N-(2-METHOXYPHENYL)PIPERAZINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16N2O
Molecular Weight	192.2575
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of N-(2-METHOXYPHENYL)PIPERAZINE

Structure Search

SMILES

COC1=C(C=CC=C1)N2CCNCC2

InChI

InChIKey=VNZLQLYBRIOLFZ-UHFFFAOYSA-N

InChI=1S/C11H16N2O/c1-14-11-5-3-2-4-10(11)13-8-6-12-7-9-13/h2-5,12H,6-9H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/33259 | https://www.ncbi.nlm.nih.gov/pubmed/13628280 | https://www.ncbi.nlm.nih.gov/pubmed/19253419 | https://www.ncbi.nlm.nih.gov/pubmed/25048712 | https://www.ncbi.nlm.nih.gov/pubmed/24156012

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	Potency
Dopamine receptor 60 Target ID: CHEMBL2093868 Sources: https://www.ncbi.nlm.nih.gov/pubmed/33259	Blocker 537
Serotonin 1 (5-HT1) receptor 9 Target ID: CHEMBL2095159 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3701781 \| Jucker, E.H. (2013) Progress in Drug Research / Fortschritte der Arzneimittelforschung / Progrès des recherches pharmaceutiques, page 91, retrieved from: https://books.google.ru/books?id=mU8OBwAAQBAJ	Agonist 2678	35.0 nM [Ki]
5-hydroxytryptamine receptor 1A 54 Target ID: P19327 Gene ID: 24473.0 Gene Symbol: Htr1a Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8893838	Binding Agent 1064	68.0 nM [Ki]
5-hydroxytryptamine receptor 6 10 Target ID: P50406 Gene ID: 3362.0 Gene Symbol: HTR6 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15745826	Binding Agent 1064	1200.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13658231 https://www.ncbi.nlm.nih.gov/pubmed/13628280	Primary		Not Provided 504	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.	1993 Aug 25	8394362
Comparison of sampling methods for 1,6-hexamethylene diisocyanate, (HDI) in a commercial spray box.	2002 Jan	11827386
Development of a diffusive sampling method for determination of methyl isocyanate in air.	2002 Oct	12400911
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 Feb	12625554
Synthesis and evaluation of in vivo activity of diphenylhydantoin basic derivatives.	2004 Dec	15571863
Biological monitoring of exposure to toluene diisocyanate.	2004 Oct	15534959
Synthesis and in vitro binding of N-phenyl piperazine analogs as potential dopamine D3 receptor ligands.	2005 Jan 3	15582454
Synthesis and characterization of novel "3 + 2" oxorhenium complexes, ReO[SNO][NN].	2006 Jul 10	16813429
Tape-strip sampling for measuring dermal exposure to 1,6-hexamethylene diisocyanate.	2006 Jun	16804626
Determination of airborne isocyanates generated during the thermal degradation of car paint in body repair shops.	2006 Jun	16434466
The synthesis of L-carvone and limonene derivatives with increased antiproliferative effect and activation of ERK pathway in prostate cancer cells.	2006 Oct 1	16806947
Underestimation of toluene diisocyanate concentration using long-term sampling with 1-(2-methoxyphenyl) piperazine impregnated filters.	2008 Jul	17869179
Aniline in hydrolyzed urine and plasma--possible biomarkers for phenylisocyanate exposure.	2008 Oct	18666023
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	18800769
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	21587972
Structure-dependent inhibition of the human α1β2γ2 GABAA receptor by piperazine derivatives: A novel mode of action.	2015 Dec	26344803

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 150 uM/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Name

Type

Language

N-(2-METHOXYPHENYL)PIPERAZINE

Systematic Name

English

D-15157

Code

English

1-(2-METHOXYPHENYL)PIPERAZINE

Systematic Name

English

PIPERAZINE, 1-(2-METHOXYPHENYL)-

Systematic Name

English

2-MEOPP

Common Name

English

PIPERAZINE, 1-(O-METHOXYPHENYL)-

Systematic Name

English

Code System Code Type Description

PUBCHEM

1346