Δ-3-Tetrahydrocannabinol

Chemical compound

Δ-3-Tetrahydrocannabinol
Identifiers

IUPAC name (9S)-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydrobenzo[c]chromen-1-ol
CAS Number	95720-02-8^Y 7663-50-5 (racemic)
PubChem CID	71587360
ChemSpider	32700761
UNII	PYI73UAY3K
KEGG	C22743
CompTox Dashboard (EPA)	DTXSID40241935
Chemical and physical data
Formula	C₂₁H₃₀O₂
Molar mass	314.469 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC1=CC(=C2C3=C(CC[C@@H](C3)C)C(OC2=C1)(C)C)O
InChI InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h12-14,22H,5-11H2,1-4H3/t14-/m0/s1 Key:NEBZNJDFIPBXCS-AWEZNQCLSA-N

Δ-3-Tetrahydrocannabinol (Delta-3-THC, Δ³-THC, Δ^6a(10a)-THC, EA-1477) is a synthetic isomer of tetrahydrocannabinol, developed during the original research in the 1940s to develop synthetic routes to the natural products Δ⁸-THC and Δ⁹-THC found in the cannabis plant.^[1] While the normal trans configuration of THC is in this case flattened by the double bond, it still has two enantiomers as the 9-methyl group can exist in an (R) or (S) conformation. The (S) enantiomer has similar effects to Δ⁹-THC though with several times lower potency, while the (R) enantiomer is many times less active or inactive, depending on the assay used.^[2]^[3]^[4] It has been identified as a component of vaping liquid products.^[5]

References

^ US 2419935, Adams R, "Marihuana active compounds.", issued 1947
^ Matsumoto K, Stark P, Meister RG (January 1977). "Cannabinoids. 1. 1-Amino- and 1-mercapto-7,8,9,10-tetrahydro-6H-dibenzo [b,d]pyrans". Journal of Medicinal Chemistry. 20 (1): 17–24. doi:10.1021/jm00211a004. PMID 833820.
^ Consroe P, Martin AR, Fish BS (May 1982). "Use of a potential rabbit model for structure--behavioral activity studies of cannabinoids". Journal of Medicinal Chemistry. 25 (5): 596–9. doi:10.1021/jm00347a021. PMID 7086846.
^ Srebnik M, Lander N, Breuer A, Mechoulam R (1984). "Base-catalysed double-bond isomerizations of cannabinoids: structural and stereochemical aspects". Journal of the Chemical Society, Perkin Transactions 1: 2881–6. doi:10.1039/P19840002881.
^ Ciolino LA, Ranieri TL, Brueggemeyer JL, Taylor AM, Mohrhaus AS (2021). "EVALI Vaping Liquids Part 1: GC-MS Cannabinoids Profiles and Identification of Unnatural THC Isomers". Frontiers in Chemistry. 9: 746479. Bibcode:2021FrCh....9..726C. doi:10.3389/fchem.2021.746479. PMC 8499677. PMID 34631667.

Cannabinoids

Phytocannabinoids
(comparison)

Cannabibutols	CBB
Cannabichromenes	CBC CBCA CBCA-A CBCB CBCBA CBCP CBCPA CBCV CBCVA CBCQ
Cannabicyclols	CBL CBLA CBLB CBLP CBLPA CBLV CBLVA
Cannabidiols	CBD CBDA CBD-C1 CBD-C5 CBDB CBDBA CBDD CBDH CBDP CBDPA CBDM CBDMA CBDV CBDVA CBDQ
Cannabielsoins	CBE CBEA CBEA-A CBEA-B CBEB CBEP CBEPA CBEV
Cannabigerols	CBG CBGA CBGB CBGBA CBGM CBGAM CBGP CBGPA CBNR CBNRA CBNRA-A CBGV CBGVA CBGVA-A CBGQ
Cannabiphorols	CBP
Cannabinols	CBN CBNA CBN-C1 CBN-C2 CBN-C4 CBNM CBND CBNDA CBNP CBNPA CBVD CBVDA
Cannabitriols	CBT CBTA CBTB CBTV CBTVA CBTP CBTPA
Cannabivarins	CBV CBVA
Delta-8-tetrahydrocannabinols	Delta-8-THC Delta-8-THCA Delta-8-THCA-A Delta-8-THCB Delta-8-THCP Delta-8-THCV
Delta-9-tetrahydrocannabinols	Delta-9-THC (THC) THCA THCMA THCA-A THCA-B THCBA THCA-C4 THCC THCA-C1 THCA-A-C1 THCA-B-C1 THCB THCH THCP THCPA THCV THCVA THCQ
Delta-10-Tetrahydrocannabinols	Delta-10-THC
Miscellaneous cannabinoids	Δ8-iso-THC Δ4(8)-iso-THC 7,8-Dihydrocannabinol 8,9-Dihydrocannabidiol CBCF Cannabicitran CBF Cannabiglendol CBM CBR CBRPA Caryophyllene DCBF Alkylamides Epigallocatechin gallate Gallocatechol Hexahydrocannabinol (HHC) Perrottetinene Serinolamide A Yangonin
Active metabolites	3'-OH-THC 7-OH-CBD 8,11-DiOH-THC 11-COOH-THC 11-OH-CBN 11-OH-HHC 11-OH-Δ8-THC 11-OH-Δ9-THC

Endocannabinoids

Synthetic
cannabinoid
receptor
agonists /
neocannabinoids

Classical cannabinoids (dibenzopyrans)	9-OH-HHC 9-Nor-9β-HHC A-40174 A-41988 A-42574 Ajulemic acid AM-087 AM-411 AM-855 AM-905 AM-906 AM-919 AM-926 AM-938 AM-2389 AM-4030 AM-7438 AM-11245 AMG-1 AMG-3 AMG-36 AMG-41 CP 42,096 Delta-3-THC Delta-4-THC Delta-7-THC Delta-10-THC Dexanabinol (HU-211) DMHP Dronabinol HU-210 HU-243 JWH-051 JWH-056 JWH-057 JWH-065 JWH-091 JWH-102 JWH-103 JWH-124 JWH-130 JWH-133 JWH-138 JWH-139 JWH-142 JWH-143 JWH-161 JWH-186 JWH-187 JWH-188 JWH-189 JWH-190 JWH-191 JWH-215 JWH-216 JWH-217 JWH-224 JWH-225 JWH-226 JWH-227 JWH-229 JWH-230 JWH-233 JWH-247 JWH-254 JWH-256 JWH-277 JWH-278 JWH-298 JWH-299 JWH-300 JWH-301 JWH-310 JWH-336 JWH-338 JWH-339 JWH-340 JWH-341 JWH-349 JWH-350 JWH-352 JWH-353 JWH-354 JWH-355 JWH-356 JWH-357 JWH-358 JWH-359 JWH-360 JWH-361 JWH-362 KM-233 L-759,633 L-759,656 Levonantradol (CP 50,5561) Menabitan Nabazenil Nabidrox (Canbisol) Nabilone Nabitan Naboctate O-224 O-581 O-774 O-806 O-823 O-1057 O-1125 O-1191 O-1238 O-2048 O-2113 O-2365 O-2372 O-2373 O-2383 O-2426 O-2484 O-2545 O-2694 O-2715 O-2716 O-3223 O-3226 Parahexyl Pirnabine SP-111 THC hemisuccinate THC-O-acetate THC-O-phosphate
Non-classical cannabinoids	Cannabicyclohexanol Cannabinor CBD-DMH CP 47,497 (C6)-CP 47,497 (C9)-CP 47,497 CP 55,244 CP 55,940 Delta-6-Cannabidiol Etrinabdione HU-320 HU-331 HU-336 HU-345 HU-446 HU-465 HU-910 HUF-101 Nonabine O-1376 O-1422 O-1601 O-1656 O-1657 O-1660 O-1663 O-1871 Onternabez (HU-308) SPA-229 Tinabinol
Adamantoylindoles	5F-AKB-48 APICA STS-135
Benzimidazoles	AZ-11713908 AZD-1940 BIM-018 FUBIMINA MCHB-1 PF-03550096 RQ-00202730
Benzoylindoles	1-Butyl-3-(2-methoxybenzoyl)indole 1-Butyl-3-(4-methoxybenzoyl)indole 1-Pentyl-3-(2-methoxybenzoyl)indole AM-630 AM-679 AM-694 AM-1241 AM-2233 GW-405,833 (L-768,242) Pravadoline RCS-4 WIN 54,461
Cyclohexylphenols	CP-47,947 CP-55,940
Eicosanoids	AM-883 AM-1346 ACEA ACPA Methanandamide (AM-356) O-585 O-689 O-1812 O-1860 O-1861
Hydrocarbons	JWH-171 JWH-176 JWH-220
Indazole carboxamides	AB-PINACA AB-FUBINACA
Indazole-3- carboxamides	4F-MDMB-BINACA 4'Cl-CUMYL-PINACA 4'F-CUMYL-5F-PINACA 5Cl-APINACA 5F-ADB 5F-ADB-PINACA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-EDMB-PINACA 5F-EMB-PINACA AB-CHMINACA AB-FUBINACA AB-FUBINACA 2-fluorobenzyl isomer AB-PINACA ADB-BINACA ADB-CHMINACA ADB-HEXINACA ADB-FUBINACA ADB-PINACA ADB-4en-PINACA ADB-5'Br-PINACA Adamantyl-THPINACA ADSB-FUB-187 AMB-CHMINACA AMB-FUBINACA APINACA (AKB48) APP-FUBINACA CUMYL-4CN-BINACA CUMYL-CBMINACA CUMYL-CHSINACA CUMYL-FUBINACA CUMYL-NBMINACA CUMYL-PINACA CUMYL-THPINACA CUMYL-TSINACA EMB-FUBINACA FUB-APINACA MDMB-4en-PINACA MDMB-5Br-INACA MDMB-FUBINACA MDMB-CHMINACA MN-18 PX-2 PX-3 THQ-PINACA
Indole-3-carboxamides	4'F-CUMYL-5F-PICA 5F-ADBICA 5F-EDMB-PICA 5F-MDMB-PICA 5F-NNE1 5F-PCN 5F-SDB-006 AB-FUBICA AB-PICA ADBICA ADB-FUBICA APICA BMS-F CUMYL-BICA CUMYL-CBMICA CUMYL-CHMICA CUMYL-NBMICA CUMYL-PICA CUMYL-5F-PICA FDU-NNE1 MDMB-CHMICA MMB-CHMICA MMB-2201 MN-25 (UR-12) NNE1 PX-1 Org 28312 Org 28611 SDB-006 STS-135
Indole-3-carboxylates	5F-PB-22 FDU-PB-22 FUB-PB-22 QUCHIC (BB-22) QUPIC (PB-22) NM-2201
Naphthoylindazoles	THJ-018 THJ-2201
Naphthoylindoles	5F-JWH-398 AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 CHM-081 EAM-2201 FUB-JWH-018 JWH-004 JWH-007 JWH-009 JWH-011 JWH-015 JWH-016 JWH-018 JWH-019 JWH-020 JWH-042 JWH-043 JWH-046 JWH-047 JWH-048 JWH-049 JWH-050 JWH-070 JWH-072 JWH-073 JWH-076 JWH-077 JWH-079 JWH-080 JWH-081 JWH-082 JWH-083 JWH-093 JWH-094 JWH-095 JWH-096 JWH-097 JWH-098 JWH-099 JWH-100 JWH-116 JWH-120 JWH-122 JWH-148 JWH-149 JWH-151 JWH-153 JWH-159 JWH-160 JWH-163 JWH-164 JWH-165 JWH-166 JWH-180 JWH-181 JWH-182 JWH-189 JWH-193 JWH-198 JWH-200 JWH-210 JWH-211 JWH-212 JWH-213 JWH-234 JWH-235 JWH-236 JWH-239 JWH-240 JWH-241 JWH-242 JWH-258 JWH-259 JWH-260 JWH-261 JWH-262 JWH-265 JWH-266 JWH-267 JWH-268 JWH-387 JWH-398 JWH-416 JWH-417 JWH-422 JWH-423 JWH-424 JWH-425 MAM-1220 MAM-2201 NE-CHMIMO
Naphthoylpyrroles	JWH-030 JWH-031 JWH-032 JWH-033 JWH-036 JWH-044 JWH-045 JWH-145 JWH-146 JWH-147 JWH-150 JWH-156 JWH-243 JWH-244 JWH-245 JWH-246 JWH-292 JWH-293 JWH-307 JWH-308 JWH-309 JWH-346 JWH-347 JWH-348 JWH-363 JWH-364 JWH-365 JWH-366 JWH-367 JWH-368 JWH-369 JWH-370 JWH-371 JWH-372 JWH-373
Naphthylmethylindenes	JWH-171 JWH-176 JWH-220
Naphthylmethylindoles	JWH-175 JWH-184 JWH-185 JWH-192 JWH-194 JWH-195 JWH-196 JWH-197 JWH-199
Phenylacetylindoles	Cannabipiperidiethanone JWH-167 JWH-201 JWH-202 JWH-203 JWH-204 JWH-205 JWH-206 JWH-207 JWH-208 JWH-209 JWH-237 JWH-248 JWH-249 JWH-250 JWH-251 JWH-252 JWH-253 JWH-302 JWH-303 JWH-304 JWH-305 JWH-306 JWH-311 JWH-312 JWH-313 JWH-314 JWH-315 JWH-316 RCS-8
Pyrazolecarboxamides	5F-AB-FUPPYCA 5F-AMPPPCA AB-CHFUPYCA
Pyrrolobenzoxazines	WIN 55,212-2
Quinolinyl esters	PB-22 5F-PB-22
Tetramethylcyclo- propanoylindazoles	FAB-144
Tetramethylcyclo- propanoylindoles	5Br-UR-144 5Cl-UR-144 A-796,260 A-834,735 FUB-144 UR-144 XLR-11 XLR-12
Tetramethylcyclo- propylindoles	UR-144 XLR-11
Others	2F-QMPSB 4-HTMPIPO 4CN-CUMYL-BUT7AICA 5F-PY-PICA 5F-PY-PINACA 5F-3-pyridinoylindole 5F-ADB-P7AICA 5F-CUMYL-P7AICA 5F-CUMYL-PEGACLONE A-836,339 A-955,840 A-PONASA Abnormal cannabidiol AB-001 ADB-FUBHQUCA ADB-FUBIATA ADB-P7AICA AM-1248 AM-1714 BAY 38-7271 BAY 59-3074 BzODZ-EPyr CB-13 CB-86 CBS-0550 CUMYL-4CN-B7AICA CUMYL-CB-MEGACLONE CUMYL-CH-MEGACLONE CUMYL-PEGACLONE EG-018 GSK-554,418A GW-842,166X JTE 7-31 LASSBio-881 LBP-1 Leelamine MDA-7 MDA-19 MEPIRAPIM NESS-040C5 NMP-7 O-889 O-1269 O-1270 O-1399 O-1602 O-2220 Olorinab PF-03550096 PSB-SB-1202 PTI-1 PTI-2 PTI-3 QMPSB S-444,823 S-777,469 SER-601 Tedalinab URB-447 VSN-16 WIN 56,098