3,4-methylenedioxyphenyl-sec-butylamine

[tamtoot]

The last one with propargyl group looks like MAOI. I have a gut feeling about it's activity. Am I the only one about it?

 

[hamhurricane]

Well, yeah it looks quite a bit like selegiline...except it's a benzylamine, contains a secondary amine, and has a denuded alpha position.

 

[tamtoot]

Look

Moclobemide

Safinamide

Rasagiline(NH is 2 atoms apart from phenol and there is the same propargyl moeity which is persist in Selegeline too)

Make this look like a good candidate for MAOI activity.

Anybody can prove, we need to know MAOI SAR for this?

 

[vecktor]

from pihkal entry 100 MDA

The benzylamine counterpart (as if one were to move the amine function from the beta-carbon to the alpha-carbon of the three carbon chain of the amphetamine molecule) is α-ethyl-3,4-methylenedioxybenzylamine or 1-amino-1-(3,4-methylenedioxyphenyl)propane, ALPHA. The hydrochloride salt has a mp of 199–201 °C. At low threshold levels (10 milligram area) there were eyes-closed “dreams” with some body tingling. The compound was not anorexic at any dose (up to 140 milligrams) and was reported to produce a pleasant, positive feeling. It is very short-lived (about 3 hours). The N-methyl homologue is α-ethyl-N-methyl-3,4-methylenedioxybenzylamine or 1-methylamino-1-(3,4-methylenedioxyphenyl)propane, M-ALPHA. It is similar in action, but is perhaps twice as potent (a plus one or plus two dose is 60 milligrams) and of twice the duration.

indicates the NH2 can be moved to the benzylic position and still retain some activity though not really MDMA like.
IMO the N-propargyl compound will be expected to have activity with MAOI activity as well.

 

[Astavats]

It mentions increase in duration and intensity of amphetamine which may confirm MAOI thoughts. CRL 40,273 is the N-propargyl-piperonylamine

(2) Interaction with amphetamine

Batches of 6 rats are given an intraperitoneal injection of 2 mg/kg of amphetamine 30 minutes after the administration of CRL 40,273. It is found that:

(a) at doses of 4 mg/kg, 16 mg/kg and 64 mg/kg, CRL 40,273 increases the duration and intensity of the amphetamine-induced stereotypies, and

(b) the increase in the duration and intensity of amphetamine-induced stereotypies is much greater at a dose of 16 mg/kg of CRL 40,273 than at doses of 4 mg/kg and 64 mg/kg.

I was wondering, it mentions out of the dosages 4mg/kg, 16 mg/kg, and 64 mg/kg that 64 mg/kg is less effective in amphetamine "stereotypies" than the 16 mg/kg. Does this suggest it has direct (weak) action at NE/DA sites?

 

[tamtoot]

Previous mentioned paper contains some truly delightful medical humor. Here is the qoute:

......patient arrives...he is in coma stage 1, after 30 minutes that mojo is back in counsiousness. Here they are, our proud doctors - They do give him IM SHOT of this compund. Guess what later. He became sedated only for the first time and then... words:

2) At the end of 20 minutes after the injection

The patient is again conscious and is in the grip of a true delirious outburst -- he thinks himself a Canadian secret agent.

he is intensely hilarious,

the other one is became all-accpeting:

3) 1 hour after the injection

The patient is relaxed, calm and serene, speaks with humour (an infantile humour) and accepts her hospitalization.

Made me laugh!

 

[Hammilton]

IIRC, many simpler benzylamines have been studied and have strong MAOI activity. I'd be surprised if many of these don't as well.