Parahexyl

Overview

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.[1][2][3] WP

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.[4][5] WP

Parahexyl was occasionally used as an anxiolytic in the mid-20th century, the dosage ranging from 5 mg to 90 mg.[6][7] WP

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.[8] WP

Drug class

Cannabinoid WP

From the Wikipedia article's infobox.

Chemistry

Formula

C22H32O2 PC

CAS number

117-51-1 PC

Molar mass (g/mol)

328.5 PC

IUPAC name (computed by PubChem)

3-hexyl-6,6,9-trimethyl-7,8,9,10-tetrahydrobenzo[c]chromen-1-ol PC

SMILES

CCCCCCC1=CC(=C2C3=C(CCC(C3)C)C(OC2=C1)(C)C)O PC

InChIKey

OORFXDSWECAQLI-UHFFFAOYSA-N PC

PubChem CID

8334

IUPAC name

3-n-hexyl- 7,8,9,10-tetrahydro- 6,6,9-trimethyl- 6H-dibenzo(b,d)pyran- 1-ol WP

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Adams R, Loewe S, Jelinek C, Wolff H. Tetrahydrocannabinol Homologs with Marihuana Activity. IX1. Journal of the American Chemical Society. July 1941. doi:10.1021/ja01852a052
2. Journal / agency Adams R, Harfenist M, Loewe S. New Analogs of Tetrahydrocannabinol. XIX. Journal of the American Chemical Society. 1949. doi:10.1021/ja01173a023
3. Other Ask Dr. Shulgin Online March 7, 2001
4. Journal / agency Ono M, Shimamine M, Takahashi K, Inoue T. Studies on hallucinogens. VII Synthesis of parahexyl. Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences. 1974. PMID 4477495
5. Journal / agency Fairchild MD, Jenden DJ, Mickey MR, Yale C. EEG effects of hallucinogens and cannabinoids using sleep-waking behavior as baseline. Pharmacology, Biochemistry, and Behavior. January 1980. doi:10.1016/0091-3057(80)90422-0 · PMID 6102770
6. Other Supniewski J. Farmakologia. 1950
7. Other Synhexyl page - Supniewski J (1950). Farmakologia. Warsaw: PZWL. P. 89
8. Other 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

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.