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
Two routes to [11C-carbonyl]organo-isocyanates utilizing [11C]phosgene ([11C]organo-isocyanates from [11C]phosgene).	2001 Nov	11711319
Oxotechnetium 99mTcO[SN(R)S][S] complexes as potential 5-HT1A receptor imaging agents.	2002 Nov	12453592
Exposure to airborne isocyanates and other thermal degradation products at polyurethane-processing workplaces.	2002 Oct	12400920
Workplace monitoring of isocyanates using ion trap liquid chromatography/tandem mass spectrometry.	2003	12872271
Evaluation of some aroxyethylamine derivatives for hypotensive properties and their affinities for adrenergic receptors.	2003 Dec	14703970
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
Novel oxorhenium and oxotechnetium MO(NS)(S)2 complexes in the development of 5-HT1A receptor imaging agents.	2003 Jan 15	12576284
Biological monitoring of exposure to toluene diisocyanate.	2004 Oct	15534959
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	16322663
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
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	16996529
Effects of humidity and filter material on diffusive sampling of isocyanates using reagent-coated filters.	2006 Oct	17240907
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
Abstracts of papers presented at the 2007 pittsburgh conference.	2007	18528514
Aniline in hydrolyzed urine and plasma--possible biomarkers for phenylisocyanate exposure.	2008 Oct	18666023
'Click' D(1) receptor agonists with a 5-HT(1A) receptor pharmacophore producing D(2) receptor activity.	2009 Jul 15	19559623
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