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All 9 posts   Subject: Phenylpiperazines & Benzylpiperazines   Please login to post   Down

 
    penner
(Stranger)
11-26-03 18:36
No 473330
      Phenylpiperazines & Benzylpiperazines     

I ve read some piperazine infos, and i know that they have side effects and they can't mess with Phenethylamines although I will try them.

I'm still a litte bit confused about some statements:

- I've heard that peolpe who tried MCPP felt very overheated and nothing more. Can i also suppose that on MMPP and CPP? I wanna avoid overheating.

- I've found only trip reports about TFMPP and BZP - is that all? Had nobody tried other, maybe more interresting piperazines?
I've seen theoretical infos here about 4-methyl-2,5-dimethoxyphenylpiperazine,and 1-(2,5-Dimethoxyphenyl)-piperazine on Rhodium, but no trip reports? which other piperazines are psychoactive?
 
 
 
 
    Nicodem
(Stranger)
11-26-03 20:01
No 473336
      A lot of piperazines are active
(Rated as: excellent)
    

The piperazine moiety is one of the best for psychoactive compounds. There is lot of work done on the piperazines acting at many monoaminergic, opioid, sigma, nicotinic and other receptors and also transporters.

I'm working on piperazines almost a year and synthesized 9 new benzylpiperazines, 2 heteroarylpiperazines, one phenacylpiperazine  and 7 disubstituted piperazines, but have not finished all the bioassays yet. Of those that were tried practically 3/4 are active in some way, but only few are interesting or enjoyable. The disubstituded ones are presumably acting trough sigma receptors (one was found slightly dissociative), while the monosubstituted are reminescent of some serotoninergic actions or just plain stimulants.

The overheating effect of TFMPP and m-CPP is due to 5-HT1a agonism. I also encountered this effect with the 3-methoxy-benzylpiperazine and a little with 2,5-dimethoxy-benzylpiperazine. But the overheating is mostly felt like not noxious (though in some circumstances it can kill), worse is the anxiogenic effect of these compounds. I don't like them. A preliminary SAR for anxigenic benzylpiperazines would therefore indicate the necessity of the methoxy on the meta benzylic position. I don't know how you can avoid these overheating/anxiogenic effects, maybe with an 5-HT1a antagonist, leaving only the 5-HT2a mediated effects. I would not bother so much, there are better compounds around.

Some others benzylpiperazines having an electronwithdrawing group (Cl, Br, NO2) look much more promising, but for most of them I'm still at the threshold level so can't tell much. However, they don't give me a feeling of being a big breakthrough and I doubt there will be any comparable at all to the oldies like 2C-B or MDMA.

The good thing is that they are easy to synthesize, well at least some of them.

"The real drug problem is that we more and better drugs" - J.Ott
 
 
 
 
    Rhodium
(Chief Bee)
02-17-04 21:51
No 489392
User Picture 
      TFMPP - Metabolism and Toxicological Detection
(Rated as: good read)
    

New designer drug 1-(3-trifluoromethylphenyl) piperazine (TFMPP): GC-MS and LC-MS studies on its metabolism and its detection in urine
Roland F. Staack, Gieselher Fritschi, Hans H. Maurer
DOI:10.1002/jms.513
Journal of Mass Spectrometry 38(9), 971-981 (2003) (https://www.rhodium.ws/pdf/tfmpp-metabolism.pdf)

Abstract
Studies are described on the phase I and II metabolism and the toxicological analysis of the piperazine-derived designer drug 1-(3-trifluoromethylphenyl)piperazine (TFMPP) in rat urine using gas chromatography/mass spectrometry (GC/MS) and liquid chromatography/mass spectrometry (LC/MS). The identified metabolites indicated that TFMPP was extensively metabolized, mainly by hydroxylation of the aromatic ring and by degradation of the piperazine moiety to N-(3-trifluoromethylphenyl)ethylenediamine, N-(hydroxy-3-trifluoromethylphenyl)ethylenediamine, 3-trifluoromethylaniline, and hydroxy-3-trifluoromethylaniline. Phase II reactions included glucuronidation, sulfatation and acetylation of phase I metabolites. The authors' systematic toxicological analysis (STA) procedure using full-scan GC/MS after acid hydrolysis, liquid-liquid extraction and microwave-assisted acetylation allowed the detection of TFMPP and its above-mentioned metabolites in rat urine after single administration of a dose calculated from the doses commonly taken by drug users. Assuming similar metabolism, the described STA procedure should be suitable for proof of an intake of TFMPP in human urine.

The Hive - Clandestine Chemists Without Borders
 
 
 
 
    Nicodem
(Hive Bee)
02-18-04 14:04
No 489533
      More forensic stuff about piperazines
(Rated as: excellent)
    

Piperazine-like compounds: a new group of designer drugs-of-abuse on the European market.

Douwe de Boer, Ingrid J. Bosmanb, Elöd Hidvégic, Carmo Manzonia, András A. Benkö, Lourenço J. A. L. dos Reys and Robert A. A. Maes.
Forensic Science International 121, Issues 1-2 , 15 September 2001, Pages 47-56
DOI:10.1016/S0379-0738(01)00452-2


Abstract
1-Aryl-piperazine compounds are, depending on their substituents, selective for certain serotonin receptors and together with their easy availability and their so-called legal status, this group of psychoactive compounds are potential designer drugs-of-abuse. Internet in that respect is an important source of information and distribution facilities. Because this development may have consequences for the interpretation of future clinical and forensic toxicological case studies, some analytical aspects of 1-benzyl-piperazine (BZP), 1-[4-methoxyphenyl]-piperazine (pMeOPP) and 1-[3-trifluoromethylphenyl]-piperazine (TFMPP) were studied. BZP was not detected by the AxSYM® FPIA technology designed to determine amphetamine-like compounds, but had showed some cross reactivity with EMIT® d.a.u.®. The cross reactivities at 300 and 12,000 ng/ml (RS)-amphetamine equivalents were 0.4 and 1.3%, respectively. Although BZP was not identified directly by the REMEDi™ HS Drug Profiling System, it can be detected by this HPLC/UV scanning system. Using GC/NPD without derivatisation, BZP, pMeOPP and TFMPP can be analysed for and applying GC/MS without or with acetylation or trifluoroacetylation, these compounds can be identified unambiguously. The usefulness of GC/NPD and GC/MS in this respect was demonstrated by the quantitative and qualitative analysis of the content of a capsule with the synthetic stimulant A2, which proved to contain 86.4 mg of BZP.

“The real drug-problem is that we need more and better drugs.” – J. Ott
 
 
 
 
    Rhodium
(Chief Bee)
04-19-04 11:19
No 501604
User Picture 
      A2 (N-Benzylpiperazine) a New Drug of Abuse
(Rated as: excellent)
    

A2 (N-Benzylpiperazine) a New Drug of Abuse in Sweden
Maria Wikström, Per Holmgren, and Johan Ahlner
Journal of Analytical Toxicology, Vol. 28, 67-70 (2004) (https://www.rhodium.ws/pdf/forensic/jatox.bzp-a2.pdf)

Abstract
N-Benzylpiperazine was tested in the beginning of the 1970s as a possible antidepressant drug. However, in both animal and human studies, it was shown to possess amphetamine-like properties, and any further studies were stopped. In a forensic autopsy case in 1999, we found a substance so far unknown to us in the chromatogram of our method used for amphetamines. We could swiftly identify this compound as N-benzylpiperazine because of information given to us by a newly formed network comprising, among others, customs and the police. Since then, we have found N-benzylpiperazine in several cases, among them 11 cases from a number of prisons.

The Hive - Clandestine Chemists Without Borders
 
 
 
 
    Rhodium
(Chief Bee)
05-17-04 00:02
No 507574
User Picture 
      Dexamphetamine vs. 1-Benzylpiperazine
(Rated as: excellent)
    

A Comparison of the Effects of 1-Benzylpiperazine and Dexamphetamine on Human Performance Tests
C. Bye, A. D. Munro-Faure, A. W. Peck and P. A. Young
Europ. J. Clin. Pharmacol. 6, 163-169 (1973) (https://www.rhodium.ws/pdf/bzp.vs.d-amph.performance.pdf)

Abstract
The effects of dexamphetamine (1 mg to 7.5 mg) and 1-benzylpiperazine (20 mg to 100 mg) on performance tests and cardiovascular responses were measured in two groups of 12 normal subjects. Drugs and dummy control were administered orally under double blind conditions at weekly intervals according to a balanced design. Significant (p<0.05) improvement occurred in an auditory vigilance test following both drugs, and this test was sufficiently sensitive to detect the changes produced by dexamphetamine 1 mg at the time of peak drug action. Subjective effects were only detected by the subjects after dexamphetamine 7.5 mg and 1-benzylpiperazine 100 mg. Significant changes attributable to drug treatment were not found in tests of short duration such as tapping rate, hand steadiness and arithmetic. Both drugs produced significant increases in heart rate and systolic blood pressure. It was concluded that 1-benzylpiperazine has psychomotor stimulant activity similar to dexamphetamine and that this was most reliably detected by using a prolonged signal detection test. The effects of 1-benzylpiperazine eye-drops (2%) on pupil diameter was investigated in 6 subjects who had had one eye pretreated with guanethidine (5%) eye-drops. 1-Benzylpiperazine gave effects similar to tyramine but significantly different from methoxamine indicating an indirect sympathomimetic action.
____ ___ __ _

Comparison of the Effects of Dexamphetamine and 1-Benzylpiperazine in Former Addicts
H. Campbell, W. Cline, M. Evans, J. Lloyd and A. W. Peck
Europ. J. Clin. Pharmacol. 6, 170-176 (1973) (https://www.rhodium.ws/pdf/bzp.vs.d-amph.in.addicts.pdf)

Abstract
The subjective, behavioural and autonomic effects of dexamphetamine 10 mg, 1-benzylpiperazine 100 mg and lactose dummy were compared in a group of 18 former amphetamine addicts. All subjects received the three preparations according to a balanced design under double blind conditions. 1-Benzylpiperazine and dexamphetamine produced indistinguishable subjective effects and both were liked. The effects of both compounds differed significantly from the effects following the dummy preparation. Increases in pulse rate and both systolic and diastolic blood pressure were similar following the two active compounds, but 1-benzylpiperazine produced pupillary dilation whereas no significant change in pupil size followed dummy or dexamphetamine. It was concluded that 1-benzylpiperazine is a compound liable to abuse by an addict population, and that this type of study might be of value in predicting abuse liability of other new drugs.
____ ___ __ _

1-Phenylpiperazines: Potential Antagonists of Lysergic Acid Diethylamide
K. Brewster, D. B. Coult and K. M. Pinder
Chimie Thérapeutique 87-91 (1972) (https://www.rhodium.ws/pdf/phenylpiperazines.pdf)

Abstract
A series of 1-phenylpiperazines was prepared by reaction of anilines with 2,2'-dichlorodiethylamine or its N-methyl derivative. Unlike their straightchain analogues the phenylethylenediamines. the 1-phenylpiperazines did not have opposite effects to those produced by lysergic and diethylamide (LSD) on the caeruloplasmin-catalysed oxidations of 5-hydroxytryptamine and noradrenaline. Moreover, they did n re LSD-induced hyperthermia in rabbits and they had little behavioural activity per se. The significance of the use of caeruloplasmin as a model for the action of LSD on the central nervous system in discussed.

The Hive - Clandestine Chemists Without Borders
 
 
 
 
    Rhodium
(Chief Bee)
07-08-04 17:53
No 518190
User Picture 
      N-Benzylpiperazine: Metabolism & Detection
(Rated as: good read)
    

Studies on the metabolism and toxicological detection of the new designer drug N-benzylpiperazine in urine using gas chromatography–mass spectrometry
Roland F. Staack, Giselher Fritschi and Hans H. Maurer
Journal of Chromatography B, 773(1), 35-46 (2002) (https://www.rhodium.ws/pdf/bzp.metabolism-detection.pdf)

Abstract
Studies are described on the metabolism and on the toxicological analysis of the piperazine-like designer drug N-benzylpiperazine (BZP, scene name "A2") in rat and human urine using gas chromatography–mass spectrometry (GC–MS). The identified metabolites indicated that BZP was hydroxylated at the aromatic ring and that the piperazine moiety is metabolically degraded. Our systematic toxicological analysis (STA) procedure using full-scan GC–MS after acid hydrolysis, liquid–liquid extraction and microwave-assisted acetylation allowed the detection of the parent compound as well as of the above mentioned metabolites in rat urine after single administration of a dose calculated from the doses commonly taken by drug users. It has also proved to be applicable in authentic clinical or forensic cases. However, it should be considered that BZP is also a metabolite of the medicament piberaline.

The Hive - Clandestine Chemists Without Borders
 
 
 
 
    Rhodium
(Chief Bee)
10-01-04 23:43
No 534081
User Picture 
      1-(3,4-methylenedioxybenzyl)-piperazine (MDBP)
(Rated as: good read)
    

Pharmacology & Bioassays:
Post 338275 (Rhodium: "Shulgin on Methylenedioxy-Piperazines", General Discourse)
Post 291455 (Nemo_Tenetur: "No effects!", Novel Discourse)
Post 301368 (toad: "MD-phenylpiperazine", Novel Discourse)
Chemistry & Synthesis:
Post 398438 (pHarmacist: "Piperonyl-piperazine synth. (french)", Novel Discourse)
Post 299533 (foxy2: "Reference", Novel Discourse)
Post 291374 (foxy2: "1-(3,4-Methylenedioxyphenyl)piperazine synthesis", Novel Discourse)


New designer drug 1-(3,4-methylenedioxybenzyl) piperazine (MDBP):
Studies on its metabolism and toxicological detection in rat urine using GC/MS

Staack RF, Maurer HH, J. Mass Spect. 39(3), 255-261 (2004)
   
34-md-bzp.gif

Abstract
Studies are described on the metabolism and toxicological analysis of the piperazine-derived designer drug 1-(3,4-methylenedioxybenzyl)piperazine (MDBP) in rat urine using gas chromatography/mass spectrometry (GC/MS). The identified metabolites indicated that MDBP was metabolized by demethylenation and subsequent methylation to N-(4-hydroxy-3-methoxybenzyl)piperazine followed by partial glucuronidation or sulfation. Additionally, degradation of the piperazine moiety to N(3,4-methylenedioxybenzyl)ethylenediamine and 3,4-methylenedioxybenzylamine and N-dealkylation to piperazine were observed. The authors' systematic toxicological analysis (STA) procedure using full-scan GC/MS after acid hydrolysis, liquid/liquid extraction and microwave-assisted acetylation allowed the detection of MDBP and its above-mentioned metabolites in rat urine after single administration of a dose calculated from the doses commonly taken by drug users. Assuming similar metabolism, the described STA procedure should be suitable for proof of an intake of MDBP by analysis of human urine.

The Hive - Clandestine Chemists Without Borders
 
 
 
 
    er0x
(Stranger)
10-06-04 04:07
No 534633
      I too am fascinated with the seemingly endless     

I too am fascinated with the seemingly endless possibilities for very interesting psychoactive piperazines.
3,4methylendioxy methyl benzylpiperazine
2,5dimethoxy 4bromo benzylpiperazine
phenylcyclohexyl methylpiperazine
anda huge list of potential unknowns, Shulgin may have to live another lifetime so he can wright Pihkal2 the piperazine story.
 
 

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