Chemistry:Tetrahydrocannabihexol

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Short description: Chemical compound
Tetrahydrocannabihexol
D9THCH structure.png
THCH 3D BS.png
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC22H32O2
Molar mass328.496 g·mol−1
3D model (JSmol)

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 Delta-8-THC itself being a degraded form of Delta-9-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. "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. December 2020. doi:10.1038/s41598-020-79042-2. PMID 33328530. Bibcode2020NatSR..1022019L. 
  2. "Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis". Molecules 26 (9): 2774. May 2021. doi:10.3390/molecules26092774. PMID 34066753. 
  3. "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. 1988. doi:10.1007/BF03189936. PMID 2853671. 
  4. "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics 290 (3): 1065–79. September 1999. PMID 10454479. 
  5. "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry 8: 17–39. 2016. doi:10.4137/PMC.S32171. PMID 27398024. 
  6. https://pubs.acs.org/doi/abs/10.1021/ja01255a061