9-Hydroxyhexahydrocannabinol

9-Hydroxyhexahydrocannabinol
Identifiers
	IUPAC name (6aR,10aR)-6,6,9-trimethyl-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzo[c]chromene-1,9-diol;
CAS Number	36028-45-2 ; 52522-56-2;
PubChem CID	71579182;
ChemSpider	148443;
Chemical and physical data
Formula	C21H32O3
Molar mass	332.484 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC1=CC(=C2C3CC(CCC3C(OC2=C1)(C)C)(C)O)O;
	InChI InChI=1S/C21H32O3/c1-5-6-7-8-14-11-17(22)19-15-13-21(4,23)10-9-16(15)20(2,3)24-18(19)12-14/h11-12,15-16,22-23H,5-10,13H2,1-4H3/t15-,16-,21?/m1/s1; Key:KSGRDIFQZVURIF-BLRYKZMTSA-N;

9-Hydroxyhexahydrocannabinol (9-OH-HHC) is a semi-synthetic derivative of tetrahydrocannabinol. It is formed as an impurity in the synthesis of Delta-8-THC,^[1] and retains activity in animal studies though with only around 1/10 the potency of Δ⁹-THC, with the 9α- and 9β- enantiomers having around the same potency.^[2]

References

^ Garrett ER, Gouyette AJ, Roseboom H (January 1978). "Stability of tetrahydrocannabinols II". Journal of Pharmaceutical Sciences. 67 (1): 27–32. doi:10.1002/jps.2600670108. PMID 22740.
^ Reggio PH, McGaughey GB, Odear DF, Seltzman HH, Compton DR, Martin BR (November 1991). "A rational search for the separation of psychoactivity and analgesia in cannabinoids". Pharmacology, Biochemistry, and Behavior. 40 (3): 479–86. doi:10.1016/0091-3057(91)90350-b. PMID 1806940. S2CID 23939720.

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[pmid22740-1] Garrett ER, Gouyette AJ, Roseboom H (January 1978). "Stability of tetrahydrocannabinols II". Journal of Pharmaceutical Sciences. 67 (1): 27–32. doi:10.1002/jps.2600670108. PMID 22740.

[pmid1806940-2] Reggio PH, McGaughey GB, Odear DF, Seltzman HH, Compton DR, Martin BR (November 1991). "A rational search for the separation of psychoactivity and analgesia in cannabinoids". Pharmacology, Biochemistry, and Behavior. 40 (3): 479–86. doi:10.1016/0091-3057(91)90350-b. PMID 1806940. S2CID 23939720.

[1]

[2]

Identifiers

IUPAC name (6aR,10aR)-6,6,9-trimethyl-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzo[c]chromene-1,9-diol
CAS Number	36028-45-2 52522-56-2
PubChem CID	71579182
ChemSpider	148443
Chemical and physical data
Formula	C₂₁H₃₂O₃
Molar mass	332.484 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC1=CC(=C2C3CC(CCC3C(OC2=C1)(C)C)(C)O)O
InChI InChI=1S/C21H32O3/c1-5-6-7-8-14-11-17(22)19-15-13-21(4,23)10-9-16(15)20(2,3)24-18(19)12-14/h11-12,15-16,22-23H,5-10,13H2,1-4H3/t15-,16-,21?/m1/s1 Key:KSGRDIFQZVURIF-BLRYKZMTSA-N

9-Hydroxyhexahydrocannabinol

See also

References