Chlorphenesin carbamate

Chlorphenesin carbamate (Maolate, Musil) is a centrally acting muscle relaxant used to treat muscle pain and spasms.[1][2] Chlorphenesin carbamate is no longer used for this purpose in most developed nations due to the availability of much safer spasmolytics such as benzodiazepines.

Chlorphenesin carbamate
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
ATC code
Pharmacokinetic data
Excretionurine
Identifiers
  • (3-(4-chlorophenoxy)-2-hydroxypropyl)carbamate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.902
Chemical and physical data
FormulaC10H12ClNO4
Molar mass245.66 g·mol−1
3D model (JSmol)
Melting point86 to 92 °C (187 to 198 °F)
  • c1cc(ccc1OCC(COC(=O)N)O)Cl
  • InChI=1S/C10H12ClNO4/c11-7-1-3-9(4-2-7)15-5-8(13)6-16-10(12)14/h1-4,8,13H,5-6H2,(H2,12,14)
  • Key:SKPLBLUECSEIFO-UHFFFAOYSA-N

Other central effects include sedation, anxiolysis, and dizziness.

Chlorphenesin

A related chemical, chlorphenesin (C9H11ClO3) without the carbamate group, is used as a preservative in products such as cosmetics. It has antifungal and some antibacterial properties, and is classified as an antifungal for topical use by the WHO.[3]

The major adverse effect from this preservative on skin is allergic contact sensitivity.[4][5] Systemic intoxication from transdermal use has not been observed, although the FDA discourages its use as an ingredient in nipple cream for nursing mothers.[6]

See also

References
  1. Okuyama S, Aihara H (February 1987). "Antinociceptive effect of chlorphenesin carbamate in adjuvant arthritic rats". Research Communications in Chemical Pathology and Pharmacology. 55 (2): 147–60. PMID 3823606.
  2. Kurachi M, Aihara H (September 1984). "Effect of a muscle relaxant, chlorphenesin carbamate, on the spinal neurons of rats". Japanese Journal of Pharmacology. 36 (1): 7–13. doi:10.1254/jjp.36.7. PMID 6503049.
  3. ATC code D01AE07
  4. Brown R (May 1981). "Chlorphenesin sensitivity". Contact Dermatitis. 7 (3): 162. doi:10.1111/j.1600-0536.1981.tb04601.x. PMID 6456118. S2CID 37580364.
  5. Burns DA (April 1986). "Allergic contact sensitivity to chlorphenesin". Contact Dermatitis. 14 (4): 246. doi:10.1111/j.1600-0536.1986.tb01234.x. PMID 2941223. S2CID 43810471.
  6. "FDA Warns Consumers Against Using Mommy's Bliss Nipple Cream Product can be harmful to nursing infants". Food and Drug Administration.
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