|AHFS/Drugs.com||International Drug Names|
|ATC code||N02BG05 (WHO)|
|Chemical and physical data|
|Molar mass||362.94 g/mol|
|3D model (Jmol)||Interactive image|
|(what is this?)|
Viminol (marketed under the brandname Dividol) is an opioid analgesic developed by a team at the drugs company Zambon in the 1960s. Viminol is based on the α-Pyrryl-2-Amino-Ethanol structure, unlike any other class of opioids.
Viminol has both antitussive (cough suppressing) and analgesic (pain reducing) effects. It has six different stereoisomers which have varying properties. 4 are inactive, the 1S-(R,R)-disecbutyl isomer being a μ-opioid full agonist around 5.5 times more potent than morphine while the 1S-(S,S)-disecbutyl isomer is an antagonist. Since vimonol is supplied as a racemic mixture of isomers, the overall effect produces a mixed agonist–antagonist profile similar to that of opioids such as pentazocine, although with somewhat fewer side effects.
Later work showed that replacing the -Cl moiety with an -F or a -CF3 produced a compound with twice the potency and half the acute toxicity. A later team at Zambon modified the pyrrolidine with a pyrrolidone could produce an analogue some 318x morphine in its analgesic activity in animal studies (the latter overlays beta hydroxy fentanyl). A number of related compounds were found to be active allowing a QSAR to be constructed.
Side effects are similar to other opioids, and can include:
However, since viminol is supplied as a racemic mixture of agonist and antagonist isomers, the abuse potential and respiratory depression tends to be less than that of μ-opioid full agonist drugs.
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- Franco Conti (10 April 1979). "US Patent 4148907 - Stereoisomers of 1-(1'benzyl-2'pyrryl)-2-di-sec.-butylaminoethanol and pharmaceutical compositions comprising same". Etablissement Viridis.
- Angelo Carenzi, Dario Chiarino, Davide Della Bella, Gian Carlo Grancini, Carlo Veneziani (2 October 1990). "US Patent 4960788 - Pyrrolidone-2 compounds and their use for central analgesic activity". Zambon Group S.P.A.