Parahexyl

Parahexyl

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule II DE: Anlage I (Controlled) UK: Class A US: 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 Y
PubChem (CID)	8334
ChemSpider	8031 Y
UNII	450N174F9W Y
Chemical and physical data
Formula	C22H32O2
Molar mass	328.488 g/mol
3D model (Jmol)	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 Y Key:OORFXDSWECAQLI-UHFFFAOYSA-N Y

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.

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 classic cannabis agonist effects 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 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.

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