• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

p-alkyl-amphetamines

T

twodogs

Greenlighter
Joined
Oct 16, 2008
Messages
4
Does anyone have a report on the effects of p-alkyl-amphetamines. I know that p-alkoxy eg methoxy are dangerous but what about p-methyl, p-ethyl or p-propyl?
 
4-methylamphetamine and 4-methylmethamphetamine are both known compounds, one of those SAR reviews the DEA put out in the 1990s mentions that they had been found as street drugs. Presumably they would be acceptable recreational drugs seeing as 4-methylmethcathinone has been quite successful.

Shulgin mentions that 2,4-dimethylamphetamine and 3,4-dimethylamphetamine were both researched as appetite suppressants, and that 3,4,5-trimethylamphetamine had been made and tested in animals, and was "very hard on the cats"...

4-(n-pentyl)methamphetamine was sold in France for a while as an appetite suppressant under the name amfepentorex.

So presumably there would be a wide range of simple 4-alkyl amphetamine derivatives that could be made, with or without a methyl (or indeed ethyl) on the nitrogen.
 
Steric bulk and polarity is OK (activity therefore almost ensured) and toxicity of a toluene-moitety expected to be quite low at the respective doses.

I didn't read any reports about it but IMO mad_Scientist must be correct.

Peace! Murphy
 
The problem with them (as I recall) was that they caused caused 5HT2B agonism, and as such had negative cardiac consequences.
 
I can't say for sure, I'm really curious as to whether there are any refs with SAR data for 4-substituted amphetamines and 5HT agonism/releasing ability.

I have a bad feeling about them though, given stuff like 4-MeO-A and 4-EtO-A.
 
p-methylmethamphetamine is in PiHKAL. Shulgin tried it and didn't like it.

I've heard p-ethylamphetamine is the best of this group.

I would think p-alkyl-m-MeO-amphetamines would be better than simple
p-alkylamphetamines.

I would like to try both.
 
I couldn't find 4-methyl-amphetamine in PIKHAL. If p-ethyl amphetamine is better what do you think p-isopropyl would be like?
 
I would expect para-isopropylamphetamine to be more sedating than amphetamine. To really get off, I think you would need a couple hundred milligrams.
 
nuke said:
The problem with them (as I recall) was that they caused caused 5HT2B agonism, and as such had negative cardiac consequences.
Click to expand...

The thing to note about 5HT2B agonism and heart valve disease though is that there is a strong correlation between the cumulative dose and the inappropriate proliferation of cardiac fibroblasts that leads to the valvopathy.

Bear in mind that the patients who developed heart valve disease after taking fenfluramine or cabergoline had been taking fairly substantial doses, every day, usually for years on end before any clinically significant damage became evident. [1]

If this kind of cardiotoxicity occurred with moderate occasional use then we would be seeing thousands of mid-20 year olds showing up with heart valve disease, because MDMA itself is a reasonably potent 5HT2B agonist, and indeed its actions on 5HT2B receptors in the brain are crucial to its serotonin-releasing effects. [2]

The fact that these kind of problems have not been found to occur in recreational MDMA users tends to suggest that chronic daily use, or at least extremely regular use, of 5HT2B agonists is required to produce cardiac valvopathies. Of course MDMA has been associated with heart problems, and we may see an epidemic of cardiac fibrosis among todays pill-poppers once they reach their 50s and 60s, but you'd think if that was going to happen then we would have seen some signs of it already considering the 80s party people are getting pretty old by now...

[1] New England Journal of Medicine. 2007 Jan 4;356(1):39-46.
[2] Journal of Neuroscience. 2008 Mar 12;28(11):2933–2940.
 
4-methyl amphetamine is known in Russia and Ukraine. This is a drug of the sort you'd better never ever touch.

It is mostly like MDMA with pronounced dopaminergic effects for the majority of people, sometimes with the faint tones of anguish and hysteria breaking through euphoria and empathy. Some people feel almost nothing at all, and it's effects are generally more variable from one person to another than those of MDMA. They last 4 hours.

It has noticeable after-effects that turn into long lasting insomnia of a very specific kind, mood disturbances, disturbances of memory and cognition upon repeated dosing, pointing at serotonin depletion and possibly marked neurotoxicity. They can include a depression so black, that only heavy cocaine use comes to mind to compare it with.

And yes, the 5-HT2B. Long term use of such a drug may probably result in cardiac muscle damage or other cardiac diseases nobody would be happy to encounter.


The N-methylated version is of much lower potency and duration.
 
Hmmm that doesn't sound very nice! So the p-methyl is no good but the p-pentyl has been used as an appetite suppressant and is described as a stimulant so I imagine that p-butyl and p-propyl are somewhere in between.
 
Erny said:
4-methyl amphetamine is known in Russia and Ukraine. This is a drug of the sort you'd better never ever touch.

It is mostly like MDMA with pronounced dopaminergic effects for the majority of people, sometimes with the faint tones of anguish and hysteria breaking through euphoria and empathy. Some people feel almost nothing at all, and it's effects are generally more variable from one person to another than those of MDMA. They last 4 hours.

It has noticeable after-effects that turn into long lasting insomnia of a very specific kind, mood disturbances, disturbances of memory and cognition upon repeated dosing, pointing at serotonin depletion and possibly marked neurotoxicity. They can include a depression so black, that only heavy cocaine use comes to mind to compare it with.

And yes, the 5-HT2B. Long term use of such a drug may probably result in cardiac muscle damage or other cardiac diseases nobody would be happy to encounter.


The N-methylated version is of much lower potency and duration.
Click to expand...

Are you sure you're talking about 4-methyl and not 4-methoxy? PMA (para-methoxy-amphetamine) has been seen quite often, and causes those things.
 
I thought I've been talking clearly, 4-methyl is 4-methyl, not 4-methoxy.

I don't know much about 4-ethyl amphetamine other than that it is active, definitely 5-HT releasing, and seems to be quite pleasurable.
 
You must log in or register to reply here.
Top