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D5891

Sigma-Aldrich

1,1-Dimethyl-4-phenylpiperazinium iodide

≥98% (TLC or titration)

Synonym(s):

DMPP

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About This Item

Empirical Formula (Hill Notation):
C12H19IN2
CAS Number:
54-77-3
Molecular Weight:
318.20
Beilstein:
3746109
EC Number:
200-213-0
MDL number:
MFCD00011976
UNSPSC Code:
12352200
PubChem Substance ID:
24277832
NACRES:
NA.77

Assay

≥98% (TLC or titration)

form

powder

mp

234-238 °C (lit.)

solubility

H2O: 21 mg/mL

storage temp.

−20°C

SMILES string

[I-].C[N+]1(C)CCN(CC1)c2ccccc2

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

InChI key

XFZJGFIKQCCLGK-UHFFFAOYSA-M

Gene Information

human ... CHRNA1(1134) , CHRNA10(57053) , CHRNA2(1135) , CHRNA3(1136) , CHRNA4(1137) , CHRNA5(1138) , CHRNA6(8973) , CHRNA7(1139) , CHRNA9(55584) , CHRNB1(1140) , CHRNB2(1141) , CHRNB3(1142) , CHRNB4(1143)
rat ... Chrna2(170945) , Chrna3(25101) , Chrna4(25590) , Chrnb2(54239) , Chrnb4(25103)

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Application

1,1-Dimethyl-4-phenylpiperazinium iodide (DMPP) has been used as a non-selective nicotinic acetylcholine receptor (nAchR) agonist:
  • to study the roles of α7 and α4β2 nAchRs in autonomic regulation of cardiovascular responses in urethane-anesthetized mice
  • to study the mechanism involved in improving glucose tolerance in diet-induced obese (DIO) mice treated with DMPP
  • to study its pharmacological effect on enteric viscerofugal neurons in the myenteric plexus of guinea-pig colon

Biochem/physiol Actions

1,1-Dimethyl-4-phenylpiperazinium iodide (DMPP) is a non-selective nicotinic acetylcholine receptor (nAchR) agonist. It acts as a stimulating agent for sympathetic ganglia. DMPP exhibits specific action on ganglia and adrenal medullary tissue hence, it finds its application in the diagnosis of pheochromocytoma.

Features and Benefits

This compound is featured on the Acetylcholine Receptors (Nicotinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D Manetti et al.
Bioorganic & medicinal chemistry, 7(3), 457-465 (1999-04-29)
A series of piperazine derivatives, obtained by hybridization of N1-acetyl-N4-dimethyl-piperazinium iodide (1, ADMP) and N1-phenyl-N4-dimethyl-piperazinium iodide (3, DMPP) or of the corresponding tertiary bases (2, 4) with arecoline (5) and arecolone (6) or by isosteric substitution of the phenyl ring
T J Hibberd et al.
Neuroscience, 275, 272-284 (2014-05-13)
Enteric viscerofugal neurons are mechanosensory interneurons that form the afferent limb of intestino-intestinal reflexes involving prevertebral sympathetic neurons. Fast synaptic inputs to viscerofugal neurons arise from other enteric neurons, but their sources are unknown. We aimed to describe the origins
Taisuke Nakazawa et al.
Vascular pharmacology, 49(2-3), 77-83 (2008-07-01)
We investigated the effects of epinephrine and dopamine on retinal blood vessels in streptozotocin (STZ, 80 mg/kg, i.p.)-treated rats and age-matched control rats to determine whether diabetes mellitus alters the retinal vascular responses to circulating catecholamines. Experiments were performed 6-8
Cardiovascular action of 1,1-dimethyl-4-phenylpiperazinium iodide (DMPP); a ganglion stimulating agent useful in the diagnosis of pheochromocytoma.
I H PAGE et al.
The American journal of medicine, 15(5), 675-683 (1953-11-01)
J P P Foong et al.
Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society, 22(11), 1209-1216 (2010-07-16)
Vasoactive intestinal peptide (VIP) submucosal neurons, the main regulators of gut secretion, display inhibitory postsynaptic potentials mediated by somatostatin (SOM) acting on SST(1) and SST(2) receptors (SSTR(1), SSTR(2)) in the guinea-pig small intestine. We investigated the implications of this for
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