Etorphine

Etorphine
Clinical data
AHFS/Drugs.com	International Drug Names
ATCvet code	QN02AE90 (WHO) ;
Legal status
Legal status	AU: S9 (Prohibited substance); BR: Class F1 (Prohibited narcotics); CA: Schedule I; DE: Anlage III (Special prescription form required); UK: Class A; US: Schedule I and Schedule II; UN: Narcotic Schedules I and IV; EU: List I (Netherlands);
Identifiers
	IUPAC name (5α,6β,14β,18R)-18-[(2R)-2-Hydroxy-2-pentanyl]-6-methoxy-17-methyl-7,8-didehydro-18,19-dihydro-4,5-epoxy-6,14-ethenomorphinan-3-ol;
CAS Number	14521-96-1 ;
PubChem CID	644209;
IUPHAR/BPS	1625;
DrugBank	DB01497 ;
ChemSpider	559231 ;
UNII	42M2Y6NU9O;
KEGG	D07937 ;
ChEBI	CHEBI:4912 ;
ChEMBL	ChEMBL140050;
CompTox Dashboard (EPA)	DTXSID40878669 DTXSID40878667, DTXSID40878669 ;
ECHA InfoCard	100.035.017
Chemical and physical data
Formula	C25H33NO4
Molar mass	411.542 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@](CCC)(O)[C@H]1C[C@]23C=C[C@]1(OC)[C@@H]4Oc5c(O)ccc6C[C@H]2N(C)CC[C@]43c65;
	InChI InChI=1S/C25H33NO4/c1-5-8-22(2,28)17-14-23-9-10-25(17,29-4)21-24(23)11-12-26(3)18(23)13-15-6-7-16(27)20(30-21)19(15)24/h6-7,9-10,17-18,21,27-28H,5,8,11-14H2,1-4H3/t17-,18-,21-,22-,23-,24+,25-/m1/s1 ; Key:CAHCBJPUTCKATP-FAWZKKEFSA-N ;
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Etorphine (M99) is a semi-synthetic opioid possessing an analgesic potency approximately 1,000–3,000 times that of morphine.^[1] It was first prepared in 1960 from oripavine, which does not generally occur in opium poppy extract but rather the related plants Papaver orientale and Papaver bracteatum.^[2] It was reproduced in 1963 by a research group at MacFarlan Smith in Edinburgh, led by Kenneth Bentley.^[3] It can be produced from thebaine.^[4]

^ Bentley KW, Hardy DG (June 1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. 3. Alcohols of the 6,14-endo-ethenotetrahydrooripavine series and derived analogs of N-allylnormorphine and -norcodeine". Journal of the American Chemical Society. 89 (13): 3281–3292. doi:10.1021/ja00989a032. PMID 6042764.
^ Aggrawal A (1995). "Chapter 3 Opium: the king of narcotics". Narcotic Drugs. New Delhi: National Book Trust. pp. xvi+161. ISBN 81-237-1383-5.
^ Bentley KW, Hardy DG (1963). "New potent analgesics in the morphine series". Proceedings of the Chemical Society. 220: 189–228. doi:10.1039/PS9630000189.
^ Huang XR, Srimurugan S, Lee GH, Chen C (February 2011). "A Facile Synthesis and Structural Verification of Etorphine and Dihydroetorphine from Codeine". Journal of the Chinese Chemical Society. 58 (1): 101–107. doi:10.1002/jccs.201190048. ISSN 0009-4536.

[pmid6042764-1] Bentley KW, Hardy DG (June 1967). "Novel analgesics and molecular rearrangements in the morphine-thebaine group. 3. Alcohols of the 6,14-endo-ethenotetrahydrooripavine series and derived analogs of N-allylnormorphine and -norcodeine". Journal of the American Chemical Society. 89 (13): 3281–3292. doi:10.1021/ja00989a032. PMID 6042764.

[urlOpium:_the_king_of_narcotics-2] Aggrawal A (1995). "Chapter 3 Opium: the king of narcotics". Narcotic Drugs. New Delhi: National Book Trust. pp. xvi+161. ISBN 81-237-1383-5.

[3] Bentley KW, Hardy DG (1963). "New potent analgesics in the morphine series". Proceedings of the Chemical Society. 220: 189–228. doi:10.1039/PS9630000189.

[4] Huang XR, Srimurugan S, Lee GH, Chen C (February 2011). "A Facile Synthesis and Structural Verification of Etorphine and Dihydroetorphine from Codeine". Journal of the Chinese Chemical Society. 58 (1): 101–107. doi:10.1002/jccs.201190048. ISSN 0009-4536.

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