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{{Short description|Chemical compound}} |
{{Short description|Chemical compound}} |
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{{Infobox drug |
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| synonyms = |
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| IUPAC_name = (6aR,10aR)-6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-octyl-6H-Dibenzo[b,d]pyran-1-ol |
| IUPAC_name = (6aR,10aR)-6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-octyl-6H-Dibenzo[b,d]pyran-1-ol |
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'''JWH-138''' ('''THC-Octyl''', '''Δ<sup>8</sup>-THC-C8''') is a synthetic [[cannabinoid]] first synthesised by [[John W. Huffman]], with a [[Dissociation constant|K<sub>i</sub>]] of 8.5nM at the CB<sub>1</sub> [[cannabinoid receptor]].<ref name="pmid10454479">{{cite journal | vauthors = Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK | display-authors = 6 | 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 = 1065–1079 | date = September 1999 | pmid = 10454479 | doi = }}</ref> |
'''JWH-138''' ('''THC-Octyl''', '''Δ<sup>8</sup>-THC-C8''') is a synthetic [[cannabinoid]] first synthesised by [[John W. Huffman]], with a [[Dissociation constant|K<sub>i</sub>]] of 8.5nM at the CB<sub>1</sub> [[cannabinoid receptor]].<ref name="pmid10454479">{{cite journal | vauthors = Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK | display-authors = 6 | 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 = 1065–1079 | date = September 1999 | pmid = 10454479 | doi = }}</ref> THC-Octyl and its hydrogenated analog HHC-Octyl was synthesized and 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 | last1=Adams | first1=Roger | last2=Loewe | first2=S. | last3=Smith | first3=C. M. | last4=McPhee | first4=W. D. | journal=Journal of the American Chemical Society | volume=64 | issue=3 | pages=694–697 }}</ref> |
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==Isomers== |
==Isomers== |
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[[File:D3-THC-C8_structure.png|220px|thumb|left|Δ<sup>3</sup>-THC-C8]]{{clear |
[[File:D3-THC-C8_structure.png|220px|thumb|left|Δ<sup>3</sup>-THC-C8]]{{clear left}} |
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[[File:d9-THC-C8_structure.png|220px|thumb|left|Δ<sup>9</sup>-THC-C8, CAS# 2552798-63-5]]{{clear |
[[File:d9-THC-C8_structure.png|220px|thumb|left|Δ<sup>9</sup>-THC-C8 (Tetrahydrocannabioctyl), CAS# 2552798-63-5]]{{clear left}}The Δ<sup>3</sup>/Δ<sup>6a(10a)</sup> isomer was synthesised in 1941, but was found to be slightly less active than [[Delta-3-Tetrahydrocannabinol|Δ<sup>3</sup>-THC]] itself.<ref>{{cite journal | vauthors = Adams R, Loewe S, Jelinek C, Wolff H | title = Tetrahydrocannabinol Homologs with Marihuana Activity. IX. | journal = Journal of the American Chemical Society | date = July 1941 | volume = 63 | issue = 7 | pages = 1971–1973 | doi = 10.1021/ja01852a052 }}</ref> The alternate isomer Δ<sup>9</sup>-THC-C8 has also been synthesised,<ref>{{cite patent |country=WO |number=2020232545|status=application|pubdate=2020-11-26|title=Catalytic cannabinoid processes and precursors|assign1=Kare Chemical Technologies Inc.|inventor1-last=Abdur-Rashid|inventor1-first=Kamaluddin|inventor2-last=Jia|inventor2-first=Wenli|inventor3-last=Abdur-Rashid|inventor3-first=Kareem|postscript = . }}</ref> and both the Δ<sup>8</sup> and Δ<sup>9</sup> isomers are included within the definition of an "intoxicating cannabinoid" in Colorado under the name '''tetrahydrocannabioctyl''',<ref>[https://leg.colorado.gov/sites/default/files/documents/2023A/bills/2023a_271_rev.pdf Senate Bill 23-271, General Assembly, State of Colorado]</ref> but it is unclear if it has been identified as a natural product. Tetrahydrocannabioctyl is sometimes referred to as THC-Octyl or THCO, which may cause confusion with [[THC-O-acetate]] which is commonly known as THC-O. |
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== See also == |
== See also == |
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* [[1,2-Didehydro-3-oxo-THCO]] |
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* [[Cannabicyclohexanol]] |
* [[Cannabicyclohexanol]] |
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* [[Parahexyl]] |
* [[Parahexyl]] |
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{{cannabinoid-stub}} |
{{cannabinoid-stub}} |
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[[Category: |
[[Category:Cannabinoids]] |
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Latest revision as of 18:33, 14 February 2024
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| Chemical and physical data | |
| Formula | C24H36O2 |
| Molar mass | 356.550 g·mol−1 |
| 3D model (JSmol) | |
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JWH-138 (THC-Octyl, Δ8-THC-C8) is a synthetic cannabinoid first synthesised by John W. Huffman, with a Ki of 8.5nM at the CB1 cannabinoid receptor.[1] THC-Octyl and its hydrogenated analog HHC-Octyl was synthesized and studied by Roger Adams as early as 1942.[2]
Isomers[edit]
The Δ3/Δ6a(10a) isomer was synthesised in 1941, but was found to be slightly less active than Δ3-THC itself.[3] The alternate isomer Δ9-THC-C8 has also been synthesised,[4] and both the Δ8 and Δ9 isomers are included within the definition of an "intoxicating cannabinoid" in Colorado under the name tetrahydrocannabioctyl,[5] but it is unclear if it has been identified as a natural product. Tetrahydrocannabioctyl is sometimes referred to as THC-Octyl or THCO, which may cause confusion with THC-O-acetate which is commonly known as THC-O.
See also[edit]
References[edit]
- ^ 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): 1065–1079. PMID 10454479.
- ^ Adams, Roger; Loewe, S.; Smith, C. M.; McPhee, W. D. (1942). "Tetrahydrocannabinol Homologs and Analogs with Marihuana Activity. XIII1". Journal of the American Chemical Society. 64 (3): 694–697. doi:10.1021/ja01255a061.
- ^ Adams R, Loewe S, Jelinek C, Wolff H (July 1941). "Tetrahydrocannabinol Homologs with Marihuana Activity. IX". Journal of the American Chemical Society. 63 (7): 1971–1973. doi:10.1021/ja01852a052.
- ^ WO application 2020232545, Abdur-Rashid, Kamaluddin; Jia, Wenli & Abdur-Rashid, Kareem, "Catalytic cannabinoid processes and precursors", published 2020-11-26, assigned to Kare Chemical Technologies Inc..
- ^ Senate Bill 23-271, General Assembly, State of Colorado