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Details

Stereochemistry ACHIRAL
Molecular Formula C12H19N2.I
Molecular Weight 318.1971
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMETHYLPHENYLPIPERAZINIUM IODIDE

SMILES

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

InChI

InChIKey=XFZJGFIKQCCLGK-UHFFFAOYSA-M
InChI=1S/C12H19N2.HI/c1-14(2)10-8-13(9-11-14)12-6-4-3-5-7-12;/h3-7H,8-11H2,1-2H3;1H/q+1;/p-1

HIDE SMILES / InChI
Molecular Formula HI
Molecular Weight 127.9124
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

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

CNS Activity

CNS Active
3913
Curator's Comment: Dimethylphenylpiperazinium (DMPP) is CNS active in animals. However DMPP does not easily cross the blood-brain barrier; thus, it has minimal central effects. No human data available.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Mediation of nicotine-induced convulsions by central nicotinic receptors of the 'C6' type.
1983 Mar
Characterization of human recombinant neuronal nicotinic acetylcholine receptor subunit combinations alpha2beta4, alpha3beta4 and alpha4beta4 stably expressed in HEK293 cells.
1998 Feb
Noncompetitive inhibition by camphor of nicotinic acetylcholine receptors.
2001 Apr 1
Excitatory synaptic inputs on myenteric Dogiel type II neurones of the pig ileum.
2001 Apr 2
Potentiation of motilin-induced contraction by nitric oxide synthase inhibition in the isolated chicken gastrointestinal tract.
2002 Feb
Pharmacological properties of nicotinic acetylcholine receptors expressed by guinea pig small intestinal myenteric neurons.
2002 Sep
Phthalates suppress the calcium signaling of nicotinic acetylcholine receptors in bovine adrenal chromaffin cells.
2002 Sep 1
Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.
2003 Dec
Butyl benzyl phthalate blocks Ca2+ signaling and catecholamine secretion coupled with nicotinic acetylcholine receptors in bovine adrenal chromaffin cells.
2003 Jan
Regulation of atrial natriuretic peptide secretion by cholinergic and PACAP neurons of the gastric antrum.
2003 Jan
Inhibition and facilitation by pimobendan, a calcium sensitizer, of catecholamine secretion from bovine adrenal chromaffin cells.
2003 Mar
Regulation of epileptiform activity in hippocampus by nicotinic acetylcholine receptor activation.
2003 Sep
GABAergic systems modulate nicotinic receptor-mediated seizures in mice.
2003 Sep
Mechanism of action of botulinum toxin on the internal anal sphincter.
2004 Feb
Influence of lobeline on catecholamine release from the isolated perfused rat adrenal gland.
2004 Jan 30
TNF-alpha hyperpolarizes membrane potential and potentiates the response to nicotinic receptor stimulation in cultured rat myenteric neurones.
2004 May
Phytoestrogen cimicifugoside-mediated inhibition of catecholamine secretion by blocking nicotinic acetylcholine receptor in bovine adrenal chromaffin cells.
2004 May
Prevention of diminished parasympathetic control of the heart in experimental heart failure.
2004 Oct
Impaired capsaicin and neurokinin-evoked colonic motility in inflammatory bowel disease.
2005 May
Properties of cholinergic responses in neurons in the intermediate grey layer of rat superior colliculus.
2006 Dec
Functional distribution of Ca2+-coupled P2 purinergic receptors among adrenergic and noradrenergic bovine adrenal chromaffin cells.
2007 Jun 14
Effects of genistein and herbimycin, tyrosine kinase inhibitors, on catecholamine release in bovine adrenal chromaffin cells.
2007 Oct
Beta-adrenoceptor-mediated vasodilation of retinal blood vessels is reduced in streptozotocin-induced diabetic rats.
2008 Aug-Sep
Expression of neuronal nicotinic acetylcholine receptors in rat vagal pulmonary sensory neurons.
2008 Mar 20
Activation of neuronal SST₁ and SST₂ receptors decreases neurogenic secretion in the guinea-pig jejunum.
2010 Nov
Human α3β4 neuronal nicotinic receptors show different stoichiometry if they are expressed in Xenopus oocytes or mammalian HEK293 cells.
2010 Oct 26
Patents

Patents

WO1996018738A2
2

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 20:05:24 GMT 2023
Edited
by admin
on Fri Dec 15 20:05:24 GMT 2023
Record UNII
X95H7DRX99
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMETHYLPHENYLPIPERAZINIUM IODIDE
Systematic Name English
NSC-89754
Code English
DMPP IODIDE
Common Name English
PIPERAZINIUM, 1,1-DIMETHYL-4-PHENYL-, IODIDE (1:1)
Systematic Name English
N,N-DIMETHYL-N'-PHENYLPIPERAZINIUM IODIDE
Systematic Name English
1,1-DIMETHYL-4-PHENYLPIPERAZINIUM IODIDE
Systematic Name English
Code System Code Type Description
CAS
54-77-3
Created by admin on Fri Dec 15 20:05:24 GMT 2023 , Edited by admin on Fri Dec 15 20:05:24 GMT 2023
PRIMARY
NSC
89754
Created by admin on Fri Dec 15 20:05:24 GMT 2023 , Edited by admin on Fri Dec 15 20:05:24 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-213-0
Created by admin on Fri Dec 15 20:05:24 GMT 2023 , Edited by admin on Fri Dec 15 20:05:24 GMT 2023
PRIMARY
PUBCHEM
5911
Created by admin on Fri Dec 15 20:05:24 GMT 2023 , Edited by admin on Fri Dec 15 20:05:24 GMT 2023
PRIMARY
CHEBI
4290
Created by admin on Fri Dec 15 20:05:24 GMT 2023 , Edited by admin on Fri Dec 15 20:05:24 GMT 2023
PRIMARY
FDA UNII
X95H7DRX99
Created by admin on Fri Dec 15 20:05:24 GMT 2023 , Edited by admin on Fri Dec 15 20:05:24 GMT 2023
PRIMARY
MESH
D004246
Created by admin on Fri Dec 15 20:05:24 GMT 2023 , Edited by admin on Fri Dec 15 20:05:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID90968822
Created by admin on Fri Dec 15 20:05:24 GMT 2023 , Edited by admin on Fri Dec 15 20:05:24 GMT 2023
PRIMARY
Related Record Type Details
Structure of DIMETHYLPHENYLPIPERAZINIUM
PARENT -> SALT/SOLVATE
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