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Muscimol information


Muscimol
Names
IUPAC name
5-(Aminomethyl)-1,2-oxazol-3(2H)-one
Other names
Agarin, Pantherine, Agarine, Pantherin
Identifiers
CAS Number
  • 2763-96-4 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
774694
ChEBI
  • CHEBI:7035 checkY
ChEMBL
  • ChEMBL273481 checkY
ChemSpider
  • 4116 checkY
ECHA InfoCard 100.018.574 Edit this at Wikidata
EC Number
  • 220-430-4
IUPHAR/BPS
  • 4259
KEGG
  • C08311 checkY
PubChem CID
  • 4266
UNII
  • D5M179TY2E checkY
UN number 2811 3077
CompTox Dashboard (EPA)
  • DTXSID5041069 Edit this at Wikidata
InChI
  • InChI=1S/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7) checkY
    Key: ZJQHPWUVQPJPQT-UHFFFAOYSA-N checkY
  • InChI=1/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7)
    Key: ZJQHPWUVQPJPQT-UHFFFAOYAI
SMILES
  • NCc1cc(no1)O
Properties[1]
Chemical formula
C4H6N2O2
Molar mass 114.104 g·mol−1
Melting point 184 to 185 °C (363 to 365 °F; 457 to 458 K)
Solubility in water
very soluble
Solubility in ethanol slightly soluble
Solubility in methanol very soluble
Pharmacology
Legal status
  • AU: S9 (Prohibited substance)
  • in general, uncontrolled
Hazards
GHS labelling:[2]
Pictograms
GHS06: Toxic
Signal word
Danger
Hazard statements
H300
Precautionary statements
P264, P270, P301+P316, P321, P330, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Muscimol (also known as agarin or pantherine) is one of the principal psychoactive constituents of Amanita muscaria and related species of mushroom. Muscimol is a potent and selective orthosteric agonist for the GABAA receptor[3] and displays sedative-hypnotic, depressant and hallucinogenic psychoactivity. This colorless or white solid is classified as an isoxazole.

Muscimol went under clinical trial phase I for epilepsy, but the trial was discontinued.[4]

Muscimol, an agonist for the GABAA receptor, was able to significantly alleviate pain in its peak effect, recent studies from 2023 show. It has since been federally banned in Australia and is pending FDA review in the United States, but scientists believe it may relieve pain as well as some opioids without much of the risk of addiction associated with opioids. [5]

  1. ^ The Merck Index, 12th Edition
  2. ^ "Muscimol". pubchem.ncbi.nlm.nih.gov.
  3. ^ Johnston GA (October 2014). "Muscimol as an ionotropic GABA receptor agonist". Neurochemical Research. 39 (10): 1942–1947. doi:10.1007/s11064-014-1245-y. PMID 24473816. S2CID 13364321.
  4. ^ Heiss JD, Walbridge S, Rene'Smith RN, Sato S, Oldfield EH, Lonser RR (August 2012). "174 Convection-Enhanced Delivery of Muscimol to the Epileptic FocusPreclinical and Clinical Research". Neurosurgery. 71 (2): E568. doi:10.1227/01.neu.0000417764.02569.dc. ISSN 0148-396X.
  5. ^ Ramawad HA, Paridari P, Jabermoradi S, Gharin P, Toloui A, Safari S, Yousefifard M (2023). "Muscimol as a treatment for nerve injury-related neuropathic pain: A systematic review and meta-analysis of preclinical studies". The Korean Journal of Pain. 36 (4): 425–440. doi:10.3344/kjp.23161. PMC 10551397. PMID 37732408.

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Muscimol

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Muscimol (also known as agarin or pantherine) is one of the principal psychoactive constituents of Amanita muscaria and related species of mushroom. Muscimol...

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Amanita muscaria

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hallucinogenic properties, with the main psychoactive constituents being muscimol and its neurotoxic precursor ibotenic acid. A local variety of the mushroom...

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Ibotenic acid

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temperate and boreal regions of the northern hemisphere. It is a prodrug of muscimol, broken down by the liver to that much more stable compound. It is a...

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Legal status of psychoactive Amanita mushrooms

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This is a list of the legality of muscimol mushrooms by country. "The Poisons Standard". Federal Register of Legislation. Archived from the original on...

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Amanita

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by these peoples. Amanita pantherina contains the psychoactive compound muscimol, but is used as an entheogen much less often than its much more distinguishable...

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Amanita pantherina

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poisonous. A. pantherina contains the psychoactive compounds ibotenic acid and muscimol, two psychoactive constituents which can cause effects such as hallucinations...

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Mushroom poisoning

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Clitocybe clavipes. Ibotenic acid: Decarboxylates into muscimol upon ingestion. The effects of muscimol vary, but nausea and vomiting are common. Confusion...

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Antiemetic

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help nausea or stomach pain when added into a tea or peppermint candies. Muscimol is purported to have antiemetic activity. Ajwain is purported to be antiemetic...

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Oneirogen

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people of South Africa to induce lucid dreams. Amanita muscaria (contains muscimol) Amphetamines and other stimulants can create psychotic episodes (called...

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Edible mushroom

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agaric) and Psilocybe cubensis, with the former containing alkaloids such as muscimol and the latter predominately psilocybin. Edible mushrooms include many...

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Rostral ventromedial medulla

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dorsal horn neurons." Next, the GABA A agonist muscimol was tested in conjuncture with SP. Intrathecal muscimol significantly enhanced SP-induced hypersensitivity...

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Mushroom

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A. pantherina, among others, contain the psychoactive compound muscimol. The muscimol-containing chemotaxonomic group of Amanitas contains no amatoxins...

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Recreational drug use

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ibotenic acid (found in Amanita muscaria ("Fly Agaric"); prodrug to muscimol) muscimol (also found in Amanita muscaria, a GABAergic) Dissociatives dextromethorphan...

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GABAA receptor

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GABAA receptor is the binding site for GABA and several drugs such as muscimol, gaboxadol, and bicuculline. The protein also contains a number of different...

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Muscazone

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causes visual damage, mental confusion, and memory loss. Ibotenic acid Muscimol Merck Index, 12th Edition, 6390 Robert Alan Lewis (1998). Lewis' Dictionary...

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Fish

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Fumonisin B2, Fumonisin B3, Fumonisin B4) Gliotoxin Ibotenic acid Lolitrem B Muscimol Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin...

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Gaboxadol

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4-c)pyridin-3-ol (THIP), is a conformationally constrained derivative of the alkaloid muscimol that was first synthesized in 1977 by the Danish chemist Poul Krogsgaard-Larsen...

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Methamphetamine

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oxide (recreational use) alkyl nitrites poppers amyl nitrite Ketamine MXE Muscimol Amanita muscaria PCP Salvinorin A Salvia divinorum Deliriants Atropine...

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Cocaine

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oxide (recreational use) alkyl nitrites poppers amyl nitrite Ketamine MXE Muscimol Amanita muscaria PCP Salvinorin A Salvia divinorum Deliriants Atropine...

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Psychopharmacology

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drugs include various psychoactive mushrooms containing psilocybin or muscimol and cacti containing mescaline and other chemicals, along with myriad other...

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MDMA

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oxide (recreational use) alkyl nitrites poppers amyl nitrite Ketamine MXE Muscimol Amanita muscaria PCP Salvinorin A Salvia divinorum Deliriants Atropine...

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Tofisopam

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anticonvulsant action of classical 1,4-benzodiazepines (such as diazepam) and muscimol, but not sodium valproate, carbamazepine, phenobarbital, or phenytoin....

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Nucleus raphe pallidus

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pallidus, induces an increased heart rate. Conversely, microinjections of muscimol, a GABA-a agonist, inhibit tachycardia in rats under air-stress stimuli...

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Penicillin

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Kojic amine L-838,417 Lignans (e.g., honokiol) Methylglyoxal Monastrol Muscimol Nefiracetam Neuroactive steroids (e.g., allopregnanolone) Org 20599 PF-6372865...

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