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4-t-butyl amphetamine

7

7har

Greenlighter
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Mar 16, 2011
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Has anyone seen any bioassays or articles on 4-t-butyl amphetamine (also p-t-butyl amphetamine)? Only reference I could find was effects of p-alkyl substitutions on the psychadelic amphetamines. In that article the 4-t-butyl substitution diminished most of the compounds activity.
 
Hammilton said:
maybe... is para-phenylmethyl or para-phenethyl active?
Click to expand...

Not quite sure what you mean Hammilton. Do you mean para-methylamphetamine and para-ethylamphetamine? Or diphenyls?

I believe para-methylamphetamine is definitely active but reports were from Russian forum and made it seem terrible. Too much serotonin I believe.

EDIT: Heres the bluelight thread on 4-methylamphetamine: http://www.bluelight.ru/vb/showthread.php?t=419580

Here is the report from Erny:

"Yes it is, em, interesting shit, and is very MDMA-like. We've already discussed it somewhere around here. It is known in Russia and Ukraine but is not very common, possibly also in Baltic states though I am not aware of the situation there. Known as p-TAP (p-toluaminopropane) or 4-MA. It is also one of the very few psychoactive chemicals I am really afraid of. After getting to know it, I feel it made me a different person. The changes are very light but I don't like them. It is notably dopaminergic, not very stimulating, but quite reinforcing, and may produce stereotyped behavior like amphetamine. It lasts 4 hours. As to oral activity, different people fall in two distinct groups: one either need 100-150 or 200-300 mg for full effects. Some people even state it is not very active orally, though effective upon insufflation or i/m injection. It is not a potent MAOI.

If you'll get some, never take more than a single dose in one day. Repeated dosing will quickly bring up very drastic after-effects with a clear picture of serotonin depletion like disturbed sleep, mood and cognition.

If what I wrote is not enough, feel free to ask."
 
Last edited:
I mean exactly what I said. 4-phenylethylamphetamine

it would be rather stupid to be asking if 4-methylamp or 4-ethylamp are active...
 
Ok...so your talking about:

1-(4-phenylphenyl)propan-2-amine and 1-(4-benzylphenyl)propan-2-amine. I have not heard of any bioassays on this material and a quick search revealed nothing of interest.

1-[4-(3-phenylpropyl)phenyl]propan-2-amine was found to be a 5-HT2A agonist (60nm) approximately twice as potent as its methoxy parent:

1-[4-(3-Phenylalkyl)phenyl]-2-aminopropanes as 5-HT2A Partial Agonists
Cynthia S. Dowd,,, Katharine Herrick-Davis,, Christina Egan,, Ann DuPre,, Carol Smith,, Milt Teitler, and, Richard A. Glennon,
Journal of Medicinal Chemistry 2000 43 (16), 3074-3084


Are you thinking the tert-butyl group would mimic 4-phenylethyl/4-phenylmethyl?
 
1-(4-phenylphenyl)propan-2-amine was found to be more potent than amphetamine as a norepinephrine (phenylethanolamine) N-methyltransferase inhibitor:

Directional probes of the hydrophobic component of the aromatic ring binding site of norepinephrine N-methyltransferase
Michael F. Rafferty, Ronald T. Borchardt, Gary L. Grunewald
J. Med. Chem., 1982, 25 (10), pp 1204–1208
Publication Date: October 1982 (Article)
DOI: 10.1021/jm00352a021
 
not that it would mimic, but rather that if there was too much bulk for it to be active, these these analogues with a 4-aryl group wouldn't be active either.
 
What about regular old n-butyl amphetamine. only seen one paper even involving this compound and they werent testing it for effect, it was used as a part of a study on how various amphetamines are metabolized if im not mistaken. i also believe it was listed as (d) n-butyl amphetamine although I might be confusing that with having seen the dextro form in a chemical search. Anyway I've never seen any testing of its effects in animals or humans, but it seems interesting to me.... would it be active? legal? toxic?
 
Sure, it'd be active, just not anywhere near as much as plain amphetamine. Nobody bothers with anything longer than N-ethyl.

The activity, if I seem to remember, of N-alkylated amphetamines is N-methyl > no alkylation > N-ethyl > N-propyl. N-benzylamphetamine is sort of typical of the class of amphetamines with ethyl or longer chains; it is essentially a chemical time release of plain amphetamine - not very active itself but slowly metabolized into amphetamine.
 
so its liike a prodrug?

i read a list of about a jillion compounds that are prodrugs for either amp or methamp (and one super cool one that is a prodrug for amp and chloral hydrate!)...

I'm basically trying to find something that has a similar safety/effect profile to dex or r-amp (even if its only like a 10th of the potency, or a prodrug) that would not be illegal to have made (bonus points if its already on the market or is active through any roa besides oral).

I assume if it was already on the market everyone would know about it, but on the other hand, if it USED to be on the market otc WAAAY back in the day and was removed simply due to lack of demand (for example replaced by something better that was later banned/ made rx), it seems there might be a short window -legally speaking (although I am not a lawyer)- where it would be "grandfathered in" and thus could be sold for human consumption until somebody who cared caught on and it was changed.
 
N-t-butylamphetamine is a no go (see Wellbutrin aka bupropion), but with 4-t-butylamphetamine, you might be on to something based on 2C-t-butyl being active, as per PiHKAL.
 
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