Dimethylheptylpyran

Dimethylheptylpyran

Clinical data
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited) DE: Anlage I (Controlled) UK: Class B US: Schedule I
Pharmacokinetic data
Biological half-life	20–39 hours
Identifiers
IUPAC name 6,6,9-Trimethyl-3-(3-methyl-2-octanyl)-7,8,9,10-tetrahydro-6H-benzo[c]chromen-1-ol
CAS Number	32904-22-6 Y
PubChem (CID)	36276
ChemSpider	33359 N
UNII	944O1KA97G N
ChEMBL	CHEMBL3244434 N
Chemical and physical data
Formula	C25H38O2
Molar mass	370.57 g/mol
3D model (Jmol)	Interactive image
SMILES CCCCCC(C)C(C)c1cc(c2c(c1)OC(C3=C2CC(CC3)C)(C)C)O
InChI InChI=1S/C25H38O2/c1-7-8-9-10-17(3)18(4)19-14-22(26)24-20-13-16(2)11-12-21(20)25(5,6)27-23(24)15-19/h14-18,26H,7-13H2,1-6H3 N Key:QBEFIFWEOSUTKV-UHFFFAOYSA-N N
NY (what is this?)

Dimethylheptylpyran (DMHP, 3-(1,2-dimethylheptyl)-Δ^6a,10a-THC, 1,2-dimethylheptyl-Δ³THC, A-40824, EA-2233) is a synthetic analogue of THC, which was invented in 1949 during attempts to elucidate the structure of Δ⁹-THC, one of the active components of cannabis. DMHP is a pale yellow, viscous oil which is insoluble in water, but dissolves in alcohol or non-polar solvents.

DMHP is similar in structure to THC, differing only in the position of one double bond, and the replacement of the 3-pentyl chain with a 3-(1,2-dimethylheptyl) chain. It produces similar activity to THC, such as sedative effects, but is considerably more potent, especially having much stronger analgesic and anticonvulsant effects than THC, although comparatively weaker psychological effects. It is thought to act as a CB₁ agonist, in a similar manner to other cannabinoid derivatives.

DMHP and its O-acetate ester were extensively investigated by the US military chemical weapons program in the Edgewood Arsenal experiments, as possible non-lethal incapacitating agents.

DMHP has three stereocenters and consequently has eight possible stereoisomers, which differ considerably in potency. The racemic mix of all eight isomers of the O-acetyl ester was given the code number EA-2233, with the eight individual isomers numbered EA-2233-1 through EA-2233-8. The most potent isomer was EA-2233-2, with an active dose range in humans of 0.5–2.8 μg/kg (i.e. ~35–200 μg for a 70 kg adult). Active doses varied markedly between individuals, but when the dose of EA-2233 was taken up to 1–2 mg, all volunteers were considered to be incapable of performing military duties, with the effects lasting as long as 2–3 days.