parahexyl

{{Short description|Synthetic homologue of THC}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Infobox drug

| verifiedrevid = 447736981

| class = Cannabinoid

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

| image = Parahexyl-skeletal.svg

| tradename =

| legal_AU =

| legal_BR = F2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-07-25}}

| legal_CA = Schedule II

| legal_UK = Class B

| legal_US = Schedule I

| legal_DE = Anlage I

| legal_UN = P I

| routes_of_administration =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 117-51-1

| ATC_prefix = none

| PubChem = 8334

| KEGG = C22779

| synonyms = Synhexyl, n-hexyl-Δ³-THC, (C6)-Δ^6a(10a)-THC

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8031

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 450N174F9W

| C = 22

| H = 32

| O = 2

| smiles = Oc2cc(cc1OC(C\3=C(/c12)CC(CC/3)C)(C)C)CCCCCC

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OORFXDSWECAQLI-UHFFFAOYSA-N

}}

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.{{cite journal | vauthors = Adams R, Loewe S, Jelinek C, Wolff H | title = Tetrahydrocannabinol Homologs with Marihuana Activity. IX1. | journal = Journal of the American Chemical Society | date = July 1941 | volume = 63 | issue = 7 | pages = 1971–1973| doi = 10.1021/ja01852a052 }}{{cite journal

|vauthors=Adams R, Harfenist M, Loewe S |title=New Analogs of Tetrahydrocannabinol. XIX |journal=Journal of the American Chemical Society |volume=71 |issue=5

|pages=1624–1628 |year=1949 |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 {{nowrap|3-pentyl}} chain by one CH₂ group to {{nowrap|n-hexyl}}.{{cite journal | vauthors = Ono M, Shimamine M, Takahashi K, Inoue T | title = [Studies on hallucinogens. VII Synthesis of parahexyl] | language = ja | journal = Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences | volume = 49 | issue = 92 | pages = 46–50 | year = 1974 | pmid = 4477495 }} 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.{{cite journal | vauthors = Fairchild MD, Jenden DJ, Mickey MR, Yale C | title = EEG effects of hallucinogens and cannabinoids using sleep-waking behavior as baseline | journal = Pharmacology, Biochemistry, and Behavior | volume = 12 | issue = 1 | pages = 99–105 | date = January 1980 | pmid = 6102770 | doi = 10.1016/0091-3057(80)90422-0 | s2cid = 24865915 }} 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.{{cite book | vauthors = Supniewski J |date=1950 |title=Farmakologia |location=Warsaw |publisher=PZWL |page=89}}{{cite web | url=https://imgur.com/a/cEsFXig | title=Synhexyl page - Supniewski J (1950). Farmakologia. Warsaw: PZWL. P. 89. }}

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 IReport 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 as a compound with no medical use.