Ciprefadol

Ciprefadol
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-[(4aR,8aR)-2-(cyclopropylmethyl)-1,3,4,5,6,7,8,8a-octahydroisoquinolin-4a-yl]phenol;
CAS Number	59889-36-0;
PubChem CID	333483;
ChemSpider	295505;
UNII	L6RFK0CJ8K;
ChEMBL	ChEMBL2111073;
CompTox Dashboard (EPA)	DTXSID00208605 ;
Chemical and physical data
Formula	C19H27NO
Molar mass	285.431 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1CC[C@]2(CCN(C[C@@H]2C1)CC3CC3)C4=CC(=CC=C4)O;
	InChI 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.

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[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, 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.

[5] 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.

[6] 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.

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