Parahexyl

Parahexyl
Clinical data
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−1
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 (Synhexyl, n-hexyl-Δ³-THC, (C6)-Δ^6a(10a)-THC) is a synthetic homologue of THC which was invented in 1941 during attempts to elucidate the structure of Δ⁹-THC, one of the active components of cannabis.^[2]^[3]^[4]

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.^[5] 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.^[6] Presumably, it acts as a CB₁ 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.^[7]^[8]

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^[9] as a compound with no medical use, despite the now-known medical uses for cannabinoids.

^ 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.
^ 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.
^ 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.
^ Ask Dr. Shulgin Online March 7, 2001
^ Ono M, Shimamine M, Takahashi K, Inoue T (1974). "[Studies on hallucinogens. VII Synthesis of parahexyl]". Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences (in Japanese). 49 (92): 46–50. PMID 4477495.
^ 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.
^ Supniewski J (1950). Farmakologia. Warsaw: PZWL. p. 89.
^ https://imgur.com/a/cEsFXig
^ 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

[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.

[JACS1949-3] 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

[pmid4477495-5] Ono M, Shimamine M, Takahashi K, Inoue T (1974). "[Studies on hallucinogens. VII Synthesis of parahexyl]". Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences (in Japanese). 49 (92): 46–50. PMID 4477495.

[pmid6102770-6] 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.

[Supniewski-7] Supniewski J (1950). Farmakologia. Warsaw: PZWL. p. 89.

[8] ttps://imgur.com/a/cEsFXig

[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

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Clinical data

ATC code	none
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)^[1] 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^Y
PubChem CID	8334
ChemSpider	8031^Y
UNII	450N174F9W
KEGG	C22779
CompTox Dashboard (EPA)	DTXSID90861748
Chemical and physical data
Formula	C₂₂H₃₂O₂
Molar mass	328.496 g·mol⁻¹
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^Y Key:OORFXDSWECAQLI-UHFFFAOYSA-N^Y
(verify)