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Merck

H108

Sigma-Aldrich

Hemicholinium-3

solid, ≥95% (HPLC)

Synonym(e):

2,2′-(4,4′-Biphenylene)bis(2-hydroxy-4,4-dimethylmorpholinium bromide)

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About This Item

Empirische Formel (Hill-System):
C24H34Br2N2O4
CAS-Nummer:
Molekulargewicht:
574.35
Beilstein:
5704458
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:

Qualitätsniveau

Assay

≥95% (HPLC)

Form

solid

Farbe

white

Löslichkeit

ethanol: 1.3 mg/mL
H2O: 10 mg/mL

SMILES String

[Br-].[Br-].C[N+]1(C)CCOC(O)(C1)c2ccc(cc2)-c3ccc(cc3)C4(O)C[N+](C)(C)CCO4

InChI

1S/C24H34N2O4.2BrH/c1-25(2)13-15-29-23(27,17-25)21-9-5-19(6-10-21)20-7-11-22(12-8-20)24(28)18-26(3,4)14-16-30-24;;/h5-12,27-28H,13-18H2,1-4H3;2*1H/q+2;;/p-2

InChIKey

OPYKHUMNFAMIBL-UHFFFAOYSA-L

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Anwendung

Hemicholinium-3 has been used in the preparation of Krebs-HC-3 buffer to study its effects on choline uptake and choline acetyltransferase activity in differentiated human neuroblastoma (SK-N-SH) cells.

Biochem./physiol. Wirkung

Hemicholinium-3 plays a role in blocking the neuronal choline uptake thereby inhibiting acetylcholine synthesis in the brain.

Leistungsmerkmale und Vorteile

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

Piktogramme

Skull and crossbones

Signalwort

Danger

Gefahreneinstufungen

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


Analysenzertifikate (COA)

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Zhuo Li et al.
Biochimica et biophysica acta, 1841(6), 859-867 (2014-03-04)
There is a paucity of information about phosphatidylcholine (PC) biosynthesis in bone formation. Thus, we characterized PC metabolism in both primary human osteoblasts (HOB) and human osteosarcoma MG-63 cells. Our results show that the CDP-choline pathway is the only de
Edward D Levin et al.
Behavioural brain research, 208(2), 319-327 (2009-12-18)
Developmental exposure of rats to the organophosphate (OP) pesticides leads to altered neurobehavioral function in juvenile and young adult stages. The current study was conducted to determine whether effects of neonatal parathion exposure on cognitive performance persist in older adult
Structure-activity aspects of hemicholinium-3 (HC-3) and its analogs and congeners.
J G Cannon
Medicinal research reviews, 14(5), 505-531 (1994-09-01)
Yu Kuang et al.
Molecular pharmaceutics, 7(6), 2077-2092 (2010-08-12)
Altered choline (Cho) metabolism in cancerous cells can be used as a basis for molecular imaging with PET using radiolabeled Cho. In this study, the metabolism of tracer Cho was investigated in a woodchuck hepatocellular carcinoma (HCC) cell line (WCH17)
H K Happe et al.
Journal of neurochemistry, 60(4), 1191-1201 (1993-04-01)
High-affinity choline transport (HAChT), the rate-limiting and regulatory step in acetylcholine (ACh) synthesis, is selectively localized to cholinergic neurons. Hemicholinium-3 (HC3), a potent and selective inhibitor of HAChT, has been used as a specific radioligand to quantify HAChT sites in

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