From Wikipedia, the free encyclopedia
Opioid analgesic drug
Ciprefadol
ATC code
3-[(4aR,8aR)-2-(cyclopropylmethyl)-1,3,4,5,6,7,8,8a-octahydroisoquinolin-4a-yl]phenol
CAS Number
PubChem
CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (
EPA )
Formula C 19 H 27 N O
Molar mass 285.431 g·mol−1 3D model (
JSmol )
C1CC[C@]2(CCN(C[C@@H]2C1)CC3CC3)C4=CC(=CC=C4)O
InChI=1S/C19H27NO/c21-18-6-3-5-16(12-18)19-9-2-1-4-17(19)14-20(11-10-19)13-15-7-8-15/h3,5-6,12,15,17,21H,1-2,4,7-11,13-14H2/t17-,19-/m0/s1
Key:KFIQKMINEHFZSM-HKUYNNGSSA-N
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
^
Dennis M. Zimmerman et al. N-cycloalkylmethyl decahydroisoquinolines. US Patent 4001248, Jun 7, 1974
^
David R. Brittelli et al. 4a-Aryl-trans-decahydroisoquinolines. US Patent 4419517, Apr 8, 1975
^
Henry Rapoport et al. Synthesis of 4A-aryl-decahydroisoquinolines. US Patent 4189583, Apr 26, 1978
^ Judd DB, Brown DS, Lloyd JE, McElroy AB, Scopes DI, Birch PJ, et al. (January 1992). "Synthesis, antinociceptive activity, and opioid receptor profiles of substituted trans-3-(decahydro- and octahydro-4a-isoquinolinyl)phenols". Journal of Medicinal Chemistry . 35 (1): 48–56.
doi :
10.1021/jm00079a005 .
PMID
1310115 .
^ Carroll FI, Chaudhari S, Thomas JB, Mascarella SW, Gigstad KM, Deschamps J, Navarro HA (December 2005).
"N-substituted cis-4a-(3-hydroxyphenyl)-8a-methyloctahydroisoquinolines are opioid receptor pure antagonists" . Journal of Medicinal Chemistry . 48 (26): 8182–93.
doi :
10.1021/jm058261c .
PMC
2585695 .
PMID
16366600 .
^ Zimmerman DM, Cantrell BE, Swartzendruber JK, Jones ND, Mendelsohn LG, Leander JD, Nickander RC (March 1988). "Synthesis and analgesic properties of N-substituted trans-4a-aryldecahydroisoquinolines". Journal of Medicinal Chemistry . 31 (3): 555–60.
doi :
10.1021/jm00398a011 .
PMID
2831363 .