4-dimethylaminoamphetamine

[Limpet_Chicken]

I can find no reference to the above compound, after a quick search in the literature.

Anybody know if it is active? or any others carrying ring methoxyls plus a primary, secondary or tertiary amino function at the 4-position?

 

[fastandbulbous]

It's an aniline derivative (aromatic amine) and that never makes me happy about it's possible other actions in the body

 

[MurphyClox]

...although the primary anilines are the real culprit. Considering the wide availability of Ehrlich's reagent, I can understand Limpet's inquiry. But IIRC, the 4-amines were reported to be inactive, no?

- Murphy

 

[atara]

Its 2-methylated friend is a MAOI:

http://www.sciencedirect.com/scienc...serid=10&md5=e40fe72493333d81eb8659420062261e

http://www.bluelight.ru/vb/archive/index.php/t-365731.html

 

[Limpet_Chicken]

Heh murphy, you figured the reason for wondering then Atara, that first article, sciencedirect is down for maintainance atm so they say.

For clarification, I wasn't referring to the 4-phenyl-2aminopropane, but a normal amphetamine, I.E 1-phenyl-propan-2-amine with an additional para-alkylamino (etc) group.

 

[mad_scientist]

4-aminoamphetamine is an active anorectic in dogs, according to some very old amphetamine SAR paper I have laying around somewhere. However I would share F&B's toxicity concerns. The methylamino derivative is probably the best bet, as alkyl chains branched adjacent to the ring at the 4-position (e.g. 4-isopropyl) are greatly reduced in activity iirc so this may well apply to the dimethylamino derivative also.

 

[dread]

alkyl chains branched adjacent to the ring at the 4-position (e.g. 4-isopropyl) are greatly reduced in activity

Reduced in which activity?

 

[fastandbulbous]

4-aminoamphetamine is an active anorectic in dogs, according to some very old amphetamine SAR paper I have laying around somewhere.

Just occured to me, you don't eat very much if you're being poisoned, because you feel so unwell (lead, tin & arsnic as anorexiants, what a spiffing idea! )

 

[Limpet_Chicken]

What is the usual mode of toxicity exerted by primary anilines?

 

[wungchow]

toxicity of N,N-dimethylaniline

 

[MurphyClox]

Back on topic!


The compound in questions is also known under the codes "FLA 289" and 4-DMAA. It is a MAO-inhibitor, being quite MAO-A-selective:
in vitro

IC50 (MAO-A) = 3.7 µM
IC50 (MAO-B) = 400 µM
​

in vivo

EC50 (intra-neuronal, p.o.) = 2.5 µmol/kg
EC50 (extra-neuronal, p.o.= 30 µmol/kg
rat hypothalamus​

Hence, it shares the hazards of other combined low-to-medium-potency stimulants / MAO-inhibitors. Being both agent and inhibitor of its own metabolism is not exactly what I consider as safe to use.
Ref: Br J Pharm 1985, 85, p.683; see also Biochem Pharmacol 1994, 47(8), p.1365.


The compound is also a moderate 5HT-reuptake inhibitor with a IC50 of 1.1 µM in hypothalamic synaptosomes resp. 0.32 µM (same, but reserpine-pretreated).
Ref: Naunyn-Schmiedeberg Arch Pharmacol 1987, 336, p.591


No big surprise, considering the abovementioned properties, the compound is anorexic.
Ref: J Med Chem 1963, 6(5), p.519.


Conclusion: Most probably active, mainly as stimulant. Moderate potency. Not the safest to use.


Peace! Murphy