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Tetrahydrocannabihexol
Identifiers
  • (6aR,10aR)-3-hexyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard ( EPA)
Chemical and physical data
FormulaC22H32O2
Molar mass328.496 g·mol−1
3D model ( JSmol)
  • CCCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O
  • InChI=1S/C22H32O2/c1-5-6-7-8-9-16-13-19(23)21-17-12-15(2)10-11-18(17)22(3,4)24-20(21)14-16/h12-14,17-18,23H,5-11H2,1-4H3/t17-,18-/m1/s1
  • Key:DMJVNNFBMZZLFB-QZTJIDSGSA-N

Tetrahydrocannabihexol (Δ9-THCH, Δ9-Parahexyl, n-Hexyl-Δ9-THC) is a phytocannabinoid, the hexyl homologue of tetrahydrocannabinol (THC) which was first isolated from Cannabis plant material in 2020 along with the corresponding hexyl homologue of cannabidiol, [1] [2] though it had been known for several decades prior to this as an isomer of the synthetic cannabinoid parahexyl. [3] Another isomer Δ8-THCH is also known as a synthetic cannabinoid under the code number JWH-124, [4] [5] though it is unclear whether this occurs naturally in Cannabis, but likely is due to Δ8-THC itself being a degraded form of Δ9-THC. THC-Hexyl can be synthesized from 4-hexylresorcinol and was studied by Roger Adams as early as 1942. [6]

Cannabidihexol (CBDH), 2552798-21-5 [1]
JWH-124 (Δ8-THCH), 20622-30-4 [2]

See also

References

  1. ^ Linciano P, Citti C, Russo F, Tolomeo F, Laganà A, Capriotti AL, et al. (December 2020). "Identification of a new cannabidiol n-hexyl homolog in a medicinal cannabis variety with an antinociceptive activity in mice: cannabidihexol". Scientific Reports. 10 (1): 22019. Bibcode: 2020NatSR..1022019L. doi: 10.1038/s41598-020-79042-2. PMC  7744557. PMID  33328530.
  2. ^ Radwan MM, Chandra S, Gul S, ElSohly MA (May 2021). "Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis". Molecules. 26 (9): 2774. doi: 10.3390/molecules26092774. PMC  8125862. PMID  34066753.
  3. ^ Brown NK, Harvey DJ (1988). "Metabolism of n-hexyl-homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse". European Journal of Drug Metabolism and Pharmacokinetics. 13 (3): 165–76. doi: 10.1007/BF03189936. PMID  2853671. S2CID  10612593.
  4. ^ Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, et al. (September 1999). "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics. 290 (3): 1065–79. PMID  10454479.
  5. ^ Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry. 8: 17–39. doi: 10.4137/PMC.S32171. PMC  4927043. PMID  27398024.
  6. ^ Adams R, Loewe S, Smith CM, McPhee WD (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII1". Journal of the American Chemical Society. 64 (3): 694–697. doi: 10.1021/ja01255a061.
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