DIMETHYLPHENYLPIPERAZINIUM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C12H19N2
Molecular Weight	191.2927
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	1

SHOW SMILES / InChI

Structure Search

SMILES

C[N+]1(C)CCN(CC1)C2=CC=CC=C2

InChI

InChIKey=MKGIQRNAGSSHRV-UHFFFAOYSA-N

InChI=1S/C12H19N2/c1-14(2)10-8-13(9-11-14)12-6-4-3-5-7-12/h3-7H,8-11H2,1-2H3/q+1

HIDE SMILES / InChI

Molecular Formula	C12H19N2
Molecular Weight	191.2927
Charge	1
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11689081 | https://www.ncbi.nlm.nih.gov/pubmed/14417244 | https://www.ncbi.nlm.nih.gov/pubmed/15994385

Dimethylphenylpiperazinium (DMPP) is an agonist of nicotinic acetylcholine receptor. DMPP regulates smooth muscle contractility. In addition, it exerts anti-inflammatory properties.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscle-type nicotinic acetylcholine receptor 65 Target ID: CHEMBL2362997 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9118208 \| https://www.ncbi.nlm.nih.gov/pubmed/11689081	Agonist 2678
Neuronal acetylcholine receptor 13 Target ID: CHEMBL2094110 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11689081 \| https://www.ncbi.nlm.nih.gov/pubmed/9614223	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Relationship between the increased cell surface alpha7 nicotinic receptor expression and neuroprotection induced by several nicotinic receptor agonists.	2001 Nov 15	11746376
Agonist regulation of rat alpha 3 beta 4 nicotinic acetylcholine receptors stably expressed in human embryonic kidney 293 cells.	2001 Sep	11502889
Nicotinic excitation of rat hypoglossal motoneurons.	2002	12435424
Pharmacological properties of nicotinic acetylcholine receptors expressed by guinea pig small intestinal myenteric neurons.	2002 Sep	12183644
Distinct protein kinases regulate SNAP-25 expression in chromaffin cells.	2003 Feb 1	12526024
SSR591813, a novel selective and partial alpha4beta2 nicotinic receptor agonist with potential as an aid to smoking cessation.	2003 Jul	12682217
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.	2003 Jun 12	12770692
Characterization of neuronal nicotinic acetylcholine receptors in the membrane of unmyelinated human C-fiber axons by in vitro studies.	2003 Nov	12878715
Regulation of epileptiform activity in hippocampus by nicotinic acetylcholine receptor activation.	2003 Sep	14529953
Phytoestrogen cimicifugoside-mediated inhibition of catecholamine secretion by blocking nicotinic acetylcholine receptor in bovine adrenal chromaffin cells.	2004 May	14757852
Adenosine activating A(2A)-receptors coupled to adenylate cyclase/cyclic AMP pathway downregulates nicotinic autoreceptor function at the rat myenteric nerve terminals.	2004 Oct	15234106
Activation of nicotinic acetylcholine receptors increases the frequency of spontaneous GABAergic IPSCs in rat basolateral amygdala neurons.	2005 Nov	16033935
Blockade of nicotinic receptors of bovine adrenal chromaffin cells by nanomolar concentrations of atropine.	2006 Mar 27	16530180
Airway irritation and cough evoked by inhaled cigarette smoke: role of neuronal nicotinic acetylcholine receptors.	2007	17137814
Specific subtypes of nicotinic cholinergic receptors involved in sympathetic and parasympathetic cardiovascular responses.	2009 Oct 2	19573576

Patents

Sample Use Guides

In Vivo Use Guide

guinea pig model of ovalbumin induced asthma: 0.4 and 0.8 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Incubation of cultured gastric myenteric ganglia with the nicotinic receptor agonist, 1,1-dimethyl-4-phenylpiperizinium (DMPP, 0.1 nM - 0.1 uM), for 24 h significantly increased the number of nNOS-immunoreactive cells and the density of immunoreactive nNOS bands and nNOS mRNA bands. nNOS mRNA expression stimulated by DMPP was antagonized by a protein kinase C antagonist, a phospholipase C inhibitor, and an intracellular Ca2+ chelator.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:54:53 UTC 2023` Edited by `admin` on `Fri Dec 15 18:54:53 UTC 2023`
Record UNII	2FLS86GK2A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIMETHYLPHENYLPIPERAZINIUM

Systematic Name

English

1,1-DIMETHYL-4-PHENYLPIPERAZINIUM ION

Common Name

English

N,N-DIMETHYL-N'-PHENYLPIPERAZINIUM

Systematic Name

English

1,1-DIMETHYL-4-PHENYLPIPERAZINIUM

Systematic Name

English

PIPERAZINIUM, 1,1-DIMETHYL-4-PHENYL

Common Name

English

DMPP

Common Name

English

Code System Code Type Description

CAS

114-28-3