Parahexyl

Parahexyl (Synhexyl, n-hexyl-Δ3THC) is a synthetic homologue of THC, which was invented in 1949 during attempts to elucidate the structure of Δ9-THC, one of the active components of cannabis.[1][2]

Parahexyl
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H32O2
Molar mass328.488 g/mol g·mol−1
3D model (JSmol)
  (verify)

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.[3] Parahexyl produces classic cannabis agonist effects in animals. It has a somewhat higher oral bioavailability than THC itself but is otherwise very similar.[4] 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.[5]

Parahexyl was made illegal under UN convention in 1982 on the basis of its structural similarity and similar effects profile to THC, despite never having had any recorded instances of recreational use by humans or illicit sale. Parahexyl was placed into the most restrictive Schedule 1 as a compound with no medical use.

Isomerism
Dibenzopyran and monoterpenoid numbering of tetrahydrocannabinol derivatives
7 double bond isomers of parahexyl and their 30 stereoisomers
Dibenzopyran numberingMonoterpenoid numberingNumber of stereoisomersNatural occurrenceConvention on Psychotropic Substances Schedule
Short nameChiral centersFull nameShort nameChiral centers
Δ6a(7)-parahexyl9 and 10a3-hexyl-8,9,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-olΔ4-parahexyl1 and 34Nounscheduled
Δ7-parahexyl6a, 9 and 10a3-hexyl-6a,9,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-olΔ5-parahexyl1, 3 and 48Nounscheduled
Δ8-parahexyl6a and 10a3-hexyl-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-olΔ6-parahexyl3 and 44Nounscheduled
Δ9,11-parahexyl6a and 10a3-hexyl-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-9-methylene-6H-dibenzo[b,d]pyran-1-olΔ1(7)-parahexyl3 and 44Nounscheduled
Δ9-parahexyl6a and 10a3-hexyl-6a,7,8,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-olΔ1-parahexyl3 and 44Nounscheduled
Δ10-parahexyl6a and 93-hexyl-6a,7,8,9-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-olΔ2-parahexyl1 and 44Nounscheduled
Δ6a(10a)-parahexyl93-hexyl-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-olΔ3-parahexyl12NoSchedule I

Note that 6H-dibenzo[b,d]pyran-1-ol is the same as 6H-benzo[c]chromen-1-ol.

See also: Tetrahydrocannabinol § Isomerism

See also

References
  1. Adams R, Harfenist M, Loewe S (1949). "New Analogs of Tetrahydrocannabinol. XIX". J. Am. Chem. Soc. 71 (5): 1624–1628. doi:10.1021/ja01173a023.
  2. Ask Dr. Shulgin Online March 7, 2001
  3. Ono M, Shimamine M, Takahashi K, Inoue T (1974). "[Studies on hallucinogens. VII Synthesis of parahexyl]". Eisei Shikenjo hōkoku. Bulletin of National Institute of Hygienic Sciences (in Japanese). 49 (92): 46–50. PMID 4477495.
  4. Fairchild MD, Jenden DJ, Mickey MR, Yale C (1980). "EEG effects of hallucinogens and cannabinoids using sleep-waking behavior as baseline". Pharmacol. Biochem. Behav. 12 (1): 99–105. doi:10.1016/0091-3057(80)90422-0. PMID 6102770.
  5. Supniewski, J. (1950). Farmakologia. Warsaw: PZWL. p. 89.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.