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

Molecular Formula	C11H16N2O
Molecular Weight	192.2575
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Substituted phenoxyalkylpiperazines as dopamine D3 receptor ligands.	2001 Apr	11338664
Two routes to [11C-carbonyl]organo-isocyanates utilizing [11C]phosgene ([11C]organo-isocyanates from [11C]phosgene).	2001 Nov	11711319
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	11990069
Comparison of sampling methods for 1,6-hexamethylene diisocyanate, (HDI) in a commercial spray box.	2002 Jan	11827386
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 Nov-Dec	14730096
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.	2004	15270248
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	16405981
Tape-strip sampling for measuring dermal exposure to 1,6-hexamethylene diisocyanate.	2006 Jun	16804626
Sampling and analytical methodology development for the determination of primary and secondary low molecular weight amines in ambient air.	2008 Mar	18392281
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
Synthesis and characterization of environment-sensitive fluorescent ligands for human 5-HT1A receptors with 1-arylpiperazine structure.	2009 Dec 10	19705871
'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

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 150 uM/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:07:23 GMT 2023` Edited by `admin` on `Sat Dec 16 11:07:23 GMT 2023`
Record UNII	81NJO1330A
Record Status	`Validated (UNII)`
Record Version

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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