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mephenesin
Sign in to saveMephenesin (INN), also called myanesin, 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 the inspiration for the synthesis of a derivative of 1,3-propanediol, meprobamate, by Bern
In the Vinony graph
Vinony's link graph records 347 inbound references to mephenesin, and connects out to neuromuscular-blocking drug, metocurine chloride and medication.
It is catalogued under topics including Chemical pages without DrugBank identifier, Diols and Drugboxes which contain changes to verified fields.
Vinony links it to 12 Wikipedia language editions.
Chemical data
- Formula
- C10H14O3
- Molecular weight
- 182.22 g/mol
- IUPAC name
- 3-(2-methylphenoxy)propane-1,2-diol
- SMILES
- CC1=CC=CC=C1OCC(CO)O
- InChIKey
- JWDYCNIAQWPBHD-UHFFFAOYSA-N
- XLogP
- 1.4
- Polar surface area
- 49.7 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
608 papers- Fatal mephenesin intoxication.Journal of forensic sciences · 2007
- Mephenesin poisoning.Lancet (London, England) · 1960
- Mephenesin in rheumatism.Lancet (London, England) · 1954
- Some studies on peripheral actions of mephenesin, methocarbamol and diazepam.British journal of pharmacology · 1968
- Conformational flexibility of mephenesin.The journal of physical chemistry. B · 2014
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 182.094
Show 6 more facts
- chemical formula
- C₁₀H₁₄O₃
- canonical SMILES
- CC1=CC=CC=C1OCC(CO)O
- melting point
- 70
- found in taxon
- Foeniculum vulgare
- has characteristic
- bitterness
- Commons category
- Mephenesin
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- See also
- External links
- References
Mephenesin (INN), also called myanesin, 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 the inspiration for the synthesis of a derivative of 1,3-propanediol, meprobamate, by Bernard Ludwig and Frank Berger,. 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.
Excerpted from Wikipedia’s “mephenesin” article, available under the CC BY-SA 4.0 licence.