Methyldesorphine

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−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC[C@H]2[C@H]3CC4=C5[C@]2([C@H]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 ;
	(what is this?) (verify)

Methyldesorphine is an opioid analgesic. First synthesized in Germany in 1940 and patented in the US in 1952,^[2] 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.^[3] It is approximately 15 times more potent than morphine as an analgesic^[4]^[5] 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.^[6]

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.

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[1] 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.

[2] 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.

[3] 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.

[4] Casy AF, Parfitt RY (1986). Opioid Analgesics, Chemistry and Receptors. New York: Plenum Press. pp. 37–38. ISBN 0-306-42130-5.

[5] Lenz GR, Evans SM, Walters DE, Hopfinger AJ (1986). Opiates. Academic Press. p. 63. ISBN 978-0-12-443830-9.

[6] "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Administration, U.S. Department of Justice.

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See also

References