Cis-THC

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.^[1] 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.^{[2][3][4][5][6][7][8][9]}

A diagram showing the isomers of delta-9-THC with carbon number indicated according to dibenzopyran numbering scheme. Cahn-Ingold-Prelog R/S designation is indicated. Please note that "synthetic" here refers to macroscopic quantities, and that these stereoisomers that are labeled as synthetic may be present in C. sativa or other organisms at trace levels compared to trans-(-)-d9-THC

Cis-THC

Identifiers
IUPAC name (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number	6087-73-6 43009-38-7
PubChem CID	12831993
ChemSpider	52083428
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@@H]3C(OC2=C1)(C)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/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17+/m1/s1 Key:CYQFCXCEBYINGO-SJORKVTESA-N

See also

• Abeo-HHC acetate
• Abn-CBD
• CBD-DMH
• Exo-THC
• Iso-THC
• HU-211
• Perrottetinene
• Machaeriol A