Benzylpiperazine

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16N2
Molecular Weight	176.2581
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(N1CCNCC1)C2=CC=CC=C2

InChI

InChIKey=IQXXEPZFOOTTBA-UHFFFAOYSA-N

InChI=1S/C11H16N2/c1-2-4-11(5-3-1)10-13-8-6-12-7-9-13/h1-5,12H,6-10H2

HIDE SMILES / InChI

Molecular Formula	C11H16N2
Molecular Weight	176.2581
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine transporter 183 Target ID: CHEMBL238 Sources: https://doi.org/10.1080/03036758.2011.557036	Blocker 555
Serotonin 1 (5-HT1) receptor 9 Target ID: CHEMBL2095159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2448760	Agonist 2752
Adrenergic receptor alpha-2 114 Target ID: CHEMBL2095158 Sources: Chan Wai Yeap, Chan Kee Bian, Ahmad Fahmi, Ahmad Fahmi Lim Abdullah, A Review on Benzylpiperazine and Trifluoromethylphenypiperazine: Origins, Effects, Prevalence and Legal Status. retrieved from: https://www.researchgate.net/publication/266484660_A_Review_on_Benzylpiperazine_and_Trifluoromethylphenypiperazine_Origins_Effects_Prevalence_and_Legal_Status	Antagonist 2849

PubMed

Title	Date	PubMed
Structure-dependent inhibition of the human α1β2γ2 GABAA receptor by piperazine derivatives: A novel mode of action.	2015-12	26344803
Estrogenic effects and their action mechanism of the major active components of party pill drugs.	2012-11-15	23026265
Another bitter pill: a case of toxicity from DMAA party pills.	2010-12-17	21358791
Novel alkyl- and arylcarbamate derivatives with N-benzylpiperidine and N-benzylpiperazine moieties as cholinesterases inhibitors.	2010-12	20926161
Trazodone, meta-chlorophenylpiperazine (an hallucinogenic drug and trazodone metabolite), and the hallucinogen trifluoromethylphenylpiperazine cross-react with the EMIT®II ecstasy immunoassay in urine.	2010-11	21073812
A hybrid liquid chromatography-mass spectrometry strategy in a forensic laboratory for opioid, cocaine and amphetamine classes in human urine using a hybrid linear ion trap-triple quadrupole mass spectrometer.	2010-10-29	20855077
Detection of 1-benzylpiperazine, 1-(3-trifluoromethylphenyl)-piperazine, and 1-(3-chlorophenyl)-piperazine in 3,4-methylenedioxymethamphetamine-positive urine samples.	2010-10	21819791
Validation of an LC-MS method for the detection and quantification of BZP and TFMPP and their hydroxylated metabolites in human plasma and its application to the pharmacokinetic study of TFMPP in humans.	2010-09	20533987
Randomised double-blind, placebo-controlled trial of the effects of the 'party pills' BZP/TFMPP alone and in combination with alcohol.	2010-09	19329546
Imidazo[4,5-b]pyridine derivatives as inhibitors of Aurora kinases: lead optimization studies toward the identification of an orally bioavailable preclinical development candidate.	2010-07-22	20565112
Purchasing 'legal highs' on the Internet--is there consistency in what you get?	2010-07	20413562
Qualitative drug analysis of hair extracts by comprehensive two-dimensional gas chromatography/time-of-flight mass spectrometry.	2010-06-25	20471020
Head shop compound abuse amongst attendees of the Drug Treatment Centre Board.	2010-05	20666082
Hydride transfer reactions via ion-neutral complex: fragmentation of protonated N-benzylpiperidines and protonated N-benzylpiperazines in mass spectrometry.	2010-05	20301171
New benzofuran derivatives as an antioxidant agent.	2010-03	20838529
Multiorgan failure from 1-benzylpiperazine ingestion--legal high or lethal high?	2010-03	20184432
Differences in harm from legal BZP/TFMPP party pills between North Island and South Island users in New Zealand: a case of effective industry self-regulation?	2010-01	19359158
"They're legal so they're safe, right?" What did the legal status of BZP-party pills mean to young people in New Zealand?	2010-01	19321329
Legal highs toxicity--symptomatology and clinical diagnosis in case series.	2010	21384787
Determining the subjective and physiological effects of BZP on human females.	2009-12	19777213
In vivo interactions between BZP and TFMPP (party pill drugs).	2009-09-25	19851418
Metabolic interactions with piperazine-based 'party pill' drugs.	2009-07	19589229
1-benzylpiperazine (BZP) abuse amongst attendees of the Drug Treatment Centre Board.	2009-06	19722361
Structure elucidation of a new designer benzylpiperazine: 4-bromo-2,5-dimethoxybenzylpiperazine.	2009-05-30	19345524
Party pills and drug-drug interactions.	2009-04-24	19448787
Pharmacokinetics of 'party pill' drug N-benzylpiperazine (BZP) in healthy human participants.	2009-04-15	19261399
Selective suppression of cocaine- versus food-maintained responding by monoamine releasers in rhesus monkeys: benzylpiperazine, (+)phenmetrazine, and 4-benzylpiperidine.	2009-04	19151247
A comparison of 1-benzylpiperazine and methamphetamine in their acute effects on anxiety-related behavior of hooded rats.	2009-04	19111568
Synthesis, optimization and structure-activity relationships of 3,5-disubstituted isoxazolines as new anti-tuberculosis agents.	2009-02	18524421
[Speed drugs].	2009	20301955
Dissociative and sympathomimetic toxicity associated with recreational use of 1-(3-trifluoromethylphenyl) piperazine (TFMPP) and 1-benzylpiperzine (BZP).	2008-12	19031377
Patterns of benzylpiperazine/trifluoromethylphenylpiperazine party pill use and adverse effects in a population sample in New Zealand.	2008-11	19378447
Toxicity from the recreational use of 1-benzylpiperazine.	2008-11	18821145
Partying on? Life after BZP-based party pills.	2008-10-03	18841183
Copper(I) cyanide networks: synthesis, structure, and luminescence behavior. Part 2. Piperazine ligands and hexamethylenetetramine.	2008-08-04	18597424
Detection of 1-benzylpiperazine and 1-(3-trifluoromethylphenyl)-piperazine in urine analysis specimens using GC-MS and LC-ESI-MS.	2008-07-26	18652752
2-[2-(4-Benzyl-piperazin-1-ylcarbon-yl)eth-yl]-5,6-diphenyl-pyridazin-3(2H)-one.	2008-05-10	21202554
[1-benzylpiperazine (BZP) and 1-(3-trifluorométhylphényl)pipérazine (TFMPP): emergence of two agents which lead to misuse].	2008-03	18570904
Investigation of the first deaths in the United Kingdom involving the detection and quantitation of the piperazines BZP and 3-TFMPP.	2008-03	18334102
1-Benzhydryl-4-(4-chloro-phenyl-sulfonyl)piperazine.	2008-01-04	21201390
N-benzylpiperazine has characteristics of a drug of abuse.	2007-12	17989516
Highs and lows: patterns of use, positive and negative effects of benzylpiperazine-containing party pills (BZP-party pills) amongst young people in New Zealand.	2007-11-19	18021425
MDMA-like behavioral effects of N-substituted piperazines in the mouse.	2007-11	17651790
Benzylpiperazine: a drug of abuse?	2007-11	17606471
Seizures in a night club.	2007-07-21	17658391
Chronic benzylpiperazine (BZP) exposure produces behavioral sensitization and cross-sensitization to methamphetamine (MA).	2007-05-11	17125936
Collapse, reported seizure--and an unexpected pill.	2007-04-28	17467520
Piperazine designer drugs of abuse.	2007-04-28	17467496
Party on? BZP party pills in New Zealand.	2007-02-16	17308559
Nitrofurans as novel anti-tuberculosis agents: identification, development and evaluation.	2007	17346196

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:10:57 GMT 2025` Edited by `admin` on `Mon Mar 31 19:10:57 GMT 2025`
Record UNII	3UG152ZU0E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Benzylpiperazine

Systematic Name

English

J149.807J

Preferred Name

English

4-BENZYLPIPERAZINE

Systematic Name

English

N-BENZYLPIPERAZINE

Common Name

English

BZP

Common Name

English

NSC-40889

Code

English

1-BENZYLPIPERAZINE

Systematic Name

English

Classification Tree Code System Code

WIKIPEDIA

Designer-drugs-Benzylpiperazine