Ciprefadol

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Ciprefadol
Ciprefadol structure.png
Systematic (IUPAC) name
3-[(4aR,8aR)-2-(cyclopropylmethyl)-1,3,4,5,6,7,8,8a-octahydroisoquinolin-4a-yl]phenol
Clinical data
Legal status ?
Identifiers
CAS number 59889-36-0
ATC code None
PubChem CID 333483
ChemSpider 295505
ChEMBL CHEMBL2111073
Chemical data
Formula C19H27NO 
Mol. mass 285.423 g/mol

Ciprefadol is an opioid analgesic that is an isoquinoline derivative most closely related to cyclazocine and picenadol,[1] with a number of other related compounds known.[2][3][4][5] Ciprefadol is a mixed agonist–antagonist at μ-opioid receptors and can partly block the effects of morphine at low doses, though at higher doses it acts more like a full agonist. It is also a potent κ-opioid agonist, unlike the corresponding N-methyl and N-phenethyl derivatives which are reasonably μ-selective agonists.[6]

References[edit]

  1. ^ Dennis M. Zimmerman et al. N-cycloalkylmethyl decahydroisoquinolines. US Patent 4001248, Jun 7, 1974
  2. ^ David R. Brittelli et al. 4a-Aryl-trans-decahydroisoquinolines. US Patent 4419517, Apr 8, 1975
  3. ^ Henry Rapoport et al. Synthesis of 4A-aryl-decahydroisoquinolines. US Patent 4189583, Apr 26, 1978
  4. ^ Judd DB, Brown DS, Lloyd JE, McElroy AB, Scopes DI, Birch PJ, Hayes AG, Sheehan MJ. Synthesis, antinociceptive activity, and opioid receptor profiles of substituted trans-3-(decahydro- and octahydro-4a-isoquinolinyl)phenols. Journal of Medicinal Chemistry. 1992 Jan;35(1):48-56. PMID 1310115
  5. ^ Carroll FI, Chaudhari S, Thomas JB, Mascarella SW, Gigstad KM, Deschamps J, Navarro HA. N-substituted cis-4a-(3-hydroxyphenyl)-8a-methyloctahydroisoquinolines are opioid receptor pure antagonists. Journal of Medicinal Chemistry. 2005 Dec 29;48(26):8182-93. PMID 16366600
  6. ^ Zimmerman DM, Cantrell BE, Swartzendruber JK, Jones ND, Mendelsohn LG, Leander JD, Nickander RC. Synthesis and analgesic properties of N-substituted trans-4a-aryldecahydroisoquinolines. Journal of Medicinal Chemistry. 1988 Mar;31(3):555-60. PMID 2831363