Viminol

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Viminol
Viminol2DACS.svg
Systematic (IUPAC) name
1-[1-[(2-chlorophenyl)methyl]pyrrol-2-yl]-2-[di(butan-2-yl)amino]ethanol
Clinical data
Trade names Dividol
AHFS/Drugs.com International Drug Names
Routes of
administration
Oral
Legal status
Legal status
  • OTC
Identifiers
CAS Number 21363-18-8 YesY
ATC code N02BG05 (WHO)
PubChem CID 65697
ChemSpider 59125 N
UNII TPV54G6XBG YesY
KEGG D07295 YesY
ChEMBL CHEMBL2104940 N
Synonyms Viminol, Dividol
Chemical data
Formula C21H31ClN2O
Molar mass 362.94 g/mol
 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[edit]

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[edit]

  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.