Product Name

  • Name

    Methocarbamol

  • EINECS 208-524-3
  • CAS No. 532-03-6
  • Density 1.256 g/cm3
  • Solubility
  • Melting Point 95-97oC
  • Formula C11H15NO5
  • Boiling Point 472.5 °C at 760 mmHg
  • Molecular Weight 241.244
  • Flash Point 239.6 °C
  • Transport Information
  • Appearance
  • Safety 36
  • Risk Codes 22-42/43
  • Molecular Structure Molecular Structure of 532-03-6 (Methocarbamol)
  • Hazard Symbols HarmfulXn
  • Synonyms Surquetil;Traumacut;Tresortil;guaiamar carbamate;racemic-Methocarbamol;Robinax;Robaxin;Relestrid;Neuraxin;NSC 170960;Miolaxene;Avetil;Delaxin;Etroflex;Glycerylguaiacolate carbamate;Guaiacol glyceryl ether carbamate;Lumirelax;3-(o-Methoxyphenoxy)-1,2-propanediol 1-carbamate;3-(o-Methoxyphenoxy)-2-hydroxypropyl carbamate;AHR 85;Carbamic acid,2-hydroxy-3-(o-methoxyphenoxy)propyl ester (6CI,7CI);1,2-Propanediol,3-(o-methoxyphenoxy)-, 1-carbamate (8CI);
  • PSA 91.01000
  • LogP 1.23050

Synthetic route

rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one
2049-21-0

rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
With ammonium hydroxide at 40℃; for 6h;95%
1-Carbaminoyloxy-2-benzyloxy-3-(2-methoxy-phenoxy)-propan
94997-48-5

1-Carbaminoyloxy-2-benzyloxy-3-(2-methoxy-phenoxy)-propan

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal
3-(2-methoxyphenoxy)propanediol 2-carbamate
10488-39-8

3-(2-methoxyphenoxy)propanediol 2-carbamate

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
With ammonium hydroxide
Multi-step reaction with 3 steps
1: SOCl2
3: aq. NH3
View Scheme
1-Acetoxy-2-carbaminoyloxy-3-(2-methoxy-phenoxy)-propan
92042-73-4

1-Acetoxy-2-carbaminoyloxy-3-(2-methoxy-phenoxy)-propan

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
With ammonium hydroxide
Multi-step reaction with 2 steps
1: TsOH
2: aq. NH3
View Scheme
rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one
2049-21-0

rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one

ammonia
7664-41-7

ammonia

isopropyl alcohol
67-63-0

isopropyl alcohol

A

methocarbamol
532-03-6

methocarbamol

B

3-(2-methoxyphenoxy)propanediol 2-carbamate
10488-39-8

3-(2-methoxyphenoxy)propanediol 2-carbamate

(+-)-2-carbamoyloxy-3-<2-methoxy-phenoxy>-propan-1-ol

(+-)-2-carbamoyloxy-3-<2-methoxy-phenoxy>-propan-1-ol

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
With ethanol; ammonia; sodium ethanolate
phosgene
75-44-5

phosgene

(+-)-3-<2-methoxy-phenoxy>-propane-1,2-diol

(+-)-3-<2-methoxy-phenoxy>-propane-1,2-diol

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
With pyridine; benzene anschliessendes Behandeln mit Wasser und Behandeln der Reaktionsloesung mit konz. wss. NH3;
(+-)-4-<2-methoxy-phenoxy-methyl>-<1,3>dioxolan-2-one

(+-)-4-<2-methoxy-phenoxy-methyl>-<1,3>dioxolan-2-one

A

methocarbamol
532-03-6

methocarbamol

B

(+-)-2-carbamoyloxy-3-<2-methoxy-phenoxy>-propan-1-ol

(+-)-2-carbamoyloxy-3-<2-methoxy-phenoxy>-propan-1-ol

Conditions
ConditionsYield
With ammonia; isopropyl alcohol
2-carbamoyloxy-1-chloro-3-(2-methoxy-phenoxy)-propane
2049-22-1

2-carbamoyloxy-1-chloro-3-(2-methoxy-phenoxy)-propane

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: aq. NH3
View Scheme
Multi-step reaction with 3 steps
2: TsOH
3: aq. NH3
View Scheme
1-Hydroxy-2-benzyloxy-3-(2-methoxy-phenoxy)-propan
94824-19-8

1-Hydroxy-2-benzyloxy-3-(2-methoxy-phenoxy)-propan

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (i) Et3N, (ii) NH3
2: H2 / Pd-C
View Scheme
1-benzyloxy-2-carbamoyloxy-3-(2-methoxy-phenoxy)-propane
93950-95-9

1-benzyloxy-2-carbamoyloxy-3-(2-methoxy-phenoxy)-propane

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / Pd-C
2: aq. NH3
View Scheme
Multi-step reaction with 4 steps
1: H2 / Pd-C
2: SOCl2
4: aq. NH3
View Scheme
1-benzyloxy-3-(2-methoxy-phenoxy)-propan-2-ol
93728-27-9

1-benzyloxy-3-(2-methoxy-phenoxy)-propan-2-ol

methocarbamol
532-03-6

methocarbamol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) Et3N, (ii) NH3
2: H2 / Pd-C
3: aq. NH3
View Scheme
Multi-step reaction with 5 steps
1: (i) Et3N, (ii) NH3
2: H2 / Pd-C
3: SOCl2
5: aq. NH3
View Scheme
methocarbamol
532-03-6

methocarbamol

cyclohexane
110-82-7

cyclohexane

C17H25NO5

C17H25NO5

Conditions
ConditionsYield
With di-tert-butyl peroxide; copper diacetate; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 25℃; for 12h; Inert atmosphere; Irradiation; chemoselective reaction;55%
3-nitrophthalic acid anhydride
641-70-3

3-nitrophthalic acid anhydride

methocarbamol
532-03-6

methocarbamol

Methocarbamol-mono-3-nitro-phthalat

Methocarbamol-mono-3-nitro-phthalat

methocarbamol
532-03-6

methocarbamol

2,4-dinitrobenzenesulfenyl chloride
528-76-7

2,4-dinitrobenzenesulfenyl chloride

C17H17N3O9S

C17H17N3O9S

Conditions
ConditionsYield
With pyridine
methocarbamol
532-03-6

methocarbamol

1-Naphthyl isocyanate
86-84-0

1-Naphthyl isocyanate

Methocarbamol-(1-naphthylcarbamat)

Methocarbamol-(1-naphthylcarbamat)

Conditions
ConditionsYield
With stannous octoate In toluene
methocarbamol
532-03-6

methocarbamol

A

3-(2-methoxyphenoxy)propanediol 2-carbamate
10488-39-8

3-(2-methoxyphenoxy)propanediol 2-carbamate

B

guaifenesin
93-14-1

guaifenesin

Conditions
ConditionsYield
With water at 70℃; Product distribution; Rate constant; further temperatures, pH 8.0-10.0;
pyridine
110-86-1

pyridine

thionyl chloride
7719-09-7

thionyl chloride

methocarbamol
532-03-6

methocarbamol

benzene
71-43-2

benzene

(+-)-2-carbamoyloxy-1-chloro-3-<2-methoxy-phenoxy>-propane

(+-)-2-carbamoyloxy-1-chloro-3-<2-methoxy-phenoxy>-propane

hydrogenchloride
7647-01-0

hydrogenchloride

chloroform
67-66-3

chloroform

methocarbamol
532-03-6

methocarbamol

rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one
2049-21-0

rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one

hydrogenchloride
7647-01-0

hydrogenchloride

methocarbamol
532-03-6

methocarbamol

isopropyl alcohol
67-63-0

isopropyl alcohol

rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one
2049-21-0

rac-4-(2-methoxyphenoxymethyl)-[1,3]dioxolan-2-one

methocarbamol
532-03-6

methocarbamol

guaifenesin
93-14-1

guaifenesin

Conditions
ConditionsYield
With ethanol In water at 80℃;
copper(II) perchlorate hexahydrate

copper(II) perchlorate hexahydrate

methocarbamol
532-03-6

methocarbamol

water
7732-18-5

water

C2H6CuN2O5*4H2O

C2H6CuN2O5*4H2O

Conditions
ConditionsYield
In ethanol for 5h; Reflux;
methocarbamol
532-03-6

methocarbamol

C11H16N2O7S

C11H16N2O7S

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 3 h / 20 - 25 °C
2: hydrogenchloride / water; acetonitrile / 20 - 25 °C
View Scheme
methocarbamol
532-03-6

methocarbamol

(tert-butoxycarbonyl) (pyridin-1-ium-1-ylsulfonyl)amide pyridinium chloride

(tert-butoxycarbonyl) (pyridin-1-ium-1-ylsulfonyl)amide pyridinium chloride

C16H24N2O9S

C16H24N2O9S

Conditions
ConditionsYield
at 20 - 25℃; for 3h;

Methocarbamol Chemical Properties

IUPAC Name: [2-hydroxy-3-(2-methoxyphenoxy)propyl] Carbamate
Synonyms of Methocarbamol (CAS NO.532-03-6): Guaiacol glyceryl ether carbamate ; Glycerylguaiacolate carbamate

Molecular Structure:  
Molecular Formula : C11H15NO5
Molecular Weight:  241.24
CAS NO: 532-03-6
EINECS:  208-524-3
Mol File: 532-03-6.mol
H bond acceptors: 6
H bond donors: 3
Freely Rotating Bonds: 8
Polar Surface Area: 57.23 Å2
Index of Refraction: 1.54
Molar Refractivity: 60.31 cm3
Molar Volume: 192 cm3
Index of Refraction: 1.54 
Surface Tension: 48.9 dyne/cm 
Density: 1.256 g/cm3 
Flash Point: 239.6 °C 
Enthalpy of Vaporization: 77.48 kJ/mol 
Boiling Point: 472.5 °C at 760 mmHg
Vapour Pressure: 9.86E-10 mmHg at 25°C 
SMILES: O=C(OCC(O)COc1ccccc1OC)N
InChI: InChI=1/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-UHFFFAOYAU
Std. 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)
Std. InChIKey: GNXFOGHNGIVQEH-UHFFFAOYSA-N
Product Categories: Active Pharmaceutical Ingredients;Organics;API's

Methocarbamol Uses

 Methocarbamol (CAS NO.532-03-6) is used for lumbar and joint ligaments of acute sprains, sciatica, hyperplastic spondylitis, rheumatoid arthritis, rheumatoid arthritis, muscle strain and so on.

Methocarbamol Toxicity Data With Reference

 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 2gm/kg (2000mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 398, 1972.
hamster LD50 intraperitoneal 1050mg/kg (1050mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
hamster LD50 oral 1410mg/kg (1410mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

BEHAVIORAL: MUSCLE WEAKNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.
mouse LD50 intraperitoneal 950mg/kg (950mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 264, 1960.
mouse LD50 intravenous 774mg/kg (774mg/kg)   Drugs in Japan Vol. 6, Pg. 836, 1982.
mouse LD50 oral 812mg/kg (812mg/kg)   Drugs in Japan Vol. 6, Pg. 836, 1982.
mouse LD50 subcutaneous 780mg/kg (780mg/kg) BEHAVIORAL: ANTICONVULSANT Acta Pharmacologica et Toxicologica. Vol. 19, Pg. 247, 1962.
rabbit LD50 intravenous 680mg/kg (680mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: REGIDITY

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
International Journal of Neuropharmacology. Vol. 5, Pg. 305, 1966.
rat LD50 intraperitoneal 815mg/kg (815mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 242, 1967.
rat LD50 oral 1320mg/kg (1320mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: ATAXIA
Journal of Pharmacology and Experimental Therapeutics. Vol. 129, Pg. 75, 1960.

Methocarbamol Safety Profile

Hazard Codes: HarmfulXn
Risk Statements 22-42/43
R22: Harmful if swallowed. 
R42/43: May cause sensitization by inhalation and skin contact.
Safety Statements: 36
S36: Wear suitable protective clothing.
WGK: Germany 3
RTECS: TY8750000

Methocarbamol Specification

1.Consumption Usage: intramuscular injection: 1 300 ~ 500mg, day 1, 5 ~ 10 as a course of treatment.
2.Note: sleepiness, dizziness, feeling of weakness,Methocarbamol (CAS NO.532-03-6) is not used with general anesthetics, hypnotics, antipsychotics . Methocarbamol is banned to the Liver dysfunction and the kidney dysfunction.
3.Because of potential for side effects, this drug is on the list for High Risk Medications in the elderly. (See NCQA’s HEDIS 4.Measure: Use of High Risk Medications in the Elderly.
5.Specifications: Injection: 500mg (5ml).

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