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D5891

Sigma-Aldrich

1,1-Dimethyl-4-phenylpiperaziniumjodid

≥98% (TLC or titration)

Synonym(e):

DMPP

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About This Item

Empirische Formel (Hill-System):
C12H19IN2
CAS-Nummer:
54-77-3
Molekulargewicht:
318.20
Beilstein:
3746109
EG-Nummer:
200-213-0
MDL-Nummer:
MFCD00011976
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24277832
NACRES:
NA.77

Assay

≥98% (TLC or titration)

Form

powder

mp (Schmelzpunkt)

234-238 °C (lit.)

Löslichkeit

H2O: 21 mg/mL

Lagertemp.

−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

InChIKey

XFZJGFIKQCCLGK-UHFFFAOYSA-M

Angaben zum Gen

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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Anwendung

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. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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E S Vizi et al.
Brain research. Brain research reviews, 30(3), 219-235 (1999-11-24)
Neuronal nicotinic acetylcholine receptors (nAChRs) belong to a family of ligand-gated channels closely related to but distinct from the muscle nAChRs. Recent progress in neurochemical and pharmacological methods supports the hypothesis of presynaptically located nAChRs on axon terminals and indicates
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
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
Anne-Françoise Ruaud et al.
Genetics, 187(1), 337-343 (2010-10-15)
Identified as a major pathway controlling entry in the facultative dauer diapause stage, the DAF-2/Insulin receptor (InsR) signaling acts in multiple developmental and physiological regulation events in Caenorhabditis elegans. Here we identified a role of the insulin-like pathway in controlling
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