Dimepheptanol

{{Short description|Synthetic opioid analgesic drug}} {{Distinguish|Oxymetholone}} {{Drugbox | verifiedrevid = 448002978 | IUPAC_name = 6-(dimethylamino)-4,4-diphenylheptan-3-ol | image = Dimepheptanol.svg | image_class = skin-invert-image | width = 160

| tradename = | pregnancy_AU =  | pregnancy_US =  | 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_UK =  | legal_US = Schedule I | legal_DE = Anlage I | routes_of_administration =

| CAS_number = 545-90-4 | ATC_prefix = None | ATC_suffix = | PubChem = 28397 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB19094 | ChEMBL = 368591 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = NNB4I01PA7 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D12673 | ChEBI = 135332 | ChemSpiderID = 26418

| C = 21 | H = 29 | N = 1 | O = 1 | smiles = CCC(C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2)O | 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 | StdInChIKey = QIRAYNIFEOXSPW-UHFFFAOYSA-N }}

'''Dimepheptanol''' (INN; '''Amidol''', '''Pangerin'''), also known as '''methadol''' or '''racemethadol''', is a synthetic opioid analgesic related to methadone. It has similar effects to other opioids, including analgesia, sedation and euphoria, as well as side effects like itching, nausea and respiratory depression.

Dimepheptanol is a mixture of two isomers, alphamethadol (α-methadol) and betamethadol (β-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> These are also available separately, and this drug has three separate entries in many national and international lists of illegal drugs, which refer to the racemic mixture dimepheptanol, and the two optical isomers.<ref name="Crime2006" /> Each of these isomers is itself a mixture of two isomers, and so there are in fact four isomers of dimepheptanol in total; L-α-methadol, D-α-methadol, L-β-methadol and D-β-methadol.<ref name="Crime2006" />

class=skin-invert-image|400px

The isomer L-α-methadol is the active metabolite of the long-acting opioid substitute drug levomethadyl acetate (LAAM), and has been used much more widely than β-methadol or the racemic mixture of dimepheptanol.

Both in US Controlled Substances Act 1970 Schedule I, the two isomers both have annual manufacturing quotas of 2 grammes and the ACSCNs of 9605 for alphamethadol and 9609 for betamethadol.

==See also== * Alphamethadol * Betamethadol * Acetylmethadol * Noracymethadol

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

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