Quadazocine

Quadazocine
Clinical data

ATC code	None
Identifiers
IUPAC name 1-cyclopentyl-5-[(1S,9R)-4-hydroxy-1,10,13-trimethyl-10-azatricyclo[7.3.1.0^2,7]trideca-2,4,6-trien-13-yl]-3-pentanone
CAS Number	71276-43-2^Y
PubChem CID	115077
ChemSpider	102983
UNII	X9BMD58553
CompTox Dashboard (EPA)	DTXSID30990187
Chemical and physical data
Formula	C₂₅H₃₇NO₂
Molar mass	383.576 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(CCC1CCCC1)CCC4([C@@H]3N(CC[C@]4(c2c(ccc(O)c2)C3)C)C)C
InChI InChI=1S/C25H37NO2/c1-24-14-15-26(3)23(16-19-9-11-21(28)17-22(19)24)25(24,2)13-12-20(27)10-8-18-6-4-5-7-18/h9,11,17-18,23,28H,4-8,10,12-16H2,1-3H3/t23-,24+,25?/m1/s1 Key:LOYWOYCPSWPKFH-CSIQULDISA-N

Quadazocine (WIN-44,441) is an opioid antagonist of the benzomorphan family which is used in scientific research.^[1] It acts as a silent antagonist at all three of the major opioid receptors—μ, κ, and δ,^[1]^[2] but with a significant preference in affinity for the μ receptor and the κ₂ subtype.^[3]^[4]^[5] As such, it has been touted as a "κ₂-selective" antagonist, though this is not entirely accurate on account of its similar affinity for the μ receptor.^[3]^[5] As would be expected, quadazocine reverses the effects (e.g., analgesia) of opioid agonists like morphine and fentanyl in animals.^[1]^[6]

References

^ ^a ^b ^c Ward SJ, Pierson AK, Michne WF (1983). "Multiple opioid receptor profile in vitro and activity in vivo of the potent opioid antagonist Win 44,441-3". Life Sciences. 33 (Suppl 1): 303–6. doi:10.1016/0024-3205(83)90503-9. PMID 6319882.
^ Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J (2006). "Pharmacological profiles of opioid ligands at kappa opioid receptors". BMC Pharmacology. 6: 3. doi:10.1186/1471-2210-6-3. PMC 1403760. PMID 16433932.
^ ^a ^b Porreca F (1 September 1995). "Pharmacological characterization of opioid delta and kappa receptors". In Tseng LF (ed.). Pharmacology of Opioid Peptides. CRC Press. p. 238. ISBN 978-3-7186-5632-5. Retrieved 22 April 2012.
^ Rapaka RS, Sadée W (13 June 2008). Drug Addiction: From Basic Research to Therapy. Springer. p. 421. ISBN 978-0-387-76677-5. Retrieved 22 April 2012.
^ ^a ^b Zhang WM, Wu S, Yu XC, Wang HX, Bian JS, Wong TM (February 1999). "Effects of U50488 and bremazocine on [Ca2+]i and cAMP in naive and tolerant rat ventricular myocytes: evidence of kappa opioid receptor multiplicity in the heart". Journal of Molecular and Cellular Cardiology. 31 (2): 355–62. doi:10.1006/jmcc.1998.9998. PMID 10093048.
^ Negus SS, Zuzga DS, Mello NK (June 2002). "Sex differences in opioid antinociception in rhesus monkeys: antagonism of fentanyl and U50,488 by quadazocine". The Journal of Pain. 3 (3): 218–26. doi:10.1054/jpai.2002.124734. PMID 14622776.