Muscimol

Muscimol
Names
	IUPAC name 5-(Aminomethyl)-1,2-oxazol-3(2H)-one
	Other names Agarin, Pantherine, Agarine, Pantherin
Identifiers
CAS Number	2763-96-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	774694
ChEBI	CHEBI:7035 ;
ChEMBL	ChEMBL273481 ;
ChemSpider	4116 ;
ECHA InfoCard	100.018.574
EC Number	220-430-4;
IUPHAR/BPS	4259;
KEGG	C08311 ;
PubChem CID	4266;
UNII	D5M179TY2E ;
UN number	2811 3077
CompTox Dashboard (EPA)	DTXSID5041069 ;
	InChI InChI=1S/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7) Key: ZJQHPWUVQPJPQT-UHFFFAOYSA-N ; 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
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:
Pictograms
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). verify (what is ?) 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 GABA_A 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 GABA_A 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]

^ The Merck Index, 12th Edition
^ "Muscimol". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ 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.
^ 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.

[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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