Betamethadol

{{Short description|Synthetic opioid analgesic drug}} {{technical|date=September 2017}} {{Drugbox | IUPAC_name = (3''S'',6''R'')-6-(dimethylamino)-4,4-diphenyl-3-heptanol | image = Betamethadol.svg | image_class = skin-invert-image | alt = Skeletal formula | width = 190 | image2 = Betamethadol molecule ball.png | image_class2 = bg-transparent | alt2 = Ball-and-stick model of betamethadol | CAS_number = 17199-55-2 | CAS_supplemental = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 57ANR1Z628 | ATC_prefix = None | ATC_suffix = | PubChem = 10064061 | KEGG = D12675 | ChEMBL = 162243 | ChemSpiderID = 8239601 | C = 21 | H = 29 | N = 1 | O = 1 | smiles = O[C@H](C(c1ccccc1)(c2ccccc2)C[C@H](N(C)C)C)CC | StdInChI = 1S/C21H29NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17,20,23H,5,16H2,1-4H3/t17-,20+/m1/s1 | StdInChIKey = QIRAYNIFEOXSPW-XLIONFOSSA-N | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion = | pregnancy_category = | legal_AU = S9 | legal_BR = A1 | legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}</ref> | legal_CA = Schedule I | legal_US = Schedule I | legal_DE = Anlage I | dependency_liability = High | routes_of_administration = }}

'''Betamethadol''' (INN), or '''β-methadol''', also known as '''betametadol''', is a synthetic opioid analgesic.<ref name="Macdonald1997">{{cite book | author = F.. Macdonald | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=A0THacd46ZsC&pg=PA1294 | accessdate = 15 May 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 1294}}</ref> It is an isomer of dimepheptanol (methadol), the other being alphamethadol (α-methadol).<ref name="Crime2006">{{cite book | author = United Nations Office on Drugs and Crime | title = Dictionnaire Multilingue Des Stupéfiants Et Des Substances Psychotropes Placés Sous Contrôle International | url = https://books.google.com/books?id=RPAphv7h4-IC&pg=PA103 | accessdate = 15 May 2012 | year = 2006 | publisher = United Nations Publications | isbn = 978-92-1-048117-5 | page = 103}}</ref> Betamethadol is composed of two isomers itself, <small>L</small>-β-methadol, and <small>D</small>-β-methadol.<ref name="Crime2006" /> Based on structure-activity relationships it can be inferred that both isomers are likely to be active as opioid analgesics, similarly to those of betacetylmethadol (β-acetylmethadol).<ref name="pmid12373424">{{cite journal | vauthors = Newman JL, Vann RE, May EL, Beardsley PM | title = Heroin discriminative stimulus effects of methadone, LAAM and other isomers of acetylmethadol in rats | journal = Psychopharmacology | volume = 164 | issue = 1 | pages = 108–14 |date=October 2002 | pmid = 12373424 | doi = 10.1007/s00213-002-1198-8 | s2cid = 19815273 }}</ref>

== See also == * Dimepheptanol * Alphamethadol * Betacetylmethadol

== References == {{reflist}}

Category:Secondary alcohols Category:Dimethylamino compounds Category:Analgesics Category:Mu-opioid receptor agonists Category:Synthetic opioids