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4-CAB (4-chloro-a-ethyl-phenethylamine)

dread

dread

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Anyone have any further information about this chemical? I find it highly interesting on paper...

http://en.wikipedia.org/wiki/4-Chlorophenylisobutylamine seems to claim that it is less neurotoxic than MDMA, at least on a mg-to-mg basis. How it would be on comparable dosages, who knows...

I wonder if this will ever make it to sale though... seems to me PCA has such a sinister reputation that it would be hard to sell anything with such a similar structure to it... Then again, there's always idiots that will take anything, as is evident by the popularity of the *drones... so who knows, eh.
 
I can see it having potential as an entactogen, but I can't help thinking that as a simple isobutylamine homologue of PCA, it would still be neurotoxic as fuck. Guess I'm just fundamentally biased against all those p-halosubstituted phenethylamines.

Less neurotoxic than MDMA, well, the wiki entry also claims it's less effective than PCA as a serotonergic neurotoxin. Not entirely comforting, as PCA has been used to selectively ablate serotonergic neurons in animal models (yeah, I geuss we've all heard this by now). Could the purporteldy reduced toxicity be attributed to a (very) low dopaminergic activity? I'm slightly confused, as wiki and the article abstract seem to focus on 4-CAB's dopamine and serotonin reuptake inhibitor activity, whereas PCA acts primarily as a dopamine and serotonin releaser, as far as I know.

I don't have access from home to the full-text Johnson article cited by wiki, but I'll certainly look into it when I'm back at work.
 
Nomenclature

Just a point of nomenclature. The compound referred to is not an isobutylamine, it is a secondary butylamine. 8) Its correct name would be 1-(4-chlorophenyl)-2-butanamine. Isobutylamine has a branched chain. This is a mistake based on the amphetamine, which really is an isopropylamine. Extending the linear chain of an isopropyl does not make it an isobutyl.
 
I was thinking of something like this, but with the 4-fluoro instead of a para-chloro (my inconsistency in naming here is consistent with the common names 4-FA and PCA). 4-FA was actually a pretty interesting compound, and it seems that by extending the alpha chain, you would get less stimulating and more entactogenic, as is seen with MDA vs. BDB.
 
yeah, given the relatively low potency of 4-FA and the as of yet undetermined threshold for 2c-f i would be inclined to agree. What about putting an alkyl group on the 4? Both amphetamines and phenethylamines with 4-alkyls tend to be popular. I suppose a bromine or iodine would fit, but that may well make it potentially more toxic. Thoughts?

In as far as toxicity of this compound goes, if the dosage is roughly equivalent to MDMA, serotonergic toxicity shouldn't be much of a problem. In rats a dosage equivalent to a ~125mg in humans showed only a 20% reduction in 5HT markers. However I don't see any data for other types of toxicity.
 
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What about putting an alkyl group on the 4? Both amphetamines and phenethylamines with 4-alkyls tend to be popular. I suppose a bromine or iodine would fit, but that may well make it potentially more toxic. Thoughts?
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There's a wikipage on 4-MAB, the methyl analogue, but there's not much info about it. Only that it's a stimulant if I recall correctly.

I suspect you are right about bromine and iodine. The 3-carbon counterparts are hideously toxic at least.

But a trifluoromethyl could be worth a shot. Or nitrile or fluoroethyl...

In as far as toxicity of this compound goes, if the dosage is roughly equivalent to MDMA, serotonergic toxicity shouldn't be much of a problem. In rats a dosage equivalent to a ~125mg in humans showed only a 20% reduction in 5HT markers. However I don't see any data for other types of toxicity.
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My thoughts exactly. I would be worried about possible cardiotoxicity...
 
tryp2fun said:
Just a point of nomenclature. The compound referred to is not an isobutylamine, it is a secondary butylamine. 8) Its correct name would be 1-(4-chlorophenyl)-2-butanamine. Isobutylamine has a branched chain. This is a mistake based on the amphetamine, which really is an isopropylamine. Extending the linear chain of an isopropyl does not make it an isobutyl.
Click to expand...

I guess it would be a secbutylamine.
 
It must have a pretty low potency, and its remote resemblance to oxidopamine could be an issue (with the concern being 5-ht not dopamine).

Honestly its rather hard to say, but there are certainly more potent, proven and available compounds whose safety profiles are better established....
 
I presume - I don't know for certain - that the two enantiomers of 4-CAB would be vastly different in terms of activity and toxicity. Specifically, they'll have different receptor affinities and therefore exert different activity as serotonin and dopamine releasers and/or reuptake inhibitors, different degree of direct 5-HT2b agonism etc. Assuming that 4-CAB would be available as a racemate, its close structural relative chlorphentermine might give us an idea of its side effect profile. I'm not too enthused.
 
Aephetamine itself is crap, so why bother with its chlorinated analog???
 
hugo24 said:
Aephetamine itself is crap, so why bother with its chlorinated analog???
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Because they are different chemicals?

That's like saying codeine is crap, so why bother with it's demethylated analog... (yes, crappy analogy, but makes the point...)

A better analogy might be 2C-H and 2C-C. 2C-H is inactive so let's not bother putting a chlorine in the para-position, what good could it possibly do...

I presume - I don't know for certain - that the two enantiomers of 4-CAB would be vastly different in terms of activity and toxicity.
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Makes sense. I remember a study where the S-isomer of MDE was found to be far less neurotoxic than the racemate or R-isomer. However this doesn't necessarily correlate with 4-CAB since it's a very different structure...

Anyway I would assume the S-isomer to be more dopaminergic than the R.
 
I know what you mean dread but all SAR data point towards it. Actually, my comment was a prognosis based on all available facts, nothing more. Though I'm quite confident I'll be right ;).

The scientist likes to make prognosis, and he likes to be proven wrong most of the time =D
 
hugo24 said:
Aephetamine itself is crap, so why bother with its chlorinated analog???
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Did you think so? While it's not amphetamine, I wouldn't call it crap.

Of the aephetamine derivatives, I wonder what 1-phenyl-2-(1-pyrrolidino)butane would be like as is prolintane with a methylene unit removed from the sidechain (prolintane is quite OK as a stimulant). Is there any data about 1-phenyl-2-(1-pyrrolidino)propane (the amphetamine analogue of prolintane)?
.
 
I don't understand why 1-(4-fluorophenyl)butane-2amine wouldn't be a better version of 4-FA? Wouldn't extending the alpha-methyl to alpha-ethyl lead to better retention of serotonergic activity? Or because that leads to higher selectivity of catehcolaminergic neurons, aka reducing the overall potency of the molecule (making the serotonergic activity more selective and longer lasting compared to the release of say DA and NE [basically serotonergic effects are more pronounced due to lack of other catecholamine activity per dose]). Longer chains on the alpha leads to inactivity because of this right? Making the amine into a secondary rather than a primary amine (n-methyl or n-ethyl) would result in lower potency, attenuation serotonin transmitter and receptor quantities over time. Messing with the alpha sub would be silly, and the n-alkyl sub potentially lead to a more neurotoxic counter part than than their primary amine buddies (4-fa < 4-fma in neurotoxcity).

Would it be worth trying to making the alpha-methyl into an alpha-ethyl on 3-FA (1-(3-fluorophenyl)butane-2amine) to increase the serotonergic activity to make it close to that of 4-FA, so it might have a slightly higher potency than 1-(4-fluorophenyl)butane-2amine making it actually usable as a recreational drug, and also decreasing some attenuation of serotonin transmitter and receptor levels.

Just curious as I was looking at an amphetamine SARs article
 
To me, 3-FA feels almost as if it is the closest thing ever produced (as in, widely distributed and available) that is as closest to a pure DA releaser. So having some of that around can result in some interesting experiments.... i like to mix 2-FMA with 3-FA sometimes. Smoked 2-FMA seems more NE release (? why) i mean i'm jacked the fuck up like lets get this shit done come on /whack/. I smoked some 3-FA , and about immediately went to bed.

maybe a bad place or wrong thread but since i'm already off subject, i wonder about (since the chemical companies are in a mood to play around with sticking the F in various spots) beta-fluoro-amphetamine or its N-methyl version. Found a study.. that directly compared 2-FA (or FMA i forget) with its beta-F version, and to the animals (primates of some type i believe) they acted much more like they were on true d-meth. I think the only reason they picked flluorine was so they can make it radioactive and do tests etc. So, closer in effects which is what "we" would love (the people that want a way out of chasing down street speed that 'bomb shit' is considered 50% cut, with whatever they use to make it solid xtals/shards). Maybe something less electronegative there that won't fall off, or if it falls off won't do damage ;) Iodo?

But i'm GOOD. No more chasing for me, i just found a place 2-FMA is the best they got, they're (act like it anyway) too dumb to know what i mean be beta-fluoro so i took whats the closest we have now to meth and bought a truckload for a lifetime supply. I should go on chemboards more often but am i correct we dont really know how toxic this 2-fma is? i'm willing to 'donate my pee to science" since i've been taking it daily, for a loooooong time now". Somebody with a LC / GC/MS NMR etc would probably help us make a better "educated guess" as to if 2-FMA is safe or not. It certainly feels safer. No (less than plain amp) serotonin release so no worries about that type of meth neurotoxicity...

Sorry if i went too off track..
 
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