Muscimol

Names

[ Name ]:
Muscimol

[Synonym ]:
5-(aminomethyl)-1,2-oxazol-3-one
5-Aminomethyl-3-hydroxy-isoxazol
PANTHERINE
5-(Aminomethyl)isoxazol-3(2H)-one
Agarine
5-Aminomethyl-3-hydroxyisoxazole
UNII:D5M179TY2E
3(2H)-Isoxazolone, 5-(aminomethyl)-
3-Hydroxy-5-aminomethylisoxazole
MFCD00057894
5-aminomethyl-isoxazol-3-one
Agarin
EINECS 220-430-4
5-(Aminomethyl)-1,2-oxazol-3(2H)-one
Pantherin
3-Hydroxy-5-aminomethyl-isoxazole 5-Aminomethyl-3-hydroxy-isoxazole 5-Aminomethyl-3-isoxazolol

Biological Activity

[Description]:

Muscimol (Agarin), a psychoactive isoxazole, is a selective neurotransmitter GABA agonist. Muscimol 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. Muscimol passes the blood-brain barrier (BBB) and has memory-disrupting effects[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> GABA Receptor

Research Areas >> Neurological Disease

Signaling Pathways >> Neuronal Signaling >> GABA Receptor

[References]

[1]. S M Dunn, et al. Reconstitution of purified GABAA receptors: ligand binding and chloride transporting properties. Biochemistry. 1994 Jan 25;33(3):755-63.

[2]. Donna R Ramirez, et al. The role of the GABA(A) agonist muscimol on memory performance: reward contingencies determine the nature of the deficit. Neurobiol Learn Mem. 2005 Nov;84(3):184-91.

[3]. M Irifune, et al. Propofol anaesthesia in mice is potentiated by muscimol and reversed by bicuculline. Br J Anaesth. 1999 Oct;83(4):665-7.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
325.0±27.0 °C at 760 mmHg

[ Melting Point ]:
175-176ºC

[ Molecular Formula ]:
C₄H₆N₂O₂

[ Molecular Weight ]:
114.103

[ Flash Point ]:
150.4±23.7 °C

[ Exact Mass ]:
114.042931

[ PSA ]:
72.28000

[ LogP ]:
-0.93

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.556

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NY3325000

CHEMICAL NAME :: 3-Isoxazolol, 5-(aminomethyl)-

CAS REGISTRY NUMBER :: 2763-96-4

LAST UPDATED :: 199701

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C4-H6-N2-O2

MOLECULAR WEIGHT :: 114.12

WISWESSER LINE NOTATION :: T5NOJ C1Z EQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human

DOSE/DURATION :: 109 ug/kg

TOXIC EFFECTS :: Behavioral - sleep Behavioral - hallucinations, distorted perceptions Gastrointestinal - nausea or vomiting

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 18,311,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 45 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 18,311,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 18,311,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 22 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #0000338

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2500 ug/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 18,311,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3800 ug/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 18,311,1968

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5620 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#11824

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 10 mg/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 18,311,1968

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
25

[ Safety Phrases ]:
S22;S45;S36/S37/S39

[ RIDADR ]:
UN 1544 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
NY3345000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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Related Compounds

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