Viminol

Viminol
Clinical data
Trade namesDividol
Other namesDividol, viminolo, diviminol
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Legal status
Legal status
Identifiers
  • 1-[1-[(2-Chlorophenyl)methyl]pyrrol-2-yl]-2-[di(butan-2-yl)amino]ethanol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.040.301 Edit this at Wikidata
Chemical and physical data
FormulaC21H31ClN2O
Molar mass362.94 g·mol−1
3D model (JSmol)
  • CCC(C)N(C(C)CC)CC(O)C1=CC=CN1CC2=CC=CC=C2Cl
  • InChI=1S/C21H31ClN2O/c1-5-16(3)24(17(4)6-2)15-21(25)20-12-9-13-23(20)14-18-10-7-8-11-19(18)22/h7-13,16-17,21,25H,5-6,14-15H2,1-4H3 ☒N
  • Key:ZILPIBYANAFGMS-UHFFFAOYSA-N ☒N
 ☒NcheckY (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 viminol 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]

  1. ^ Anvisa (2024-05-28). "RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União. Archived from the original on 2024-09-25. Retrieved 2024-09-25.
  2. ^ US 3539589, Teotino UM, Bella DD, "1-(α-Pyrryl)-2-amino Ethanols", issued 10 November 1970, assigned to Whitefin Holding SA 
  3. ^ Contri AM (April 1981). "[Chromatographic separation of diastereoisomers of aminoalcohol salts and their densitometric determination]". Il Farmaco; Edizione Pratica (in Italian). 36 (4): 215–22. PMID 6894429.
  4. ^ Neto JM, Murad JE, Monteiro SS (December 1977). "Psychopharmacological properties of the viminol-p-hydroxybenzoate". Revista Brasileira de Pesquisas Medicas e Biologicas. 10 (6): 361–8. PMID 609773.
  5. ^ US 3857857, Della D, Bella CV, Monza DC, Tiotino UM, "Stereoisomers of 1(1'(-O-Chlorobenzyl)-2'-Pyrryl)-2-Disec.Butylamino-Ethanol", issued 31 December 1974, assigned to Whitefin Holding SA 
  6. ^ Shook JE, Kallman MJ, Dewey WL (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. S2CID 11418389.
  7. ^ Cinelli M, Costa V, Ventresca GP, Lodola E (May 1986). "Viminol R2 analgesic activity in patients with postoperative pain: comparison with pentazocine". International Journal of Clinical Pharmacology, Therapy, and Toxicology. 24 (5): 232–5. PMID 3525423.