Viminol

Viminol
Clinical data
Trade names	Dividol
Other names	Viminol, Dividol
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	N02BG05 (WHO) ;
Legal status
Legal status	In general: Over-the-counter (OTC);
Identifiers
	IUPAC name 1-[1-[(2-chlorophenyl)methyl]pyrrol-2-yl]-2-[di(butan-2-yl)amino]ethanol;
CAS Number	21363-18-8 ;
PubChem CID	65697;
ChemSpider	59125 ;
UNII	TPV54G6XBG;
KEGG	D07295 ;
ChEMBL	ChEMBL2104940 ;
CompTox Dashboard (EPA)	DTXSID00864987 ;
ECHA InfoCard	100.040.301
Chemical and physical data
Formula	C21H31ClN2O
Molar mass	362.94 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(C)N(C(C)CC)CC(O)C1=CC=CN1CC2=CC=CC=C2Cl;
	InChI 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 ; Key:ZILPIBYANAFGMS-UHFFFAOYSA-N ;
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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.

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:

Itching
Nausea
Sedation
Respiratory depression - can be potentially life-threatening

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

^ 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.{{cite journal}}: 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.{{cite web}}: 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.{{cite journal}}: 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.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: year (link)
^ 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.{{cite web}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite web}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[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.{{cite journal}}: CS1 maint: multiple names: authors list (link) CS1 maint: year (link)

[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.{{cite web}}: CS1 maint: multiple names: authors list (link)

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