Quadazocine

Quadazocine

Quadazocine
Systematic (IUPAC) name
1-cyclopentyl-5-[(1S,9R)-4-hydroxy-1,10,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2,4,6-trien-13-yl]-3-pentanone
Clinical data
Legal status
?
Identifiers
CAS number
ATC code None
PubChem
ChemSpider
UNII  YesY
Chemical data
Formula C25H37NO2 
Mol. mass 383.567 g/mol

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 receptorsμ, 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, of course, 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

  1. ^ 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.  
  2. ^ Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J (2006). "Pharmacological profiles of opioid ligands at kappa opioid receptors". BMC Pharmacology 6: 3.  
  3. ^ a b Leon F. Tseng (1 September 1995). Pharmacology of Opioid Peptides. CRC Press. p. 238.  
  4. ^ Rao S. Rapaka; Wolfgang Sadée (13 June 2008). Drug Addiction: From Basic Research to Therapy. Springer. p. 421.  
  5. ^ 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.  
  6. ^ 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 : Official Journal of the American Pain Society 3 (3): 218–26.