ContaminantDB: Muscimol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (12)XML

Record Information

Version

1.0

Creation Date

2009-07-03 21:01:06 UTC

Update Date

2026-05-14 19:21:50 UTC

Accession Number

CHEM002045

Identification

Common Name

Muscimol

Class

Small Molecule

Description

Muscimol (Agarin, Pantherine) is the major psychoactive alkaloid present in many mushrooms of the Amanita genus. Unlike psilocybin, a tryptamine, muscimol is a potent, selective agonist of the GABAA receptor. Amanita muscaria contains two main active ingredients, Ibotenic acid and its derivative Muscimol. Muscimol is the product of the decarboxylation or drying of ibotenic acid and it is thought that muscimol is as much as ten times more potent than ibotenic acid. (2)

Contaminant Sources

Clean Air Act Chemicals
T3DB toxins

Contaminant Type

Amine
Fungal Toxin
Mycotoxin
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5-(Aminomethyl)-3(2H)-isoxazolone	ChEBI
Agarin	MeSH
Pantherine	MeSH

Chemical Formula

C₄H₆N₂O₂

Average Molecular Mass

114.103 g/mol

Monoisotopic Mass

114.043 g/mol

CAS Registry Number

18174-72-6

IUPAC Name

5-(aminomethyl)-2,3-dihydro-1,2-oxazol-3-one

Traditional Name

muscimol

SMILES

NCC1=CC(O)=NO1

InChI Identifier

InChI=1S/C4H6N2O2/c5-2-3-1-4(7)6-8-3/h1H,2,5H2,(H,6,7)

InChI Key

ZJQHPWUVQPJPQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Azole
Isoxazole
Heteroaromatic compound
Lactam
Organoheterocyclic compound
Oxacycle
Azacycle
Organic oxygen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

alkaloid (CHEBI:7035 )
primary amino compound (CHEBI:7035 )
isoxazoles (CHEBI:7035 )
Alkaloids (C08311 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	184-185°C
Boiling Point	Not Available
Solubility	Solubility in water: very soluble Solubility in ethanol: slightly soluble Solubility in methanol: very soluble

Predicted Properties

Property	Value	Source
Water Solubility	57.9 g/L	ALOGPS
logP	-0.95	ALOGPS
logP	-1.4	ChemAxon
logS	-0.29	ALOGPS
pKa (Strongest Acidic)	5.78	ChemAxon
pKa (Strongest Basic)	7.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.28 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.15 m³·mol⁻¹	ChemAxon
Polarizability	10.53 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-003r-9000000000-8a5c7c8119385828f867	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-9200000000-9b83d1483d2e2c7ddeb6	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-3900000000-68483046cfeb7ca5d01b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0002-9000000000-6de63da45a13d454cce3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00kb-9000000000-6b5110dcd6fa6b4422e8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014i-9000000000-c2fbac7befc44bdfbe43	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-014r-9000000000-f4eda66dfcf7c0a3918c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3900000000-b58c956f64f0f049a64c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9600000000-164169f85b3f6f6c94db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-100u-9000000000-04ba67371609e08956ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3900000000-2b5bf5ca3739d495ccc9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-9800000000-ac88ce1ff672c846f8b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-2bbb93920e5a57deff3a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kb-9400000000-f76809dd9d9cfaa33245	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9100000000-6f3f42f82def807255c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-aa53a456f47c4c6734b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01ot-9500000000-e072f5ae3316e619c7f7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-4072272fb0cceffda304	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9000000000-79bfba881e929cb7e2c1	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Oral, dermal, inhalation, and parenteral (contaminated drugs). (1)

Mechanism of Toxicity

Muscimol is a potent GABAA agonist, activating the receptor for the brain's major inhibitory neurotransmitter, GABA. Muscimol actually binds to the same binding site on the GABAA receptor complex as GABA itself, as opposed to other GABAergic drugs such as barbiturates and benzodiazepines which bind to separate regulatory sites. GABAA receptors are widely distributed in the brain, and so when muscimol is administered, it alters neuronal activity in multiple regions including the cerebral cortex, hippocampus, and cerebellum. However while muscimol is conventionally thought of as a selective GABAA agonist, it is also a potent partial agonist at the GABAC receptor, and so its effects profile results from a combined action at both targets. (2)

Metabolism

Not Available

Toxicity Values

LD50: 3.8 mg/kg (Subcutaneous, Mouse) (2) LD50: 2.5 mg/kg (Intraperitoneal, Mouse) (2) LD50: 4.5 mg/kg (Intravenous, Rat) (2) LD50: 45 mg/kg (Oral, Rat) (2)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Muscimol is produced naturally in the mushrooms Amanita muscaria, Amanita pantherina, and Amanita gemmata, along with muscarine, muscazone, and ibotenic acid. (2)

Minimum Risk Level

Not Available

Health Effects

Muscimol is neurotoxic and produces hallucinations. (2)

Symptoms

Muscimol is hallucinogenic. (2)

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID