Parahexyl

Drugbox
IUPAC_name = 3-n-Hexyl-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo(b,d)pyran-1-ol


width= 200
CAS_number= 117-51-1
ATC_prefix=
ATC_suffix=
PubChem= 8334
DrugBank=
C=22 | H=32 | O=2
molecular_weight = 328.488 g/mol
bioavailability=
metabolism =
elimination_half-life=
excretion =
pregnancy_category =
legal_status = Schedule I / Class A
routes_of_administration=

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.cite journal
author=Adams R, Harfenist M, Loewe S
title=New Analogs of Tetrahydrocannabinol. XIX
journal=J. Am. Chem. Soc.
volume=71
issue=5
pages=1624–1628
year=1949
pmid=
doi=10.1021/ja01173a023] [ [http://www.cognitiveliberty.org/shulgin/adsarchive/parahexl.htm Ask Dr. Shulgin Online March 7, 2001 ] ]

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. cite journal
author=Ono M, Shimamine M, Takahashi K, Inoue T
title= [Studies on hallucinogens. VII Synthesis of parahexyl]
language=Japanese
journal=Eisei Shikenjo hōkoku. Bulletin of National Institute of Hygienic Sciences
volume=49
issue=92
pages=46–50
year=1974
pmid=4477495
doi=] Parahexyl produces classic cannabis agonist effects in animals. It has a somewhat higher oral bioavailability than THC itself but is otherwise very similar. cite journal
author=Fairchild MD, Jenden DJ, Mickey MR, Yale C
title=EEG effects of hallucinogens and cannabinoids using sleep-waking behavior as baseline
journal=Pharmacol. Biochem. Behav.
volume=12
issue=1
pages=99–105
year=1980
pmid=6102770
doi=] 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 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 abuse by humans or illicit sale. Parahexyl was placed into the most restrictive Schedule 1 as a compound with no medical use, even though it has never been properly researched to see whether it might have medical use or not.

References