MUSCIMOL

MUSCIMOL Structure
CAS No.
2763-96-4
Chemical Name:
MUSCIMOL
Synonyms
AGARIN;agarine;MUSCIMOL;pantherin;NSC 333569;PANTHERINE;MUSCIMOL(P);MUSCIMOL (RG);Pyroibotenic acid;Arylex Impurity 8
CBNumber:
CB6231349
Molecular Formula:
C4H6N2O2
Molecular Weight:
114.1
MOL File:
2763-96-4.mol
Modify Date:
2024/3/14 15:18:27

MUSCIMOL Properties

Melting point 175-176°C
Boiling point 213.59°C (rough estimate)
Density 1.291
refractive index 1.4487 (estimate)
storage temp. 2-8°C
solubility ethanol: 1 mg/mL
form powder
pka 12.19±0.40(Predicted)
color white to off-white
Water Solubility Soluble in water (10 mg/ml), methanol, ethanol, 0.05 M HCl (20 mg/ml), DMSO (sparingly soluble), DMF (sparingly soluble), and PBS (pH 7.2) (10 mg/ml).
Merck 13,6336
BRN 1618960
Stability Hygroscopic, Store in Freezer at -20°C
EPA Substance Registry System 5-(Aminomethyl)-3-isoxazolol (2763-96-4)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Signal word  Danger
Hazard statements  H300-H336
Precautionary statements  P261-P264-P270-P271-P301+P310-P304+P340+P312
Hazard Codes  T
Risk Statements  25
Safety Statements  22-36/37/39-45
RIDADR  UN 1544 6.1/PG 2
WGK Germany  3
RTECS  NY3345000
3-10
TSCA  Yes
HazardClass  6.1(a)
PackingGroup  II
HS Code  29349990
Toxicity LD50 in mice (mg/kg): 3.8 s.c., 2.5 i.p.; in rats (mg/kg): 4.5 i.v., 45 orally (Theobald)
NFPA 704
0
3 0

MUSCIMOL price More Price(4)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) M1523 Muscimol powder 2763-96-4 5MG ₹17049.38 2022-06-14 Buy
Sigma-Aldrich(India) M1523 Muscimol powder 2763-96-4 10MG ₹24323.78 2022-06-14 Buy
Sigma-Aldrich(India) M1523 Muscimol powder 2763-96-4 25MG ₹53269.83 2022-06-14 Buy
Sigma-Aldrich(India) 5.06044 Muscimol - CAS 2763-96-4 - Calbiochem Muscimol is a constituent and psychoactive ingredient of the mushroom Amanita muscaria, that acts as a potent agonist of GABAA receptors. 2763-96-4 1MG ₹10049.99 2022-06-14 Buy
Product number Packaging Price Buy
M1523 5MG ₹17049.38 Buy
M1523 10MG ₹24323.78 Buy
M1523 25MG ₹53269.83 Buy
5.06044 1MG ₹10049.99 Buy

MUSCIMOL Chemical Properties,Uses,Production

Description

The amino acid γ-aminobutyric acid (GABA) is an inhibitory neurotransmitter that acts through two families of heteromeric ligand-gated ion channels, GABAA and GABAC and a G protein-coupled receptor, GABAB. Muscimol is a full GABAA agonist and partial GABAC agonist. It binds GABAA on both high- and low-affinity sites (Kd = 10 and 270 nM, respectively), stimulating chloride efflux with an EC50 value of 200 nM. Benzodiazepines enhance the effects of muscimol via GABAA without altering its binding. Muscimol activates GABAC receptors with an EC50 value of 1.3 μM. It also acts as an inhibitor of GABAA uptake and a substrate for the GABA-metabolizing enzyme GABA transaminase. Muscimol impairs memory formation and retrieval in mice and attenuates airway constriction in guinea pigs in vivo.

Chemical Properties

Tan Solid

Uses

A potent but toxic structural analogue of g-aminobutyric acid (GABA), with a zwitterionic structure that can cross the blood-brain barrier

Definition

ChEBI: 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.

General Description

Crystals. Formerly used as a sedative and an anti-emetic.

Reactivity Profile

MUSCIMOL is a ketone and an amine. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides

Health Hazard

MUSCIMOL is a natural constituent of amanita mushrooms and is extremely toxic. It is a potent central nervous system depressant, and is believed to be responsible for most of the nervous system effects that result from eating this mushroom. The lowest toxic dose in humans has been reported at 109 mg/kg.

Fire Hazard

When heated to decomposition, MUSCIMOL emits toxic fumes of nitrogen oxides.

Biological Activity

Potent GABA A receptor agonist and partial GABA C receptor agonist. Inhibits memory retention and attenuates airway constriction in vivo .

Purification Methods

Recrystallise muscimol from MeOH/tetrahydrofuran or EtOH and sublime it at 110-140o (bath) at 10-4 mm to give a yellow spot with ninhydrin which slowly turns purple [NMR: Bowden et al. J Chem Soc (C) 172 1968]. It can also be purified by dissolving in the minimum volume of hot H2O and adding EtOH dropwise until cloudy, cool, and colourless crystals separate; IR: max 3445w, 3000-2560w br, 2156w, 1635s and 1475s cm-1. [NMR: Jager & Frey Justus Liebigs Ann Chem 817 1982.] Alternatively it has been purified by two successive chromatographic treatments on Dowex-1 x 8, with the first elution with 2M AcOH and a second with a linear gradient between 0—2M AcOH, evaporating the desired fractions and recrystallising the residue from MeOH. [McCarry & Savard Tetrahedron Lett 22 5153 1981, Nakamura Chem Pharm Bull Jpn 19 46 1971.]

MUSCIMOL Preparation Products And Raw materials

Raw materials

Preparation Products

5-(aminomethyl)isoxazol-3-ol hydrate MUSCIMOL CRYSTALLINE Containsupto10%Ethanol 5-Aminomethyl-3-hydroxyisoxazole, 5-(Aminomethyl)-3(2H)-isoxazolone Muscimol: (5-Aminomethyl-3-isoxyzole) 5-Aminomethylisoxazol-3(2H)-one Muscimol hydrate,98% Muscimol hydrate5-(Aminomethyl)-3-isoxazolol AGARIN 3-HYDROXY-5-AMINOMETHYL-ISOXAZOLE 3-HYDROXY-5-AMINOMETHYLISOXAZOLE HYDROBROMIDE 5-(AMINOMETHYL)-3(2H)-ISOXAZOLONE 5-(AMINOMETHYL)-3(2H)-ISOXAZOLONE, HYDROBROMIDE 5-AMINOMETHYL-3-ISOXAZOLOL 5-AMINOMETHYL-3-HYDROXYISOAZOLE, HBR 5-AMINOMETHYL-3-HYDROXYISOOXAZOLE 5-AMINOMETHYL-3-HYDROXYISOXAZOLE 3-Hydroxy-5-aminomethyl-isoxazole, 5-Aminomethyl-3-hydroxy-isoxazole, 5-Aminomethyl-3-isoxazolol MUSCIMOL (RG) NSC 333569 Agarin, Pantherine pantherin rcrawastenumberp007 PANTHERINE MUSCIMOL MUSCIMOL HYDROBROMIDE 5-Aminomethylisoxazol-3-one MUSCIMOL(P) Pyroibotenic acid 5-(aminomethyl)isoxazol-3-ol 3(2h)isoxazoione,5-(aminomethyl)- 3-hydroxy-5-aminomethylisoxazole-agarin 5-(aminomethyl)-3(2h)-isoxazolon 5-(aminomethyl)-3-isoxazolo 5-aminomethyl-3-isoxyzole agarine Arylex Impurity 8 2763-96-4 C4H7BrN2O2 C4H6N2O2xH2O Building Blocks BioChemical Cell Signaling and Neuroscience Cell Biology Ligand-Gated Ion Channels Isoxazoles Ion Channels GABA and Glycine Receptor Modulators Heterocyclic Building Blocks Heterocycles GABA/Glycine receptor Bioactive Small Molecules Building Blocks Cell Biology Chemical Synthesis Heterocyclic Building Blocks Enzyme substrates Neurochemicals