Zenazocine

Zenazocine
Clinical data
ATC code	None;
Legal status
Legal status	In general: non-regulated;
Identifiers
	IUPAC name 1-[(1S,9R)-4-hydroxy-1,10,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-13-yl]-6-methyl-3-heptanone;
CAS Number	74559-85-6;
PubChem CID	9885108;
ChemSpider	8060782;
UNII	8WIL6L9U01;
CompTox Dashboard (EPA)	DTXSID20996077 ;
Chemical and physical data
Formula	C23H35NO2
Molar mass	357.538 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(CCC(C)C)CCC3([C@@H]2N(CC[C@]3(c1c(ccc(O)c1)C2)C)C)C;
	InChI InChI=1S/C23H35NO2/c1-16(2)6-8-18(25)10-11-23(4)21-14-17-7-9-19(26)15-20(17)22(23,3)12-13-24(21)5/h7,9,15-16,21,26H,6,8,10-14H2,1-5H3/t21-,22 ,23?/m1/s1; Key:JZFZEWWOIOYBTQ-AXWGZAFASA-N;

Zenazocine (INN; WIN-42,964) is an opioid analgesic of the benzomorphan family which made it to phase II clinical trials before development was ultimately halted and it was never marketed.^[1]^[2] It acts as a partial agonist of the μ- and δ-opioid receptors, with less intrinsic activity at the former receptor and more at the latter receptor (hence, it behaves more antagonistically at the former and more agonistically at the latter), and produces antinociceptive effects in animal studies.^[1]

References

^ ^a ^b Ward SJ, Pierson AK, Michne WF (February 1985). "Pharmacological profiles of tonazocine (Win 42156) and zenazocine (Win 42964)". Neuropeptides. 5 (4–6): 375–8. doi:10.1016/0143-4179(85)90032-0. PMID 2860595. S2CID 20674308.
^ Cotton R, James R (1985). "Chapter 3. Analgesics, Opioids and Opioid Receptors". In Bailey DM (ed.). Annual Reports in Medicinal Chemistry. Vol. 20. Academic Press. pp. 21–30. doi:10.1016/S0065-7743(08)61029-5. ISBN 978-0-12-040520-6.