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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:
312-45-8
Molekulargewicht:
574.35
Beilstein:
5704458
EG-Nummer:
206-227-3
MDL-Nummer:
MFCD00011978
UNSPSC-Code:
12352200
PubChem Substanz-ID:
24278169
NACRES:
NA.77

Qualitätsniveau

100

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
GHS06

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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HEPES ≥99.5% (titration)

Sigma-Aldrich

H3375

HEPES

Effect of hemicholinium-3 on the hypothalamic concentration of a cytochemically detectable glucose-6-phosphate dehydrogenase-stimulating substance.
Vargas, H M, et al.
Journal of Cardiovascular Pharmacology, 24(5), 773-778 (1994)
Determination of high-affinity choline uptake (HACU) and choline acetyltransferase (ChAT) activity in the same population of cultured cells
Ray B, et al.
Brain Research, 1297(5), 160-168 (2009)
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
Theodore A Slotkin et al.
Environmental health perspectives, 117(6), 916-922 (2009-07-11)
Developmental exposure to a wide variety of developmental neurotoxicants, including organophosphate pesticides, evokes late-emerging and persistent abnormalities in acetylcholine (ACh) systems. We are seeking interventions that can ameliorate or reverse the effects later in life. We administered parathion to neonatal
Sebastian A Müller et al.
European journal of nuclear medicine and molecular imaging, 36(9), 1434-1442 (2009-04-09)
Choline derivatives labelled with positron emitters are successfully used for PET imaging of prostate cancer patients. Since little is known about uptake mechanisms, the aim of this study was to characterize choline uptake in prostate cancer cells, also following anti-androgen
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