Viminol (marketed under the brandname Dividol) is an opioid analgesic developed by a team at the drug company Zambon in the 1960s. Viminol is based on the α-pyrryl-2-aminoethanol structure, unlike any other class of opioids.
|Synonyms||Dividol, viminolo, diviminol|
|AHFS/Drugs.com||International Drug Names|
|Chemical and physical data|
|Molar mass||362.94 g·mol−1|
|3D model (JSmol)|
|(what is this?)|
Viminol has both antitussive (cough suppressing) and analgesic (pain reducing) effects. Viminol has additional effects similar to other opioids including sedation and euphoria. It has six different stereoisomers which have varying properties. Four are inactive, but the 1S-(R,R)-disecbutyl isomer is a μ-opioid full agonist around 5.5 times more potent than morphine and the 1S-(S,S)-disecbutyl isomer is an antagonist. Since vimonol is supplied as a racemic mixture of isomers, the overall effect is a mixed agonist–antagonist profile similar to that of opioids such as pentazocine, although with somewhat fewer side effects.
Side effects are similar to other opioids, and can include:[medical citation needed]
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.[medical citation needed]
Later work showed that replacing the chlorine atom with an fluorine atom (2F-Viminol) or with a trifluoromethyl group produced a compound with twice the potency and half the acute toxicity. A later team at Zambon found that one isomer of a pyrrolidone analog is 318 times as potent as morphine in its analgesic activity in animal studies. A number of related compounds were also found to be active, allowing a QSAR model to be constructed.
- Uberto M. Teotino, Davide Della Bella (10 November 1970). "US Patent 3539589 - 1-(α-PYRRYL)-2-AMINO ETHANOLS". Whitefin Holding Sa.
- A. M. Contri (April 1981). "[Chromatographic separation of diastereoisomers of aminoalcohol salts and their densitometric determination]". Il Farmaco (in Italian). 36 (4): 215–222. PMID 6894429.
- J. M Neto, J.E. Murad, S.S. Monteiro (December 1977). "Psychopharmacological properties of the viminol-p-hydroxybenzoate". Revista Brasileira de Pesquisas Medicas e Biologicas. 10 (6): 361–368. PMID 609773.CS1 maint: multiple names: authors list (link)
- Davide Della Bella, Carlo Veneziani Bresso, Dario Chiarnio Monza, Uberio Maria Tiotino (31 December 1974). "US Patent 3857857 - Stereoisomers of 1(1'(-O-Chlorobenzyl)-2'-Pyrryl)-2-Disec.Butylamino-Ethanol". Whitefin Holding Sa.CS1 maint: multiple names: authors list (link)
- Jennifer E. Shook, Mary Jeanne Kallman, William L. Dewey (January 1984). "The discriminative stimulus properties of the R2 isomer of viminol". Pharmacology Biochemistry and Behavior. 20 (1): 59–62. doi:10.1016/0091-3057(84)90101-1. PMID 6546450.CS1 maint: multiple names: authors list (link)
- M. Cinelli, V. Costa, G. P. Ventresca, E. Lodola (May 1986). "Viminol R2 analgesic activity in patients with postoperative pain: comparison with pentazocine". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 24 (5): 232–235. PMID 3525423.CS1 maint: multiple names: authors list (link)
- Turkiewicz, G.; Baltieri, D. A. (2009). "Dependence on Viminol". Journal of Substance Use. 12 (4): 301. doi:10.1080/14659890701237124.
- 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.CS1 maint: multiple names: authors list (link)