Compound: muscimol
SMILES: O=c1[nH]oc(c1)CN
InChIKey: ZJQHPWUVQPJPQT-UHFFFAOYSA-N
Synonyms: muscimol, 2763-96-4, Agarin, Pantherine, Agarine, 3(2H)-Isoxazolone, 5-(aminomethyl)-, 5-(Aminomethyl)-3(2H)-isoxazolone, 5-Aminomethyl-3-hydroxyisoxazole, Pantherin, 3-Hydroxy-5-aminomethylisoxazole, 5-(Aminomethyl)-3-isoxazolol, 5-Aminomethyl-3-isoxyzole, 3-Isoxazolol, 5-(aminomethyl)-, 5-(aminomethyl)-1,2-oxazol-3-ol, 3-Hydroxy-5-aminomethylisoxazole-agarin, 5-(aminomethyl)-1,2-oxazol-3-one, NSC-333569, CHEBI:7035, D5M179TY2E, DTXSID5041069, 5-(aminomethyl)-2,3-dihydro-1,2-oxazol-3-one, 5-(azaniumylmethyl)-1,2-oxazol-3-olate, RefChem:819660, DTXCID3021069, 220-430-4, RCRA waste number P007, NSC 333569, MFCD00057894, 5-(aminomethyl)isoxazol-3-one, CHEMBL273481, A1IIN, CCRIS 3720, HSDB 6036, 3-Hydroxy-5-aminomethyl-isoxazole, EINECS 220-430-4, RCRA waste no. P007, 5-(Aminomethyl)isoxazol-3-ol hydrate, UNII-D5M179TY2E, SR-01000075619, Muscimol, powder, [3H]muscimol, [3H]-muscimol, 5-(Aminomethyl)isoxazol-3(2H)-one, [3 H]-muscimol, ZINC22064260, Tocris-0289, MUSCIMOL [HSDB], Lopac-G-019, MUSCIMOL [MI], Biomol-NT_000255, Lopac0_000591, WLN: T5NOJ C1Z EQ, SCHEMBL149693, SCHEMBL149694, BPBio1_000926, GTPL4090, GTPL4259, 5-(aminomethyl)-isoxazol-3-ol, BDBM23183, HMS3266G03, HMS3414F05, HMS3678F05, 5(aminomethyl)-3(2h)-isooxazolone, BDBM50052792, HB0887, MSK7265-100M, NSC333569, AKOS006223439, AKOS022719658, CCG-204680, DB12458, EBC-198032, FM26103, SDCCGSBI-0050573.P002, SMP1_000201, NCGC00015459-01, NCGC00015459-02, NCGC00015459-03, NCGC00015459-04, NCGC00015459-05, NCGC00024526-01, NCGC00024526-02, NCGC00024526-03, Muscimol Solution in Methanol, 100ug/mL, 5-(aminomethyl)-1,2-oxazol-3(2H)-one, NS00028339, UPCMLD00X18174-72-6:001, C08311, EN300-333440, G85421, Q412504, SR-01000075619-3, BRD-K60441002-001-04-8, 3-Hydroxy-5-aminomethyl-isoxazole;5-Aminomethyl-3-isoxazolol;5-Aminomethyl-3-hydroxy-isoxazole
Theoretical properties:
molecular_formula: C4H6N2O2
molecular_weight: 114.10 g/mol
exact_mass: 114.042927438 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 8
topological_polar_surface_area: 64.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals
color: Crystals
melting_point: 347 °F decomposes (EPA, 1998)
vapor_pressure: 0.000294 [mmHg]
Descriptions:
{"pubchem": "Muscimol is a member of the class of isoxazoles that is 1,2-oxazol-3(2H)-one substituted by an aminomethyl group at position 5. It has been isolated from mushrooms of the genus Amanita. It has a role as a oneirogen, a psychotropic drug, a GABA agonist and a fungal metabolite. It is an alkaloid, a primary amino compound and a member of isoxazoles.", "chebi": "A member of the class of isoxazoles that is 1,2-oxazol-3(2<em>H</em>)-one substituted by an aminomethyl group at position 5. It has been isolated from mushrooms of the genus <em>Amanita</em>.", "chembl": "MUSCIMOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 1.0.", "wikipedia": "Muscimol, also known as agarin, pantherine, or pyroibotenic acid, is a GABAA receptor agonist with sedative and hallucinogenic effects and the principal psychoactive constituent of Amanita mushrooms such as Amanita muscaria (fly agaric) and Amanita pantherina (panther cap). It is a 3-hydroxyisoxazole alkaloid and is closely related structurally to the neurotransmitter \u03b3-aminobutyric acid (GABA). The compound is widely used as a ligand and agonist of the GABAA receptor in scientific research. Muscimol is typically taken orally, but may also be smoked. Peak effects occur after 1 to 3 hours orally and its duration is 4 to 8 hours but up to 24 hours.\nThe effects of muscimol in humans include central depression, sedation, sleep, cognitive and motor impairment, hallucinations, perceptual distortion, and muscle twitching, among others. Muscimol acts as a potent GABAA receptor full agonist. It is also a potent GABAA-\u03c1 receptor partial agonist and a weak GABA reuptake inhibitor. The drug is inactive at the GABAB receptor but is a substrate of GABA transaminase (GABA-T). Muscimol mostly exerts its effects via GABAA receptor activation. It is very different from drugs like benzodiazepines and barbiturates as it is an orthosteric agonist of the GABAA receptor rather than an allosteric modulator. Unlike GABA, muscimol crosses the blood\u2013brain barrier and hence is centrally active. Muscimol, which is also known chemically as 5-aminomethylisoxazol-3-ol, is a conformationally restrained analogue of GABA. The related compound and Amanita spp. constituent ibotenic acid is a prodrug of muscimol.\nMuscimol was first isolated from Amanita muscaria and hence was discovered in 1964. It has been limitedly clinically studied as a potential pharmaceutical drug for a number of uses, such as treatment of epilepsy. In addition, analogues and derivatives of muscimol, such as the selective GABAA receptor agonist gaboxadol (THIP; LU-2-030) and the selective GABA reuptake inhibitor tiagabine (Gabitril), have been developed as pharmaceutical drugs. Muscimol and Amanita muscaria mushrooms have rarely been used as recreational drugs historically. By the mid-2020s however, use of these substances, including recreational use for hallucinogenic effects and microdosing for claimed therapeutic benefits, has become increasingly prominent. The most commonly cited therapeutic reason for their use is to improve sleep. Muscimol is not a controlled substance and is unregulated in most of the world, including in most of the United States and Europe."}