viminol

{{Short description|Opioid analgesic medicine}}

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 448072389

| IUPAC_name = 1-[1-[(2-Chlorophenyl)methyl]pyrrol-2-yl]-2-[di(butan-2-yl)amino]ethanol

| image = Viminol2DACS.svg

| image_class = skin-invert-image

| width = 180

| tradename = Dividol

| Drugs.com = {{drugs.com|international|viminol}}

| pregnancy_AU =

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| legal_US =

| legal_BR = A1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2024-05-28 |title=RDC Nº 877 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 877 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-da-diretoria-colegiada-anvisa-n-877-de-28-de-maio-de-2024-562758149 |url-status=live |archive-url=https://web.archive.org/web/20240925040323/https://www.in.gov.br/en/web/dou/-/resolucao-da-diretoria-colegiada-anvisa-n-877-de-28-de-maio-de-2024-562758149 |archive-date=2024-09-25 |access-date=2024-09-25 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2024-05-28}}

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| routes_of_administration = Oral

| bioavailability =

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| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 21363-18-8

| ATC_prefix = N02

| ATC_suffix = BG05

| PubChem = 65697

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104940

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = TPV54G6XBG

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07295

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 59125

| C=21 | H=31 | Cl=1 | N=2 | O=1

| smiles = CCC(C)N(C(C)CC)CC(O)C1=CC=CN1CC2=CC=CC=C2Cl

| synonyms = Dividol, viminolo, diviminol

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZILPIBYANAFGMS-UHFFFAOYSA-N

|drug_name=|alt=|caption=|type=|MedlinePlus=|licence_EU=|licence_US=}}

Viminol (marketed under the brandname Dividol) is an opioid analgesic developed by a team at the drug company Zambon in the 1960s.{{cite patent | url=http://www.google.com/patents/US3539589 | country = US | number = 3539589 | title = 1-(α-Pyrryl)-2-amino Ethanols | assign1 = Whitefin Holding SA | gdate=10 November 1970 | inventor = Teotino UM, Bella DD }} Viminol is based on the α-pyrryl-2-aminoethanol structure, unlike any other class of opioids.{{cite journal | vauthors = Contri AM | title = [Chromatographic separation of diastereoisomers of aminoalcohol salts and their densitometric determination] | language = Italian | journal = Il Farmaco; Edizione Pratica | volume = 36 | issue = 4 | pages = 215–22 | date = April 1981 | pmid = 6894429 }}{{cite journal | vauthors = Neto JM, Murad JE, Monteiro SS | title = Psychopharmacological properties of the viminol-p-hydroxybenzoate | journal = Revista Brasileira de Pesquisas Médicas e Biológicas | volume = 10 | issue = 6 | pages = 361–8 | date = December 1977 | pmid = 609773 }}

Viminol has both antitussive (cough suppressing) and analgesic (pain reducing) effects. Viminol has additional effects similar to other opioids including sedation and euphoria.{{cn|date=April 2017}} 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.{{cite patent | url=https://www.google.com/patents/US3857857 | country = US | number = 3857857 | title = Stereoisomers of 1(1'(-O-Chlorobenzyl)-2'-Pyrryl)-2-Disec.Butylamino-Ethanol | assign1 = Whitefin Holding SA | gdate=31 December 1974 | inventor = Della D, Bella CV, Monza DC, Tiotino UM }}{{cite journal | vauthors = Shook JE, Kallman MJ, Dewey WL | title = The discriminative stimulus properties of the R2 isomer of viminol | journal = Pharmacology, Biochemistry, and Behavior | volume = 20 | issue = 1 | pages = 59–62 | date = January 1984 | pmid = 6546450 | doi = 10.1016/0091-3057(84)90101-1 | s2cid = 11418389 }} 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.{{cite journal | vauthors = Cinelli M, Costa V, Ventresca GP, Lodola E | title = Viminol R2 analgesic activity in patients with postoperative pain: comparison with pentazocine | journal = International Journal of Clinical Pharmacology, Therapy, and Toxicology | volume = 24 | issue = 5 | pages = 232–5 | date = May 1986 | pmid = 3525423 }}