Parahexyl

Parahexyl
Clinical data
Other namesSynhexyl, n-hexyl-Δ3-THC, (C6)-Δ6a(10a)-THC
Drug classCannabinoid
ATC code
  • none
Legal status
Legal status
Identifiers
  • 3-n-hexyl- 7,8,9,10-tetrahydro- 6,6,9-trimethyl- 6H-dibenzo(b,d)pyran- 1-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H32O2
Molar mass328.496 g·mol−1
3D model (JSmol)
  • Oc2cc(cc1OC(C\3=C(/c12)CC(CC/3)C)(C)C)CCCCCC
  • 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 checkY
  • Key:OORFXDSWECAQLI-UHFFFAOYSA-N checkY
  (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 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 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.[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.

  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). "[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.
  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