Methopholine
Encyclopedia
Methopholine is an opioid
analgesic
drug discovered in the 1950s by a team of Swiss researchers at Hoffmann-La Roche.
Methopholine is an isoquinoline
derivative which is not structurally related to most other opioids. It has around the same efficacy as an analgesic as codeine
, and was evaluated for the treatment of postoperative pain. Methopholine tablets were marketed in the United States under the brand name of Versidyne, but the drug was withdrawn from the market in 1965 due to the occurrence of ophthalmic
side-effects and the discovery that it could produce corneal opacities in dogs.
Methopholine has two enantiomer
s, with the levo (R) enantiomer being the active form, around 3x the potency of codeine, and the (S) enantiomer being inactive. Analogues where the 4'-chloro group has been replaced by other groups have also been tested, the fluoro derivative being slightly more potent than chloro, and the nitro derivative being most potent of all, with the racemic 4'-nitromethopholine being around 20x the potency of codeine.
Opioid
An opioid is a psychoactive chemical that works by binding to opioid receptors, which are found principally in the central and peripheral nervous system and the gastrointestinal tract...
analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
drug discovered in the 1950s by a team of Swiss researchers at Hoffmann-La Roche.
Methopholine is an isoquinoline
Isoquinoline
Isoquinoline is a heterocyclic aromatic organic compound. It is a structural isomer of quinoline. Isoquinoline and quinoline are benzopyridines, which are composed of a benzene ring fused to a pyridine ring. In a broader sense, the term isoquinoline is used to make reference to isoquinoline...
derivative which is not structurally related to most other opioids. It has around the same efficacy as an analgesic as codeine
Codeine
Codeine or 3-methylmorphine is an opiate used for its analgesic, antitussive, and antidiarrheal properties...
, and was evaluated for the treatment of postoperative pain. Methopholine tablets were marketed in the United States under the brand name of Versidyne, but the drug was withdrawn from the market in 1965 due to the occurrence of ophthalmic
Ophthalmic
Ophthalmic means pertaining to the eye, and can refer to:* Ophthalmology* Ophthalmic nerve* Ophthalmic artery* Ophthalmic veins* Ophthalmic drug administration, as with eye dropsSee also:* Ophthalmia...
side-effects and the discovery that it could produce corneal opacities in dogs.
Methopholine has two enantiomer
Enantiomer
In chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
s, with the levo (R) enantiomer being the active form, around 3x the potency of codeine, and the (S) enantiomer being inactive. Analogues where the 4'-chloro group has been replaced by other groups have also been tested, the fluoro derivative being slightly more potent than chloro, and the nitro derivative being most potent of all, with the racemic 4'-nitromethopholine being around 20x the potency of codeine.