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Hemicholinium-3

Alias: HC-3; HC 3; HC3
Cat No.:V22113 Purity: ≥98%
Hemicholinium 3 is a competitive high-affinity choline transporter (HACU) inhibitor (antagonist) with Ki of 25 nM.
Hemicholinium-3
Hemicholinium-3 Chemical Structure CAS No.: 312-45-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Hemicholinium 3 is a competitive high-affinity choline transporter (HACU) inhibitor (antagonist) with Ki of 25 nM. Hemicholinium 3 inhibits the synthesis and release of acetylcholine (ACh) and works as a neuromuscular blocker. Hemicholinium 3 inhibits Epibatidine-induced contraction and [3H]acetylcholine release with IC50 of 897 nM and 693 nM, respectively.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
In the damaged area of myenteric neurons isolated from guinea pig longitudinal muscle strips, hemicholinium 3 (HC-3) inhibits nAChRs[2]. With a Ki value of 13.3 μM, hemicholinium 3 (HC-3) inhibits [3H]choline solution in NCI-H69 cells [3]. At a high affinity choline dosage (IC50=18 nM), hemicholinium 3 (HC-3) (1 mM) strongly reduces sodium cell inhibition in NCI-H69 cells [4].
ln Vivo
Learning about space is hampered by hemicholinium-3. The capacity to learn spatially is impaired by hemicholinium-3 (2.5, 5.0 μg/bag/ICV; 1 hour before training) computing devices [5].
Cell Assay
Cell Viability Assay [3]
Cell Types: The Human Small Cell Lung Cancer Cell Line NCI-H69
Tested Concentrations: 1 mM
Incubation Duration: Add daily for 2 days.
Experimental Results: Dramatically inhibited cell viability.
References

[1]. Inhibition by Hemicholinium-3 of [14C] Acetylcholine Synthesis and [3H] Choline High-Affinity Uptake in Rat Striatal Synaptosomes.Molecular Pharmacology September 1973, 9 (5) 630-639.

[2]. Inhibitory effect of hemicholinium-3 on presynaptic nicotinic acetylcholine receptors located on the terminal region of myenteric motoneurons. Neurochem Int. 2006 Sep;49(4):327-33.

[3]. Functional expression of choline transporter-like protein 1 (CTL1) in small cell lung carcinoma cells: a target molecule for lung cancer therapy. Pharmacol Res. 2013 Oct;76:119-31.

[4]. Methylpiperidine analog of hemicholinium-3: a selective, high affinity non-competitive inhibitor of sodium dependent choline uptake system. Eur J Pharmacol. 1988 May 10;149(3):241-8.

[5]. Hemicholinium-3 impairs spatial learning and the deficit is reversed by cholinomimetics. Psychopharmacology (Berl). 1989;98(3):347-56.

Additional Infomation
A potent inhibitor of the high affinity uptake system for CHOLINE. It has less effect on the low affinity uptake system. Since choline is one of the components of ACETYLCHOLINE, treatment with hemicholinium can deplete acetylcholine from cholinergic terminals. Hemicholinium 3 is commonly used as a research tool in animal and in vitro experiments.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C24H34BR2N2O4
Molecular Weight
574.35
Exact Mass
572.089
CAS #
312-45-8
PubChem CID
9399
Appearance
White to off-white solid powder
Melting Point
180 °C
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
3
Heavy Atom Count
32
Complexity
544
Defined Atom Stereocenter Count
0
InChi Key
OPYKHUMNFAMIBL-UHFFFAOYSA-L
InChi Code
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
Chemical Name
2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol;dibromide
Synonyms
HC-3; HC 3; HC3
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment, avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ~33.33 mg/mL (~58.03 mM)
Solubility (In Vivo)
Solubility in Formulation 1: 10 mg/mL (17.41 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication (<60°C).

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.7411 mL 8.7055 mL 17.4110 mL
5 mM 0.3482 mL 1.7411 mL 3.4822 mL
10 mM 0.1741 mL 0.8705 mL 1.7411 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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