Tonazocine

Tonazocine
Clinical data
ATC code	None;
Legal status
Legal status	In general: non-regulated;
Identifiers
	IUPAC name 1-[(2S,6R,11S)-8-hydroxy-3,6,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-11-yl]octan-3-one;
CAS Number	71461-18-2;
PubChem CID	72177;
ChemSpider	65150;
UNII	J356A16LLK;
Chemical and physical data
Formula	C23H35NO2
Molar mass	357.538 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(CCCCC)CC[C@@]3([C@H]2N(CC[C@@]3(c1c(ccc(O)c1)C2)C)C)C;
	InChI InChI=1S/C23H35NO2/c1-5-6-7-8-18(25)11-12-23(3)21-15-17-9-10-19(26)16-20(17)22(23,2)13-14-24(21)4/h9-10,16,21,26H,5-8,11-15H2,1-4H3/t21-,22+,23+/m0/s1; Key:UDNUCVYCLQJJBY-YTFSRNRJSA-N;

Tonazocine (WIN-42,156) is an opioid analgesic of the benzomorphan family which made it to phase II clinical trials for the treatment of postoperative pain,^[1] but development was apparently ceased and ultimately it was never marketed. Tonazocine is a partial agonist at both the mu-opioid and delta-opioid receptors, but acting more like an antagonist at the former and more like an agonist at the latter.^[2]^[3] It lacks most of the side effects of other opioids such as adverse effects on the cardiovascular system and respiratory depression, but it can cause sedation (although to a lesser degree of typical opioids), and in some patients it may induce hallucinations (probably via binding to and activating the κ-opioid receptor).^[4]

References