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
PubChem CID
ChemSpider
Chemical and physical data
FormulaC21H32O3
Molar mass332.484 g·mol−1
3D model (JSmol)
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 1/10th the potency of Δ9-THC, with the 9α- and 9β- enantiomers having around the same potency.[2]

See also

References

  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.
  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.
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