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Parahexyl

Synthetic homologue of THC

Field	Value
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
image_class	skin-invert-image
legal_AU
legal_BR	F2
legal_BR_comment
legal_CA	Schedule II
legal_UK	Class B
legal_US	Schedule I
legal_DE	Anlage I
legal_UN	P I
routes_of_administration
excretion
CAS_number_Ref
CAS_number	117-51-1
ATC_prefix	none
PubChem	8334
KEGG	C22779
synonyms	Synhexyl, n-hexyl-Δ3-THC, (C6)-Δ6a(10a)-THC
ChemSpiderID_Ref
ChemSpiderID	8031
UNII_Ref
UNII	450N174F9W
<!--Chemical data-->	C	22
H	32
O	2
smiles	Oc2cc(cc1OC(C\3=C(/c12)CC(CC/3)C)(C)C)CCCCCC
StdInChI_Ref
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
StdInChIKey	OORFXDSWECAQLI-UHFFFAOYSA-N

| elimination_half-life =

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

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.

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 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.

Isomerism

At least three isomers of parahexyl have been studied and are known to be active as cannabinoids. Parahexyl itself (i.e. the Δ6a(10a) isomer) has not had any significant use in scientific research since it was banned internationally in the early 1980s; however, the Δ8 and Δ9 isomers are both known to be cannabinoid receptor agonists, and Δ8-parahexyl has the code number JWH-124, while Δ9-parahexyl has been isolated from Cannabis plant material and assigned the name tetrahydrocannabihexol (THCH).

Dibenzopyran and monoterpenoid numbering of tetrahydrocannabinol derivatives

7 double bond isomers of parahexyl and their 30 stereoisomers	Dibenzopyran numbering	Monoterpenoid numbering	Number of stereoisomers	Natural occurrence	Convention on Psychotropic Substances Schedule	Short name	Chiral centers
Δ6a(7)-parahexyl	9 and 10a	3-hexyl-8,9,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol	Δ4-parahexyl	1 and 3	4	No	unscheduled
Δ7-parahexyl	6a, 9 and 10a	3-hexyl-6a,9,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol	Δ5-parahexyl	1, 3 and 4	8	No	unscheduled
Δ8-parahexyl	6a and 10a	3-hexyl-6a,7,10,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol	Δ6-parahexyl	3 and 4	4	No	unscheduled
Δ9,11-parahexyl	6a and 10a	3-hexyl-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-9-methylene-6H-dibenzo[b,d]pyran-1-ol	Δ1(7)-parahexyl	3 and 4	4	No	unscheduled
Δ9-parahexyl	6a and 10a	3-hexyl-6a,7,8,10a-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol	Δ1-parahexyl	3 and 4	4	No	unscheduled
Δ10-parahexyl	6a and 9	3-hexyl-6a,7,8,9-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol	Δ2-parahexyl	1 and 4	4	No	unscheduled
Δ6a(10a)-parahexyl	9	3-hexyl-7,8,9,10-tetrahydro-6,6,9-trimethyl-6H-dibenzo[b,d]pyran-1-ol	Δ3-parahexyl	1	2	No	Schedule I

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

References

Anvisa. (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial". [[Diário Oficial da União]].
(July 1941). "Tetrahydrocannabinol Homologs with Marihuana Activity. IX1.". Journal of the American Chemical Society.
[http://www.cognitiveliberty.org/shulgin/adsarchive/parahexl.htm Ask Dr. Shulgin Online March 7, 2001]
(1974). "[Studies on hallucinogens. VII Synthesis of parahexyl]". Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences.
(January 1980). "EEG effects of hallucinogens and cannabinoids using sleep-waking behavior as baseline". Pharmacology, Biochemistry, and Behavior.
(1950). "Farmakologia". PZWL.
"Synhexyl page - Supniewski J (1950). Farmakologia. Warsaw: PZWL. P. 89.".
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
(September 1999). "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics.
(2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation". Perspectives in Medicinal Chemistry.
(December 2020). "Identification of a new cannabidiol n-hexyl homolog in a medicinal cannabis variety with an antinociceptive activity in mice: cannabidihexol". Scientific Reports.

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