pressure of carbon dioxide (PaCO2) both induce further decreases in blood pressure, as well as increases in blood glucose, epinephrine and norepinephrine.[22] In humans, methoxyflurane produces some decrease in blood pressure, but cardiac output, stroke volume, and total peripheral resistance are only minimally depressed. Its effect on the pulmonary circulation is negligible, and it does not predispose the heart to cardiac dysrhythmias.[18][23][24][25]
Respiratory effects
Unlike diethyl ether, methoxyflurane is a significant respiratory depressant. In dogs, methoxyflurane causes a dose-dependent decrease in respiratory rate and a marked decrease in respiratory minute volume, with a relatively mild decrease in tidal volume. In humans, methoxyflurane causes a dose-dependent decrease in tidal volume and minute volume, with respiratory rate relatively constant.[21] The net effect of these changes is profound respiratory depression, as evidenced by CO2 retention with a concomitant decrease in arterial pH (this is referred to as a respiratory acidosis) when anesthetized subjects are allowed to breathe spontaneously for any length of time.[18]
Gastrointestinal effects
In a series of 500 consecutive obstetric patients, Boisvert and Hudon observed vomiting in 12 (4.8%) patients during or after administration of methoxyflurane anesthesia. These findings compared favorably with those reported for cyclopropane (42%), trichloroethylene (28%) and halothane (4.6%).[26] In another study of 645 obstetric patients, Romagnoli and Korman observed 8 cases (1.2%) of postoperative vomiting, one of whom was retching before the administration of the anesthetic.[27]
Analgesic effects
Although the high blood solubility of methoxyflurane is often undesirable, this property makes it useful in certain situations—it persists in the lipid compartment of the body for a long time, providing sedation and analgesia well into the postoperative period.[17][21] There is substantial data to indicate that methoxyflurane is an effective analgesic and sedative agent at subanesthetic doses.[3][4][5][6][28][29][30][31][32][33][34][35][36] Supervised self-administration of methoxyflurane in children and adults can briefly lead to deep sedation,[4] and it has been used as a patient controlled analgesic for painful procedures in children in hospital emergency departments.[7] During childbirth, administration of methoxyflurane produces significantly better analgesia, less psychomotor agitation, and only slightly more somnolence than trichloroethylene.[28]
In 1968, Robert Wexler of Abbott Laboratories developed the Analgizer, a disposable inhaler that allowed the self-administration of methoxyflurane vapor in air for analgesia.[37] The Analgizer consisted of a polyethylene cylinder 5 inches long and 1 inch in diameter with a 1 inch long mouthpiece. The device contained a rolled wick of polypropylene felt which held 15 milliliters of methoxyflurane. Because of the simplicity of the Analgizer and the pharmacological characteristics of methoxyflurane, it was easy for patients to self-administer the drug and rapidly achieve a level of conscious analgesia which could be maintained and adjusted as necessary over a period of time lasting from a few minutes to several hours. The 15 milliliter supply of methoxyflurane would typically last for two to three hours, during which time the user would often be partly amnesic to the sense of pain; the device could be refilled if necessary.[31] The Analgizer was found to be safe, effective, and simple to administer in obstetric patients during childbirth, as well as for patients with bone fractures and joint dislocations,[31] and for dressing changes on burn patients.[30] When used for labor analgesia, the Analgizer allows labor to progress normally and with no apparent adverse effect on Apgar scores.[31] All vital signs remain normal in obstetric patients, newborns, and injured patients.[31] The Analgizer was widely utilized for analgesia and sedation until the early 1970s, in a manner that foreshadowed the patient-controlled analgesia infusion pumps of today.[28][29][32][33] The Analgizer inhaler was withdrawn in 1974, but use of methoxyflurane as a sedative and analgesic continues in Australia and New Zealand in the form of the Penthrox inhaler.[3][4][7][8] Trials of methoxyflurane as an analgesic in emergency medicine are going on in the UK.
Biodegradation and toxicity[edit]
Further information: Drug metabolism and Fluoride poisoning
The first report of nephrotoxicity appeared in 1964, when Paddock and colleagues reported three cases of acute renal insufficiency, two of whom were found to have calcium oxalate crystals in the renal tubules at autopsy.[38] In 1966, Crandell and colleagues reported a series in which 17/95 (18%) of patients developed an unusual type of nephropathy after operations in which methoxyflurane was used as a general anesthetic. This particular type of renal insufficiency was characterized by vasopressin-resistant high-output renal failure (production of large volumes of poorly concentrated urine) with a negative fluid balance, pronounced weight loss, elevation of serum sodium, chloride, osmolality and blood urea nitrogen. The urine of these patients was of a relatively fixed specific gravity and an osmolality very similar to that of the serum. Furthermore, the high urine output persisted a challenge test of fluid deprivation. Most cases resolved within 2–3 weeks, but evidence of renal dysfunction persisted for more than one year in 3 of these 17 cases (18%), and more than two years in one case (6%).[39]
Reports of severe and even fatal hepatotoxicity related to the use of methoxyflurane began to appear in 1966.[40][41][42][43][44][45][46][47][48] These reports prompted anesthesiologists to subject this agent to intense and systematic scrutiny. A study published in 1973 by Cousins and Mazze demonstrated that compared with halothane, methoxyflurane produces dose-dependent and deleterious abnormalities in renal function. The authors showed that subclinical nephrotoxicity occurred following methoxyflurane at minimum alveolar concentration (MAC) for 2.5 to 3 hours (2.5 to 3 MAC hours), while overt toxicity was present in all patients at dosages greater than five MAC hours.[49] This landmark study provided a model that would be used for the assessment of the nephrotoxicity of volatile anesthetics for the next two decades.[50]
The biodegradation of methoxyflurane begins immediately after the onset of exposure. The kidney and liver toxicity observed after anesthetic doses is attributable to one or more metabolites produced by O-demethylation of methoxyflurane. Significant products of this catabolic process include methoxyfluoroacetic acid (MFAA), dichloroacetic acid (DCAA), and inorganic fluoride.[51] Methoxyflurane nephrotoxicity is dose dependent[39][52][53] and irreversible, resulting from O-demethylation of methoxyflurane to fluoride and DCAA.[9] This effect is so predictable and reproducible that methoxyflurane now serves as a pharmacologic model of fluoride-related nephrotoxicity, one with which newer drugs are compared.[50] It is not entirely clear whether the fluoride itself is toxic—it may simply be a surrogate measure for some other toxic metabolite.[54] The concurrent formation of inorganic fluoride and DCAA is unique to methoxyflurane biotransformation compared with other volatile anesthetics, and this combination is more toxic than fluoride alone. This may explain why fluoride formation from methoxyflurane is associated with nephrotoxicity, while fluoride formation from other volatile anesthetics (such as enflurane and sevoflurane) is not.[55] Furthermore, the concurrent use of tetracyclines and methoxyflurane has been reported to result in fatal renal toxicity.[56]
Based on the findings of these and other studies in the early 1970s, the current consensus is that the use of methoxyflurane should be restricted only to healthy individuals, in situations where it offers specific advantages and even then, only at dosages less than 2.5 MAC hours.[49][51] Partly because of these warnings, but also because of the development of newer volatile anesthetics such as enflurane, isoflurane, desflurane and sevoflurane, the clinical use of methoxyflurane as a general anesthetic in humans was largely abandoned in the mid-1970s.
The National Institute for Occupational Safety and Health maintains a recommended exposure limit for methoxyflurane as waste anesthetic gas of 2 ppm (13.5 mg/m3) over 60 minutes.[57]
History[edit]
All of the currently used volatile anesthetic agents are organofluorine compounds. Aside from the synthesis of Freon (Thomas Midgley, Jr. and Charles F. Kettering, 1928)[58] and the discovery of Teflon (Roy J. Plunkett, 1938),[59] the field of organofluorine chemistry had not attracted a great deal of attention up to 1940 because of the extreme reactivity of elemental fluorine, which had to be produced in situ for use in chemical reactions. The development of organofluorine chemistry was a spin-off from the Manhattan Project, during which elemental fluorine was produced on an industrial scale for the first time.
The need for fluorine arose from the need to separate the isotope235U from 238U because the former, present in natural uranium at a concentration of less than 1% is fissile (capable of sustaining a nuclear chain reaction of nuclear fission with thermal neutrons),[60] whereas the latter is not. Members of the MAUD Committee (especially Francis Simon and Nicholas Kurti) proposed the use of gaseous diffusion for isotope separation, since, according to Graham's law the rate of diffusion is inversely proportional to molecular mass.[61] After an extensive search, uranium hexafluoride, UF6, was determined to be the most suitable compound of uranium to be used for the gaseous diffusion process.[62] Elemental fluorine is needed in the production of UF6.
Significant obstacles had to be overcome in the handling of both fluorine and UF6. Before the K-25 gaseous diffusion plant could be built, it was first necessary to develop non-reactive chemical compounds that could be used as coatings, lubricants and gaskets for the surfaces which would come into contact with the UF6 gas (a highly reactive and corrosive substance). William T. Miller,[63] professor of organic chemistry at Cornell University, was co-opted to develop such materials, because of his expertise in organofluorine chemistry. Miller and his team developed several novel non-reactive chlorofluorocarbon polymers that were used in this application.
Charles Suckling synthesized halothane in 1951. Halothane was the first organofluorine anesthetic agent to be introduced into clinical practice in 1956.[64] Miller and his team continued to develop organofluorine chemistry after the end of World War II and methoxyflurane was synthesized in 1948.[1]
Notes[edit]
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^ Jump up to: a b Johnston S, Wilkes GJ, Thompson JA, Ziman M, Brightwell R (2011). "Inhaled methoxyflurane and intranasal fentanyl for prehospital management of visceral pain in an Australian ambulance service". Emergency Medicine Journal. 28 (1): 57–63. doi:10.1136/emj.2009.078717. PMID 20466829.
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^ Jump up to: a b Packer KJ, Titel JH (1969). "Methoxyflurane analgesia for burns dressings: experience with the Analgizer". British Journal of Anaesthesia. 41 (12): 1080–5. doi:10.1093/bja/41.12.1080. PMID 4903969.
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^ Jump up to: a b Josephson CA, Schwartz W (1974). "The Cardiff inhaler and Penthrane. A method of sedation analgesia in routine dentistry". Journal of the Dental Association of South Africa. 29 (2): 77–80. PMID 4534883.
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Jump up ^ Komesaroff D (1995). "Pre-hospital pain relief: Penthrane or Entonox". Australian Journal of Emergency Care. 2 (2): 28–9. ISSN 1322-3127.
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^ Jump up to: a b Crandell WB, Pappas SG, Macdonald A (1966). "Nephrotoxicity associated with methoxyflurane anesthesia". Anesthesiology. 27 (5): 591–607. doi:10.1097/00000542-196609000-00010. PMID 5918999.
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^ Jump up to: a b Cousins MJ, Mazze RI (1973). "Methoxyflurane nephrotoxicity: a study of dose response in man (abstract)". Journal of the American Medical Association. 225 (13): 1611–6. doi:10.1001/jama.1973.03220410023005. PMID 4740737.
^ Jump up to: a b Barash, Cullen and Stoelting (2009), Ebert and Schmid, Chapter 17: Inhaled Anesthetics, pp. 413–43
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References[edit]
Barash, PG; Cullen, BF; Stoelting, RK; Cahalan, MK; Stock, MC, eds. (2009). Clinical anesthesia (6th ed.). Philadelphia: Lippincott Williams & Wilkins. ISBN 978-0-7817-8763-5.
Cotton S (2006). Lanthanide and actinide chemistry (1st ed.). Chichester, England: John Wiley and Sons, Ltd. ISBN 978-0-470-01006-8.
Rhodes, R (1986). The making of the atomic bomb. New York: Simon & Schuster. ISBN 978-0-684-81378-3.
Sneader W (2005). Drug discovery: a history. Chichester, England: John Wiley and Sons, Ltd. ISBN 978-0-471-89980-8.
Further reading[edit]
Brennan, R.; Pearlstein, A.; Miller, S. (1988). "Computed tomography of the kidneys in a patient with methoxyflurane abuse". Journal of computer assisted tomography. 12 (1): 155–156. doi:10.1097/00004728-198801000-00033. PMID 3335658.
Clark, R.; Beard, A.; Thompson, D. (1979). "Renal function in newborns and mothers exposed to methoxyflurane analgesia for labor and delivery". Anesthesiology. 51 (5): 464–466. doi:10.1097/00000542-197911000-00020. PMID 496064.
Corbett, T.; Ball, G. (1971). "Chronic exposure to methoxyflurane: A possible occupational hazard to anesthesiologists". Anesthesiology. 34 (6): 532–537. doi:10.1097/00000542-197106000-00012. PMID 5556243.
Crankshaw DP, Eagle A, Komesaroff D (2004). "Methoxyflurane dosage with the Penthrox inhaler for analgesia during short painful procedures (abstract)". Anaesth. Intensive Care. 32 (3): 428.
Dahlgren, B. (1979). "Fluoride concentrations in urine of delivery ward personnel following exposure to low concentrations of methoxyflurane". Journal of Occupational Medicine. 21 (9): 624–626. PMID 490224.
Dahlgren, B. (1980). "Hepatic and renal effects of low concentrations of methoxyflurane in exposed delivery ward personnel". Journal of Occupational Medicine. 22 (12): 817–819. doi:10.1097/00043764-198012000-00017. PMID 7218059.
Dahlgren, B.; Olander, L.; Ovrum, P. (1979). "Pollution of delivery ward air by nitrous oxide--methoxyflurane". American Industrial Hygiene Association journal. 40 (8): 666–672. doi:10.1080/15298667991430136. PMID 495468.
De Francisco, C. (1971). "Pentrane dependence: A case report". The British Journal of Psychiatry. 119 (553): 609–610. doi:10.1192/bjp.119.553.609. PMID 5143658.
Edmunds, D.; Rosen, M. (1975). "Inhalation sedation for conservative dentistry. A comparison between nitrous oxide and methoxyflurane". British dental journal. 139 (10): 398–402. doi:10.1038/sj.bdj.4803643. PMID 1059442.
Elder, B.; Beal, H.; Dewald, W.; Cobb, S. (1971). "Exacerbation of subclinical myasthenia by occupational exposure to an anesthetic". Anesthesia and Analgesia. 50 (3): 383–387. doi:10.1213/00000539-197105000-00023. PMID 5103772.
Kharasch, E.; Hankins, D.; Thummel, K. (1995). "Human kidney methoxyflurane and sevoflurane metabolism. Intrarenal fluoride production as a possible mechanism of methoxyflurane nephrotoxicity". Anesthesiology. 82 (3): 689–699. doi:10.1097/00000542-199503000-00011. PMID 7879937.
Klemmer, P.; Hadler, N. (1978). "Subacute fluorosis: A consequence of abuse of an organofluoride anesthetic". Annals of Internal Medicine. 89 (5 Pt 1): 607–611. doi:10.7326/0003-4819-89-5-607. PMID 717928.
Komesaroff D; Crankshaw DP (2004). Methoxyflurane analgesia with the Penthrox Inhaler: Emergency Department and Hospital Ward Applications. Teaching and Research Conference. Victoria University of Technology, Melbourne, Australia.
Laird SM, Gray BM. Intermittent inhalation of methoxyflurane and trichloroethylene as an analgesic in burns dressings procedures. Br. J. Anaesth. 1971; 43: 149–59.
Lindblad P, Zack M, Adami HO, Ericson A (1992). "Maternal and perinatal risk factors for Wilms' tumor: a nationwide nested case control study in Sweden". International Journal of Cancer. 51 (1): 38–41. doi:10.1002/ijc.2910510108. PMID 1314230.
Major, V.; Rosen, M.; Mushin, W. (1967). "Concentration of methoxyflurane for obstetric analgesia by self-administered intermittent inhalation". British Medical Journal. 4 (5582): 767–770. doi:10.1136/bmj.4.5582.767. PMC 1749043  . PMID 6081001.
Metropolitan Ambulance Service/Rural Ambulance Service. Clinical practice guideline D020. Version 4, 2005. Methoxyflurane (Penthrane).
Miller WT (1981). "My early days in fluorine chemistry" (PDF). Journal of Fluorine Chemistry. 18 (4): 305–21. doi:10.1016/S0022-1139(00)82652-4.
Novak, M.; Roth, A.; Levine, M. (1988). "Calcium oxalate retinopathy associated with methoxyflurane abuse". Retina (Philadelphia, Pa.). 8 (4): 230–236. doi:10.1097/00006982-198808040-00002. PMID 3231916.
National Institute for Occupational Safety and Health. Pocket guide to chemical hazards, methoxyflurane. Publication number 2005-149.
Rosen, M.; Latto, P.; Asscher, A. (1972). "Kidney function after methoxyflurane analgesia during labour". British Medical Journal. 1 (5792): 81–83. doi:10.1136/bmj.1.5792.81. PMC 1789263  . PMID 5007074.
Rosen, M.; Mushin, W.; Jones, P.; Jones, E. (1969). "Field trial of methoxyflurane, nitrous oxide, and trichloroethylene as obstetric analgesics". British Medical Journal. 3 (5665): 263–267. doi:10.1136/bmj.3.5665.263. PMC 1984095  . PMID 4895340.
Toomath, R.; Morrison, R. (1987). "Renal failure following methoxyflurane analgesia". The New Zealand medical journal. 100 (836): 707–708. PMID 3452163.
External links[edit]
Sheffield Museum of Anaesthesia: the Analgizer
Medical Developments International Limited: Penthrox (methoxyflurane)
Centers for Disease Control and Prevention: NIOSH Pocket Guide to Chemical Hazards
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Nicodicodeine
Nicomorphine
Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone)
Oxymorphone
Thebacon
Synthetic
Alfentanil
Alphaprodine
Anileridine
Butorphanol
Carfentanil
Dextromoramide
Dextropropoxyphene
Dezocine
Fentanyl# (+fluanisone)
Ketobemidone
Levorphanol
Lofentanil
Meptazinol
Methadone#
Nalbuphine
NFEPP
Pentazocine
Pethidine (meperidine)
Phenadoxone
Phenazocine
Piminodine
Piritramide
Propiram
Remifentanil
Sufentanil
Tapentadol
Tilidine
Tramadol
Paracetamol-type
Acetanilide‡
Bucetin‡
Butacetin‡
Paracetamol (acetaminophen)#
Parapropamol‡
Phenacetin‡
Propacetamol‡
NSAIDs
Propionates
Fenoprofen
Flurbiprofen
Ibuprofen#
Ketoprofen
Naproxen
Oxaprozin
Oxicams
Meloxicam
Piroxicam
Acetates
Diclofenac
Indometacin
Ketorolac
Nabumetone
Sulindac
Tolmetin
COX-2 inhibitors
Celecoxib
Etoricoxib
Lumiracoxib
Parecoxib
Rofecoxib ‡
Valdecoxib ‡
Fenamates
Meclofenamic acid
Mefenamic acid
Salicylates
Aspirin (acetylsalicylic acid)# (+paracetamol/caffeine)
Benorylate
Diflunisal
Ethenzamide
Magnesium salicylate
Salicin
Salicylamide
Salsalate
Wintergreen (methyl salicylate)
Pyrazolones
Aminophenazone‡
Ampyrone
Metamizole (dipyrone)
Nifenazone
Phenazone
Propyphenazone (+paracetamol/caffeine)
Others
Glafenine
Cannabinoids
Cannabidiol
Cannabis
Nabilone
Nabiximols
Tetrahydrocannabinol (dronabinol)
Ion channel
modulators
Calcium blockers
Gabapentin
Gabapentin enacarbil
Pregabalin
Ziconotide
Sodium blockers
Carbamazepine
Lacosamide
Local anesthetics (e.g., cocaine, lidocaine)
Mexiletine
Nefopam
Tricyclic antidepressants (e.g., amitriptyline#)
Nav1.7/1.8-selective: DSP-2230§
Funapide§
PF-05089771§
Raxatrigine§
Potassium openers
Flupirtine
Myorelaxants
Carisoprodol
Chlorzoxazone
Cyclobenzaprine
Mephenoxalone
Methocarbamol
Orphenadrine
Others
Analgesic adjuvant
Analgecine
Camphor
Capsaicin
Clonidine
Ketamine
Menthol
Methoxyflurane
Nefopam
Proglumide
Tricyclic antidepressants (e.g., amitriptyline#)
#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
[show]
Pharmacodynamics
[show]
v
t
e
GABAA receptor positive modulators
Alcohols
Brometone
Butanol
Chloralodol
Chlorobutanol (cloretone)
Ethanol (alcohol) (alcoholic drink)
Ethchlorvynol
Isobutanol
Isopropanol
Menthol
Methanol
Methylpentynol
Pentanol
Petrichloral
Propanol
tert-Butanol (2M2P)
tert-Pentanol (2M2B)
Tribromoethanol
Trichloroethanol
Triclofos
Trifluoroethanol
Barbiturates
(-)-DMBB
Allobarbital
Alphenal
Amobarbital
Aprobarbital
Barbexaclone
Barbital
Benzobarbital
Benzylbutylbarbiturate
Brallobarbital
Brophebarbital
Butabarbital/Secbutabarbital
Butalbital
Buthalital
Butobarbital
Butallylonal
Carbubarb
Crotylbarbital
Cyclobarbital
Cyclopentobarbital
Difebarbamate
Enallylpropymal
Ethallobarbital
Eterobarb
Febarbamate
Heptabarb
Heptobarbital
Hexethal
Hexobarbital
Metharbital
Methitural
Methohexital
Methylphenobarbital
Narcobarbital
Nealbarbital
Pentobarbital
Phenallymal
Phenobarbital
Phetharbital
Primidone
Probarbital
Propallylonal
Propylbarbital
Proxibarbital
Reposal
Secobarbital
Sigmodal
Spirobarbital
Talbutal
Tetrabamate
Tetrabarbital
Thialbarbital
Thiamylal
Thiobarbital
Thiobutabarbital
Thiopental
Thiotetrabarbital
Valofane
Vinbarbital
Vinylbital
Benzodiazepines
2-Oxoquazepam
3-Hydroxyphenazepam
Adinazolam
Alprazolam
Arfendazam
Avizafone
Bentazepam
Bretazenil
Bromazepam
Brotizolam
Camazepam
Carburazepam
Chlordiazepoxide
Ciclotizolam
Cinazepam
Cinolazepam
Clazolam
Climazolam
Clobazam
Clonazepam
Clonazolam
Cloniprazepam
Clorazepate
Clotiazepam
Cloxazolam
CP-1414S
Cyprazepam
Delorazepam
Demoxepam
Diazepam
Diclazepam
Doxefazepam
Elfazepam
Estazolam
Ethyl carfluzepate
Ethyl dirazepate
Ethyl loflazepate
Etizolam
EVT-201
FG-8205
Fletazepam
Flubromazepam
Flubromazolam
Fludiazepam
Flunitrazepam
Flunitrazolam
Flurazepam
Flutazolam
Flutemazepam
Flutoprazepam
Fosazepam
Gidazepam
Halazepam
Haloxazolam
Iclazepam
Imidazenil
Irazepine
Ketazolam
Lofendazam
Lopirazepam
Loprazolam
Lorazepam
Lormetazepam
Meclonazepam
Medazepam
Menitrazepam
Metaclazepam
Mexazolam
Midazolam
Motrazepam
N-Desalkylflurazepam
Nifoxipam
Nimetazepam
Nitrazepam
Nitrazepate
Nitrazolam
Nordazepam
Nortetrazepam
Oxazepam
Oxazolam
Phenazepam
Pinazepam
Pivoxazepam
Prazepam
Premazepam
Proflazepam
Pyrazolam
QH-II-66
Quazepam
Reclazepam
Remimazolam
Rilmazafone
Ripazepam
Ro48-6791
Ro48-8684
SH-053-R-CH3-2′F
Sulazepam
Temazepam
Tetrazepam
Tolufazepam
Triazolam
Triflubazam
Triflunordazepam (Ro5-2904)
Tuclazepam
Uldazepam
Zapizolam
Zolazepam
Zomebazam
Carbamates
Carisbamate
Carisoprodol
Clocental
Cyclarbamate
Difebarbamate
Emylcamate
Ethinamate
Febarbamate
Felbamate
Hexapropymate
Lorbamate
Mebutamate
Meprobamate
Nisobamate
Pentabamate
Phenprobamate
Procymate
Styramate
Tetrabamate
Tybamate
Flavonoids
6-Methylapigenin
Ampelopsin (dihydromyricetin)
Apigenin
Baicalein
Baicalin
Catechin
EGC
EGCG
Hispidulin
Linarin
Luteolin
Rc-OMe
Skullcap constituents (e.g., baicalin)
Wogonin
Imidazoles
Etomidate
Metomidate
Propoxate
Kava constituents
10-Methoxyyangonin
11-Methoxyyangonin
11-Hydroxyyangonin
Desmethoxyyangonin
11-Methoxy-12-hydroxydehydrokavain
7,8-Dihydroyangonin
Kavain
5-Hydroxykavain
5,6-Dihydroyangonin
7,8-Dihydrokavain
5,6,7,8-Tetrahydroyangonin
5,6-Dehydromethysticin
Methysticin
7,8-Dihydromethysticin
Yangonin
Monoureides
Acecarbromal
Apronal (apronalide)
Bromisoval
Carbromal
Capuride
Ectylurea
Neuroactive steroids
Acebrochol
Allopregnanolone (brexanolone)
Alfadolone
Alfaxalone
3α-Androstanediol
Androstenol
Androsterone
Certain anabolic-androgenic steroids
Cholesterol
DHDOC
3α-DHP
5α-DHP
5β-DHP
DHT
Etiocholanolone
Ganaxolone
Hydroxydione
Minaxolone
ORG-20599
ORG-21465
P1-185
Pregnanolone (eltanolone)
Progesterone
Renanolone
SAGE-105
SAGE-217
SAGE-324
SAGE-516
SAGE-689
SAGE-872
Testosterone
THDOC
Nonbenzodiazepines
β-Carbolines: Abecarnil
Gedocarnil
Harmane
SL-651,498
ZK-93423
Cyclopyrrolones: Eszopiclone
Pagoclone
Pazinaclone
Suproclone
Suriclone
Zopiclone
Imidazopyridines: Alpidem
DS-1
Necopidem
Saripidem
Zolpidem
Pyrazolopyrimidines: Divaplon
Fasiplon
Indiplon
Lorediplon
Ocinaplon
Panadiplon
Taniplon
Zaleplon
Others: Adipiplon
CGS-8216
CGS-9896
CGS-13767
CGS-20625
CL-218,872
CP-615,003
CTP-354
ELB-139
GBLD-345
Imepitoin
JM-1232
L-838,417
Lirequinil (Ro41-3696)
NS-2664
NS-2710
NS-11394
Pipequaline
ROD-188
RWJ-51204
SB-205,384
SX-3228
TGSC01AA
TP-003
TPA-023
TP-13
U-89843A
U-90042
Viqualine
Y-23684
Phenols
Fospropofol
Propofol
Thymol
Piperidinediones
Glutethimide
Methyprylon
Piperidione
Pyrithyldione
Pyrazolopyridines
Cartazolate
Etazolate
ICI-190,622
Tracazolate
Quinazolinones
Afloqualone
Cloroqualone
Diproqualone
Etaqualone
Mebroqualone
Mecloqualone
Methaqualone
Methylmethaqualone
Nitromethaqualone
SL-164
Volatiles/gases
Acetone
Acetophenone
Acetylglycinamide chloral hydrate
Aliflurane
Benzene
Butane
Butylene
Centalun
Chloral
Chloral betaine
Chloral hydrate
Chloroform
Cryofluorane
Desflurane
Dichloralphenazone
Dichloromethane
Diethyl ether
Enflurane
Ethyl chloride
Ethylene
Fluroxene
Gasoline
Halopropane
Halothane
Isoflurane
Kerosine
Methoxyflurane
Methoxypropane
Nitric oxide
Nitrogen
Nitrous oxide
Norflurane
Paraldehyde
Propane
Propylene
Roflurane
Sevoflurane
Synthane
Teflurane
Toluene
Trichloroethane (methyl chloroform)
Trichloroethylene
Vinyl ether
Others/unsorted
3-Hydroxybutanal
α-EMTBL
AA-29504
Avermectins (e.g., ivermectin)
Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
DEABL
Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine))
DS2
Efavirenz
Etazepine
Etifoxine
Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid)
Fluoxetine
Flupirtine
Hopantenic acid
Lanthanum
Lavender oil
Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
Loreclezole
Menthyl isovalerate (validolum)
Monastrol
Niacin
Nicotinamide (niacinamide)
Org 25,435
Phenytoin
Propanidid
Retigabine (ezogabine)
Safranal
Seproxetine
Stiripentol
Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional)
Terpenoids (e.g., borneol)
Topiramate
Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)
Unsorted benzodiazepine site positive modulators: α-Pinene
MRK-409 (MK-0343)
TCS-1105
TCS-1205
See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators
[show]
v
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Glycine receptor modulators
Receptor
(ligands)
GlyR
Agonists: β-Alanine
β-ABA (BABA)
β-AIBA
Caesium
D-Alanine
D-Serine
GABA
Glycine
Hypotaurine
Ivermectin
L-Alanine
L-Proline
L-Serine
L-Threonine
MDL-27531
Milacemide
Picolinic acid
Propofol
Quisqualamine
Sarcosine
Taurine
Positive modulators: Alcohols (e.g., brometone, chlorobutanol (chloretone), ethanol (alcohol), tert-butanol (2M2P), tribromoethanol, trichloroethanol, trifluoroethanol)
Alkylbenzene sulfonate
Anandamide
Barbiturates (e.g., pentobarbital, sodium thiopental)
Chlormethiazole
D12-116
Dihydropyridines (e.g., nicardipine)
Etomidate
Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf))
Glutamic acid (glutamate)
Ivermectin
Ketamine
Neuroactive steroids (e.g., alfaxolone, pregnenolone (eltanolone), pregnenolone acetate, minaxolone, ORG-20599)
Nitrous oxide
Penicillin G
Propofol
Tamoxifen
Tetrahydrocannabinol
Triclofos
Tropeines (e.g., atropine, bemesetron, cocaine, LY-278584, tropisetron, zatosetron)
Volatiles/gases (e.g., chloral hydrate, chloroform, desflurane, diethyl ether (ether), enflurane, halothane, isoflurane, methoxyflurane, sevoflurane, toluene, trichloroethane (methyl chloroform), trichloroethylene)
Xenon
Zinc
Antagonists: 2-Aminostrychnine
2-Nitrostrychnine
4-Phenyl-4-formyl-N-methylpiperidine
αEMBTL
Bicuculline
Brucine
Cacotheline
Caffeine
Colchicine
Colubrine
Cyanotriphenylborate
Dendrobine
Diaboline
Endocannabinoids (e.g., 2-AG, anandamide (AEA))
Gaboxadol (THIP)
Gelsemine
iso-THAZ
Isobutyric acid
Isonipecotic acid
Isostrychnine
Laudanosine
N-Methylbicuculline
N-Methylstrychnine
N,N-Dimethylmuscimol
Nipecotic acid
Pitrazepin
Pseudostrychnine
Quinolines (e.g., 4-hydroxyquinoline, 4-hydroxyquinoline-3-carboxylic acid, 5,7-CIQA, 7-CIQ, 7-TFQ, 7-TFQA)
RU-5135
Sinomenine
Strychnine
Thiocolchicoside
Tutin
Negative modulators: Amiloride
Benzodiazepines (e.g., bromazepam, clonazepam, diazepam, flunitrazepam, flurazepam)
Corymine
Cyanotriphenylborate
Daidzein
Dihydropyridines (e.g., nicardipine, nifedipine, nitrendipine)
Furosemide
Genistein
Ginkgo constituents (e.g., bilobalide, ginkgolides (e.g., ginkgolide A, ginkgolide B, ginkgolide C, ginkgolide J, ginkgolide M))
Imipramine
NBQX
Neuroactive steroids (e.g., 3α-androsterone sulfate, 3β-androsterone sulfate, deoxycorticosterone, DHEA sulfate, pregnenolone sulfate, progesterone)
Opioids (e.g., codeine, dextromethorphan, dextrorphan, levomethadone, levorphanol, morphine, oripavine, pethidine, thebaine)
Picrotoxin (i.e., picrotin and picrotoxinin)
PMBA
Riluzole
Tropeines (e.g., bemesetron, LY-278584, tropisetron, zatosetron)
Verapamil
Zinc
NMDAR
See here instead.
Transporter
(blockers)
GlyT1
ACPPB
ALX-1393
ALX-5407 (NFPS)
AMG-747
ASP2535
Bitopertin (RG1678/RO4917838)
CP-802079
Ethanol (alcohol)
Glycyldodecylamide
GSK1018921
LY-2365109
ORG-24598
ORG-25935 (SCH-900435)
PF-02545920
PF-03463275
PF-04958242
Sarcosine
SSR-103,800
SSR-504,734
GlyT2
Amoxapine
Ethanol (alcohol)
NAGly
Opiranserin (VVZ-149)
ORG-25543
VVZ-368
See also
Receptor/signaling modulators
GABA receptor modulators
GABAA receptor positive modulators
Ionotropic glutamate receptor modulators
[show]
v
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Ionotropic glutamate receptor modulators
AMPAR
Agonists: Main site agonists: 5-Fluorowillardiine
Acromelic acid (acromelate)
AMPA
BOAA
Domoic acid
Glutamate
Ibotenic acid
Proline
Quisqualic acid
Willardiine; Positive allosteric modulators: Aniracetam
Cyclothiazide
CX-516
CX-546
CX-614
Farampator (CX-691, ORG-24448)
CX-717
CX-1739
CX-1942
Diazoxide
Hydrochlorothiazide (HCTZ)
IDRA-21
LY-392098
LY-395153
LY-404187
LY-451646
LY-503430
Mibampator (LY-451395)
Nooglutyl
ORG-26576
Oxiracetam
PEPA
PF-04958242
Piracetam
Pramiracetam
S-18986
Tulrampator (S-47445, CX-1632)
Antagonists: ACEA-1011
ATPO
Becampanel
Caroverine
CNQX
Dasolampanel
DNQX
Fanapanel (MPQX)
GAMS
Kaitocephalin
Kynurenic acid
Kynurenine
Licostinel (ACEA-1021)
NBQX
PNQX
Selurampanel
Tezampanel
Theanine
Topiramate
YM90K
Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
Cyclopropane
Enflurane
Ethanol (alcohol)
Evans blue
GYKI-52466
GYKI-53655
Halothane
Irampanel
Isoflurane
Perampanel
Pregnenolone sulfate
Sevoflurane
Talampanel; Unknown/unsorted antagonists: Minocycline
KAR
Agonists: Main site agonists: 5-Bromowillardiine
5-Iodowillardiine
Acromelic acid (acromelate)
AMPA
ATPA
Domoic acid
Glutamate
Ibotenic acid
Kainic acid
LY-339434
Proline
Quisqualic acid
SYM-2081; Positive allosteric modulators: Cyclothiazide
Diazoxide
Enflurane
Halothane
Isoflurane
Antagonists: ACEA-1011
CNQX
Dasolampanel
DNQX
GAMS
Kaitocephalin
Kynurenic acid
Licostinel (ACEA-1021)
LY-382884
NBQX
NS102
Selurampanel
Tezampanel
Theanine
Topiramate
UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental)
Enflurane
Ethanol (alcohol)
Evans blue
NS-3763
Pregnenolone sulfate
NMDAR
Agonists: Main site agonists: AMAA
Aspartate
Glutamate
Homocysteic acid (L-HCA)
Homoquinolinic acid
Ibotenic acid
NMDA
Proline
Quinolinic acid
Tetrazolylglycine
Theanine; Glycine site agonists: β-Fluoro-D-alanine
ACBD
ACC (ACPC)
ACPD
AK-51
Apimostinel (NRX-1074)
B6B21
CCG
D-Alanine
D-Cycloserine
D-Serine
DHPG
Dimethylglycine
Glycine
HA-966
L-687414
L-Alanine
L-Serine
Milacemide
Neboglamine (nebostinel)
Rapastinel (GLYX-13)
Sarcosine; Polyamine site agonists: Neomycin
Spermidine
Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol
DHEA (prasterone)
DHEA sulfate (prasterone sulfate)
Epipregnanolone sulfate
Pregnenolone sulfate
SAGE-201
SAGE-301
SAGE-718
Antagonists: Competitive antagonists: AP5 (APV)
AP7
CGP-37849
CGP-39551
CGP-39653
CGP-40116
CGS-19755
CPP
Kaitocephalin
LY-233053
LY-235959
LY-274614
MDL-100453
Midafotel (d-CPPene)
NPC-12626
NPC-17742
PBPD
PEAQX
Perzinfotel
PPDA
SDZ-220581
Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101)
5,7-DCKA
7-CKA
ACC
ACEA-1011
ACEA-1328
Apimostinel (NRX-1074)
AV-101
Carisoprodol
CGP-39653
CNQX
D-Cycloserine
DNQX
Felbamate
Gavestinel
GV-196771
Harkoseride
Kynurenic acid
Kynurenine
L-689560
L-701324
Licostinel (ACEA-1021)
LU-73068
MDL-105519
Meprobamate
MRZ 2/576
PNQX
Rapastinel (GLYX-13)
ZD-9379; Polyamine site antagonists: Arcaine
Co 101676
Diaminopropane
Diethylenetriamine
Huperzine A
Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP
3-HO-PCP
3-MeO-PCE
3-MeO-PCMo
3-MeO-PCP
4-MeO-PCP
8A-PDHQ
18-MC
α-Endopsychosin
Alaproclate
Alazocine (SKF-10047)
Amantadine
Aptiganel
Argiotoxin-636
Arketamine
ARL-12495
ARL-15896-AR
ARL-16247
Budipine
Coronaridine
Delucemine (NPS-1506)
Dexoxadrol
Dextrallorphan
Dextromethadone
Dextromethorphan
Dextrorphan
Dieticyclidine
Diphenidine
Dizocilpine
Ephenidine
Esketamine
Etoxadrol
Eticyclidine
Fluorolintane
Gacyclidine
Ibogaine
Ibogamine
Indantadol
Ketamine
Ketobemidone
Lanicemine
Levomethadone
Levomethorphan
Levomilnacipran
Levorphanol
Loperamide
Memantine
Methadone
Methorphan
Methoxetamine
Methoxphenidine
Milnacipran
Morphanol
NEFA
Neramexane
Nitromemantine
Noribogaine
Norketamine
Orphenadrine
PCPr
PD-137889
Pethidine (meperidine)
Phencyclamine
Phencyclidine
Propoxyphene
Remacemide
Rhynchophylline
Rimantadine
Rolicyclidine
Sabeluzole
Tabernanthine
Tenocyclidine
Tiletamine
Tramadol; Ifenprodil (NR2B) site antagonists:
Besonprodil
Buphenine (nylidrin)
CO-101244 (PD-174494)
Eliprodil
Haloperidol
Isoxsuprine
Radiprodil (RGH-896)
Rislenemdaz (CERC-301, MK-0657)
Ro 8-4304
Ro 25-6981
Safaprodil
Traxoprodil (CP-101606); NR2A-selective antagonists: MPX-004
MPX-007
TCN-201
TCN-213; Cations: Hydrogen
Magnesium
Zinc; Alcohols/volatile anesthetics/related: Benzene
Butane
Chloroform
Cyclopropane
Desflurane
Diethyl ether
Enflurane
Ethanol (alcohol)
Halothane
Hexanol
Isoflurane
Methoxyflurane
Nitrous oxide
Octanol
Sevoflurane
Toluene
Trichloroethane
Trichloroethanol
Trichloroethylene
Urethane
Xenon
Xylene; Unknown/unsorted antagonists: ARR-15896
Bumetanide
Caroverine
D-αAA
Dexanabinol
Flufenamic acid
Flupirtine
FPL-12495
FR-115427
Furosemide
Hodgkinsine
Ipenoxazone (MLV-6976)
MDL-27266
Metaphit
Minocycline
MPEP
Niflumic acid
Pentamidine
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See also: Receptor/signaling modulators
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