312-45-8

Basic information

• Product Name: HEMICHOLINIUM-3
• Synonyms: 2,2’-(1,1’-biphenyl)-4,4’-diylbis(2-hydroxy-4,4-dimethyl-morpholinium)dibrom;2,2’-(4,4’-biphenylylene)bis(2-hydroxy-4,4-dimethyl-morpholiniudibromide;hc-3;hemicholine;hemicholinium-3bromide;hemicholinium-3dibromide;hemicholiniumbromide;hemicholiniumdibromide
• CAS NO: 312-45-8
• Molecular Formula: 2Br*C₂₄H₃₄N₂O₄
• Molecular Weight: 574.351
• EINECS: 206-227-3
• Mol File: 312-45-8.mol
• Article Data: 1

Chemical Properties

• Melting Point: 180°; mp 226- 228° (dec)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/solid
• Density: g/cm³
• Solubility: ethanol: 1.3 mg/mL
• Merck: 13,4660
• BRN: 5704458
• CAS DataBase Reference: HEMICHOLINIUM-3(CAS DataBase Reference)
• NIST Chemistry Reference: HEMICHOLINIUM-3(312-45-8)
• EPA Substance Registry System: HEMICHOLINIUM-3(312-45-8)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: QF2450000
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 312-45-8(Hazardous Substances Data)

Usage

Description

HEMICHOLINIUM-3 is a compound that acts as an acetylcholine stores depletor. It is known for its ability to inhibit the high-affinity uptake of choline, which is a precursor for the synthesis of acetylcholine. This property makes it a valuable tool in the study of cholinergic systems and the regulation of acetylcholine synthesis.

Uses

Used in Neuroscience Research:
HEMICHOLINIUM-3 is used as a research tool for studying cholinergic systems. It serves as a cholinergic probe to deplete acetylcholine stores, which helps researchers understand the role of acetylcholine in various neurological processes and disorders.
Used in Cell Culture Studies:
HEMICHOLINIUM-3 is used in the preparation of Krebs-HC-3 buffer, which is utilized to study its effects on choline uptake and choline acetyltransferase activity in differentiated human neuroblastoma (SK-N-SH) cells. This application aids in the investigation of the mechanisms underlying cholinergic neurotransmission and the potential therapeutic targets for related conditions.

Biochem/physiol Actions

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

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 4072-67-7 4,4'-bis(bromoacetyl)biphenyl 

Relevant articles and documents

Synthesis and biodistribution of new radiolabeled high-affinity choline transporter inhibitors [11C]hemicholinium-3 and [18F]hemicholinium-3

The high-affinity choline transporter (CHT1) system is an attractive target for the development of positron emission tomography (PET) biomarkers to probe brain, cardiac, and cancer diseases. An efficient and convenient synthesis of new radiolabeled CHT1 inhibitors [11C]hemicholinium-3 and [18F]hemicholinium-3 by solid-phase extraction (SPE) technique using a cation-exchange CM Sep-Pak cartridge has been well developed. The preliminary evaluation of both tracers through biodistribution studies in 9L-glioma rats has been performed, and the uptakes in the heart and tumor were observed, while very low brain uptake was seen.