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Neurotoxicity of Halogenated amphetamines

Smyth

Smyth

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Does anybody know why halogenated amphetamines are neurotoxic? [This might belong in another thread]. People hired by the government also say MDMA is 'neurotoxic' as is cocaine. I just wanted to know what the deal is that something like p-bromo-amphetamine or particularly something like 3,4-dichloromethamphetamine is considered so dangerous.

I would bet that they woud cause the dreaded 'serotonin syndrome'. But does anybody know exactly what the score is with these chemicals since it is all one big mystery to me.
 
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People "hired" AKA funded, by the government, as well as people funded by politically nutral, and private funds, show that MDMA is far more neurotoxic than cocaine (cocaine isn't classically neurotoxic).

I don't think we know how the proto-typic neurotoxic hallogenated amphetamine (p-chloroamphetamine) is neurotoxic. It releases serotonin in a classical amphetamine like manner, and then burns out serotonergic terminals in a non-MAO-B-dependent manner. It's another free-radicle mediated neurotoxin.

It would only cause serotonin syndrome at massive doses, or in combination with a MAO inhibitor (just like MDMA).
 
It may be a case of energetic exhaustion: Overheating impairs ATP production, the axons can no longer maintain membrane polarization, Ca++ flows in, and the axon's metabolism gets FUBARed (to use the technical term.) :-)

Anyway...most amphetamines are probably neurotoxic. I don't recall specific research on p-bromoamphetamine, but it's rather certainly neurotoxic as well. Whether that would translate into a danger to humans at 'recreational' doses is less clear, although I would approach untested halogenated amphetamines with GREAT caution.
 
Just wanted to mention that p-chloroamphetamine was once used clinically:

Considerable clinical application of 4-CA has been made, and it has been found effective as an antidepressant when used chronically at levels of 75 mg/day (van Praag et al., 1971; van Praag and Korf, 1976). There are very few side effects noted and the drug is tolerated very well. However, indications of raphe-nucleus degeneration (Yunger et al., 1974) and related neurotoxicity (Harvey and McMaster, 1976) in experimental animals have discouraged further clinical study.
Click to expand...
http://www.erowid.org/archive/rhodium/chemistry/shulgin.pea.sar.hop.html#35
 
>However, indications of raphe-nucleus
>degeneration (Yunger et al., 1974) and
>related neurotoxicity (Harvey and
>, 1976) in experimental animals
>have discouraged further clinical study

Makes me very curious if we could see the same toxicity with other para-chlorinated phenethylamines, such as DOC, 2C-C, 2C-CDF and DOCDF. I'd expect any possible toxicity to be most associated with 2C-C because of the high dosage needed (20mg to 40mg) compared to things such as DOC where the dosage is 1/10th the amount.
 
The halogenated amphetamines being discussed here exert their actions via the serotonin (and catchecolamine) transporters whereas the 4-halo 2C-x/DOx compounds are specific 5HT2a agonists. I don't know if any of the 2C-x/DOx compounds have any effects on the monoamine reuptake mechanisms, but if not, I'd doubt that they'd exhibit neurotoxicity in the same was as the 4-haloamphetamines

BTW are 4-psueudohalogenated amphetamines (eg 4-cyanoamphetamine) known to be neurotoxic or work in the same way as 4-chloroamphetamine etc.?
 
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4-vinyl amphetamine is possible to make from 4-bromo-amphetamine.

J. Med. Chem. 2000, 43, 1215-1222
Further SAR Studies of Piperidine-Based Analogues of Cocaine. 2. Potent Dopamine and Serotonin Reuptake Inhibitors
 
Isn't 4-flouro-amphetamine for whatever reason considered "safer" and relatively OK compared to the others? 4-FA is definitely, good stuff.

Yeah i'd wonder what something like 4-triflouro-amphetamine would do, or if just being 'heavier' there makes it neurotoxic for whatever reason.
 
^^

uh, oh well, i mean, when i have eaten a nice dose (> 150-170mg) of it, its provided me with an experience that made my brain record, "good shit" :)
 
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