Mephenesin

Mephenesin

Systematic (IUPAC) name
3-(2-methylphenoxy)propane-1,2-diol
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	59-47-2
ATC code	M03BX06 (WHO)
PubChem	CID 4059
ChemSpider	3919
UNII	7B8PIR2954
KEGG	D02595
ChEMBL	CHEMBL229128
NIAID ChemDB	017830
Chemical data
Formula	C10H14O3
Molar mass	182.216 g/mol
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 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 Dr. Bernard Ludwig and Dr. Frank Milan Berger to synthesize meprobamate, the first tranquilizer to see widespread clinical use. Mephenesin is no longer available in North America but is used in France, Italy and a few other countries.^[2] Its use has largely been replaced by the related drug methocarbamol, which is better absorbed^[3]

Mephenesin may be an NMDA receptor antagonist.^[4]

See also

• Chlorphenesin
• Guaifenesin
• Mephenoxalone
• Methocarbamol

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. "Comparative Plasma Levels of Mephenesin, Mephenesin Carbamate and Methocarbamol". Experimental Biology & Medicine. 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.