CP 47,497

CP 47,497
Legal status
Legal status	CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); UK: Class B; US: Schedule I; Illegal in France, Latvia, Lithuania, Sweden, Romania;
Identifiers
	IUPAC name 2-[(1S,3R)-3-hydroxycyclohexyl]-5-(2-methyloctan-2-yl)phenol;
CAS Number	(1S,3R): 70434-82-1 ;
PubChem CID	(1S,3R): 125835; (1R,3S): 15942731;
ChemSpider	(1S,3R): 10205286; (1R,3S): 111910;
UNII	(1S,3R): FAPQAUKC04;
ChEMBL	(1S,3R): ChEMBL163701 ;
CompTox Dashboard (EPA)	(1S,3R): DTXSID201017793 DTXSID401009968, DTXSID201017793 ;
Chemical and physical data
Formula	C21H34O2
Molar mass	318.501 g·mol−1
3D model (JSmol)	(1S,3R): Interactive image; (1R,3S): Interactive image;
	SMILES (1S,3R): CCCCCCC(C)(C)c1ccc(c(c1)O)[C@H]2CCC[C@H](C2)O; ; (1R,3S): CCCCCCC(C)(C)c1ccc(c(c1)O)[C@@H]2CCC[C@@H](C2)O;
	InChI (1S,3R): InChI=1S/C21H34O2/c1-4-5-6-7-13-21(2,3)17-11-12-19(20(23)15-17)16-9-8-10-18(22)14-16/h11-12,15-16,18,22-23H,4-10,13-14H2,1-3H3/t16-,18+/m0/s1; Key:ZWWRREXSUJTKNN-FUHWJXTLSA-N; ; (1R,3S): InChI=1S/C21H34O2/c1-4-5-6-7-13-21(2,3)17-11-12-19(20(23)15-17)16-9-8-10-18(22)14-16/h11-12,15-16,18,22-23H,4-10,13-14H2,1-3H3/t16-,18+/m1/s1; Key:ZWWRREXSUJTKNN-AEFFLSMTSA-N;

CP 47,497 or (C7)-CP 47,497 is a cannabinoid receptor agonist drug, developed by Pfizer in the 1980s.^[1] It has analgesic effects and is used in scientific research. It is a potent CB₁ agonist with a K_d of 2.1 nM.^[2]^[3]^[4]

^ Weissman A, Milne GM, Melvin LS (November 1982). "Cannabimimetic activity from CP-47,497, a derivative of 3-phenylcyclohexanol". The Journal of Pharmacology and Experimental Therapeutics. 223 (2): 516–23. PMID 6290642.
^ Shim JY, Welsh WJ, Howlett AC (2003). "Homology model of the CB1 cannabinoid receptor: sites critical for nonclassical cannabinoid agonist interaction". Biopolymers. 71 (2): 169–89. doi:10.1002/bip.10424. PMID 12767117. S2CID 7909397.
^ Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168. Springer. ISBN 3-540-22565-X
^ Little PJ, Compton DR, Johnson MR, Melvin LS, Martin BR (December 1988). "Pharmacology and stereoselectivity of structurally novel cannabinoids in mice". The Journal of Pharmacology and Experimental Therapeutics. 247 (3): 1046–51. PMID 2849657.

[1] Weissman A, Milne GM, Melvin LS (November 1982). "Cannabimimetic activity from CP-47,497, a derivative of 3-phenylcyclohexanol". The Journal of Pharmacology and Experimental Therapeutics. 223 (2): 516–23. PMID 6290642.

[2] Shim JY, Welsh WJ, Howlett AC (2003). "Homology model of the CB1 cannabinoid receptor: sites critical for nonclassical cannabinoid agonist interaction". Biopolymers. 71 (2): 169–89. doi:10.1002/bip.10424. PMID 12767117. S2CID 7909397.

[3] Roger Pertwee. Cannabinoids. Handbook of Experimental Pharmacology Volume 168. Springer. ISBN 3-540-22565-X

[4] Little PJ, Compton DR, Johnson MR, Melvin LS, Martin BR (December 1988). "Pharmacology and stereoselectivity of structurally novel cannabinoids in mice". The Journal of Pharmacology and Experimental Therapeutics. 247 (3): 1046–51. PMID 2849657.

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Legal status

Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) UK: Class B US: Schedule I Illegal in France, Latvia, Lithuania, Sweden, Romania
Identifiers
IUPAC name 2-[(1S,3R)-3-hydroxycyclohexyl]-5-(2-methyloctan-2-yl)phenol
CAS Number	(1S,3R): 70434-82-1^Y
PubChem CID	(1S,3R): 125835 (1R,3S): 15942731
ChemSpider	(1S,3R): 10205286 (1R,3S): 111910
UNII	(1S,3R): FAPQAUKC04
ChEMBL	(1S,3R): ChEMBL163701^Y
CompTox Dashboard (EPA)	(1S,3R): DTXSID201017793 DTXSID401009968, DTXSID201017793
Chemical and physical data
Formula	C₂₁H₃₄O₂
Molar mass	318.501 g·mol⁻¹
3D model (JSmol)	(1S,3R): Interactive image (1R,3S): Interactive image
SMILES (1S,3R): CCCCCCC(C)(C)c1ccc(c(c1)O)[C@H]2CCC[C@H](C2)O (1R,3S): CCCCCCC(C)(C)c1ccc(c(c1)O)[C@@H]2CCC[C@@H](C2)O
InChI (1S,3R): InChI=1S/C21H34O2/c1-4-5-6-7-13-21(2,3)17-11-12-19(20(23)15-17)16-9-8-10-18(22)14-16/h11-12,15-16,18,22-23H,4-10,13-14H2,1-3H3/t16-,18+/m0/s1 Key:ZWWRREXSUJTKNN-FUHWJXTLSA-N (1R,3S): InChI=1S/C21H34O2/c1-4-5-6-7-13-21(2,3)17-11-12-19(20(23)15-17)16-9-8-10-18(22)14-16/h11-12,15-16,18,22-23H,4-10,13-14H2,1-3H3/t16-,18+/m1/s1 Key:ZWWRREXSUJTKNN-AEFFLSMTSA-N