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{{Short description|Opioid analgesic medicine}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 409095147 | verifiedrevid = 448072389
| IUPAC_name = 1-- 2-(di-''sec''-butylamino) ethanol | IUPAC_name = 1-pyrrol-2-yl]-2-ethanol
| image = Viminol.png | image = Viminol2DACS.svg
| width = 180 | width = 180


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Dividol
| Drugs.com = {{drugs.com|international|viminol}} | Drugs.com = {{drugs.com|international|viminol}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
Line 15: Line 17:
| legal_CA = <!-- Schedule I --> | legal_CA = <!-- Schedule I -->
| legal_UK = <!-- Unscheduled --> | legal_UK = <!-- Unscheduled -->
| legal_US = <!-- (Most likely) Schedule I --> | legal_US = <!-- Most likely Schedule I -->
| legal_status = OTC | legal_BR = A1
| legal_BR_comment = <ref>{{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=] |language=pt-BR |publication-date=2024-05-28}}</ref>
| legal_status =
| routes_of_administration = Oral | routes_of_administration = Oral


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| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion = | excretion =


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 21363-18-8 | CAS_number = 21363-18-8
| ATC_prefix = N02 | ATC_prefix = N02
| ATC_suffix = BG05 | ATC_suffix = BG05
| PubChem = 65697 | PubChem = 65697
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2104940
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = TPV54G6XBG | UNII = TPV54G6XBG
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07295 | KEGG = D07295
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 59125


<!--Chemical data--> <!--Chemical data-->
| C=21 | H=31 | Cl=1 | N=2 | O=1 | 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
| molecular_weight = 362.94 g/mol
| synonyms = Viminol, Dividol | 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 ] '''Dividol''') is an ] ] developed by a team at the drug company ] in the 1960s.<ref>{{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 }}</ref> Viminol is based on the α-pyrryl-2-aminoethanol structure, unlike any other class of opioids.<ref>{{cite journal | vauthors = Contri AM | title = | language = Italian | journal = Il Farmaco; Edizione Pratica | volume = 36 | issue = 4 | pages = 215–22 | date = April 1981 | pmid = 6894429 }}</ref><ref>{{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 }}</ref>
'''Viminol''' (marketed under the ] '''Dividol''') is an ] ] developed by the drugs company ] in the 1960s.<ref>{{ cite patent
| country = US
| number = 3539589
| status = patent
| title = 1-(α-PYRRYL)-2-AMINO ETHANOLS
| pubdate = 1967-05-08
| gdate = 1970-10-11
| inventor = Uberto M Teotino and Davide Della Bella
}}</ref> It has an unusual chemical structure that is not similar to other opioids.<ref>Contri AM. Chromatographic separation of diastereoisomers of aminoalcohol salts and their densitometric determination. (Italian). ''Il Farmaco''. 1981 Apr;36(4):215-22.</ref><ref>Neto JM, Murad JE, Monteiro SS. Psychopharmacological properties of the viminol-p-hydroxybenzoate. ''Revista Brasileira de Pesquisas Medicas e Biologicas''. 1977 Dec;10(6):361-8.</ref>


Viminol has both ] (cough suppressing) and ] (pain reducing) effects. It has six different ]s which have varying properties, with the 2-(''R'') isomer being a ] full agonist around 5 times more potent than ]<ref>US Patent 3857857 - Davide Della Bella, Carlo Veneziani Bresso, Dario Chiarnio Monza & Uberio Maria Tiotino 'Stereoisomers of 1(1'(-O-Chlorobenzyl)-2'-Pyrryl)-2-Disec.Butylamino-Ethanol'</ref>, while the 2-(''S'') isomer is an antagonist.<ref>Shook JE, Kallman MJ, Dewey WL. The discriminative stimulus properties of the R2 isomer of viminol. ''Pharmacology, Biochemistry and Behaviour''. 1984 Jan;20(1):59-62.</ref> Since vimonol is supplied as a ] mixture of isomers, the overall effect produces a mixed agonist-antagonist profile similar to that of opioids such as ], although with somewhat less side effects.<ref>Cinelli M, Costa V, Ventresca GP, Lodola E. Viminol R2 analgesic activity in patients with postoperative pain: comparison with pentazocine. ''International Journal of Clinical Pharmacology, Therapy and Toxicology''. 1986 May;24(5):232-5.</ref> Viminol has both ] (cough suppressing) and ] (pain reducing) effects. Viminol has additional effects similar to other opioids including ] and ].{{cn|date=April 2017}} It has six different ]s which have varying properties. Four are inactive, but the 1''S''-(''R'',''R'')-disecbutyl isomer is a ] full agonist around 5.5 times more potent than ] and the 1''S''-(''S'',''S'')-disecbutyl isomer is an ].<ref>{{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 }}</ref><ref>{{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 }}</ref> Since viminol is supplied as a ] mixture of isomers, the overall effect is a mixed ] profile similar to that of opioids such as ], although with somewhat fewer side effects.<ref>{{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 }}</ref>


⚫ ==Side effects==
Viminol has similar effects to other opioids, and produces analgesia, ] and ].
⚫ Side effects are similar to other opioids, and can include:{{medcn|date=April 2017}}


* ]
⚫ ==Side Effects==
⚫ * ]
⚫ Side effects are similar to other opioids, and can include:
*] * ]
⚫ * ] - can be potentially life-threatening
⚫ *]
*]
⚫ *] - can be potentially life-threatening


However, since viminol is supplied as a racemic mixture of agonist and antagonist isomers, the ] and respiratory depression tends to be less than that of μ-opioid full agonist drugs. However, since viminol is supplied as a racemic mixture of agonist and antagonist isomers, the ] and respiratory depression tends to be less than that of μ-opioid full agonist drugs.{{medcn|date=April 2017}}

] may occur.<ref>{{cite journal | doi = 10.1080/14659890701237124| title = Dependence on Viminol| journal = Journal of Substance Use| volume = 12| issue = 4| pages = 301–305| year = 2009| vauthors = Turkiewicz G, Baltieri DA | s2cid = 71184621}}</ref>

==Related compounds==
Later work showed that replacing the chlorine atom with an fluorine atom (''']''') or with a ] group produced a compound with twice the potency and half the acute toxicity.<ref>{{cite patent | url= http://www.google.com/patents/US4148907 | country = US | number = 4148907 | title = Stereoisomers of 1-(1'benzyl-2'pyrryl)-2-di-sec.-butylaminoethanol and pharmaceutical compositions comprising same | assign1 = Etablissement Viridis | gdate=10 April 1979 | inventor = Conti F }}</ref> A later team at Zambon found that one isomer of a ] ] is 318 times as potent as morphine in its analgesic activity in animal studies.<ref>{{cite patent | url=http://www.google.com/patents/US4960788 | country = US | number = 4960788 | title = Pyrrolidone-2 compounds and their use for central analgesic activity | assign1 = Zambon Group S.P.A. | gdate=2 October 1990 | inventor = Carenzi A, Chiarino D, Bella DD, Grancini GC, Veneziani C }}</ref> A number of related compounds were also found to be active, allowing a ] to be constructed.

{{Multiple image
| align = left
| direction = horizontal
| image1 = Viminol trifluoromethyl derivative.svg
| caption1 = Trifluoromethyl analog
| image2 = 2F-Viminol_structure.png
| caption2 = Fluoro analog "2F-Viminol"
| image3 = Viminol pyrrolidone derivative.svg
| caption3 = Pyrrolidone analog, ]<ref>{{cite journal | vauthors = Napoletano M, Fraire C, Grancini G, Mosotto C, Ricciardi S, Zambon C, Della Bella D | display-authors = 6 | title = Stereoselective synthesis and evaluation of all stereoisomers of Z4349, a novel and selective μ-opioid analgesic. | journal = Bioorganic & Medicinal Chemistry Letters | date = 1995 | volume = 6 | issue = 5 | pages = 589–592 | doi = 10.1016/0960-894X(95)00077-7 }}</ref>
⚫ }}
{{clear-left}}


== References == == References ==
{{reflist}} {{Reflist|2}}


{{opioids}} {{Opioidergics}}


] ]
] ]
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{{analgesic-stub}}

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