Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H16N2O.BrH |
| Molecular Weight | 273.169 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Br.COC1=C(C=CC=C1)N2CCNCC2
InChI
InChIKey=QPAHBXFXDDEKNB-UHFFFAOYSA-N
InChI=1S/C11H16N2O.BrH/c1-14-11-5-3-2-4-10(11)13-8-6-12-7-9-13;/h2-5,12H,6-9H2,1H3;1H
1-(2-methoxyphenyl)piperazine is an effective blocker of striatal dopaminergic receptors in rat brain and is apparently the simplest chemical structure known to exert dopaminergic blocking activity. It is exhibited pronounced antihypertensive and weak sympatholytic activities in experimental animals. Blood pressure was also lowered in hypertensive patients and this effect was sometimes accompanied by a strong sedation, and after large repeated doses, by disorientation and stupor. In a filter paper bioassay 1-(2-methoxyphenyl)piperazine demonstrated acaricidal activity. 1-(2-methoxyphenyl)piperazine is a building block of many serotonergic and dopaminergic agents. Some of them have antidepressant activity.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2093868 |
|||
| 35.0 nM [Ki] | |||
Target ID: P19327 Gene ID: 24473.0 Gene Symbol: Htr1a Target Organism: Rattus norvegicus (Rat) |
68.0 nM [Ki] | ||
Target ID: P50406 Gene ID: 3362.0 Gene Symbol: HTR6 Target Organism: Homo sapiens (Human) |
1200.0 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype. | 1993 Aug 25 |
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| Substituted phenoxyalkylpiperazines as dopamine D3 receptor ligands. | 2001 Apr |
|
| Development of novel mixed-ligand oxotechnetium [SNS/S] complexes as potential 5-HT1A receptor imaging agents. | 2001 Mar |
|
| A comparison of solid sampler methods for the determination of hexamethylene-based isocyanates in spray-painting operations. | 2001 Mar-Apr |
|
| Two routes to [11C-carbonyl]organo-isocyanates utilizing [11C]phosgene ([11C]organo-isocyanates from [11C]phosgene). | 2001 Nov |
|
| 2-H- and 2-acyl-9- [omega-[4-(2-methoxyphenyl)piperazinyl]-alkyl]-1,2,3,4-tetrahydro-beta-carbolines as ligands of 5-HT1A and 5-HT2A receptors. | 2001 Sep-Oct |
|
| Comparison of sampling methods for 1,6-hexamethylene diisocyanate, (HDI) in a commercial spray box. | 2002 Jan |
|
| Exposure to airborne isocyanates and other thermal degradation products at polyurethane-processing workplaces. | 2002 Oct |
|
| Development of a diffusive sampling method for determination of methyl isocyanate in air. | 2002 Oct |
|
| Novel oxorhenium and oxotechnetium MO(NS)(S)2 complexes in the development of 5-HT1A receptor imaging agents. | 2003 Jan 15 |
|
| Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L. | 2004 |
|
| Synthesis and evaluation of in vivo activity of diphenylhydantoin basic derivatives. | 2004 Dec |
|
| New imide 5-HT1A receptor ligands - modification of terminal fragment geometry. | 2004 Feb 28 |
|
| A survey of airborne isocyanate exposure in 13 Swedish polyurethane industries. | 2004 Jul |
|
| Biological monitoring of exposure to toluene diisocyanate. | 2004 Oct |
|
| Selective antagonist at D3 receptors, but not non-selective partial agonists, influences the expression of cocaine-induced conditioned place preference in free-feeding rats. | 2005 Dec |
|
| Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. | 2005 Jan 3 |
|
| Tape-strip sampling for measuring dermal exposure to 1,6-hexamethylene diisocyanate. | 2006 Jun |
|
| Determination of airborne isocyanates generated during the thermal degradation of car paint in body repair shops. | 2006 Jun |
|
| Validation of a diffusive sampling method for airborne low-molecular isocyanates using 4-nitro-7-piperazinobenzo-2-oxa-1,3-diazole-impregnated filters and liquid chromatography-tandem mass spectrometry. | 2006 Nov 17 |
|
| The synthesis of L-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells. | 2006 Oct 1 |
|
| Abstracts of papers presented at the 2007 pittsburgh conference. | 2007 |
|
| Quantitative monitoring of dermal and inhalation exposure to 1,6-hexamethylene diisocyanate monomer and oligomers. | 2008 Apr |
|
| Synthesis, alpha 1-adrenoceptor antagonist activity, and SAR study of novel arylpiperazine derivatives of phenytoin. | 2008 Jun 1 |
|
| Sampling and analytical methodology development for the determination of primary and secondary low molecular weight amines in ambient air. | 2008 Mar |
|
| Aniline in hydrolyzed urine and plasma--possible biomarkers for phenylisocyanate exposure. | 2008 Oct |
|
| Structural modifications of N-(1,2,3,4-tetrahydronaphthalen-1-yl)-4-aryl-1-piperazinehexanamides: influence on lipophilicity and 5-HT7 receptor activity. Part III. | 2008 Sep 25 |
|
| Synthesis and characterization of environment-sensitive fluorescent ligands for human 5-HT1A receptors with 1-arylpiperazine structure. | 2009 Dec 10 |
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| 'Click' D(1) receptor agonists with a 5-HT(1A) receptor pharmacophore producing D(2) receptor activity. | 2009 Jul 15 |
|
| [(18)F]-labeled 2-methoxyphenylpiperazine derivative as a potential brain positron emission tomography imaging agent. | 2009 Nov |
|
| 3-(1-Adamant-yl)-1-{[4-(2-meth-oxy-phen-yl)piperazin-1-yl]meth-yl}-4-methyl-1H-1,2,4-triazole-5(4H)-thione. | 2010 Jun 23 |
|
| Structure-dependent inhibition of the human α1β2γ2 GABAA receptor by piperazine derivatives: A novel mode of action. | 2015 Dec |
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DTXSID40641012
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100939-96-6
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24720997
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2N1ZY78316
Created by
admin on Sat Dec 16 11:18:12 GMT 2023 , Edited by admin on Sat Dec 16 11:18:12 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD
