Benzylpiperidine (BENZYL PIPERAZINE) activity & identification

[haribo1]

Has someone got a list of all the Benzypiperidine class of drug that has made it to the market? I seem to remember that the title compound does little by itself, but boosts the effects of the meta trifluoromethyl (for example). In addition, is there a simple test (like a marquis reagent that will a)confirm the presence of a benzyl piperidine & b)give a guide to WHICH of the class it is?
I know the drugs were first commercialised in New Zealand, but can anyone fill in a more detailed history? I seem to remember someone in alt.drugs.chemistry talking about 'accidentally' putting 100mg of benzylpiperizine and 30mg of meta trifluoromethyl benzylpiperidine on his and his girlfriends KFC and going to see a band. I think that was in about 1992.

Many thanks in advance...

PS What the hell do these chemically DO in the body? They do not sound like much fun, but I hear that in the US, in particular, a lot of X pills are infact the piperizines...

 

[haribo1]

Which of these have been lumbered onto the public?

 

[fastandbulbous]

^ All of the above are benzylpiperazines, not benzylpiperidines (piperidines only contain one heterocyclic nitrogen). Benzylpiperidines are things like methylphenidate, pipradrol, desoxypipradrol etc

 

[haribo1]

^Sorry, I realize I was 1/2 asleep. So, it's benzylpiperizines!!! Sorry for my stupidity folks...

 

[MattPsy]

I've tried lots of piperazines.

In chronological order of market introduction to the best of my knowledge (I live in New Zealand), and with included methods of action:

BZP (1-benzylpiperazine)
- Amphetamine-like actions at DA & NE, slight nonselective 5-HT2 agonism.
TFMPP (1-(3-trifluoromethyl)phenylpiperazine)
- 5-HT2A+C agonist.
pFPP (1-(4-fluoro)phenylpiperazine)
- Mostly 5-HT2A agonist, some activity at 5-HT1 and 5-HT2C.
MBZP (4-methyl-1-benzylpiperazine)
- The same as BZP, but less potent by weight and intensity of effect.
mCPP (1-(3-chloro)phenylpiperazine)
- Mostly 5-HT2C agonist, some 5-HT2A agonism.
MeOPP (1-(4-methoxy)phenylpiperazine)
- DA + NE + 5-HT reuptake inhibition, some 5-HT2A agonism.

I've also tried MDBZP, 2-BZP and one of my own, para-nitro-benzylpiperazine.
The first seems to be a SERT inhibitor and very weak 5-HT2A agonist from what I could tell from the effects. The second is a nice stimulant + weak psychedelic combomolecule. The third seems to be a SERT inhibitor - I used it to make a MDMA experience last many many hours by taking it after MDMA a few times.

I assure you BZP doesn't do nothing by itself, it can be a plenty powerful stimulant, just with more side effects than amphetamines.
TFMPP doesn't do too much by itself unless at higher doses, until you take BZP with it - it seems to potentiate it, making it a mild psychedelic at doses like 100mg, whereas by itself you need about 300mg for it to be psychedelic.

 

[Reminisant B]

^Sorry, I realize I was 1/2 asleep. So, it's benzylpiperizines!!! Sorry for my stupidity folks...

and substituted Phenyl-piperazines.

Many people get benzylpiperazines (BZP, MBZP) confused with the substituted phenylpiperazines (MEOPP, MCPP, TFMPP) in terms of the molecule.


Not phenylpiperazine itself though. (I.e not substituted) erowid have corrected the following incorrect trip report.
http://www.erowid.org/experiences/exp.php?ID=22420

 

[fastandbulbous]

Wouldn't touch a piperazine with a 10' shitty stick to be honest. I saw the phenylpiperazines classified as panicogens & my experience with yohimbine is enough to put me off taking anythimng with a clinically significant anxiety/panic attack causing activity

 

[Bondmaker]

I've made..

i'm not a brraggard but i've made at least 25 new phenylpiperazines/ piperidines; and worked with literally hundreds of them, both benzl piperazines and piperidines, as well as the phenylpiperidies/piperazines. Never tasted one of them, but certainly absorbed lots of them by skin contact. Never felt weird by absorbtion of small amounts, so they can't be extremely potent compounds Benzyl piperazines/piperidines have use as synthons for CNS active antidepressants and neuroleptics. When they are metabolized, the parent piperidine/ piperazine often is a metabolite, which is from what i've read active in many cases by itself, or causes "unwanted" side effects. LIke fastandbulbous, i wouldn't touch one to my tongue for all the tea in China. Especially don't like the 4 Aryl piperidines. Too MPTP like in stucture to mess around with!!!

 

[fastandbulbous]

I've also tried MDBZP, 2-BZP and one of my own, para-nitro-benzylpiperazine.

Did you have no dread of taking an aromatic nitro compound? Lots of them are nasty chemicals that decouple oxidative phosphorylation in cells so the energy is released as heat - it's lead to industrial diseases like women who worked in munitions factories in WWII, turning yellow & uncontrollable heatstroke in some cases due to poisoning with aromatic nitro explosives (trinitrotoluene/TNT; trinitrobenzene; picric acid/2,4,6,-trinitrophenol etc). Even the dyes aromatic nitro groups are virtually toxic and they're a long way removed from TNT etc than the nitrobenzylpiperidine you mention.

If they get reduced by some means to the aromatic amine (aniline derivatives), you just swap one set of ugly toxicities for another. I've no desire to try DON or 2C-N & I think very highly of the psychedelic phenethylamines, purely because of he aromatic nitro group. It's not a bad idea to try and track down the toxicology of close relatives (or the compound itself if you can find it) before consuming a chemical with almost bog all known of its pharmacology - and the 5HT2c agonism that gets them the property of being 'panicogens' (apparently anxiogenic just wasn't descriptive enough!) that just screams "avoid" at me. That's without even touching (again! ) on the phenylpiperizines being aniline derivatives...

 

[MattPsy]

Yeah I was aware of the potential (probable?) toxicity involved but it was more of a "let's see what activity it has" than a "let's take this lots of times" sort of thing, in an effort to see the effect of different electron densities on the ring for the BZP and PP derivs.
In any case it didn't feel toxic or anything, no methaemoglobinaemia symptoms... although I was quite preocupied at the time with mild SS symptoms, oops... not that that is a green light or anything, haha. I suppose it is comparably toxic to nitrobenzene.

Nitrobenzene: ORAL (LD50): Acute: 780 mg/kg [Rat]. 590 mg/kg [Mouse].