Mephenesin

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.[1] 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is no longer available in North America but is used in Italy and a few other countries.[2] Its use has largely been replaced by the related drug methocarbamol, which is better absorbed.[3]

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
PubChem CID	4059
ChemSpider	3919
UNII	7B8PIR2954
KEGG	D02595
ChEMBL	ChEMBL229128
NIAID ChemDB	017830
CompTox Dashboard (EPA)	DTXSID4023254
ECHA InfoCard	100.000.389
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 Key:JWDYCNIAQWPBHD-UHFFFAOYSA-N
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Mephenesin may be an NMDA receptor antagonist.[4]

See also

• Chlorphenesin
• Guaifenesin
• Mephenoxalone
• Methocarbamol
• Prenderol

External links

• Bachmeyer C, Blum L, Fléchet M, Duriez P, Cabane J, Imbert J (1996). "[Severe contact dermatitis caused by mephenesin]". Ann Dermatol Venereol. 123 (3): 185–7. PMID 8761781.
• Ono H, Nakamura T, Ito H, Oka J, Fukuda H (1987). "Rigidity in rats due to radio frequency decerebration and effects of chlorpromazine and mephenesin". Gen Pharmacol. 18 (1): 57–9. doi:10.1016/0306-3623(87)90170-4. PMID 3557053.

References

1. "Mephenesin". MIMS.
2. "Mephenesin". Drugs.com.
3. Huf, Ernst; et al. (1959). "Comparative Plasma Levels of Mephenesin, Mephenesin Carbamate and Methocarbamol". Proceedings of the Society for Experimental Biology and Medicine. Experimental Biology & Medicine. 102 (2): 276–7. doi:10.3181/00379727-102-25218. PMID 14403806. S2CID 37483102. Retrieved 8 January 2014.
4. Keshavarz M, Showraki A, Emamghoreishi M (2013). "Anticonvulsant Effect of Guaifenesin against Pentylenetetrazol-Induced Seizure in Mice". Iran J Med Sci. 38 (2): 116–21. PMC 3700057. PMID 23825891.