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Cannabinoid

Tetrahydrocannabihexol

Also called THCH, n-Hexyl-delta-9-thc

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Mixing

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Overview

Tetrahydrocannabihexol (THCH) is a phytocannabinoid. PW

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, though it had been known for several decades prior to this as an isomer of the synthetic cannabinoid parahexyl. Another isomer Δ⁸-THCH is also known as a synthetic cannabinoid under the code number JWH-124, 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.[1–6] WP

History

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Pharmacology

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Chemistry

Formula
C22H32O2 PC
CAS number
36482-24-3 PC
Molar mass (g/mol)
328.5 PC
IUPAC name (computed by PubChem)
(6aR,10aR)-3-hexyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol PC
SMILES
CCCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C)O PC
InChIKey
DMJVNNFBMZZLFB-QZTJIDSGSA-N PC
PubChem CID
161906

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References

  1. Journal / agency Linciano P, Citti C, Russo F, Tolomeo F, Laganà A, Capriotti AL, Luongo L, Iannotta M, Belardo C, Maione S, Forni F, Vandelli MA, Gigli G, Cannazza G. Identification of a new cannabidiol n-hexyl homolog in a medicinal cannabis variety with an antinociceptive activity in mice: cannabidihexol. Scientific Reports. December 2020. doi:10.1038/s41598-020-79042-2 · PMID 33328530 · PMC7744557
  2. Journal / agency Radwan MM, Chandra S, Gul S, ElSohly MA. Cannabinoids, Phenolics, Terpenes and Alkaloids of Cannabis. Molecules. May 2021. doi:10.3390/molecules26092774 · PMID 34066753 · PMC8125862
  3. Journal / agency Brown NK, Harvey DJ. Metabolism of n-hexyl-homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse. European Journal of Drug Metabolism and Pharmacokinetics. 1988. doi:10.1007/BF03189936 · PMID 2853671
  4. Journal / agency Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK. Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists. The Journal of Pharmacology and Experimental Therapeutics. September 1999. PMID 10454479
  5. Journal / agency Bow EW, Rimoldi JM. The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation. Perspectives in Medicinal Chemistry. 2016. doi:10.4137/PMC.S32171 · PMID 27398024 · PMC4927043
  6. Journal / agency Adams R, Loewe S, Smith CM, McPhee WD. Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII¹. Journal of the American Chemical Society. 1942. doi:10.1021/ja01255a061

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