2-p-Tolyl-cyclopropylamine/2-PTC

[Someone13232]

so i finally decided to make an account after years of lingering about... i saw this chemical (2ptc) on what i consider to be a rather dodgy looking chinese and badly translated website (who care not for breaking laws), and came across this thread, and decided to stear clear...
BUT, upon checking the lists of my favourite legal EU RC vendor who has been a reliable source for me and many associates for years now, i see not only 2-PTC, but 3,4-DFPTC... what do you guys think? i really wanna know what this crazy shit is about man...

 

[Black]

so i finally decided to make an account after years of lingering about... i saw this chemical (2ptc) on what i consider to be a rather dodgy looking chinese and badly translated website (who care not for breaking laws), and came across this thread, and decided to stear clear...
BUT, upon checking the lists of my favourite legal EU RC vendor who has been a reliable source for me and many associates for years now, i see not only 2-PTC, but 3,4-DFPTC... what do you guys think? i really wanna know what this crazy shit is about man...

there's a thread about the diflouro-version in NPD. i'd rather stay clear. if the difluoro-compound is an mao-inhibitor as well as a serotonin releaser, it might well be "serotonin syndrome in a single pill".

so this shit is basically about making money from selling compounds that look remotely like mephedrone or mdma.

 

[Black]

Hi all, medicinal chemist here to clear up some confusion. First and foremost, this product is being labeled as (r)-MDMA but let's be clear, the product in question is 2-(p-tolyl)-cyclopropylamine (CAS #90874-49-0 as the HCl salt).

Second, people here are screaming about the toxicity of cyclopropane groups. This is categorically incorrect. A number of drugs (Livalo and moxifloxacin immediately come to mind) have cyclopropane rings and exhibit no significant toxicity related to this functional group. Someone mentioned alkylation of DNA which is completely untrue. The nitrogen mustards utilize reactive aziridine rings to alkylate DNA, not cyclopropane rings

As far as MAOI risk, you cannot simply say "oh, well the demethylated derivative is an MAOI so this probably will be too." The fact of that matter is if you're willing to take the obscene risk of snorting a bunch of chemicals synthesized in China, no one can make an educated guess whether this one is more or less toxic than anything else you've put up your nose. The fact of that matter is there is literally zero tox research into any research chemicals. The only data we have are medical case reports when someone presents to the emergency room.

For the wanna-be chemists in the group, para hydroxylation is a major route of metabolism (and eventual excretion) and blocking this action by p-methylation radically alters the pharmacokinetics of the drug. In addition, this can radically alter the enzyme binding affinity and it would not surprise me at all for this compound to have substantially different MAOI activity (higher or lower) than trans-2-phenyl-cyclopropylamine (the original compound in question).

It absolutely amazes me how much misinformation makes its way onto this site. Hopefully everyone takes what's said here with a HUGE grain of salt.

biochemist here. sure cycopropane groups aren't inherently toxic, but how would you describe the mechanism of how tranylcypromine to non-chemists? you cannot deny that a cyclopropane ring has a lot of ring strain and easily opens and attaches to anything suitible in the vicinity when compared to most other functional groups present in recreational drugs. i never said that any cyclopropane ring randomly springs open and alkylates anything in sight, but binding to MAO certainly is enough to make that happen with tranylcypramine (with MAO being "anything in sight" in that case; sure it's still a bit of an oversimplification but being a medicinal chemist i'm sure you understand what i mean).

besides, fitting into MAO is more dependent on the side chain than on what's attached to the phenyl ring. adding a para-methyl sure influences the pharmakokinetics, but is very unlikely to dramatically alter the pharmacodynamics in this case.
while there obviously are no studies on the toxicology of this compound, our job here on bluelight (as a harm reduction forum) is to make our best guesses and estimates concerning the possible effects and dangers associated with the things that turn up. taking an irreversible MAOI as an MDMA substitute can kill the unsuspecting users.
so when a new compound turns up on the radar that raises multiple red flags (especially since we're in MED and not NPD, and considering the reactions of the people after your post) i'd rather use a (perhaps a bit too) graphic description of its likely effects than to downplay the risks. and saying that it's probably no more dangerous than any other RC definitely falls into that category when we have good reason to believe that it's at least an MAOI. of course as of yet, we do not know what it does at all, but that doesn't mean we have no idea what it might do and what particular dangers might be the consequence.


edit:
according to this paper, at least with 2-fluoro-tranylcypramine derivatives, putting a methyl-group in the para position doesn't change the MAOI activity much at all, while replacing the methyl with a fluorine actually increases the potency as an MAOI.

 

[wzrd420]

so is this what is being sold as R Mdma and has a brown tan powder and root beer smell?

 

[LucidSDreamr]

not only that (well, that's bad enough [might not be quite as bad, seeing as cypenamine is used as a pharmaceutical drug], but it gets worse)

cypenamine has no ringstrain associated with it because it is a 5-ring, thus won't do such nasty things as this compound most likely would.

 

[LucidSDreamr]

Second, people here are screaming about the toxicity of cyclopropane groups. This is categorically incorrect. A number of drugs (Livalo and moxifloxacin immediately come to mind) have cyclopropane rings and exhibit no significant toxicity related to this functional group. Someone mentioned alkylation of DNA which is completely untrue. The nitrogen mustards utilize reactive aziridine rings to alkylate DNA, not cyclopropane rings


It absolutely amazes me how much misinformation makes its way onto this site. Hopefully everyone takes what's said here with a HUGE grain of salt.

no what you are saying is completely untrue.

heres a peer reviewed article (one of thousands) on the use of cyclopropane containing drugs to alkylate DNA.

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC307750/pdf/nar00025-0102.pdf

c'mon man, at least do a google search before you come on here and start ripping into people. I'm not even a medicinal chemist and i knew that cyclopropane containing compounds can alkylate dna off the top of my head, its freshman year organic chemistry knowledge.

I'll admit it was wrong of me to imply that just because something contains a cyclopropane ring that alone makes it inherently nasty. Other factors need to be at work such as electronics and strain to make them nasty, besides just the ring....but here we've got the ring, so there is a starting point for something to get ugly,(btw I'm not looking to get into a discussion about how "rmdma" is or is not tuned to undergo such ringopening, because it isn't) and until the drug goes through 10-15 years of trials like the ones you looked up on google to post into this thread, you can't say that that ring being there isn't potentially a starting point for some nastiness to happen.

But you saying that its "completely untrue" that cycloprpanes can alkylate DNA is flat out wrong

 

[Black]

cypenamine has no ringstrain associated with it because it is a 5-ring, thus won't do such nasty things as this compound most likely would.

whoops, i mixed it up. i ment tranylcypromine.

 

[DKKON1]

... I'll admit it was wrong of me to imply that just because something contains a cyclopropane ring that alone makes it inherently nasty. Other factors need to be at work such as electronics and strain to make them nasty, besides just the ring....

Question: what sort of electronics are you referring to here? Hopefully its not a dumb question!

 

[Black]

Question: what sort of electronics are you referring to here? Hopefully its not a dumb question!

that would be for instance electron withdrawing groups. having halogens or nitro groups or something in the vicinity would destabilise the ring, making it more reactive.