DMPP; non-neurotoxic phenethylamine/lefetamine derivative with analgesic properties

[nuke]

The shorthand I've made up for N,N-dimethyl-1-phenyl-2-(1H-pyrrol-1-yl)ethylamine, for lack of anything better. The acronym corresponds to dimethyl pyrrole phenethylamine. Reported in this paper:

The synthesis of pyrrole analogues of the analgesic drug lefetamine is reported. These derivatives bear the 1-phenyl-2-(1H-pyrrol-1-yl)ethylamino moiety. Compounds were evaluated for analgesic activities in mice by the hot plate and Randall-Selitto tests. Antiinflammatory activity was tested by the carrageenan-induced rat paw edema method. General neuropsychopharmacological effects were also screened. The most interesting compound, N,N-dimethyl-1-phenyl-2-(1H-pyrrol-1-yl)ethylamine, showed an analgesic effect comparable to that of lefetamine, but devoid of the neurotoxicity of this drug.

http://www.ncbi.nlm.nih.gov/pubmed/2604832

Anyone have access to this paper? Another neat looking unscheduled goodie. I wonder what enantiomer is the more active one?

 

[MurphyClox]

Access is difficult as there are no (regular/official) online-pdf versions from Farmaco before january 1998 to my knowledge...watta pity...

 

[LuxEtVeritas]

structurally it is basically a subbing of a pyrrole where the methyl is on (N,N)-Dimethylamphetamine ('alpha' position)
we know DMA is a piss-poor variant of MA so why the Dimethyl and not simply N-methyl I do not have a clue on the lefetamine class...not sure what the subbing of the pyrrole over the phenyl will provide but it looks nicer, LOL

 

[LuxEtVeritas]

now is it NT or opioid mediated analgesia.....???? or both....and if so what ratio?

 

[nuke]

structurally it is basically a subbing of a pyrrole where the methyl is on (N,N)-Dimethylamphetamine ('alpha' position)
we know DMA is a piss-poor variant of MA so why the Dimethyl and not simply N-methyl I do not have a clue on the lefetamine class...not sure what the subbing of the pyrrole over the phenyl will provide but it looks nicer, LOL

My guess is it's an NDRI because of the pyrrole group being where it is (a la the pyrovalerones), and then the dimethyl group might have some opioid activity like tramadol. But that's a stretch, who knows. It could be more of a stimulant and less of an opiate than lefetamine.

I doubt the synthesis is anything too difficult.

 

[The Monkey Mantra]

That's what I'm wondering: If the analgesic activity is just standard amphetamine-variety and isn't opioid-mediated at all.

 

[(zonk)]

If I had to guess I'd say the analgesia is from a combo of opiate and nmda antagonism

 

[LuxEtVeritas]

i was thinking more likely NDRI myself...but i guess we won;t know anytime soon