Dimethylheptylpyran

Structural formula
	Mixture of several stereoisomers - simplified structural formula without stereochemistry
General
Surname	Dimethylheptylpyran
other names	Dimethylheptyltetrahydrocannabinol; 6,6,9-Trimethyl-3- (3-methyl-octan-2-yl) -7,8,9,10-tetra-hydro-6H-benzo [ c ] chromen-1-ol; 1,2-dimethylheptyl-Δ 3 -THC; DMHP; A-40824; EA-1476;
Molecular formula	C 25 H 38 O 2
Brief description	Light yellow, viscous oil
External identifiers / databases
PubChem	36276
ChemSpider	33359
Wikidata	Q5277339
properties
Molar mass	370.57 g · mol -1
solubility	Almost insoluble in water, soluble in alcohol and non-polar solvents
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
Toxicological data	63 mg kg −1 ( LD 50 , mouse , iv )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dimethylheptylpyran ( DMHP ) is a synthetic analogue of Δ ⁹ - tetrahydrocannabinol (Δ ⁹ -THC).

pharmacology

Both DMHP and its acetate , DMPA, produce varying degrees of physical and mental impairment. Both compounds cause orthostatic hypotension , even in doses far below those that cause mild mental impairment.

Compared to Δ ⁹ -THC, DMHP has a significantly stronger and longer antihypertensive effect, but at the same time a much less pronounced psychological effect. The potencies of DMHP and DMHPA are more or less similar, but the acetate derivative is more stable to the damaging effects of light and air.

It is believed that DMHP acts as a CB1 agonist .

DMHP causes ataxia , mydriasis , nystagmus, and ptosis in mice, rats, rabbits, cats, dogs, and monkeys, to which it is administered intravenously .

Oral ingestion in humans causes thirst, hypotension , blurred vision and a marked urge to move. After parenteral and intravenous uptake by humans, the substance also unfolds its effectiveness. The half-life in plasma is about 20 hours in rats and rabbits and 39 hours in humans.

toxicity

Studies on the acute toxicity of DMHP were carried out on mice, rats, rabbits, cats, dogs and macaques , the mean lethal dose (LD ₅₀ ) in the case of mice being 63 mg / kg intravenously. The mean effective dose, on the other hand, is 0.075 mg / kg, which means a high therapeutic range of 840, which, for example, exceeds that of fentanyl .

In dogs, however, the toxic effects increased when DMHP was administered together with cocaine , caffeine , D - amphetamine or nalorphine ( N- allyl normorphine, an opioid antagonist that has not been used for a long time).

No study on DMHP revealed mutagenic , teratogenic or carcinogenic effects.

chemistry

The isomers of DMHP were isolated as acetates and named EA 2233-1 to EA 2233-8 by their discoverers, Aaron and Ferguson.

In air, DMHP rapidly auto- oxidizes, which at room temperature is a pale yellow, viscous oil that is not soluble in water, but is soluble in alcohol and benzene .

Legal position

In Germany, dimethylheptyltetrahydrocannabinol (DMHP) is classified in Appendix I of the Narcotics Act (BtMG) as a non-marketable narcotic .

literature

National Research Council (US). Committee on Toxicology: Possible Long-term Health Effects of Short-term Exposure to Chemical Agents , National Academy Press , Washington 1984.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k National Research Council (US). Committee on Toxicology: Possible long-term health effects of short-term exposure to chemical agents. National Academy Press, 1982, Washington, DC, pp. 80-94.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b S. N. Pradhan: Pharmacology of some synthetic tetrahydrocannabinols. In: Neuroscience & Biobehavioral Reviews 8, 1984, pp. 369-385, doi : 10.1016 / 0149-7634 (84) 90058-7 .
↑ LA Parker, R. Mechoulam: Cannabinoid agonists and antagonists modulate lithium-induced conditioned gaping in rats. In: Integrative physiological and behavioral science: the official journal of the Pavlovian Society. Volume 38, Number 2, 2003, pp. 133-145, PMID 14527182 .

[NAP1982-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k National Research Council (US). Committee on Toxicology: Possible long-term health effects of short-term exposure to chemical agents. National Academy Press, 1982, Washington, DC, pp. 80-94.

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[DOI10.1016/0149-7634(84)90058-7-3] S. N. Pradhan: Pharmacology of some synthetic tetrahydrocannabinols. In: Neuroscience & Biobehavioral Reviews 8, 1984, pp. 369-385, doi : 10.1016 / 0149-7634 (84) 90058-7 .

[PMID14527182-4] LA Parker, R. Mechoulam: Cannabinoid agonists and antagonists modulate lithium-induced conditioned gaping in rats. In: Integrative physiological and behavioral science: the official journal of the Pavlovian Society. Volume 38, Number 2, 2003, pp. 133-145, PMID 14527182 .