Δ-4-Tetrahydrocannabinol

Δ-4-Tetrahydrocannabinol
Identifiers
	IUPAC name (9R,10aR)-6,6,9-trimethyl-3-pentyl-8,9,10,10a-tetrahydrobenzo[c]chromen-1-ol;
CAS Number	59042-44-3;
PubChem CID	91936925;
ChemSpider	26608727;
UNII	0M4C88EI3H;
KEGG	C22744;
CompTox Dashboard (EPA)	DTXSID701336770 ;
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@@H](CC=C3C(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/h10,12-14,16,22H,5-9,11H2,1-4H3/t14-,16-/m1/s1; Key:UQOUHXDCXBITSF-GDBMZVCRSA-N;

Δ-4-Tetrahydrocannabinol (Delta-4-THC, Δ⁴-THC, Δ^6a(7)-THC) is a synthetic isomer of tetrahydrocannabinol, developed in the 1970s during research to develop improved synthetic routes to the natural forms Δ⁸-THC and Δ⁹-THC. Only the (9R, 10aR) enantiomer has been synthesised, though other isomers are possible.^[1]^[2]

References

^ Arnone A, Merlini L, Servi S (1975). "Hashish: Synthesis of (+)-Δ4-tetrahydrocannabinol". Tetrahedron. 31 (24): 3093–3096. doi:10.1016/0040-4020(75)80154-2.
^ WHO Expert Committee on Drug Dependence Critical Review. Isomers of THC (PDF) (Report). World Health Organization. 2018.

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[1] Arnone A, Merlini L, Servi S (1975). "Hashish: Synthesis of (+)-Δ4-tetrahydrocannabinol". Tetrahedron. 31 (24): 3093–3096. doi:10.1016/0040-4020(75)80154-2.

[2] WHO Expert Committee on Drug Dependence Critical Review. Isomers of THC (PDF) (Report). World Health Organization. 2018.

[1]

[2]

Identifiers

IUPAC name (9R,10aR)-6,6,9-trimethyl-3-pentyl-8,9,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number	59042-44-3
PubChem CID	91936925
ChemSpider	26608727
UNII	0M4C88EI3H
KEGG	C22744
CompTox Dashboard (EPA)	DTXSID701336770
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@@H](CC=C3C(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/h10,12-14,16,22H,5-9,11H2,1-4H3/t14-,16-/m1/s1 Key:UQOUHXDCXBITSF-GDBMZVCRSA-N

Δ-4-Tetrahydrocannabinol

See also

References