Muscimol

Base Information

• Chemical Name: Muscimol
• CAS No.: 2763-96-4
• Deprecated CAS: 2489-10-3
• Molecular Formula: C4H6N2O2
• Molecular Weight: 114.104
• Hs Code.: 29349990
• European Community (EC) Number: 220-430-4
• NSC Number: 333569
• UN Number: 2811,3077
• UNII: D5M179TY2E
• DSSTox Substance ID: DTXSID5041069
• Nikkaji Number: J7.909J
• Wikipedia: Muscimol
• Wikidata: Q412504
• Pharos Ligand ID: 2Y9PPVMX7U7V
• Metabolomics Workbench ID: 67474
• ChEMBL ID: CHEMBL273481
• Mol file: 2763-96-4.mol

Synonyms:Agarin;Muscimol;Pantherine

Chemical Property of Muscimol

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: 175-176°C
• Refractive Index: 1.4487 (estimate)
• Boiling Point: 325°Cat760mmHg
• PKA: 12.19±0.40(Predicted)
• Flash Point: 150.4°C
• PSA: 72.28000
• Density: 1.291g/cm³
• LogP: 0.53920
• Storage Temp.: 2-8°C
• Solubility.: ethanol: 1 mg/mL
• Water Solubility.: Soluble in water (10 mg/ml), methanol, ethanol, 0.05 M HCl (20 mg/ml), DMSO (sparingly soluble), DMF (sparingly soluble), and PB
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 114.042927438
• Heavy Atom Count: 8
• Complexity: 141
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Muscimol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 25
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Mushroom Toxins
• Canonical SMILES: C1=C(ONC1=O)CN
• Recent ClinicalTrials: Brain Infusion of Muscimol to Treat Epilepsy
• 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.
• Uses: A potent but toxic structural analogue of g-aminobutyric acid (GABA), with a zwitterionic structure that can cross the blood-brain barrier As a molecular probe to study GABA receptors.

Technology Process of Muscimol

There total 11 articles about Muscimol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 64.0%

5-aminomethyl-3-methoxyisoxazole hydrochloride (2763-95-3) → muscimol (2763-96-4)

Guidance literature:

With hydrogen bromide; In acetic acid; for 0.166667h; Heating;

DOI:10.1016/S0040-4039(00)84748-6

Reference yield: 62.0%

5-aminomethyl-3-methoxyisoxazole (2763-94-2) → muscimol (2763-96-4)

Guidance literature:

With DOWEX W₅₀x8-200 mesh (H⁺-form); hydrogen bromide; In acetic acid; for 0.25h; Heating;

DOI:10.1080/00397919208021324

Reference yield: 51.0%

muscimol hydrochloride (3579-03-1) → muscimol (2763-96-4)

Guidance literature:

With ion exchanger (Lewatit S 100 G₁); In water;

DOI:10.1002/jlac.198219820423

upstream raw materials:

5-aminomethyl-3-methoxyisoxazole

3-hydroxy-5-isoxazolylmethyl chloride

C₈H₈N₂O₅

muscimol hydrochloride

Downstream raw materials:

Z-Glycylmuscimol

5-acetamidomethyl-3-acetoxyisoxazole

5-acetamidomethyl-2-acetyl-3-isoxazolone

5-acetamidomethyl-3-hydroxyisoxazole

Refernces

• 1、 Chiarino, D.,Napoletano, M.,Sala, A.. "A CONVENIENT SYNTHESIS OF MUSCIMOL BY A 1,3-DIPOLAR CYCLOADDITION REACTION". . p. 3181 - 3182. Retrieved 1986.
• 2、 Pevarello,Varasi. "An improved synthesis of muscimol". . p. 1939 - 1948. Retrieved 2007/10/02.