Methyldesorphine: Difference between revisions

{{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

| 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 }}</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:Mu-opioid receptor agonists]]

[[Category:Opioids]]

[[Category:Phenols]]