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Beta-aminopropylbenzene and analogues

H

hexxx

Bluelighter
Joined
Jan 30, 2008
Messages
817
Location
South Africa
I'm sorry if this is a bit too basic for you guys, if it is please move it. What I want to know is if the definition of this class of drugs:

Beta-aminopropylbenzene and beta-aminoisopropylbenzene derivatives,
being any compound structurally derived from either of these substances
by substitution in the side chain or by ring closure therein (or by both such
substitution and such ring closure);
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Contains all analogues and RC chemicals such as mephedrone, methylone etc. I worked out that Beta-aminopropylbenzene is a synonym for amphetamine/d-amp, am I correct? If I'm way off, please let me know.

What exactly does it cover? I know that ephedrine, pseudoephedrine and norephedrine fit into that category. Would it be equivalent to the US definition under the infamous analogue act?

Thanks!
 
Why not call this amphetamine and analogues? Beta-aminoisopropyl is beta-methylphenethylamine. I've never seen this explicitly scheduled, and IIRC, there's even a product sold in the US that contains beta-me-PEA, which is so obviously an amphetamine analogue, I can't believe they're so stupid enough to do so.

What do they mean by ring closure? Are they talking about 3-phenylpiperidine or 3-methyl-1,2,3,4-tetrahydroisoquinoline sorts of things, or something that's not even occured to me?
 
So it is a synonym for amphetamine? I've quoted exactly what is written by my country's scheduling laws, I'm trying to ascertain what is legal and what isn't. My knowledge of organic chemistry is limited, I didn't even know that beta-aminopropylbenze was amphetamine for sure. Do you think that including this definition includes all analogues, or is it a bit unclear? Or stupid? (wouldn't be surprised given our previous minister of health)

Methcathinone and MDMA/MDA are specifically mentioned in the list with no reference given to beta-aminopropylbenze or anything. In fact MDMA has an explicit inclusion of analogues added to the same scheduling class.

Here is the complete definition of the group in the particular scheduling class:
Beta-aminopropylbenzene and beta-aminoisopropylbenzene:
a. any compound structurally derived from either of these substances by substitution in the side chain or
by ring closure therein (or by both such substitution and such ring closure); and
b. any salt or substance falling under the above, and
c. except preparations and mixtures of the above when used as vasoconstrictors and decongestants in
antihistamine nose and eye preparations; (S1) and
d. except when contained in appliances for inhalation in which the substance is absorbed onto solid
material; (S1, S7) and
e. excluding cathine «+)-norpseudoephedrine), ephedrine, etafedrine, N-methylephedrine,
N-diethylaminoethylephedrine, phenylpropanolamine, prenylamine and preparations and mixtures
thereof; and
f. except substances listed in Schedule 7. (S1, S2, S6)
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Yep: pretty much everything tht contains the PEA backbone will be scheduled. Well, actually, I take that back. I don't think this covers plain PEAs at all.
 
Damn. At least it's only S5, ie same as benzos. But that makes it illegal for me to bring in or try to produce anything. Also, not legal to possess but nothing severe enough to warrant a criminal record, but I'll make sure about that first when I speak to a lawyer friend.

Thanks. Not all PEAs are restricted so I don't think it covers all of them.

Just anything loosely based on the amphetamine structure with small changes surely? Like cathinones, ephedrine and stuff like FMA (sorry can't remember exactly what it was called - fleuro methamphetamine or something) and PMA. Would cathinones even fall into the category at all? I am most interested in the designer varieties of this class, I want to see what all the fuss is about but will skip it if it's going to get me into trouble.
 
It's NOT amphetamine, hexx. Amphetamine would be *alpha*-methyl phenethylamine, hence A-m-phe-tamine. As far as I know, though, it's weak as hell and unscheduled. I wouldn't fuck around with its legality, but naw, it's not amphetamine.
 
No, that's wrong.

beta-aminopropylbenzene is a synonym for amphetamine or
2-amino-1-phenylpropane in IUPAC, and there's nothing weak about it.
 
The Monkey Mantra said:
It's NOT amphetamine, hexx. Amphetamine would be *alpha*-methyl phenethylamine, hence A-m-phe-tamine. As far as I know, though, it's weak as hell and unscheduled. I wouldn't fuck around with its legality, but naw, it's not amphetamine.
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Do you think before you decide to post or not? Bored and just feel like saying something contrary for the hell of it? I do this, all the time really, but I prefer to make sure that it's accurate first.

You realize that alpha-methyl-phenethylamine isn't really standard naming? The standard is IUPAC, but there are numerous ways to name something without it or based on it. I made note of this, that this is a nonstandard naming, and given that it's so unused, that it was strange to use it in the law.

Still, the title compound is quite obviously amphetamine. Picture a benzene ring. Of of this ring, add three carbons (propyl). Now picture the middle carbon of those three. Either way you want to start counting (from the benzene other end of the propyl chain), you get the middle carbon as the #2 carbon, or the beta carbon. In typical amphetamine terminology, this is the alpha carbon, but then the alpha is thought of as the substitution. In this terminology, the amine is the substitution.

So you have an propylbenzene molecule (PEA with the amine replaced by a CH3 group), with an amine on the middle carbon... something like this:

(C6H5)-CH2-CH-CH3
.....................l
....................NH2

The Beta-aminoisopropylbenzene, again, is

(C6H5)-CH-CH2-NH2
...............l
..............CH3

Why don't you get a copy of ChemDraw and that whole package? It's incredibly useful and can do most anything you want, unless you want to do receptor modeling stuff, for which it really isn't set up to do.
 
The second first compound Hammilton just produced is 1-Phenylpropan-2-amine. It not is an amphetamine, as the nitrogen here is secondary. Amphetamines must contain the 1-Phenylpropan-2-amine skeleton (hence why amphetamine, the most simple amphetamine, is 1-Phenylpropan-2-amine) and therefore possess a primary secondary amine as well. 2-Phenylpropan-1-amine (second compound) is a positional and constitutional isomer of amphetamine. These compounds have more in common with benzylamines than they do amphetamines.

beta-Aminopropylbenzene is a synonym for amphetamine which upon further examination is inexplicably named? The alpha carbon is always the carbon connected to the functional group, in this case an amine. But, they seem to be using benzene as the functional group. That would make the second compound Hammilton presented correct, but the amine would clearly have functional group priority here and rather the compound would be named beta-phenylisopropylamine. Methamphetamine would be Methyl-beta-phenylisopropylamine. I don't know what's going with the law here.

2-amino-1-phenylpropane in IUPAC
Click to expand...
Incorrect, the amine group has priority over both the alkane group and the arene group. Therefore the name is correctly 1-Phenylpropan-2-amine or 1-Phenyl-2-propanamine.
 
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Hammy, do you stop and think about how WHY you feel the need to play the "I can insult you because I'm smart" game? I *know* you're better than that. I took a look again and figured out what the heck was going on with the non-IUPAC nomenclature, but I don't appreciate how you responded to me. What's your deal, dude? I do my best to post literate, helpful shit, and the moment I space out you call me a moron. What the fuck?

I like you and I'd like to be your friend. I'm just gonna assume you're having a shitty day/week/year. I hope you feel better soon, dude.
 
The second compound Hammilton just produced is 2-Phenylpropan-1-amine. It's not an amphetamine, as the nitrogen here is secondary. Amphetamines must contain the 1-Phenylpropan-2-amine skeleton (hence why amphetamine, the most simple amphetamine, is 1-Phenylpropan-2-amine) and therefore possess a primary amine as well. It is a positional and constitutional isomer of amphetamine. These compounds have more in common with benzylamines than they do amphetamines.
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Wait, what the heck?

Unless you're seeing a substitutent that I'm not, 2-Phenylpropan-1-amine IS a primary amine- hence the reason there are two hydrogen atoms connected to it. It is NOT a benzylamine, and has nothing more in with these than amphetamine does. It's the second compound mentioned in the law, beta-aminopropylbenzene and beta-aminoisopropylbenzene. The first is drawn first, the second, second, naturally.

The structures I drew were both correct. Text isn't a good medium to 'draw' in, so maybe this will make it easier.

A real drawing of the second structure.
AM00109.gif
 
Hammilton said:
Wait, what the heck?

Unless you're seeing a substitutent that I'm not, 2-Phenylpropan-1-amine IS a primary amine- hence the reason there are two hydrogen atoms connected to it. It is NOT a benzylamine, and has nothing more in with these than amphetamine does. It's the second compound mentioned in the law, beta-aminopropylbenzene and beta-aminoisopropylbenzene. The first is drawn first, the second, second, naturally.

The structures I drew were both correct. Text isn't a good medium to 'draw' in, so maybe this will make it easier.

A real drawing of the second structure.
AM00109.gif
Click to expand...

Yeah, that was backwards, chalk it up to a viral infection and dyslexia. Amphetamine has a secondary amine while the other compound is a primary amine. I was switching the nitrogen and erm what a confusing thread.

It's the second compound mentioned in the law, beta-aminopropylbenzene and beta-aminoisopropylbenzene.
Click to expand...
β-Phenylisopropylamine has historically always referred to amphetamine. It appears to refer to isopropylamine in this case, from which the β-group is phenyl, hence beta-Phenylisopropylamine.

But upon further investigation, it appears you're correct, although I've never heard anything about 2-Phenylpropan-1-amine abuse. Do you (or anyone) have anything from the literature? I don't understand why it would be made illegal if there is not a history of abuse (the reports from this thread make it out to be pseudoephedrine-like).
 
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Amphetamine has a secondary amine while the other compound is a primary amine. I was switching the nitrogen and erm what a confusing thread.
Click to expand...

No, they're both primary amines. They only difference is the location of the methyl group, one is located on the beta carbon, the other the alpha (to use more common terminology). Both amines are NH2, so primary.

β-Phenylisopropylamine has historically always referred to amphetamine. It appears to refer to isopropylamine in this case, from which the β-group is phenyl, hence beta-Phenylisopropylamine.
Click to expand...

Yeah. This is why I use Chembiodraw, it does a pretty good job of getting the right structure out of various terminology. The way they're naming is all backwards.

But upon further investigation, it appears you're correct, although I've never heard anything about 2-Phenylpropan-1-amine abuse. Do you (or anyone) have anything from the literature?
Click to expand...

Outside of the few websites selling a proprietary product containing beta-methyl-PEA, no, a few body building websites have mini reports regarding it, but nothing interesting.
 
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