Skip to Content
Merck
All Photos(1)

Documents

H108

Sigma-Aldrich

Hemicholinium-3

solid, ≥95% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C24H34Br2N2O4
CAS Number:
312-45-8
Molecular Weight:
574.35
Beilstein:
5704458
EC Number:
206-227-3
MDL number:
MFCD00011978
UNSPSC Code:
12352200
PubChem Substance ID:
24278169
NACRES:
NA.77

Assay

≥95% (HPLC)

form

solid

color

white

solubility

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

InChI key

OPYKHUMNFAMIBL-UHFFFAOYSA-L

Looking for similar products? Visit Product Comparison Guide

Application

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 Actions

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

Features and Benefits

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.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

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

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 3

1 of 3

Capsaicin ≥95%, from Capsicum sp.

Sigma-Aldrich

M2028

Capsaicin

Choline chloride ≥99%

Sigma-Aldrich

C7017

Choline chloride

HEPES ≥99.5% (titration)

Sigma-Aldrich

H3375

HEPES

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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service