Methyldesorphine - Misplaced Pages

Chemical compound Pharmaceutical compound

Methyldesorphine
Clinical data

Other names	3-Hydroxy-6,N-dimethyl- 4,5-epoxymorphin-6-en
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs) CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name (5α)-6,17-Dimethyl-6,7-didehydro-4,5-epoxymorphinan-3-ol
CAS Number	16008-36-9
PubChem CID	5362518
ChemSpider	4515065
UNII	Y460N7W76B
KEGG	D12691
CompTox Dashboard (EPA)	DTXSID60166797
ECHA InfoCard	100.036.474
Chemical and physical data
Formula	C₁₈H₂₁NO₂
Molar mass	283.371 g·mol
3D model (JSmol)	Interactive image
SMILES CC1=CC23CC4=C52(1OC5=C(C=C4)O)CCN3C
InChI InChI=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 Key:CUFWYVOFDYVCPM-GGNLRSJOSA-N
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Methyldesorphine is an opioid analgesic. First synthesized in Germany in 1940 and patented in the US in 1952, 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. It is approximately 15 times more potent than morphine as an analgesic 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.

References

Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
US patent 2694068, Payne GB, Pfister III K, "Δ6-Desoxymorphine Compounds and Process of Producing the Same", published 1952-08-05, issued 1954-09-11, assigned to Merck & Co., Inc.
Savchuk SA, Barsegyan SS, Barsegyan IB, Kolesov GM (2008). "Chromatographic Study of Expert and Biological Samples Containing Desomorphine". Journal of Analytical Chemistry. 63 (4): 361–370. doi:10.1007/s10809-008-4009-5. S2CID 195068778.
Casy AF, Parfitt RY (1986). Opioid Analgesics, Chemistry and Receptors. New York: Plenum Press. pp. 37–38. ISBN 0-306-42130-5.
Lenz GR, Evans SM, Walters DE, Hopfinger AJ (1986). Opiates. Academic Press. p. 63. ISBN 978-0-12-443830-9.
"Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Administration, U.S. Department of Justice.