Hemicholinium-3 | CAS# 312-45-8 | Choline Transport Antagonist

Hemicholinium-3
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 564739

CAS#: 312-45-8

Description: Hemicholinium-3 is a competitive antagonist of CHT-mediated choline transport.

Chemical Structure

Hemicholinium-3

CAS# 312-45-8

Instruction

Theoretical Analysis

MedKoo Cat#: 564739
Name: Hemicholinium-3
CAS#: 312-45-8
Chemical Formula: C24H34Br2N2O4
Exact Mass: 0.00
Molecular Weight: 574.350
Elemental Analysis: C, 50.19; H, 5.97; Br, 27.82; N, 4.88; O, 11.14

Price and Availability

Size	Price	Availability
100mg	USD 350	2 Weeks
500mg	USD 1050	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: HC3; HC 3; HC-3; Hemicholinium3; Hemicholinium 3; Hemicholinium-3

IUPAC/Chemical Name: 2,2'-([1,1'-biphenyl]-4,4'-diyl)bis(2-hydroxy-4,4-dimethylmorpholin-4-ium) bromide

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

SMILES Code: OC1(C2=CC=C(C3=CC=C(C4(O)OCC[N+](C)(C)C4)C=C3)C=C2)OCC[N+](C)(C)C1.[Br-].[Br-]

Appearance: Solid powder

Purity: >95% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 574.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Koshy Cherian A, Parikh V, Wu Q, Mao-Draayer Y, Wang Q, Blakely RD, Sarter M. Hemicholinium-3 sensitive choline transport in human T lymphocytes: Evidence for use as a proxy for brain choline transporter (CHT) capacity. Neurochem Int. 2017 Sep;108:410-416. doi: 10.1016/j.neuint.2017.05.022. Epub 2017 May 31. PubMed PMID: 28577989; PubMed Central PMCID: PMC5524217.

2: Soukup O, Kristofikova Z, Jun D, Tambor V, Ripova D, Kuca K. The interaction of standard oxime reactivators with hemicholinium-3 sensitive choline carriers. Toxicol Lett. 2012 Aug 3;212(3):315-9. doi: 10.1016/j.toxlet.2012.05.027. Epub 2012 Jun 6. PubMed PMID: 22683831.

3: Hong BS, Allali-Hassani A, Tempel W, Finerty PJ Jr, Mackenzie F, Dimov S, Vedadi M, Park HW. Crystal structures of human choline kinase isoforms in complex with hemicholinium-3: single amino acid near the active site influences inhibitor sensitivity. J Biol Chem. 2010 May 21;285(21):16330-40. doi: 10.1074/jbc.M109.039024. Epub 2010 Mar 18. PubMed PMID: 20299452; PubMed Central PMCID: PMC2871500.

4: Kristofiková Z, Kopecký V Jr, Hofbauerová K, Hovorková P, Rípová D. Complex of amyloid beta peptides with 24-hydroxycholesterol and its effect on hemicholinium-3 sensitive carriers. Neurochem Res. 2008 Mar;33(3):412-21. Epub 2007 Aug 24. PubMed PMID: 17717740.

5: Zheng QH, Gao M, Mock BH, Wang S, Hara T, Nazih R, Miller MA, Receveur TJ, Lopshire JC, Groh WJ, Zipes DP, Hutchins GD, DeGrado TR. Synthesis and biodistribution of new radiolabeled high-affinity choline transporter inhibitors [11C]hemicholinium-3 and [18F]hemicholinium-3. Bioorg Med Chem Lett. 2007 Apr 15;17(8):2220-4. Epub 2007 Feb 4. PubMed PMID: 17303422.

6: Mandl P, Kiss JP. 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. Epub 2006 Apr 18. PubMed PMID: 16621160.

7: Boccia MM, Acosta GB, Blake MG, Baratti CM. Memory consolidation and reconsolidation of an inhibitory avoidance response in mice: effects of i.c.v. injections of hemicholinium-3. Neuroscience. 2004;124(4):735-41. PubMed PMID: 15026114.

8: Ribeiro FM, Alves-Silva J, Volknandt W, Martins-Silva C, Mahmud H, Wilhelm A, Gomez MV, Rylett RJ, Ferguson SS, Prado VF, Prado MA. The hemicholinium-3 sensitive high affinity choline transporter is internalized by clathrin-mediated endocytosis and is present in endosomes and synaptic vesicles. J Neurochem. 2003 Oct;87(1):136-46. PubMed PMID: 12969261.

9: Kristofiková Z, Platilová V, Klaschka J. Age- and sex-dependent effects of ethanol on hippocampal hemicholinium-3 sensitive choline carriers during postnatal development of rats. Neurochem Res. 2003 Apr;28(3-4):397-405. PubMed PMID: 12675122.

10: Kristofiková Z, Tejkalová H, Klaschka J. Amyloid beta peptide 1-40 and the function of rat hippocampal hemicholinium-3 sensitive choline carriers: effects of a proteolytic degradation in vitro. Neurochem Res. 2001 Mar;26(3):203-12. PubMed PMID: 11495543.

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