Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

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 2

1 of 2

Choline chloride ≥99%

Sigma-Aldrich

C7017

Choline chloride

HEPES ≥99.5% (titration)

Sigma-Aldrich

H3375

HEPES

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
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)
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)
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
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
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