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
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.
ID Source | ID |
---|---|
PubMed CID | 75994 |
CHEMBL ID | 113600 |
CHEBI ID | 83537 |
SCHEMBL ID | 83548 |
MeSH ID | M0049461 |
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 |
Excerpt | Reference | Relevance |
---|---|---|
" 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 |
Excerpt | Reference | Relevance |
---|---|---|
"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 |
Excerpt | Relevance | Reference |
---|---|---|
" 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 |
Role | Description |
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xenobiotic | A 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 contaminant | Any minor or unwanted substance introduced into the environment that can have undesired effects. |
psychotropic drug | A loosely defined grouping of drugs that have effects on psychological function. |
serotonergic agonist | An 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] |
Class | Description |
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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 | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
5-hydroxytryptamine receptor 2C | Rattus norvegicus (Norway rat) | Ki | 10.0000 | 0.0002 | 0.6677 | 10.0000 | AID4755; AID5225 |
5-hydroxytryptamine receptor 2A | Rattus norvegicus (Norway rat) | Ki | 10.0000 | 0.0001 | 0.6017 | 10.0000 | AID5225 |
5-hydroxytryptamine receptor 2B | Rattus norvegicus (Norway rat) | Ki | 10.0000 | 0.0002 | 0.5909 | 10.0000 | AID5225 |
Caspase-3 | Homo sapiens (human) | IC50 (µMol) | 100.0000 | 0.0002 | 1.1979 | 8.8000 | AID503719 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Caspase-3 | Homo sapiens (human) | EC50 (µMol) | 50.0000 | 0.2200 | 1.8225 | 4.0800 | AID1799387; AID503695 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Process | via Protein(s) | Taxonomy |
---|---|---|
nucleus | Caspase-3 | Homo sapiens (human) |
cytoplasm | Caspase-3 | Homo sapiens (human) |
nucleus | Caspase-3 | Homo sapiens (human) |
nucleoplasm | Caspase-3 | Homo sapiens (human) |
cytosol | Caspase-3 | Homo sapiens (human) |
neuronal cell body | Caspase-3 | Homo sapiens (human) |
death-inducing signaling complex | Caspase-3 | Homo sapiens (human) |
[Information is prepared from geneontology information from the June-17-2024 release] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID5225 | Binding affinity against 5-hydroxytryptamine 2 receptor in rat using [3H]ketanserin as radioligand | 1992 | Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26 | Ketanserin analogues: structure-affinity relationships for 5-HT2 and 5-HT1C serotonin receptor binding. |
AID204444 | Binding affinity towards sigma receptor in guinea pig brain membranes using [3H]DTG as radioligand | 1991 | Journal of medicinal chemistry, Dec, Volume: 34, Issue:12 | Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high-affinity sigma ligands. |
AID503695 | Activation 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-PAGE | 2006 | Nature chemical biology, Oct, Volume: 2, Issue:10 | Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy. |
AID4755 | Binding affinity against 5-hydroxytryptamine 1C receptor in rat using [3H]mesulergine as radioligand | 1992 | Journal of medicinal chemistry, Dec-25, Volume: 35, Issue:26 | Ketanserin analogues: structure-affinity relationships for 5-HT2 and 5-HT1C serotonin receptor binding. |
AID503719 | Activation of procaspase-3-mediated human HL60 cell death after 72 hrs by MTS/PMS assay | 2006 | Nature chemical biology, Oct, Volume: 2, Issue:10 | Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy. |
AID1799387 | Procaspase-3 Activation Assay from Article 10.1038/nchembio814: \\Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy.\\ | 2006 | Nature chemical biology, Oct, Volume: 2, Issue:10 | Small-molecule activation of procaspase-3 to caspase-3 as a personalized anticancer strategy. |
AID493017 | Wombat Data for BeliefDocking | 1991 | Journal 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 3 (3.66) | 18.7374 |
1990's | 3 (3.66) | 18.2507 |
2000's | 29 (35.37) | 29.6817 |
2010's | 44 (53.66) | 24.3611 |
2020's | 3 (3.66) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (43.89) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 7 (7.61%) | 5.53% |
Reviews | 13 (14.13%) | 6.00% |
Case Studies | 7 (7.61%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 65 (70.65%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |