Page last updated: 2024-11-06

1-benzylpiperazine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1-Benzylpiperazine is a heterocyclic organic compound with the formula C12H16N2. It is a colorless liquid that is soluble in organic solvents. 1-Benzylpiperazine is a precursor to several pharmaceutical drugs, including the antihistamine fexofenadine (Allegra) and the antidepressant trazodone (Desyrel). It is also used as a reagent in organic synthesis. 1-Benzylpiperazine is a potent serotonin reuptake inhibitor (SSRI) with a high affinity for the 5-HT2A receptor. It has been shown to have antidepressant, anxiolytic, and antipsychotic activity in animal studies. 1-Benzylpiperazine is also a substrate for the enzyme monoamine oxidase (MAO), which is involved in the breakdown of neurotransmitters such as serotonin and dopamine. This suggests that 1-Benzylpiperazine may have therapeutic potential for the treatment of neurological and psychiatric disorders.'

1-benzylpiperazine: possesses psychomotor stimulant activity similar to dextroamphetamine; RN given refers to parent cpd; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

1-benzylpiperazine : A tertiary amino compound that is piperazine substituted by a benzyl group at position 1. It is a serotonergic agonist used as a recreational drug. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID75994
CHEMBL ID113600
CHEBI ID83537
SCHEMBL ID83548
MeSH IDM0049461

Synonyms (72)

Synonym
dea no. 7493
3ug152zu0e ,
unii-3ug152zu0e
1-benzylpiperazine
4-benzylpiperazine
n-benzylpiperazine
nsc40889
2759-28-6
piperazine, 1-(phenylmethyl)-
nsc-40889
benzylpiperazine
piperazine, 1-benzyl-
1-(phenylmethyl)piperazine
STK298724
stratospheres(tm) pl-ppz (piperazine) resin, 50-100 mesh, extent of labeling: >5.0 mmol/g loading, 1 % cross-linked
ai3-52573
einecs 220-423-6
nsc 40889
1-benzylpiperazine, >=97.0% (gc)
AC-11628
iqxxepzfoottba-uhfffaoysa-
inchi=1/c11h16n2/c1-2-4-11(5-3-1)10-13-8-6-12-7-9-13/h1-5,12h,6-10h2
AKOS000264277
1-benzyl-piperazine
chebi:83537 ,
CHEMBL113600 ,
1-benzyl-piperazine, 10
bdbm50004308
1-(phenylmethyl)-piperazin;piperazine, 1-(phenylmethyl)-;piperazine, 1-benzyl-
A25584
860027-50-5
2759-17-3
FT-0689815
FT-0634469
LF-0548
SCHEMBL83548
j149.807j ,
1-benylpiperazine
4-benzyl-piperazine
benzyl piperazine
mono benzyl piperazine
n-benzyl-piperazine
1-benzyl piperazine
n-(phenylmethyl)piperazine
1-(benzyl)piperazine
1-(phenyl-methyl)piperazine
4-(phenylmethyl)piperazine
(phenylmethyl)piperazine
1-(phenylmethyl)-piperazine
n-phenylmethylpiperazine
1 -benzylpiperazine
4-benzylpiperzine
1-(benzyl)-piperazine
4-benzyl piperazine
n-benzyl piperazine
1-n-benzylpiperazine
1-phenylmethylpiperazine
n-benzylpiprazine
AM85333
W-107101
AC-28091
DTXSID0022197
VU0488792-1
1-benzylpiperazine dihcl
thiourea,n,n'-bis(2,3-dihydro-1h-indol-7-yl)-
BCP04193
n-benylpiperazine
piperazine,1-(phenylmethyl)-(9ci)
n-(phenylmethyl)piperaine
Q161585
SB36348
PD093542

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" This study explores the relationship between plasma BZP level and adverse effects experienced by users."( Toxicity from the recreational use of 1-benzylpiperazine.
Gee, P; Gilbert, M; Graham, P; Moore, G; Paterson, S; Richardson, S, 2008
)
0.62
" The legal status of these 'party pills' conveys mixed messages to young people and whilst being seen as potentially safe and of good quality, this often leads to higher than 'recommended' doses being used."( "They're legal so they're safe, right?" What did the legal status of BZP-party pills mean to young people in New Zealand?
Butler, R; Sheridan, J, 2010
)
0.36
" The use of these party pills has been associated with adverse health effects."( Patterns of benzylpiperazine/trifluoromethylphenylpiperazine party pill use and adverse effects in a population sample in New Zealand.
Girling, M; Sweetsur, P; Wilkins, C, 2008
)
0.35
" Multiple logistic regression analysis was used to identify independent predictors of having experienced adverse side effects from party pills."( Patterns of benzylpiperazine/trifluoromethylphenylpiperazine party pill use and adverse effects in a population sample in New Zealand.
Girling, M; Sweetsur, P; Wilkins, C, 2008
)
0.35
" Being female, using cannabis and other drugs concurrently with BZP/TFMPP party pills, taking large quantities of party pills in a single session and taking 5-hydroxytryptophan (5-HTP) recovery pills at the same time as party pills were independent predictors of having experienced an adverse problem from party pills."( Patterns of benzylpiperazine/trifluoromethylphenylpiperazine party pill use and adverse effects in a population sample in New Zealand.
Girling, M; Sweetsur, P; Wilkins, C, 2008
)
0.35
" Taking 5-HTP 'recovery' pills with party pills may increase the risk of adverse effects as both substances increase users' levels of serotonin."( Patterns of benzylpiperazine/trifluoromethylphenylpiperazine party pill use and adverse effects in a population sample in New Zealand.
Girling, M; Sweetsur, P; Wilkins, C, 2008
)
0.35
" Many people (ab)use BZP-based party pills usually without any significant toxic effects."( Nephrotoxicity of recreational party drugs.
Berney-Meyer, L; Putt, T; Schollum, J; Walker, R, 2012
)
0.38
"Lack of quality control in party pill manufacture may have led to the toxic effects reported by users unaware of the true content and release of drug from pills."( Pharmaceutical quality of "party pills" raises additional safety concerns in the use of illicit recreational drugs.
Antia, U; Fredatovich, JD; Na, Y; Neale, PT; Roberts, AF; Russell, B; Thrimawithana, TR; Young, SA; Zhou, H, 2013
)
0.39
" The aim of this work was to evaluate the toxic effects of BZP, MeOPP and MDBP using Caenorhabditis elegans as in vivo model for acute toxicity, development, reproduction and behavior testing."( Piperazine designer drugs elicit toxicity in the alternative in vivo model Caenorhabditis elegans.
Arbo, MD; Ávila, DS; Bastos, ML; Carmo, H; Cestonaro, LV; Eifler-Lima, V; Garcia, I; Garcia, SC; Göethel, G; Peruzzi, CP; Souto, C, 2020
)
0.56

Compound-Compound Interactions

ExcerptReferenceRelevance
"The objective of this study was to determine the clinical effects of party pills containing benzylpiperazine (BZP) and trifluoromethylphenylpiperazine (TFMPP) when taken alone and in combination with alcohol."( Randomised double-blind, placebo-controlled trial of the effects of the 'party pills' BZP/TFMPP alone and in combination with alcohol.
Aldington, S; Beasley, R; Caldwell, B; Dickson, S; Lucas, N; McDowall, J; Robinson, G; Thompson, I; Weatherall, M; Williams, G, 2010
)
0.36
" The purpose of this study is to further investigate the subjective and physiological responses following an oral dose of BZP combined with TFMPP in males."( Determining the subjective and physiological effects of BZP combined with TFMPP in human males.
Jan, RK; Jensen, MA; Kydd, RR; Lee, H; Lin, JC; Russell, BR, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
" The time-course excretion profiles of BZP, p-OH-BZP, and m-OH-BZP in the rats were investigated after a single intraperitoneal dosing of 5 mg/kg BZP, by using an optimized analytical procedure that combines solid-phase extraction and LC-ESI MS determination."( Metabolism and the urinary excretion profile of the recently scheduled designer drug N-Benzylpiperazine (BZP) in the rat.
Inoue, H; Kamata, T; Katagi, M; Kishi, T; Miki, A; Nakajima, K; Shima, N; Tsuchihashi, H; Tsutsumi, H,
)
0.13
" Users from both Islands commonly exceeded the dosage of BZP/TFMPP recommended by STANZ suggesting the STANZ code of conduct was largely ineffective."( 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?
Sweetsur, P; Wilkins, C, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
xenobioticA xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
environmental contaminantAny minor or unwanted substance introduced into the environment that can have undesired effects.
psychotropic drugA loosely defined grouping of drugs that have effects on psychological function.
serotonergic agonistAn agent that has an affinity for serotonin receptors and is able to mimic the effects of serotonin by stimulating the physiologic activity at the cell receptors. Serotonin agonists are used as antidepressants, anxiolytics, and in the treatment of migraine disorders.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
N-alkylpiperazine
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
5-hydroxytryptamine receptor 2CRattus norvegicus (Norway rat)Ki10.00000.00020.667710.0000AID4755; AID5225
5-hydroxytryptamine receptor 2ARattus norvegicus (Norway rat)Ki10.00000.00010.601710.0000AID5225
5-hydroxytryptamine receptor 2BRattus norvegicus (Norway rat)Ki10.00000.00020.590910.0000AID5225
Caspase-3Homo sapiens (human)IC50 (µMol)100.00000.00021.19798.8000AID503719
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Caspase-3Homo sapiens (human)EC50 (µMol)50.00000.22001.82254.0800AID1799387; AID503695
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (56)

Processvia Protein(s)Taxonomy
neurotrophin TRK receptor signaling pathwayCaspase-3Homo sapiens (human)
luteolysisCaspase-3Homo sapiens (human)
response to hypoxiaCaspase-3Homo sapiens (human)
B cell homeostasisCaspase-3Homo sapiens (human)
negative regulation of cytokine productionCaspase-3Homo sapiens (human)
proteolysisCaspase-3Homo sapiens (human)
apoptotic processCaspase-3Homo sapiens (human)
DNA damage responseCaspase-3Homo sapiens (human)
axonal fasciculationCaspase-3Homo sapiens (human)
heart developmentCaspase-3Homo sapiens (human)
sensory perception of soundCaspase-3Homo sapiens (human)
learning or memoryCaspase-3Homo sapiens (human)
intrinsic apoptotic signaling pathway in response to osmotic stressCaspase-3Homo sapiens (human)
response to xenobiotic stimulusCaspase-3Homo sapiens (human)
response to UVCaspase-3Homo sapiens (human)
response to woundingCaspase-3Homo sapiens (human)
response to glucoseCaspase-3Homo sapiens (human)
response to X-rayCaspase-3Homo sapiens (human)
regulation of macroautophagyCaspase-3Homo sapiens (human)
protein processingCaspase-3Homo sapiens (human)
hippocampus developmentCaspase-3Homo sapiens (human)
protein catabolic processCaspase-3Homo sapiens (human)
erythrocyte differentiationCaspase-3Homo sapiens (human)
platelet formationCaspase-3Homo sapiens (human)
negative regulation of B cell proliferationCaspase-3Homo sapiens (human)
regulation of protein stabilityCaspase-3Homo sapiens (human)
response to cobalt ionCaspase-3Homo sapiens (human)
response to estradiolCaspase-3Homo sapiens (human)
response to lipopolysaccharideCaspase-3Homo sapiens (human)
glial cell apoptotic processCaspase-3Homo sapiens (human)
response to tumor necrosis factorCaspase-3Homo sapiens (human)
response to nicotineCaspase-3Homo sapiens (human)
response to hydrogen peroxideCaspase-3Homo sapiens (human)
T cell homeostasisCaspase-3Homo sapiens (human)
response to amino acidCaspase-3Homo sapiens (human)
fibroblast apoptotic processCaspase-3Homo sapiens (human)
cell fate commitmentCaspase-3Homo sapiens (human)
negative regulation of cell cycleCaspase-3Homo sapiens (human)
negative regulation of activated T cell proliferationCaspase-3Homo sapiens (human)
striated muscle cell differentiationCaspase-3Homo sapiens (human)
response to glucocorticoidCaspase-3Homo sapiens (human)
neuron apoptotic processCaspase-3Homo sapiens (human)
protein maturationCaspase-3Homo sapiens (human)
anterior neural tube closureCaspase-3Homo sapiens (human)
pyroptosisCaspase-3Homo sapiens (human)
leukocyte apoptotic processCaspase-3Homo sapiens (human)
cellular response to staurosporineCaspase-3Homo sapiens (human)
apoptotic signaling pathwayCaspase-3Homo sapiens (human)
intrinsic apoptotic signaling pathwayCaspase-3Homo sapiens (human)
execution phase of apoptosisCaspase-3Homo sapiens (human)
positive regulation of pyroptosisCaspase-3Homo sapiens (human)
positive regulation of amyloid-beta formationCaspase-3Homo sapiens (human)
epithelial cell apoptotic processCaspase-3Homo sapiens (human)
keratinocyte differentiationCaspase-3Homo sapiens (human)
positive regulation of neuron apoptotic processCaspase-3Homo sapiens (human)
neuron differentiationCaspase-3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
protease bindingCaspase-3Homo sapiens (human)
aspartic-type endopeptidase activityCaspase-3Homo sapiens (human)
cysteine-type endopeptidase activityCaspase-3Homo sapiens (human)
cyclin-dependent protein serine/threonine kinase inhibitor activityCaspase-3Homo sapiens (human)
death receptor bindingCaspase-3Homo sapiens (human)
protein bindingCaspase-3Homo sapiens (human)
peptidase activityCaspase-3Homo sapiens (human)
phospholipase A2 activator activityCaspase-3Homo sapiens (human)
protein-containing complex bindingCaspase-3Homo sapiens (human)
cysteine-type endopeptidase activity involved in apoptotic processCaspase-3Homo sapiens (human)
cysteine-type endopeptidase activity involved in apoptotic signaling pathwayCaspase-3Homo sapiens (human)
cysteine-type endopeptidase activity involved in execution phase of apoptosisCaspase-3Homo sapiens (human)
enzyme activator activityCaspase-3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
nucleusCaspase-3Homo sapiens (human)
cytoplasmCaspase-3Homo sapiens (human)
nucleusCaspase-3Homo sapiens (human)
nucleoplasmCaspase-3Homo sapiens (human)
cytosolCaspase-3Homo sapiens (human)
neuronal cell bodyCaspase-3Homo sapiens (human)
death-inducing signaling complexCaspase-3Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID5225Binding affinity against 5-hydroxytryptamine 2 receptor in rat using [3H]ketanserin as radioligand1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Ketanserin analogues: structure-affinity relationships for 5-HT2 and 5-HT1C serotonin receptor binding.
AID204444Binding affinity towards sigma receptor in guinea pig brain membranes using [3H]DTG as radioligand1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
AID503695Activation of N-terminal His6-tagged recombinant procaspase-3 expressed in Escherichia coli assessed as hydrolysis of acetyl-DEVD-p-nitroanilide after 2 hrs by SDS-PAGE2006Nature chemical biology, Oct, Volume: 2, Issue:10
Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy.
AID4755Binding affinity against 5-hydroxytryptamine 1C receptor in rat using [3H]mesulergine as radioligand1992Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26
Ketanserin analogues: structure-affinity relationships for 5-HT2 and 5-HT1C serotonin receptor binding.
AID503719Activation of procaspase-3-mediated human HL60 cell death after 72 hrs by MTS/PMS assay2006Nature chemical biology, Oct, Volume: 2, Issue:10
Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy.
AID1799387Procaspase-3 Activation Assay from Article 10.1038/nchembio814: \\Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy.\\2006Nature chemical biology, Oct, Volume: 2, Issue:10
Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy.
AID493017Wombat Data for BeliefDocking1991Journal of medicinal chemistry, Dec, Volume: 34, Issue:12
Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (82)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (3.66)18.7374
1990's3 (3.66)18.2507
2000's29 (35.37)29.6817
2010's44 (53.66)24.3611
2020's3 (3.66)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 43.89

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index43.89 (24.57)
Research Supply Index4.61 (2.92)
Research Growth Index5.61 (4.65)
Search Engine Demand Index65.76 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (43.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials7 (7.61%)5.53%
Reviews13 (14.13%)6.00%
Case Studies7 (7.61%)4.05%
Observational0 (0.00%)0.25%
Other65 (70.65%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]