Parahexyl

Parahexyl
Clinical data
ATC code	none;
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); CA: Schedule II; DE: Anlage I (Authorized scientific use only); UK: Class B; US: Schedule I; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name 3-n-hexyl- 7,8,9,10-tetrahydro- 6,6,9-trimethyl- 6H-dibenzo(b,d)pyran- 1-ol;
CAS Number	117-51-1 ;
PubChem CID	8334;
ChemSpider	8031 ;
UNII	450N174F9W;
KEGG	C22779;
Chemical and physical data
Formula	C22H32O2
Molar mass	328.496 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Oc2cc(cc1OC(C\3=C(/c12)CC(CC/3)C)(C)C)CCCCCC;
	InChI 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 ; Key:OORFXDSWECAQLI-UHFFFAOYSA-N ;
	(verify)

Parahexyl (Synhexyl, n-hexyl-Δ³-THC, (C6)-Δ^6a(10a)-THC) is a synthetic homologue of THC which was invented in 1941 during attempts to elucidate the structure of Δ⁹-THC, one of the active components of cannabis.

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 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.

Parahexyl was made illegal under UN convention in 1982 on the basis of its structural similarity and similar effects profile to THC. Parahexyl was placed into the most restrictive Schedule 1 as a compound with no medical use, despite the now-known medical uses for cannabinoids.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.