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Eth? your opinion guys?

/navarone/

/navarone/

Bluelighter
Joined
Dec 26, 2003
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Under your bed, masturbating...
Hello fellas.

I haven't posted here for a long time but recently i had this big curiosity on the possible potency of this amphetamine i have thought of.

Months ago i read a thread about N-dimethylamphetamine, the title caught my attention since i'm a fan of amphetamines and i always wondered what dimethylamphetamine would be like. Sadly i discovered that its no big deal due to a matter of receptor affinity and its psychoactive potency wasn't even as good as amphetamine. From that i understood that the amine group should be left with at least a hydrogen bonded to it when speaking of psychoactive potency and receptor affinity (am i right?). So i came up with this new curiosity, i looked everywhere on google and came up with nothing so i should ask some 'experts' like u guys.

So the substance i was pondering about is N-Ethyl-amphetamine (D isomer of course), yup thats right....and ethyl group instead of a methyl group on the amine group.
Based on your predictions (cuz i doubt anybody has tried it), what would be the potency of this substance compared to amphetamine and methamphetamine? would it have any recreational advantages or is it just another disappointment?

And since we r speaking of amphetamines and its effect on dopamine receptors, could anybody briefly explain to me how the dopamine receptor affinity works please?

Any info would be apreciated, thanks.
 
PS: i already know that affinity has to do with the shape of the molecule with the attaching site, eg. like a cube in a cubic hole, but thats all i know about it. however i know its waaaay more complex than that, so if u could please explain what goes on when different molecules attach to the receptor...especially the dopamine receptor. thanks
 
Well amphetamines on the whole don't have any affinity for dopamine receptors.

When ligands do bind to receptors, they do so through a largely simple lock and key mechanism, except that not only does the ligand have to be the right shape, but it has to have positive charges where the receptor has negative, and vise versa, and be neutral in neutral places. Of course, only in the active site.
 
i heard n-propylamphetamine is good stuff.. dose is higher than amph. but its way smoother and somewhat longer lasting. Felt somewhere inbetween how meth feels and reg. amph, the person i believe also said they definitely preffered it over amphetamine.
 
yoyoman said:
i heard n-propylamphetamine is good stuff.. dose is higher than amph. but its way smoother and somewhat longer lasting. Felt somewhere inbetween how meth feels and reg. amph, the person i believe also said they definitely preffered it over amphetamine.
Click to expand...


Do you think the subjective "smoothness" is more an effect of differing metabolic profiles or something directly related to the actions of the original compound?
 
Ethlyampthetamine and especially Methlyamphetamine slide thru BloodBrain barrier better than Amphetamine or Propylamphetamine, but Eth gets metabolized to EtOH and Amp first while Meth goes to MeOH and Amp, and EtOH is preferable to MeOH b/c...

EtOH -[bodily oxidation]-> CH3COOH (Acetic Acid)
MeOH -[bodily oxidation]-> Formic Acid

and on a Toxicity Scale

Formic Acid > Acetic Acid
 
Interesting...

Helios. said:
Ethlyampthetamine and especially Methlyamphetamine slide thru BloodBrain barrier better than Amphetamine or Propylamphetamine, but Eth gets metabolized to EtOH and Amp first while Meth goes to MeOH and Amp, and EtOH is preferable to MeOH b/c...

EtOH -[bodily oxidation]-> CH3COOH (Acetic Acid)
MeOH -[bodily oxidation]-> Formic Acid

and on a Toxicity Scale

Formic Acid > Acetic Acid
Click to expand...

Very interesting info helios:D ....(if thats true and demonstrated) that explains a lot of the toxicity and the hangovers caused by meth. its methanol poisoning which is some nasty shit. From what i read, methanol is extremely toxic for the nerves, brain and sight even in small doses.(is this right?)8(

This also suggets sumthing else about ethamphetamine.
It should be less toxic and heavy on the body than meth since it metabolizes into ethanol and amphetamine, ethanol is way less toxic and neurotoxic than methanol and the ammount metabolized by one dose of ethamphetamine (lets say 120mg) isn't even enought to give anybody the slightest tipsiness.
This solves the methanol poisoning from meth without even giving symptoms of heavy ethanol poisoning.=D

Am I wrong?
 
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Ethlyampthetamine and especially Methlyamphetamine slide thru BloodBrain barrier better than Amphetamine or Propylamphetamine, but Eth gets metabolized to EtOH and Amp first while Meth goes to MeOH and Amp, and EtOH is preferable to MeOH b/c...
Click to expand...

I don't believe you. Firstly, Eth amphetamine should go through the BBB faster because it is less polar. Secondly, I don't believe that methanol is a product of methamphetamine metabolism. Do you have any references to your strange claims?
 
There's no need to argue. Eth is less polar but sterically more hindered.
My predictions will be borne out by experiment (or not).
 
i remember i was told that meth goes in and out of ur body unchanged becuz it dint get mebaolized. that there are traces of methamphetamine in urines and sweat. but that could also be untrue.

ill try to find some article about the metabolism of meth...this thread really intrigues me. if what helios said was true, it could be an interesting piece of info.

catch you later...
 
From:
http://www.rxlist.com/cgi/generic2/methamphetamine_cp.htm

"In humans, methamphetamine is rapidly absorbed from the gastrointestinal tract. The primary site of metabolism is in the liver by aromatic hydroxylation, N-dealkylation and deamination. At least seven metabolites have been identified in the urine. The biological half-life has been reported in the range of 4 to 5 hours. Excretion occurs primarily in the urine and is dependent on urine pH. Alkaline urine will significantly increase the drug half-life. Approximately 62% of an oral dose is eliminated in the urine within the first 24 hours with about one-third as intact drug and the remainder as metabolites."

I hope this is true, lol i never knew methamphetamine had so many metabolites. the story of meth leaving ur body unchanged sounded a bit odd to me.
Anyway if N-dealkylation really takes place that means that methanol is in fact a metabolite of methamphetamine, and that ethamphetamine should release ethanol as a metabolite.

This is also an interesting article:
http://www.erowid.org/references/refs_view.php?A=ShowDocPartFrame&ID=394&DocPartID=357

If whats written there is true, that signifies that the metabolites of meth are methanol (by N-dealkylation), ammonia (by deamination) which further on turns into urea, and a resulting phenol (by the aromatic dehydroxylation) with a propan-2-ol attached to it (the OH should be formed during deamination i think).
 
Anyway if N-dealkylation really takes place that means that methanol is in fact a metabolite of methamphetamine, and that ethamphetamine should release ethanol as a metabolite.
Click to expand...

No, that means that meth and eth are dealkylated. What happens to the methyl and ethyl group that were there, is not known, as far as I'm aware.

Edit: and methanol is a metabolite of aspartame, with hydrolysis yielding 10% of the weight, and used as a sugar substitute it doesn't seem to produce many problems. the maximum amount of methanol you could get from helios' described metabolism is 22% of the original weight, and the doses of aspartame are much higher than those used by meth users.

this article described the urinary metabolites for humans:
"In two male human subjects receiving the drug orally (20mg per person) about 90% of the 14C was excreted in the urine in 4 days. The urine ofthe first day was examined for metabolites, and the main metabolites were the unchanged drug (22% of the dose) and 4-hydroxymethamphetamine (15 %). Minor metabolites were hippuric acid, norephedrine, 4-hydroxyamphetamine, 4-hydroxynorephedrine and an acid-labile precursor of benzyl methyl ketone." http://www.biochemj.org/bj/129/0011/1290011.pdf
 
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Ive glossed over this thread and my views are that the reason why meth and rit are popular is not only because pseudo is naturally occuring and a cheap commodity. On top of this there is the simple fact that the methylated versions are more potent than other alkyl chains occupying these positions. The postulation surrounding methanol toxicity even if true is not a powerful enough argument for somone to seek out the ethylated versions.

I mean you could try and use the reasoning that the ethylated versions are to be preferred in that the offset in potency is compensated for by lessened hypertension and mania for example. However this would be an intrinsic property of the drug itself, and not its metabolites, that are to be held accountable for this.
 
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meth metabolism

Even if meth was only metabolised by oxidative dealkylation and all the ingested dose was metabolised solely to methanol, the dose of methanol would be in the order of 30mgs or so. Far less than exposure caused by drinking asartame sweetened drinks, most people reading this right now contain 30-40 mg of methanol..entirely naturally, more if you drink wine spirits or fruit juices.

In reality demethylation is a minor metabolic path in man. the majority is excreted unchanged or as 4-OH methamfetamin
In short the methanol hypothesis is rubbish

there are some interesting papers on meth metabolism,

http://www.biochemj.org/bj/129/0011/1290011.pdf

it is interesting that one of the primary metabolites p-hydoxy metamfetamin is supposed stronger CNS and sympathomimetic stimulant than meth, p-hydroxy methamphetamine would be too polar to cross the BBB but the acetyl derivative might, I have never hear of p-acetoxy methamfetamin being tasted
 
nuke said:
No, that means that meth and eth are dealkylated. What happens to the methyl and ethyl group that were there, is not known, as far as I'm aware.

Edit: and methanol is a metabolite of aspartame, with hydrolysis yielding 10% of the weight, and used as a sugar substitute it doesn't seem to produce many problems. the maximum amount of methanol you could get from helios' described metabolism is 22% of the original weight, and the doses of aspartame are much higher than those used by meth users.

this article described the urinary metabolites for humans:
"In two male human subjects receiving the drug orally (20mg per person) about 90% of the 14C was excreted in the urine in 4 days. The urine ofthe first day was examined for metabolites, and the main metabolites were the unchanged drug (22% of the dose) and 4-hydroxymethamphetamine (15 %). Minor metabolites were hippuric acid, norephedrine, 4-hydroxyamphetamine, 4-hydroxynorephedrine and an acid-labile precursor of benzyl methyl ketone." http://www.biochemj.org/bj/129/0011/1290011.pdf
Click to expand...

From what i know N-dealkylation takes places thanks to an enzyme which 'splits' the molecule into the amine and the alkyl group, water interacts in this process and it also splits giving the H+ to the amine and the OH- to the alkane.
Imagine if bubbles of methane/ethane poped up in your liver? that would be a mess. It is true though that this process wont occur for all the methamphetamine molecules present, sorry if i generalized a bit to much.

Funny coincidence about aspartame. i actually wrote a school essay a few months ago proposing a new molecular model of aspartame which held ethanol instead of methanol in its structure, so that during hydrolysis it would give ethanol instead of methanol. The purpose of the Biology essay was to propose a solution to a modern problem and i took inspiration from all the recent protests against aspartame and its methanol releasing property.

It is true that the ammounts of methanol released are silly, still it is a disadvantage against ethylamphetamine, i know its a small detail but i wated to verify it that was actually true.

Anyway the purpouse of this thread was investigate/predict the psychoactive potency of ethylamphetamine compared to meth and amphetamine.
So im gonna go back to that question.
Smyth maybe what u said is true, that the methylated version of amphetamine is more potent than other alkylations, but there is no evidence for that so far. I've hear contraddicting rumors on the matter and i would like to find out which one is true, there might be a possibility that ethylamphetamine is more potent as in effects than meth but its hard to tell because nobody every tried it i think.

If anybody could explain or find evidence on why the methylated verson of amphetamine is so much more potent than amphetamine itself, maybe it could be possible to predict the potency of ethylamphetamine. From what i have tried and read meth is the strongest stimulant around (talking about effects) so the possibility of a stronger stimulant intrigues me.

(BTW even if meth and amphetamine dont have a big affinity for the dopamine receptor, do they still attach and interact with it? or doest the high work in another way?)
 
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