Methocarbamol Chemical Properties

Melting point:

95-97°C

Boiling point:

384.01°C (rough estimate)

Density 

1.2611 (rough estimate)

refractive index 

1.5080 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

13.08±0.20(Predicted)

color 

White to Off-White

Merck 

14,5980

InChI

InChI=1S/C11H15NO5/c1-15-9-4-2-3-5-10(9)16-6-8(13)7-17-11(12)14/h2-5,8,13H,6-7H2,1H3,(H2,12,14)

InChIKey

GNXFOGHNGIVQEH-UHFFFAOYSA-N

SMILES

C(OC(=O)N)C(O)COC1=CC=CC=C1OC

CAS DataBase Reference

532-03-6(CAS DataBase Reference)

NIST Chemistry Reference

Methocarbamol(532-03-6)

EPA Substance Registry System

Methocarbamol (532-03-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-42/43

Safety Statements 

36

WGK Germany 

3

RTECS 

TY8750000

HS Code 

29222990

Hazardous Substances Data

532-03-6(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

Methocarbamol Usage And Synthesis

Chemical Properties

White Solid

Originator

Robaxin ,Robins,US,1957

Uses

Methocarbamol suppresses multisynaptic pathways in the spinal cord. It is used for relieving spasms and skeletal muscle pain as well as for treating tetanus. Synonyms of this drug are delaxin, forbaxin, robamol, robaxin, and tresortil.

Uses

For use as an adjunct to rest, physical therapy, and other measures for the relief of discomforts associated with acute, painful musculoskeletal conditions.

Uses

A muscle relaxant (skeletal).

Definition

ChEBI: 2-hydroxy-3-(2-methoxyphenoxy)propyl carbamate is a carbamate ester that is glycerol in which one of the primary alcohol groups has been converted to its 2-methoxyphenyl ether while the other has been converted to the corresponding carbamate ester. It is a carbamate ester, a secondary alcohol and an aromatic ether.

Manufacturing Process

The starting material for methocarbamol is 3-o-methoxyphenoxy-1,2- propanediol (guaiacol glyceryl ether) (see entry under Guaifenesin for its preparation). To a stirred suspension of 198.2 g (1.0 mol) of 3-omethoxyphenoxy-1,2-propanediol in 1,000 ml of dry benzene contained in a 5-liter, 3-neck, round bottom flask equipped with a thermometer, dropping funnel and blade stirrer, was added dropwise (in 30 minutes) a solution of 98.9 g (1.0 mol) of phosgene in 400 ml of cold dry benzene. The mixture was stirred at 30°C until all solid material dissolved (about 3 hours was required) and stirring was continued for 30 minutes longer. To this mixture was added dropwise 79.1 g (1.0 mol) of dry pyridine, the temperature being held below 30°C by cooling. After addition of the pyridine, stirring at 30°C was continued for 30 minutes.
The mixture was cooled to 7°C, extracted with two 500-cc portions of ice water to remove pyridine hydrochloride, and the benzene solution of 3-omethoxyphenoxy-2-hydroxypropyl chlorocarbonate was added to 500 ml of cold concentrated ammonium hydroxide. The mixture was vigorously stirred at 5°C for 6 hours, then the crude white precipitate of 3-o-methoxyphenoxy-2- hydroxypropyl carbamate was filtered off, dissolved in 1,500 ml of hot benzene and completely dried by codistillation of last traces of water with benzene, treated with decolorizing carbon and filtered while hot. On cooling 160 g of product crystallized as white needles melting at 88° to 90°C.

brand name

Delaxin (Ferndale); Forbaxin (Forest); Robaxin (Baxter Healthcare).

Therapeutic Function

Muscle relaxant

Synthesis Reference(s)

The Journal of Organic Chemistry, 22, p. 1595, 1957 DOI: 10.1021/jo01363a016

General Description

Methocarbamol, 3-(o-methoxyphenoxy)-1,2-propanediol 1-carbamate (Robaxin), issaid to be more sustained in effect than mephenesin. Likelysites for metabolic attack include the secondary hydroxylgroup and the two ring positions opposite the ether functions.The dihydric parent compound, guaifenesin, is used asan expectorant.

Synthesis

Methocarbamol, 3-(2-methoxyphenoxy)-1,2-propanediol-1 carbamate (15.3.13), is synthesized by successive reaction with phosgene and then ammonia into 3- (2-methoxyphenoxy)propanediol-1,2.

Veterinary Drugs and Treatments

In dogs and cats, methocarbamol is indicated (FDA approved) “as adjunctive therapy of acute inflammatory and traumatic conditions of the skeletal muscle and to reduce muscular spasms.” In horses, intravenous use is indicated (FDA approved) “as adjunctive therapy of acute inflammatory and traumatic conditions of the skeletal muscle to reduce muscular spasms, and effect striated muscle relaxation.” (Package insert; Robaxin?V—Robins)

Methocarbamol(532-03-6)Related Product Information

• Ethylbenzene
• 2-Butoxyethanol
• Chlorpropham
• 4-Aminobenzoic acid
• Dimethyl ether
• POLYURETHANE
• Oxydipropyl dibenzoate
• PETROLEUM ETHER
• GLYCERYL MONORICINOLEATE
• Urethane
• Propylene glycol
• Methyl anthranilate
• Guaifenesin
• Diethyl ether
• Anthranilic acid
• 2-(2-HYDROXYETHOXY)PHENOL
• Guaiacol
• 1-(2-METHOXYPHENOXY)-2-PROPANOL