{{Short description|Chemical compound}} {{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 411440631 | IUPAC_name = (5α)-6,17-Dimethyl-6,7-didehydro-4,5-epoxymorphinan-3-ol | image = Methyldesorphine.svg | image_class = skin-invert-image | width = 180
<!--Clinical data--> | 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 =
<!--Pharmacokinetic data--> | bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 16008-36-9 | ATC_prefix = none | ATC_suffix = | PubChem = 5362518 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | UNII_Ref = {{fdacite|changed|FDA}} | UNII = Y460N7W76B | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 4515065 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D12691
<!--Chemical data--> | C=18 | H=21 | N=1 | O=2 | smiles = CC1=CC[C@H]2[C@H]3CC4=C5[C@]2([C@H]1OC5=C(C=C4)O)CCN3C | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C18H21NO2/c1-10-3-5-12-13-9-11-4-6-14(20)16-15(11)18(12,17(10)21-16)7-8-19(13)2/h3-4,6,12-13,17,20H,5,7-9H2,1-2H3/t12-,13+,17-,18-/m0/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = CUFWYVOFDYVCPM-GGNLRSJOSA-N | synonyms = <small>3-Hydroxy-6,''N''-dimethyl-4,5-epoxymorphin-6-en</small> }}
'''Methyldesorphine''' is an opioid analgesic. First synthesized in Germany in 1940 and patented in the US in 1952,<ref>{{cite patent | country = US | number = 2694068 | status = patent | title = Δ6-Desoxymorphine Compounds and Process of Producing the Same | pubdate = 1952-08-05 | gdate = 1954-09-11 | inventor = Payne GB, Pfister III K | assign1 = Merck & Co., Inc. }}</ref> it has a high potential for abuse as with any potent opioid agonist, and is sometimes found along with desomorphine as a component of the home-made opioid mixture known as "Krokodil" used in Russia and the neighboring former Soviet republics.<ref>{{cite journal | vauthors = Savchuk SA, Barsegyan SS, Barsegyan IB, Kolesov GM | s2cid = 195068778 | title = Chromatographic Study of Expert and Biological Samples Containing Desomorphine | doi = 10.1007/s10809-008-4009-5 | journal = Journal of Analytical Chemistry | volume = 63 | issue = 4 | pages = 361–370| year = 2008 | doi-access = free }}</ref> It is approximately 15 times more potent than morphine as an analgesic,<ref>{{ cite book | vauthors = Casy AF, Parfitt RY | title = Opioid Analgesics, Chemistry and Receptors | year = 1986 | publisher = Plenum Press | location = New York | pages = 37–38 | isbn = 0-306-42130-5 }}</ref><ref>{{cite book | vauthors = Lenz GR, Evans SM, Walters DE, Hopfinger AJ | title = Opiates | year = 1986 | page = 63 | publisher = Academic Press | isbn = 978-0-12-443830-9 }}</ref> but if the 6-7 bond is saturated, the β isomer is some 50 times more potent than morphine.
Methyldesorphine is listed as a Schedule I Narcotic controlled substance under the Controlled Substances Act 1970 in the United States with a DEA ACSCN of 9302 and zero annual aggregate manufacturing quota. The free base conversion ratio of the hydrochloride is 0.89.<ref>{{cite web | title = Conversion Factors for Controlled Substances | url = http://www.deadiversion.usdoj.gov/quotas/conv_factor/index.html | work = Diversion Control Division | publisher = Drug Enforcement Administration, U.S. Department of Justice }}</ref>
== See also == * 6-Methylenedihydrodesoxymorphine
== References == {{Reflist|2}}
{{Opioidergics}}
Category:4,5-Epoxymorphinans Category:Ethers Category:Mu-opioid receptor agonists Category:Opioids Category:Hydroxyarenes Category:Semisynthetic opioids
{{analgesic-stub}}