Viminol

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

Clinical data
Trade names	Dividol
Other names	Dividol, viminolo, diviminol
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	N02BG05 (WHO)
Legal status
Legal status	BR: Class A1 (Narcotic drugs)[1]
Identifiers
IUPAC name 1-[1-[(2-Chlorophenyl)methyl]pyrrol-2-yl]-2-[di(butan-2-yl)amino]ethanol
CAS Number	21363-18-8 Y
PubChem CID	65697
ChemSpider	59125 N
UNII	TPV54G6XBG
KEGG	D07295 Y
ChEMBL	ChEMBL2104940 N
CompTox Dashboard (EPA)	DTXSID00864987
ECHA InfoCard	100.040.301
Chemical and physical data
Formula	C21H31ClN2O
Molar mass	362.94 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 N Key:ZILPIBYANAFGMS-UHFFFAOYSA-N N
NY (what is this?)  (verify)

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]

Side effects

Side effects are similar to other opioids, and can include:^{[medical citation needed]}

• 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.^{[medical citation needed]}

Drug dependence may occur.^[8]

Related compounds

Later work showed that replacing the chlorine atom with a fluorine atom (2F-Viminol) 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

Fluoro analog "2F-Viminol"

Pyrrolidone analog, Z4349^[11]