Cis-THC
{{Short description|Cis enantiomer of tetrahydrocannabidiol}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| IUPAC_name = (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
| image = CisD9THC_structure.png
| image_class = skin-invert-image
| width = 220
| image2 = Cis-d9-THC.png
| image_class2 = bg-transparent
| width2 = 220
| pregnancy_category =
| legal_status =
| routes_of_administration =
| bioavailability =
| metabolism =
| excretion =
| CAS_number = 6087-73-6
| CAS_supplemental =
43009-38-7
| PubChem = 12831993
| ChemSpiderID = 52083428
| ChEMBL =
| ChEBI =
| UNII =
| C=21 | H=30 | O=2
| smiles = CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@@H]3C(OC2=C1)(C)C)C)O
| StdInChI = 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/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m1/s1
| StdInChIKey = CYQFCXCEBYINGO-SJORKVTESA-N
}}
cis-Delta-9-Tetrahydrocannabinol ((-)-cis-Δ9-THC) is an isomer of tetrahydrocannabinol found in the Cannabis plant but in lower quantities than the more well-known trans isomer. Formation of cis-THC could take place in process of epimerization associated with acid-catalyzed cyclization of CBD to THC.{{Cite journal | vauthors = Palfreyman MG, Nivorozhkin A | title = Acid-Catalyzed Conversion of Cannabidiol to Tetrahydrocannabinols: En Route to Demystifying Manufacturing Processes and Controlling the Reaction Outcomes | journal = Cannabis and Cannabinoid Research | volume = 10 | issue = 3 | pages = 377–388 | date = 2025-06-01 | pmid = 40250991 | doi = 10.1089/can.2025.0015 | url = https://www.liebertpub.com/doi/10.1089/can.2025.0015 | language = en | issn = 2578-5125 }} It has similar psychoactive effects to trans-Δ9-THC in tests on mice, but with only around 1/5th the potency. The equivalent Δ8 isomer is also known as a synthetic compound, but has not been isolated from Cannabis plant material. All four cis/trans isomers are known, though only the (6aR,10aR) and (6aS,10aR) enantiomers are psychoactive, while the others retain activity at targets such as GPR18 and GPR55.{{cite journal | vauthors = Uliss DB, Dalzell HC, Handrick GR, Howes JF, Razdan RK | title = Hashish. Importance of the phenolic hydroxyl group in tetrahydrocannabinols | journal = Journal of Medicinal Chemistry | volume = 18 | issue = 2 | pages = 213–215 | date = February 1975 | pmid = 1120991 | doi = 10.1021/jm00236a025 }}{{cite journal | vauthors = Smith RM, Kempfert KD | title = Δ1-3, 4-cis-tetrahydrocannabinol in Cannabis sativa. | journal = Phytochemistry | volume = 16 | issue = 7 | pages = 1088–1089 | date = January 1977 | doi = 10.1016/S0031-9422(00)86745-X | bibcode = 1977PChem..16.1088S }}{{cite journal | vauthors = Churchill KT | title = Synthetic tetrahydrocannabinol | journal = Journal of Forensic Sciences | volume = 28 | issue = 3 | pages = 762–772 | date = July 1983 | pmid = 6311937 | doi = 10.1520/JFS11571J }}{{cite journal | vauthors = Ballerini E, Minuti L, Piermatti O, Pizzo F | title = High pressure Diels-Alder approach to hydroxy-substituted 6a-cyano-tetrahydro-6H-benzo[c]chromen-6-ones: a route to delta(6)-cis-cannabidiol | journal = The Journal of Organic Chemistry | volume = 74 | issue = 11 | pages = 4311–4317 | date = June 2009 | pmid = 19402693 | doi = 10.1021/jo9005365 }}{{cite journal | vauthors = Minuti L, Ballerini E | title = High-pressure access to the Δ9-cis- and Δ9-trans-tetrahydrocannabinols family | journal = The Journal of Organic Chemistry | volume = 76 | issue = 13 | pages = 5392–5403 | date = July 2011 | pmid = 21563759 | doi = 10.1021/jo200796b }}{{cite journal | vauthors = Schafroth MA, Zuccarello G, Krautwald S, Sarlah D, Carreira EM | title = Stereodivergent total synthesis of Δ9-tetrahydrocannabinols | journal = Angewandte Chemie | location = International Ed. in English | volume = 53 | issue = 50 | pages = 13898–13901 | date = December 2014 | pmid = 25303495 | doi = 10.1002/anie.201408380 }}{{cite journal | vauthors = Schafroth MA, Mazzoccanti G, Reynoso-Moreno I, Erni R, Pollastro F, Caprioglio D, Botta B, Allegrone G, Grassi G, Chicca A, Gasparrini F, Gertsch J, Carreira EM, Appendino G | title = Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology | journal = Journal of Natural Products | volume = 84 | issue = 9 | pages = 2502–2510 | date = September 2021 | pmid = 34304557 | doi = 10.1021/acs.jnatprod.1c00513 | s2cid = 236431636 | url = https://boris.unibe.ch/161548/ | hdl = 20.500.11850/508697 | hdl-access = free }}{{cite journal | vauthors = Dorsch C, Schneider C | title = Brønsted Acid Catalyzed Asymmetric Synthesis of cis-Tetrahydrocannabinoids | journal = Angewandte Chemie | location = International Ed. in English | volume = 62 | issue = 24 | pages = e202302475 | date = April 2023 | pmid = 37057742 | doi = 10.1002/anie.202302475 | s2cid = 258135845 | doi-access = free }}
See also
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