Parahexyl ATC code Legal status
CA : Schedule II
DE : Anlage I (Authorized scientific use only)
UK : Class A
US : Schedule I
3-n-hexyl- 7,8,9,10-tetrahydro- 6,6,9-trimethyl- 6H-dibenzo(b,d)pyran- 1-ol
CAS Number PubChem CID ChemSpider UNII Formula C 22 H 32 O 2 Molar mass 328.496 g·mol−1 3D model (JSmol )
Oc2cc(cc1OC(C\3=C(/c12)CC(CC/3)C)(C)C)CCCCCC
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-Δ3 -THC , (C6)-Δ6a(10a) -THC ) 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 .[1] [2]
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.[3] 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.[4] 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.[5]
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.
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 ,[6] [7] while Δ9 -parahexyl has been isolated from Cannabis plant material and assigned the name tetrahydrocannabihexol .[8]
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
Full name
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.
See also: Tetrahydrocannabinol § Isomerism
See also [ ]
References [ ]
^ Adams R, Harfenist M, Loewe S (1949). "New Analogs of Tetrahydrocannabinol. XIX". J. Am. Chem. Soc . 71 (5): 1624–1628. doi :10.1021/ja01173a023 .
^ Ask Dr. Shulgin Online March 7, 2001
^ Ono M, Shimamine M, Takahashi K, Inoue T (1974). "[Studies on hallucinogens. VII Synthesis of parahexyl]". Eisei Shikenjo Hokoku. Bulletin of National Institute of Hygienic Sciences (in Japanese). 49 (92): 46–50. PMID 4477495 .
^ Fairchild MD, Jenden DJ, Mickey MR, Yale C (January 1980). "EEG effects of hallucinogens and cannabinoids using sleep-waking behavior as baseline". Pharmacology, Biochemistry, and Behavior . 12 (1): 99–105. doi :10.1016/0091-3057(80)90422-0 . PMID 6102770 . S2CID 24865915 .
^ Supniewski J (1950). Farmakologia . Warsaw: PZWL. p. 89.
^ Martin BR, Jefferson R, Winckler R, Wiley JL, Huffman JW, Crocker PJ, Saha B, Razdan RK (September 1999). "Manipulation of the tetrahydrocannabinol side chain delineates agonists, partial agonists, and antagonists". The Journal of Pharmacology and Experimental Therapeutics . 290 (3): 1065–79. PMID 10454479 .
^ Bow EW, Rimoldi JM (2016). "The Structure-Function Relationships of Classical Cannabinoids: CB1/CB2 Modulation" . Perspectives in Medicinal Chemistry . 8 : 17–39. doi :10.4137/PMC.S32171 . PMC 4927043 . PMID 27398024 .
^ Linciano P, Citti C, Russo F, Tolomeo F, Laganà A, Capriotti AL, Luongo L, Iannotta M, Belardo C, Maione S, Forni F, Vandelli MA, Gigli G, Cannazza G (December 2020). "Identification of a new cannabidiol n-hexyl homolog in a medicinal cannabis variety with an antinociceptive activity in mice: cannabidihexol" . Scientific Reports . 10 (1): 22019. doi :10.1038/s41598-020-79042-2 . PMC 7744557 . PMID 33328530 .
Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCH
THCP
THCV
Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide)
2-Arachidonoylglycerol (2-AG)
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
2-Oleoylglycerol (2-OG)
N-Arachidonoyl dopamine (NADA)
N-Arachidonylglycine (NAGly)
N-Arachidonoyl serotonin (AA-5-HT)
Docosatetraenoylethanolamide (DEA)
Lysophosphatidylinositol (LPI)
Oleamide
Oleoylethanolamide (OEA)
Palmitoylethanolamide (PEA)
RVD-Hpα
Stearoylethanolamide (SEA)
O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles
AM-630
AM-679
AM-694
AM-1241
AM-2233
GW-405,833 (L-768,242)
Pravadoline
RCS-4
WIN 54,461
Cyclohexylphenols Eicosanoids
ACEA
ACPA
Methanandamide (AM-356)
O-1812
Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
XLR-12
Tetramethylcyclo- propylindoles Others
Allosteric CBR ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
AM-251
AM-630
AM-6545
BML-190
Drinabant (AVE1625)
Hemopressin
Ibipinabant (SLV319)
JTE-907
LY-320,135
MK-9470
NESS-0327
O-1918
O-2050
Otenabant (CP-945,598)
PF-514273
PipISB
PSB-SB-487
Rimonabant (SR141716)
Rosonabant (E-6776)
SR-144,528
Surinabant (SR147778)
Taranabant (MK-0364)
TM-38837
VCHSR
See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics
Hallucinogens
Psychedelics (5-HT2A agonists)
Benzofurans
2C-B-FLY
2CBFly-NBOMe
5-MeO-BFE
5-MeO-DiBF
Bromo-DragonFLY
F-2
F-22
TFMFly
Lyserg‐ amides
1B-LSD
1cP-LSD
1P-ETH-LAD
1P-LSD
1V-LSD
2-Butyllysergamide
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AL-LAD
ALD-52
BU-LAD
Diallyllysergamide
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ETH-LAD
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LAE-32
LPD-824
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LSM-775
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alpha -alkyltryptamines
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α-ET
α-MT
x -DALT
(Daltacetin) 4-AcO-DALT
5-MeO-DALT
DALT
x -DET
(Ethacetin) 4-AcO-DET
(Ethocin) 4-HO-DET
5-MeO-DET
(T-9) DET
(Ethocybin) 4-PO-DET
x -DiPT
(Ipracetin) 4-AcO-DiPT
(Iprocin) 4-HO-DiPT
5-MeO-DiPT
DiPT
x -DMT
4,5-DHP-DMT
2,N,N-TMT
4-AcO-DMT
4-HO-5-MeO-DMT
4-Propionyloxy-DMT
5-AcO-DMT
5-Bromo-DMT
5-MeO-DMT
5-N ,N -TMT
7,N,N-TMT
α,N,N-TMT
(Bufotenin) 5-HO-DMT
DMT
Norbaeocystin
(Psilocin) 4-HO-DMT
(Psilocybin) 4-PO-DMT
x -DPT
(Deprocin) 4-HO-DPT
5-MeO-DPT
(The Light) DPT
Ibogaine-related
18-MAC
18-MC
Coronaridine
Ibogaine
Ibogamine
ME-18-MC
Noribogaine
Tabernanthine
Voacangine
x -MET
(Metocin) 4-HO-MET
(Metocetin) 4-AcO-MET
5-MeO-MET
MET
x -MiPT
(Mipracetin) 4-AcO-MiPT
(Miprocin) 4-HO-MiPT
5-Me-MiPT
(Moxy) 5-MeO-MiPT
MiPT
Others
4-HO-DBT
4-HO-EPT
4-HO-McPT
(Lucigenol) 4-HO-MPMI
(Meprocin) 4-HO-MPT
5-MeO-EiPT
5-MeO-MALT
5-MeO-MPMI
Aeruginascin
Baeocystin
DBT
EiPT
EPT
MPT
PiPT
Others
AL-38022A
ALPHA
Dimemebfe
Efavirenz
Glaucine
Lorcaserin
M-ALPHA
RH-34 Also empathogens in general (e. g.: 5-APB , 5-MAPB , 6-APB and other substituted benzofurans ).
Dissociatives (NMDAR antagonists )
Arylcyclo‐ hexylamines
Ketamine-related
2-Fluorodeschloroketamine
Arketamine ((R)-ketamine)
Deschloroketamine
Ethketamine (N-Ethylnorketamine)
Esketamine ((S)-ketamine)
Ketamine
Methoxetamine
Methoxmetamine
Methoxyketamine
MXiPr
Norketamine
Tiletamine
PCP-related Others
Diarylethylamines Morphinans
Dextrallorphan
Dextromethorphan
Dextrorphan
Racemethorphan
Racemorphan
Others
2-EMSB
2-MDP
8A-PDHQ
Aptiganel
Budipine
Delucemine
Dexoxadrol
Dizocilpine
Etoxadrol
Herkinorin
Ibogaine
Midafotel
NEFA
Neramexane
Nitrous oxide
Noribogaine
Perzinfotel
RB-64
Remacemide
Selfotel
Xenon
Deliriants (mAChR antagonists )
Atropine
Benactyzine
Benzatropine
Benzydamine
Biperiden
Brompheniramine
BZ
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,668
Chloropyramine
Chlorphenamine
Clemastine
CS-27349
Cyclizine
Cyproheptadine
Dicycloverine
Dimenhydrinate
Diphenhydramine
Ditran
Doxylamine
EA-3167
EA-3443
EA-3580
EA-3834
Elemicin
Flavoxate
Hyoscyamine
JB-318
JB-336
Meclozine
Mepyramine
Myristicin
Orphenadrine
Oxybutynin
Pheniramine
Phenyltoloxamine
Procyclidine
Promethazine
Scopolamine
Tolterodine
Trihexyphenidyl
Tripelennamine
Triprolidine
WIN-2299
Others
Receptor (ligands )
CB1
Agonists (abridged; see here for more) : 2-AG
2-AGE (noladin ether)
11-Hydroxy-THC
α-Amyrin · β-Amyrin
AB-CHMINACA
AM-1220
AM-1221
AM-1235
AM-2201
AM-2232
Anandamide
AZ-11713908
Cannabinol
CB-13
CP 47,497
CP 55,940
Dimethylheptylpyran
DEA
ECG
EGCG
Epicatechin
Gallocatechol (gallocatechin)
Honokiol
HU-210
JWH-007
JWH-015
JWH-018
JWH-073
Kavain
L-759,633
Levonantradol
Menabitan
Nabilone
Nabitan
NADA
O-1812
Oleamide
Pravadoline
Serinolamide A
THC (dronabinol)
UR-144
WIN 55,212-2
Yangonin
Antagonists: AM-251
AM-6545
Cannabidiol
Cannabigerol
Drinabant
Falcarinol (carotatoxin)
Hemopressin
Ibipinabant
LY-320,135
MK-9470
NESS-0327
O-2050
Otenabant
PF-514273
PipISB
Rimonabant
Rosonabant
Surinabant
Taranabant
THCV
TM-38837
VCHSR
Virodhamine
CB2
Agonists: 2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-133
L-759,633
L-759,656
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Virodhamine
Antagonists: 4-O-Methylhonokiol
AM-630
BML-190
Cannabidiol
Honokiol
JTE-907
SR-144,528
WIN 54,461
WIN 56,098
NAGly (GPR18 )
Agonists: Abnormal cannabidiol
ACPA
AM251
Anandamide
Cannabidiol
NADGly
THC (dronabinol)
O-1602
GPR55
Agonists: 2-AGE (noladin ether)
Abnormal cannabidiol
AM-251
CP 55,940
Lysophosphatidylinositol
O-1602
Oleoylethanolamide
Palmitoylethanolamide
THC (dronabinol)
GPR119 Unsorted
Transporter (modulators )
eCBTs
Inhibitors:
AM-404
Arachidonoyl serotonin
Cannabidiol
Guineensine
LY-2183240
Paracetamol (acetaminophen)
URB-597
VDM-11
Enzyme (modulators )
FAAH MAGL
Inhibitors:
IDFP
JZL-184
JZL-195
MAFP
URB-602
ABHD6 ABHD12
Inhibitors: Betulinic acid
Maslinic acid
MAFP
Oleanolic acid
Orlistat (tetrahydrolipstatin)
Ursolic acid
Others
Precursors: Phosphatidylethanolamine
NAPE
Diacylglycerol
Others: (directly potentiates activity of 2-AG at CB1 receptor)
(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)