methocarbamol

Names

[ CAS No. ]:
532-03-6

[ Name ]:
methocarbamol

[Synonym ]:
Guaiacol glyceryl ether carbamate
neuraxin
Relax
Methyocarbamol
Delaxin
2-hydroxy-3-{[2-(methyloxy)phenyl]oxy}propyl carbamate
Relestrid
Carbamic Acid 2-Hydroxy-3-(2-methoxyphenoxy)propyl Ester
guaifenesin carbamate
EINECS 208-524-3
2-Hydroxy-3-(2-methoxyphenoxy)propyl carbamate
Lumirelax
Miolaxene
Robaxan
Perilax
MFCD00057662
methocarbamol
Robamol
AHR 85
Traumacut
Miowas
Robaxin
1,2-Propanediol, 3-(2-methoxyphenoxy)-, 1-carbamate
Avetil

Biological Activity

[Description]:

Methocarbamol is a central muscle relaxant used to treat skeletal muscle spasms.Target: Carbonic AnhydraseMethocarbamol is the carbamate of guaifenesin, but does not produce guaifenesin as a metabolite, because the carbamate bond is not hydrolyzed metabolically; metabolism is by Phase I ring hydroxylation and O-demethylation, followed by Phase II conjugation. All the major metabolites are unhydrolyzed carbamates. Methocarbamol is used as an adjunct in the symptomatic treatment of musculoskeletal conditions associated with painful muscle spasm [1, 2].

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Metabolic Disease

[References]

[1]. Bruce, R.B., L.B. Turnbull, and J.H. Newman, Metabolism of methocarbamol in the rat, dog, and human. J Pharm Sci, 1971. 60(1): p. 104-6.

[2]. Sica, D.A., et al., Pharmacokinetics and protein binding of methocarbamol in renal insufficiency and normals. Eur J Clin Pharmacol, 1990. 39(2): p. 193-4.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
472.5±40.0 °C at 760 mmHg

[ Melting Point ]:
95-97ºC

[ Molecular Formula ]:
C₁₁H₁₅NO₅

[ Molecular Weight ]:
241.240

[ Flash Point ]:
239.6±27.3 °C

[ Exact Mass ]:
241.095016

[ PSA ]:
91.01000

[ LogP ]:
0.55

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.541

[ Storage condition ]:
-20°C Freezer

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: TY8750000

CHEMICAL NAME :: 1,2-Propanediol, 3-(o-methoxyphenoxy)-, 1-carbamate

CAS REGISTRY NUMBER :: 532-03-6

BEILSTEIN REFERENCE NO. :: 1884446

LAST UPDATED :: 199701

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C11-H15-N-O5

MOLECULAR WEIGHT :: 241.27

WISWESSER LINE NOTATION :: ZVO1YQ1OR BO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1320 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - muscle weakness Behavioral - ataxia

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 129,75,1960

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 815 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 17,242,1967

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 812 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,836,1982

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 950 mg/kg

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

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 2,264,1960

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 780 mg/kg

TOXIC EFFECTS :: Behavioral - anticonvulsant

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 19,247,1962

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 774 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,836,1982

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 2 gm/kg

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

REFERENCE :: 27ZQAG "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972 Volume(issue)/page/year: -,398,1972

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 680 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - altered sleep time (including change in righting reflex) Behavioral - rigidity (including catalepsy)

REFERENCE :: IJNEAQ International Journal of Neuropharmacology. (New York, NY) V.1-8, 1962-69. For publisher information, see NEPHBW. Volume(issue)/page/year: 5,305,1966

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 1410 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - muscle weakness Behavioral - ataxia

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 129,75,1960

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - hamster

DOSE/DURATION :: 1050 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - muscle weakness Behavioral - ataxia

REFERENCE :: JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 129,75,1960 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84354 No. of Facilities: 350 (estimated) No. of Industries: 3 No. of Occupations: 3 No. of Employees: 1853 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 84354 No. of Facilities: 188 (estimated) No. of Industries: 1 No. of Occupations: 4 No. of Employees: 9546 (estimated) No. of Female Employees: 8341 (estimated)

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H317-H334

[ Precautionary Statements ]:
P261-P280-P284-P304 + P340-P333 + P313-P342 + P311

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22;R42/43

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
TY8750000

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

A new HPLC technique for the separation of methocarbamol enantiomers.

J. Pharm. Pharmacol. 51(7) , 873-5, (1999)

We have developed a stereoselective high-performance liquid chromatography technique for analytical separation of methocarbamol enantiomers. Precolumn derivatization was performed at room temperature ...

Spectrofluorometric determination of methocarbamol in pharmaceutical preparations and human plasma.

J. Fluoresc. 21(2) , 555-61, (2011)

A simple, sensitive and rapid spectrofluorometric method for determination of methocarbamol in pharmaceutical formulations and spiked human plasma has been developed. The proposed method is based on t...

A stability-indicating high-performance liquid chromatographic method for the determination of methocarbamol in veterinary preparations.

J. AOAC Int. 92(5) , 1602-5, (2009)

An isocratic HPLC method was developed and validated for the quantitation of methocarbamol in the presence of its degradation products. Quantitation was achieved using a reversed-phase C18 column at a...