Dimethylheptylpyran

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Dimethylheptylpyran
Systematic (IUPAC) name
6,6,9-trimethyl-3-(3-methyloctan-2-yl)- 7,8,9,10-tetrahydrobenzo[c]chromen-1-ol
Identifiers
CAS number	32904-22-6
ATC code	?
PubChem	36276
Chemical data
Formula	C25H38O2
Mol. mass	370.57 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule I / Class A
Routes	?

Dimethylheptylpyran, 1,2-dimethylheptyl-Δ³THC, or DMHP is a synthetic analogue of THC, which was invented in 1949 during attempts to elucidate the structure of Δ⁹-THC, the active component of cannabis.^[1]

[edit] Effects

DMHP is similar in both 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.^[2] It produces similar activity to THC, such as sedative effects, but is considerably more potent.^[3] It is thought to act as a CB₁ agonist, in a similar manner to other similar cannabinoid derivatives.^[4]

[edit] Legality

DMHP was made illegal under UN convention in 1982 on the basis of its structural similarity and similar effects profile to THC, despite never having had any recorded instances of abuse by humans or illicit sale. In the United States, DMHP was placed into the most restrictive Schedule I as a compound with no medical use, although it is still used in some scientific research into cannabinoid drugs.

[edit] References

1. ^ Adams R, Harfenist M, Loewe S. New Analogs of Tetrahydrocannabinol. XIX. Journal of the American Chemical Society. 1949; 71(5):1624-1628.
2. ^ Razdan RK. The Total Synthesis of Cannabinoids. Wiley-Interscience 1980.
3. ^ Wilkison DM, Pontzer N, Hosko MJ. "Slowing of cortical somatosensory evoked activity by delta 9-tetrahydrocannabinol and dimethylheptylpyran in alpha-chloralose-anesthetized cats." Neuropharmacology. 1982 Jul;21(7):705-9. PMID 6289158
4. ^ Parker LA, Mechoulam R. "Cannabinoid agonists and antagonists modulate lithium-induced conditioned gaping in rats." Integrative Physiological and Behavioural Science. 2003 Apr-Jun;38(2):133-45. PMID 14527182

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