Quadazocine

{{Short description|Chemical compound}}

{{Drugbox

| 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

| image = Quadazocine structure.svg

| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 71276-43-2

| ATC_prefix = None

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| PubChem = 115077

| ChemSpiderID = 102983

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = X9BMD58553

| C = 25 | H = 37 | N = 1 | O = 2

| smiles = O=C(CCC1CCCC1)CCC4([C@@H]3N(CC[C@]4(c2c(ccc(O)c2)C3)C)C)C

| StdInChI = 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

| StdInChIKey = LOYWOYCPSWPKFH-CSIQULDISA-N

| bioavailability =

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Quadazocine (WIN-44,441) is an opioid antagonist of the benzomorphan family which is used in scientific research.{{cite journal |vauthors=Ward SJ, Pierson AK, Michne WF | title = Multiple opioid receptor profile in vitro and activity in vivo of the potent opioid antagonist Win 44,441-3 | journal = Life Sciences | volume = 33 | pages = 303–6 | year = 1983 | issue = Suppl 1 | pmid = 6319882 | doi = 10.1016/0024-3205(83)90503-9}} It acts as a silent antagonist at all three of the major opioid receptors—μ, κ, and δ,{{cite journal |vauthors=Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J | title = Pharmacological profiles of opioid ligands at kappa opioid receptors | journal = BMC Pharmacology | volume = 6 | pages = 3 | year = 2006 | pmid = 16433932 | pmc = 1403760 | doi = 10.1186/1471-2210-6-3 | doi-access = free }} but with a significant preference in affinity for the μ receptor and the κ₂ subtype.{{cite book | vauthors = Porreca F | chapter = Pharmacological characterization of opioid delta and kappa receptors | veditors = Tseng LF | title = Pharmacology of Opioid Peptides | chapter-url = https://books.google.com/books?id=PhHTwIy9Wd8C&pg=PA238 | access-date = 22 April 2012 | date = 1 September 1995 | publisher = CRC Press | isbn = 978-3-7186-5632-5 | page = 238}}{{cite book | vauthors = Rapaka RS, Sadée W | title = Drug Addiction: From Basic Research to Therapy | url = https://books.google.com/books?id=Z36GjK1vABEC&pg=PA421 | access-date = 22 April 2012 | date = 13 June 2008 | publisher = Springer | isbn = 978-0-387-76677-5 | page = 421}}{{cite journal |vauthors=Zhang WM, Wu S, Yu XC, Wang HX, Bian JS, Wong TM | title = 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 = Journal of Molecular and Cellular Cardiology | volume = 31 | issue = 2 | pages = 355–62 |date=February 1999 | pmid = 10093048 | doi = 10.1006/jmcc.1998.9998 }} 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. As would be expected, quadazocine reverses the effects (e.g., analgesia) of opioid agonists like morphine and fentanyl in animals.{{cite journal |vauthors=Negus SS, Zuzga DS, Mello NK | title = Sex differences in opioid antinociception in rhesus monkeys: antagonism of fentanyl and U50,488 by quadazocine | journal = The Journal of Pain | volume = 3 | issue = 3 | pages = 218–26 |date=June 2002 | pmid = 14622776 | doi = 10.1054/jpai.2002.124734| doi-access = free }}