Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H16N2O.ClH |
| Molecular Weight | 228.718 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=C(C=CC=C1)N2CCNCC2
InChI
InChIKey=DDMVHGULHRJOEC-UHFFFAOYSA-N
InChI=1S/C11H16N2O.ClH/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 |
|---|---|---|
| Structure-dependent inhibition of the human α1β2γ2 GABAA receptor by piperazine derivatives: A novel mode of action. | 2015-12 |
|
| 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. | 2010-06-23 |
|
| Synthesis and characterization of environment-sensitive fluorescent ligands for human 5-HT1A receptors with 1-arylpiperazine structure. | 2009-12-10 |
|
| [(18)F]-labeled 2-methoxyphenylpiperazine derivative as a potential brain positron emission tomography imaging agent. | 2009-11 |
|
| 'Click' D(1) receptor agonists with a 5-HT(1A) receptor pharmacophore producing D(2) receptor activity. | 2009-07-15 |
|
| Aniline in hydrolyzed urine and plasma--possible biomarkers for phenylisocyanate exposure. | 2008-10 |
|
| 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. | 2008-09-25 |
|
| Underestimation of toluene diisocyanate concentration using long-term sampling with 1-(2-methoxyphenyl) piperazine impregnated filters. | 2008-07 |
|
| Synthesis, alpha 1-adrenoceptor antagonist activity, and SAR study of novel arylpiperazine derivatives of phenytoin. | 2008-06-01 |
|
| Quantitative monitoring of dermal and inhalation exposure to 1,6-hexamethylene diisocyanate monomer and oligomers. | 2008-04 |
|
| Sampling and analytical methodology development for the determination of primary and secondary low molecular weight amines in ambient air. | 2008-03 |
|
| Abstracts of papers presented at the 2007 pittsburgh conference. | 2007 |
|
| 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. | 2006-11-17 |
|
| The synthesis of L-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells. | 2006-10-01 |
|
| Effects of humidity and filter material on diffusive sampling of isocyanates using reagent-coated filters. | 2006-10 |
|
| Synthesis and characterization of novel "3 + 2" oxorhenium complexes, ReO[SNO][NN]. | 2006-07-10 |
|
| Tape-strip sampling for measuring dermal exposure to 1,6-hexamethylene diisocyanate. | 2006-06 |
|
| Determination of airborne isocyanates generated during the thermal degradation of car paint in body repair shops. | 2006-06 |
|
| Selective antagonist at D3 receptors, but not non-selective partial agonists, influences the expression of cocaine-induced conditioned place preference in free-feeding rats. | 2005-12 |
|
| Validation of a solvent-free sampler for the determination of low molecular weight aliphatic isocyanates under thermal degradation conditions. | 2005-09 |
|
| Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands. | 2005-01-03 |
|
| Characterisation of derivatised monomeric and prepolymeric isocyanates by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry and structural elucidation by tandem mass spectrometry. | 2005 |
|
| Synthesis and evaluation of in vivo activity of diphenylhydantoin basic derivatives. | 2004-12 |
|
| Biological monitoring of exposure to toluene diisocyanate. | 2004-10 |
|
| A study on application of impregnated synthetic peptide TLC stationary phases for the screening of 5-HT1A ligands. Part 2. | 2004-10 |
|
| A survey of airborne isocyanate exposure in 13 Swedish polyurethane industries. | 2004-07 |
|
| New imide 5-HT1A receptor ligands - modification of terminal fragment geometry. | 2004-02-28 |
|
| Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L. | 2004 |
|
| Toxicological detection of the new designer drug 1-(4-methoxyphenyl)piperazine and its metabolites in urine and differentiation from an intake of structurally related medicaments using gas chromatography-mass spectrometry. | 2003-12-25 |
|
| Evaluation of some aroxyethylamine derivatives for hypotensive properties and their affinities for adrenergic receptors. | 2003-12 |
|
| Synthesis, in vitro and in vivo 5-HT1A/5-HT2A serotonin receptor activity of new hybrid 1,2,3,4-tetrahydro-gamma-carbolines with 1-(2-methoxyphenyl)piperazine moiety. | 2003-11-05 |
|
| Investigation of the competitive rate of derivatization of several secondary amines with phenylisocyanate (PHI), hexamethylene-1,6-diisocyanate (HDI), 4,4'-methylenebis(phenyl isocyanate) (MDI) and toluene diisocyanate (TDI) in liquid medium. | 2003-02 |
|
| Novel oxorhenium and oxotechnetium MO(NS)(S)2 complexes in the development of 5-HT1A receptor imaging agents. | 2003-01-15 |
|
| Workplace monitoring of isocyanates using ion trap liquid chromatography/tandem mass spectrometry. | 2003 |
|
| Oxotechnetium 99mTcO[SN(R)S][S] complexes as potential 5-HT1A receptor imaging agents. | 2002-11 |
|
| Exposure to airborne isocyanates and other thermal degradation products at polyurethane-processing workplaces. | 2002-10 |
|
| Development of a diffusive sampling method for determination of methyl isocyanate in air. | 2002-10 |
|
| 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. | 2002-05-07 |
|
| Comparison of sampling methods for 1,6-hexamethylene diisocyanate, (HDI) in a commercial spray box. | 2002-01 |
|
| Two routes to [11C-carbonyl]organo-isocyanates utilizing [11C]phosgene ([11C]organo-isocyanates from [11C]phosgene). | 2001-11 |
|
| A comparison of solid sampler methods for the determination of hexamethylene-based isocyanates in spray-painting operations. | 2001-05-03 |
|
| Substituted phenoxyalkylpiperazines as dopamine D3 receptor ligands. | 2001-04 |
|
| Development of novel mixed-ligand oxotechnetium [SNS/S] complexes as potential 5-HT1A receptor imaging agents. | 2001-03 |
|
| Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype. | 1993-08-25 |
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3XQ74IHW73
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28709
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66373-53-3
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DTXSID5051440
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5464-78-8
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226-762-6
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9899402
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ACTIVE MOIETY
SUBSTANCE RECORD
