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psychedelic cathinones? are they possible

M

michael_1992

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Aug 16, 2010
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im not talking about slight psychedelic effects from methylone or any other empathogen cathinone.

We know that 2C chemicals and mescaline , which are substituted phenethylamines (but not amphetamines) are psychedelic. We also know that many of the "amphetamine versions" of the 2C chemicals are psychedelic (such as DOI). But what would be the effect of using cathinone versions of the 2C chemicals. Are there any reports of this being manufactured / used?
 
1) Cahinones tend to become unstable without N-substitution. If you look through PIHKAL as many have done there are surprisingly few compounds which are considered good psychadelics which had N-substitution. (as you mention not referring to MDMA type compounds but instead true psychadelic drugs).

2) The best bet I would predict would be beta-keto NBOMes as in these compounds (well i the PEA equivalents) the N-substitution actually increases potency.

http://www.bluelight.ru/vb/threads/609841-Beta-keto-NBOMe-s?highlight=beta+keto+nbome
 
The beta-ketone version of DOB is mentioned in a brief footnote in The Psychedelic Index Volume 1 by Shulgin. The information on it he received from one Igor in 2006 (personal communication). According to that source it is active orally at 20mg, 6-8 hours. Shulgin adds that it is not reported in the scientific litterature.
 
^need a second copy of that *gets pristine untouched version down from shelf* , very interesting hadn't read that.

I do wonder if the other problem with cathinones i.e NON-N-alkylated versions is if there is any oxidation/decomposition it would make dosing a bitch - not something to mess with when dealing with chemical analogues of DOB.
 
Are they possible? Most likely. Beta methyl (or is it methoxy?) 2C-series compounds are detailed in PiHKAL, and they are active. Insofar as stability of bk-phenethylamines lacking an N-substitution is a problem, n-benzyl-X substituted phenethylamines present a solution (as n-methyl is the kiss of death as far as psychedelic activity goes). Is there a point to bk-phenethylamine psychedelics? probably not. The beta-methyl (or methoxy?? jeez...) 2Cs explored by Shulgin had a high ratio of annoying physiological side-effects to psychedelic effects.

ebola
 
I don't think the beta-methyl or beta-methoxy PEA's should be considered as indicators for beta-ketone PEA or AMPs. Methcathinone (As far as I am aware) is not in anyway similar to it's beta-methyl or beta-methoxy equivalent? Both substitutions always stuck out as nasty to me (methyl is so hard to remove and methoxy works to protect the beta-oxygen too much)

It's true beta-ketones potentially produce beta-hydroxy metabolites often associated with sympathomimetic properties but if one was to investigate NBOME's this would likely be a minor irrelevant metabolite. Am I correct in thinking Shulgin didn't investigate beta-ketones until looking at methylone?

I hear what your saying but I personally wouldn't dismiss them so quickly. I reckon there might be a few possible ones of interest. I guess they just become less cost effective to both make and investigate compared to simple PEAS.
 
Dr. Shulgin said:
Your idea of making analogues of the psychoactive amphetamines with the carbonyl that is characteristic of CAT would probably be a disappointment. Cathinone itself is rather unstable because there is a primary amine and a ketone in the same molecule. It will tend to dimerize and become inactive. In the example of METHYLONE (as with methcathinone) the amine is a secondary amine and the compound is quite stable. But all of the psychoactive amphetamines (except for MDMA) are primary amines.
Click to expand...

http://www.cognitiveliberty.org/shulgin/blg/index.html
 
Too bad Glennon didn't assay bk-2C-B and bk-DOB when he made the beta-hydroxy and beta-methoxy analogues, which, by the way, look pretty active although the beta-hydroxys probably won't cross the BBB.
 
One thing I've wondered about in this direction, is something similar. But with the use of pthalimido protecting groups, whilst not going into details the synthesis of pthalimidopropiophenones is not difficult. Its actually an intermediate step in the Gabriel synthesis, after which, whatever target compound whoever is doing whatever, that pthalimide is cleaved off with hydrazine (fairly nasty stuff) The synthetic details are relevant here, not in detail, but the fact that these pthalimidopropiophenones are intermediates of that nature, well known, well characterised etc. as a class (I don't mean specifically of the 2,5-OCH3-beta-C=O phenethylamines, but phthalimidopropiophenones or other such well known substitution patterns on a BK-amphetamine)

The primary keto-amines undergo a dimerization and cyclization giving diphenylpyrazine products (how delightful)
To dimerise successfully to a significant degree they are going to have to be present in a concentrated enough solution, thats going to be a bugger if one was trying to work up a synthetic reaction and isolate the end product substituted cathinone (or cathinone ltself) without ending up instead, with a mess of the corresponding diphenylpyrazine, some cathinone and rxn byproduct shite, but if the concentration is dilute enough, there are not going to be enough molecules meeting to do so. The phthalimide protecting group gets cleaved off in-vivo, giving the substituted cathinone, to be diluted in stomach acid and absorbed as it does so.

Pthalimidopropiophenone itself turned up in some variety (or varieties, I don't know) of party pill, as a prodrug for cathinone. I see no reason why the principle couldn't be extended to pthalimidopropiophenones bearing the (for instance) 2,5-dimethoxy-4-R-phenyl-beta-carbonylpropan-2-amines, (R=halide, alkyl, alkoxy, thioalkyl, etc. or for ex. the 3,4,5-same.
Thing is...the body will do the same thing
 
Was there any information to suggest Pthalimidopropiophenone was actually in neo-organics capsules at any relevant quantity to be active?

I seem to remember a discussion (to which I never read an answer) over whether or not it was an artifact - i.e was it an impurity left over from synthesis present in tiny amounts (GC/MS can be very sensitive etc) or whether it was actually in quantities relevant for activity.
 
dip12 said:
Was there any information to suggest Pthalimidopropiophenone was actually in neo-organics capsules at any relevant quantity to be active?

I seem to remember a discussion (to which I never read an answer) over whether or not it was an artifact - i.e was it an impurity left over from synthesis present in tiny amounts (GC/MS can be very sensitive etc) or whether it was actually in quantities relevant for activity.
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If it were left over from the synthesis of cathinone, then why didn't they detect cathinone in the pills?
 
Somebody mentioned cathinones becoming unstable without the N-substitution which got me thinking here. So what if the molecule is unstable if it's active, it just means it doesn't really have proper shelf life and that it would have to be consumed immediately after the synthesis. This isn't practical at all though, so what about creating a stable prodrug which would get metabolized in the liver to an active yet unstable form, capable of crossing the BBB? As long as the metabolized, active form doesn't break down or further metabolize into harmful stuff, it should be safe as well right? We could even take it one step further and start designing new enzymes capable of doing this if we find our own bodies lacking. This sounds kinda futuristic to me, but whatever the case is, I have a hunch that prodrugs will eventually hit the grey markets when analogue laws get stricter and stricter worldwide. Problem is, to my understanding they're particularly tricky to create/design.

I hope I'm not just rambling non-sense.
 
atrollappears said:
I got you a present!
http://www.mediafire.com/?9mkc7zj008obksd
They say one of the pills was only phthalimidopropiophenone and 2-FMA, that's a pretty botched synthesis xD
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Trying not to sound too pedantic but that was the point (the botched synthesis was referring to the individual ingredient not the combination). I.e you can't assess whether a potential stimulant is active/to what extent when in a combination product that also contains another known potent stimulant. (Hell the could have mixed it in there thinking it was methcathinone analogue or even after a singe 'placebo' type self test). It's interesting to note ALL neo-organics 'ingredients' have been subsequently seen on the RC market - as far as I am aware phthalimidopropiophenone has not?? (I am happy to stand corrected if this is incorrect?)

FnX said:
Somebody mentioned cathinones becoming unstable without the N-substitution which got me thinking here. So what if the molecule is unstable if it's active, it just means it doesn't really have proper shelf life and that it would have to be consumed immediately after the synthesis. This isn't practical at all though, so what about creating a stable prodrug which would get metabolized in the liver to an active yet unstable form, capable of crossing the BBB? As long as the metabolized, active form doesn't break down or further metabolize into harmful stuff, it should be safe as well right? We could even take it one step further and start designing new enzymes capable of doing this if we find our own bodies lacking. This sounds kinda futuristic to me, but whatever the case is, I have a hunch that prodrugs will eventually hit the grey markets when analogue laws get stricter and stricter worldwide. Problem is, to my understanding they're particularly tricky to create/design.
Click to expand...

O_o Designing enzymes to cleave pro-drugs to circumvent drug regulation?!! I would just go for Gene-therapy or some electronic-pleasure centre-of-the-brain interface. ;)
 
dip12 said:
Trying not to sound too pedantic but that was the point (the botched synthesis was referring to the individual ingredient not the combination). I.e you can't assess whether a potential stimulant is active/to what extent when in a combination product that also contains another known potent stimulant. (Hell the could have mixed it in there thinking it was methcathinone analogue or even after a singe 'placebo' type self test). It's interesting to note ALL neo-organics 'ingredients' have been subsequently seen on the RC market - as far as I am aware phthalimidopropiophenone has not?? (I am happy to stand corrected if this is incorrect?)
Click to expand...

Yeah I assumed you meant that the phthalimidopropiophenone was an unintended byproduct in the synthesis of another cathinone. As I imagine it, it would be unlikely that an RC supplier with that much experience would synthesize entirely the wrong, inactive chemical and have no idea. It wouldn't be the first time though (see: 6-APDB -> 6-APB though 6-APB is still active) and of course we can imagine situations in which that would occur.
Good point about the RC market. If the drug is not inactive, then I'd say that maybe there was no interest in it, and/or that they speculated as you did that it may not even be active.
 
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