Chemistry:Mephenesin

Short description: Muscle relaxer & antidote for strychnine poisoning

Mephenesin

Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	M03BX06 (WHO)
Identifiers
IUPAC name 3-(2-methylphenoxy)propane-1,2-diol
CAS Number	59-47-2 N
PubChem CID	4059
ChemSpider	3919 Y
UNII	7B8PIR2954
KEGG	D02595 Y
ChEMBL	ChEMBL229128 Y
NIAID ChemDB	017830
Chemical and physical data
Formula	C10H14O3
Molar mass	182.219 g·mol−1
3D model (JSmol)	Interactive image
SMILES O(c1ccccc1C)CC(O)CO
InChI InChI=1S/C10H14O3/c1-8-4-2-3-5-10(8)13-7-9(12)6-11/h2-5,9,11-12H,6-7H2,1H3 Y Key:JWDYCNIAQWPBHD-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Mephenesin (INN) is a centrally acting muscle relaxant. It can be used as an antidote for strychnine poisoning. Mephenesin however presents with the major drawbacks of having a short duration of action and a much greater effect on the spinal cord than the brain, resulting in pronounced respiratory depression at clinical doses and therefore a very low therapeutic index. It is especially dangerous and potentially fatal in combination with alcohol and other depressants. Mephenesin was used by Bernard Ludwig and Frank Berger to synthesize meprobamate, the first tranquilizer to see widespread clinical use. Mephenesin is no longer available in North America but is used in Italy and a few other countries. Its use has largely been replaced by the related drug methocarbamol, which is better absorbed.

Mephenesin may be an NMDA receptor antagonist. Mephenesin was previously used in France as an OTC muscle relaxant called Décontractyl but was taken out of production by Sanofi Aventis and due to a French Health Ministry decree in July 2019. Mephenesin is, however, still available in Italy.

See also

• Chlorphenesin
• Guaifenesin
• Mephenoxalone
• Methocarbamol
• Prenderol

External links

• "[Severe contact dermatitis caused by mephenesin]". Ann Dermatol Venereol 123 (3): 185–7. 1996. PMID 8761781. 
• "Rigidity in rats due to radio frequency decerebration and effects of chlorpromazine and mephenesin". Gen Pharmacol 18 (1): 57–9. 1987. doi:10.1016/0306-3623(87)90170-4. PMID 3557053.