N-(2-METHOXYPHENYL)PIPERAZINE DIHYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H16N2O.2ClH
Molecular Weight	265.179
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of N-(2-METHOXYPHENYL)PIPERAZINE DIHYDROCHLORIDE

Structure Search

SMILES

Cl.Cl.COC1=C(C=CC=C1)N2CCNCC2

InChI

InChIKey=ZGWQDMTYAQEMHA-UHFFFAOYSA-N

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

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

Molecular Formula	ClH
Molecular Weight	36.461
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
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.	1993 Aug 25	8394362
Development of novel mixed-ligand oxotechnetium [SNS/S] complexes as potential 5-HT1A receptor imaging agents.	2001 Mar	11315561
A comparison of solid sampler methods for the determination of hexamethylene-based isocyanates in spray-painting operations.	2001 Mar-Apr	11331997
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
Serotonergic and dopaminergic influence of the duration of embryogenesis and intracapsular locomotion of Lymnaea stagnalis L.	2004	15270248
Synthesis and evaluation of in vivo activity of diphenylhydantoin basic derivatives.	2004 Dec	15571863
Biological monitoring of exposure to toluene diisocyanate.	2004 Oct	15534959
A study on application of impregnated synthetic peptide TLC stationary phases for the screening of 5-HT1A ligands. Part 2.	2004 Oct	15386518
Abstracts of papers presented at the 2007 pittsburgh conference.	2007	18528514
'Click' D(1) receptor agonists with a 5-HT(1A) receptor pharmacophore producing D(2) receptor activity.	2009 Jul 15	19559623
[(18)F]-labeled 2-methoxyphenylpiperazine derivative as a potential brain positron emission tomography imaging agent.	2009 Nov	19679486

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 11:38:09 GMT 2023` Edited by `admin` on `Sat Dec 16 11:38:09 GMT 2023`
Record UNII	8ES41BS53U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

N-(2-METHOXYPHENYL)PIPERAZINE DIHYDROCHLORIDE

Systematic Name

English

2-MEOPP 2HCL

Common Name

English

PIPERAZINE, 1-(2-METHOXYPHENYL)-, HYDROCHLORIDE (1:2)

Systematic Name

English

1-(2-METHOXYPHENYL)PIPERAZINE DIHYDROCHLORIDE

Systematic Name

English

PIPERAZINE, 1-(2-METHOXYPHENYL)-, DIHYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

ECHA (EC/EINECS)

254-167-1