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H108

Hemicholinium-3

≥95% (HPLC), acetylcholine synthesis inhibitor, solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C24H34Br2N2O4
CAS Number:
312-45-8
Molecular Weight:
574.35
NACRES:
NA.77
PubChem Substance ID:
24278169
UNSPSC Code:
12352200
EC Number:
206-227-3
MDL number:
MFCD00011978
Beilstein/REAXYS Number:
5704458
Assay:
≥95% (HPLC)
Form:
solid
Quality level:
100
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Product Name

Hemicholinium-3, solid, ≥95% (HPLC)

Quality Level

100

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

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

signalword

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

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

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM9975
BCCK4343
BCCH8355
BCCJ2286
BCCG5490

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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)
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
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