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
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 Dec 25	14643514
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
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
Quantitative monitoring of dermal and inhalation exposure to 1,6-hexamethylene diisocyanate monomer and oligomers.	2008 Apr	18385871
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

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

Download

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