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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

Qualitätsniveau

200

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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J J Galligan
The Journal of pharmacology and experimental therapeutics, 291(1), 92-98 (1999-09-22)
Nicotinic acetylcholine receptors (nAChRs) localized to excitatory longitudinal muscle motoneurons were studied in segments of guinea pig ileum maintained in vitro. Longitudinal muscle contractions caused by the nAChRs agonists, dimethylphenylpiperazinium (DMPP), nicotine, and cytisine were measured using isometric strain gauge
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
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
Carla Cirillo et al.
Gut, 62(2), 227-235 (2012-03-06)
Most direct understanding of enteric nerve (patho)physiology has been obtained by electrode and imaging techniques in animal models and human surgical samples. Until now, neuronal activity recordings from a more accessible human tissue source have remained a true challenge. To
C Morel et al.
Molecular psychiatry, 19(8), 930-936 (2013-12-04)
Smoking is the most important preventable cause of morbidity and mortality worldwide. Recent genome-wide association studies highlighted a human haplotype on chromosome 15 underlying the risk for tobacco dependence and lung cancer. Several polymorphisms in the CHRNA3-CHRNA5-CHRNB4 cluster coding for
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