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Parahexyl

Clinical data
Other names	Synhexyl, n-hexyl-Δ-THC, (C6)-Δ-THC
Drug class	Cannabinoid
ATC code	none
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics) CA: Schedule II DE: Anlage I (Authorized scientific use only) UK: Class B US: Schedule I UN: Psychotropic Schedule I
Identifiers
IUPAC name 3-n-hexyl- 7,8,9,10-tetrahydro- 6,6,9-trimethyl- 6H-dibenzo(b,d)pyran- 1-ol
CAS Number	117-51-1
PubChem CID	8334
ChemSpider	8031
UNII	450N174F9W
KEGG	C22779
CompTox Dashboard (EPA)	DTXSID90861748
Chemical and physical data
Formula	C22H32O2
Molar mass	328.496 g·mol
3D model (JSmol)	Interactive image
SMILES Oc2cc(cc1OC(C\3=C(/c12)CC(CC/3)C)(C)C)CCCCCC
InChI 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/h13-15,23H,5-12H2,1-4H3 Key:OORFXDSWECAQLI-UHFFFAOYSA-N
(verify)

Parahexyl, also known as synhexyl, is a synthetic homologue of tetrahydrocannabinol (THC) which was invented in 1941 during attempts to elucidate the structure of Δ-THC, one of the active components of cannabis.

Parahexyl is similar in both structure and activity to THC, differing only in the position of one double bond and the lengthening of the 3-pentyl chain by one CH₂ group to n-hexyl. Parahexyl produces effects typical of other cannabinoid receptor agonists in animals. It has a somewhat higher oral bioavailability than THC itself but is otherwise very similar. Presumably, it acts as a CB₁ receptor agonist in the same way as THC, but as there has been no research published using parahexyl since the discovery of the CB₁ receptor, this has not been definitively confirmed.

Parahexyl was occasionally used as an anxiolytic in the mid-20th century, the dosage ranging from 5 mg to 90 mg.

Parahexyl was made illegal under UN convention in 1971 on the basis of its structural similarity and similar effects profile to THC. Parahexyl was placed into the most restrictive Schedule I as a compound with no medical use.

Isomerism

At least three isomers of parahexyl have been studied and are known to be active as cannabinoids. Parahexyl itself (i.e. the Δ isomer) has not had any significant use in scientific research since it was banned internationally in the early 1980s; however, the Δ and Δ isomers are both known to be cannabinoid receptor agonists, and Δ-parahexyl has the code number JWH-124, while Δ-parahexyl has been isolated from Cannabis plant material and assigned the name tetrahydrocannabihexol (THCH).

Note that 6H-dibenzopyran-1-ol is the same as 6H-benzochromen-1-ol.

See also

• Delta-3-Tetrahydrocannabinol (delta-3-THC)
• Hexahydrocannabihexol (HHCH)
• Tetrahydrocannabutol
• Tetrahydrocannabiphorol (THCP)
• Tetrahydrocannabivarin (THCV)

References

1. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
2. Adams R, Loewe S, Jelinek C, Wolff H (July 1941). "Tetrahydrocannabinol Homologs with Marihuana Activity. IX1". Journal of the American Chemical Society. 63 (7): 1971–1973. doi:10.1021/ja01852a052.
3. Adams R, Harfenist M, Loewe S (1949). "New Analogs of Tetrahydrocannabinol. XIX". Journal of the American Chemical Society. 71 (5): 1624–1628. doi:10.1021/ja01173a023.
4. Ask Dr. Shulgin Online March 7, 2001
5. Ono M, Shimamine M, Takahashi K, Inoue T (1974). "". Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences (in Japanese). 49 (92): 46–50. PMID 4477495.
6. Fairchild MD, Jenden DJ, Mickey MR, Yale C (January 1980). "EEG effects of hallucinogens and cannabinoids using sleep-waking behavior as baseline". Pharmacology, Biochemistry, and Behavior. 12 (1): 99–105. doi:10.1016/0091-3057(80)90422-0. PMID 6102770. S2CID 24865915.
7. Supniewski J (1950). Farmakologia. Warsaw: PZWL. p. 89.
8. "Synhexyl page - Supniewski J (1950). Farmakologia. Warsaw: PZWL. P. 89".
9. Report of the Technical Committee on Schedules I, II, III and I at the United Nations Conference for the adoption of a Protocol on Psychotropic Substances. 15 February 1971. E/CONF.58/L.47
10. 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.
11. 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.
12. 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.

• Drugs not assigned an ATC code
• Benzochromenes
• Cannabinoids
• Hydroxyarenes