Viminol Article

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Viminol
Viminol2DACS.svg
Clinical data
Trade namesDividol
SynonymsDividol, viminolo, diviminol
AHFS/ Drugs.com International Drug Names
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • US: Not FDA approved
  • prescription without retention (Outside SMS/MS Ordnance 344/98)/ [1]
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.040.301 Edit this at Wikidata
Chemical and physical data
FormulaC21H31ClN2O
Molar mass362.94 g·mol−1
3D model ( JSmol)
 ☒N☑Y  (what is this?)   (verify)

Viminol (marketed under the brandname Dividol) is an opioid analgesic developed by a team at the drug company Zambon in the 1960s. [2] Viminol is based on the α-pyrryl-2-aminoethanol structure, unlike any other class of opioids. [3] [4]

Viminol has both antitussive (cough suppressing) and analgesic (pain reducing) effects. Viminol has additional effects similar to other opioids including sedation and euphoria.[ citation needed] 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. [5] [6] 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. [7]

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]

Drug dependence may occur. [8]

Related compounds

Later work showed that replacing the chlorine atom with an fluorine atom or with a trifluoromethyl group produced a compound with twice the potency and half the acute toxicity. [9] 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. [10] A number of related compounds were also found to be active, allowing a QSAR model to be constructed.

Trifluoromethyl analog
Pyrrolidone analog

References

  1. ^ http://www.anvisa.gov.br/datavisa/fila_bula/frmVisualizarBula.asp?pNuTransacao=5075802015&pIdAnexo=2670717
  2. ^ Uberto M. Teotino, Davide Della Bella (10 November 1970). "US Patent 3539589 - 1-(α-PYRRYL)-2-AMINO ETHANOLS". Whitefin Holding Sa.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ Turkiewicz, G.; Baltieri, D. A. (2009). "Dependence on Viminol". Journal of Substance Use. 12 (4): 301. doi: 10.1080/14659890701237124.
  9. ^ 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.
  10. ^ 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.