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'''Tetrahydrocannabihexol ([https://drherbals.se/kategori/thch-thcb/ THCH])''' ('''Δ<sup>9</sup>-THCH''', '''Δ<sup>9</sup>-Parahexyl''', '''n-Hexyl-Δ<sup>9</sup>-THC''') is a [[phytocannabinoid]], the hexyl [[Homologous series|homologue]] of [[tetrahydrocannabinol]] (THC) which was first isolated from ''[[Cannabis]]'' plant material in 2020 along with the corresponding hexyl homologue of [[cannabidiol]],<ref>{{cite journal | vauthors = 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 | title = Identification of a new cannabidiol n-hexyl homolog in a medicinal cannabis variety with an antinociceptive activity in mice: cannabidihexol | journal = Scientific Reports | volume = 10 | issue = 1 | pages = 22019 | date = December 2020 | pmid = 33328530 | doi = 10.1038/s41598-020-79042-2 | pmc = 7744557 | bibcode = 2020NatSR..1022019L }}</ref><ref>{{cite journal | vauthors = Radwan MM, Chandra S, Gul S, ElSohly MA | title = Cannabinoids, Phenolics, Terpenes and Alkaloids of ''Cannabis'' | journal = Molecules | volume = 26 | issue = 9 | date = May 2021 | page = 2774 | pmid = 34066753 | doi = 10.3390/molecules26092774 | pmc = 8125862 | doi-access = free }}</ref> though it had been known for several decades prior to this as an isomer of the [[synthetic cannabinoid]] [[parahexyl]].<ref name="pmid2853671">{{cite journal | vauthors = Brown NK, Harvey DJ | title = Metabolism of n-hexyl-homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 13 | issue = 3 | pages = 165–76 | date = 1988 | pmid = 2853671 | doi = 10.1007/BF03189936 | s2cid = 10612593 }}</ref> Another isomer Δ<sup>8</sup>-THCH is also known as a synthetic cannabinoid under the code number '''JWH-124''',<ref name="pmid10454479">{{cite journal | vauthors = Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK | title = Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 290 | issue = 3 | pages = 1065–79 | date = September 1999 | pmid = 10454479 }}</ref><ref name="pmid27398024">{{cite journal | vauthors = Bow EW, Rimoldi JM | title = The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation | journal = Perspectives in Medicinal Chemistry | volume = 8 | pages = 17–39 | date = 2016 | pmid = 27398024 | pmc = 4927043 | doi = 10.4137/PMC.S32171 }}</ref> though it is unclear whether this occurs naturally in ''Cannabis'', but likely is due to Δ<sup>8</sup>-THC itself being a degraded form of Δ<sup>9</sup>-THC.
'''Tetrahydrocannabihexol''' ('''Δ<sup>9</sup>-THCH''', '''Δ<sup>9</sup>-Parahexyl''', '''n-Hexyl-Δ<sup>9</sup>-THC''') is a [[phytocannabinoid]], the hexyl [[Homologous series|homologue]] of [[tetrahydrocannabinol]] (THC) which was first isolated from ''[[Cannabis]]'' plant material in 2020 along with the corresponding hexyl homologue of [[cannabidiol]],<ref>{{cite journal | vauthors = 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 | title = Identification of a new cannabidiol n-hexyl homolog in a medicinal cannabis variety with an antinociceptive activity in mice: cannabidihexol | journal = Scientific Reports | volume = 10 | issue = 1 | pages = 22019 | date = December 2020 | pmid = 33328530 | doi = 10.1038/s41598-020-79042-2 | pmc = 7744557 | bibcode = 2020NatSR..1022019L }}</ref><ref>{{cite journal | vauthors = Radwan MM, Chandra S, Gul S, ElSohly MA | title = Cannabinoids, Phenolics, Terpenes and Alkaloids of ''Cannabis'' | journal = Molecules | volume = 26 | issue = 9 | date = May 2021 | page = 2774 | pmid = 34066753 | doi = 10.3390/molecules26092774 | pmc = 8125862 | doi-access = free }}</ref> though it had been known for several decades prior to this as an isomer of the [[synthetic cannabinoid]] [[parahexyl]].<ref name="pmid2853671">{{cite journal | vauthors = Brown NK, Harvey DJ | title = Metabolism of n-hexyl-homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse | journal = European Journal of Drug Metabolism and Pharmacokinetics | volume = 13 | issue = 3 | pages = 165–76 | date = 1988 | pmid = 2853671 | doi = 10.1007/BF03189936 | s2cid = 10612593 }}</ref> Another isomer Δ<sup>8</sup>-THCH is also known as a synthetic cannabinoid under the code number '''JWH-124''',<ref name="pmid10454479">{{cite journal | vauthors = Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK | title = Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 290 | issue = 3 | pages = 1065–79 | date = September 1999 | pmid = 10454479 }}</ref><ref name="pmid27398024">{{cite journal | vauthors = Bow EW, Rimoldi JM | title = The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation | journal = Perspectives in Medicinal Chemistry | volume = 8 | pages = 17–39 | date = 2016 | pmid = 27398024 | pmc = 4927043 | doi = 10.4137/PMC.S32171 }}</ref> though it is unclear whether this occurs naturally in ''Cannabis'', but likely is due to Δ<sup>8</sup>-THC itself being a degraded form of Δ<sup>9</sup>-THC.
THC-Hexyl can be synthesized from [[4-Hexylresorcinol|4-hexylresorcinol]] and was studied by [[Roger Adams]] as early as 1942.<ref>{{cite journal | url=https://pubs.acs.org/doi/abs/10.1021/ja01255a061 | doi=10.1021/ja01255a061 | title=Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII<sup>1</sup> | date=1942 | vauthors = Adams R, Loewe S, Smith CM, McPhee WD | journal=Journal of the American Chemical Society | volume=64 | issue=3 | pages=694–697 }}</ref>
THC-Hexyl can be synthesized from [[4-Hexylresorcinol|4-hexylresorcinol]] and was studied by [[Roger Adams]] as early as 1942.<ref>{{cite journal | url=https://pubs.acs.org/doi/abs/10.1021/ja01255a061 | doi=10.1021/ja01255a061 | title=Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII<sup>1</sup> | date=1942 | vauthors = Adams R, Loewe S, Smith CM, McPhee WD | journal=Journal of the American Chemical Society | volume=64 | issue=3 | pages=694–697 }}</ref>


Latest revision as of 00:30, 15 June 2024

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[edit]

References[edit]

  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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