Viminol

Viminol
Clinical data
Trade names Dividol
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
ATC code N02BG05 (WHO)
Legal status
Legal status
  • OTC
Identifiers
Synonyms Viminol, Dividol
CAS Number 21363-18-8 YesY
PubChem (CID) 65697
ChemSpider 59125 N
UNII TPV54G6XBG YesY
KEGG D07295 YesY
ChEMBL CHEMBL2104940 N
ECHA InfoCard 100.040.301
Chemical and physical data
Formula C21H31ClN2O
Molar mass 362.94 g/mol
3D model (Jmol) Interactive image
 NYesY (what is this?)  (verify)

Viminol (marketed under the brandname Dividol) is an opioid analgesic developed by a team at the drugs company Zambon in the 1960s.[1] Viminol is based on the α-Pyrryl-2-Amino-Ethanol structure, unlike any other class of opioids.[2][3]

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.[4][5] 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.[6]

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.[7] 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).[8] A number of related compounds were found to be active allowing a QSAR to be constructed.

Alt
Trifluoromethyl derivative
Alt
Pyrrolidone derivative

Viminol has similar effects to other opioids, and produces analgesia, sedation and euphoria.

Side Effects

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.

References

  1. Uberto M. Teotino, Davide Della Bella (10 November 1970). "US Patent 3539589 - 1-(α-PYRRYL)-2-AMINO ETHANOLS". Whitefin Holding Sa.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.
  8. 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.
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