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Δ3-Tetrahydrocannabinol

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(Redirected fromΔ-3-Tetrahydrocannabinol)
Chemical compound
Pharmaceutical compound
Δ3-Tetrahydrocannabinol
Clinical data
Other namesDelta-3-THC, Δ3-THC, Δ6a(10a)-THC, EA-1477
Drug classCannabinoid
Identifiers
  • (9S)-6,6,9-trimethyl-3-pentyl-7,8,9,10-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChemCID
ChemSpider
UNII
KEGG
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • CCCCCC1=CC(=C2C3=C(CC[C@@H](C3)C)C(OC2=C1)(C)C)O
  • 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

Δ3-Tetrahydrocannabinol (often abbreviated asdelta-3-THC orΔ3-THC) is a syntheticisomer oftetrahydrocannabinol (THC) developed during the original research in the 1940s to develop synthetic routes to thenatural productsΔ8-THC and Δ9-THC found in thecannabis.[1] While the normaltrans configuration of THC is in this case flattened by the double bond, it still has twoenantiomers 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 ofvaping liquid products.[5]

Legality

[edit]

United States

[edit]

Delta-3-Tetrahydrocannabinol is federally uncontrolled, but due to its similarities with Delta-9-THC it could be prosecuted under theFederal Analogue Act

Arkansas

[edit]

As of June 25, 2025, theU.S. 8th Circuit Court of Appeals overturned a lower court's injunction, allowingArkansas to enforce its ban on hemp-derived THC products, including Delta-3 THC (listed as Delta-6a10a-THC). This ruling means that Act 629, which classifies Delta-8, Delta-9 (above 0.3%), and Delta-10 THC ("Psychoactive hemp-derived cannabinoids" as stated in Act 629) as Schedule VI controlled substances in the state, is now enforceable. Previously, sales of these products had been temporarily permitted due to the injunction.[6][7]

See also

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References

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  1. ^US 2419935, Adams R, "Marihuana active compounds.", issued 1947 
  2. ^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.
  3. ^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.
  4. ^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.
  5. ^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.
  6. ^Campbell, Matt (2025-06-24)."Federal court allows state to resume ban on sale of hemp-derived THC products".Arkansas Times. Retrieved2025-06-27.
  7. ^Mobley, Matthew Sewell | Andrew (2025-06-24)."Arkansas to ban Delta-8, other THC products after appeals court victory".KATV. Retrieved2025-06-27.
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