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MedKoo Cat#: 564739 | Name: Hemicholinium-3
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Description:

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

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

Chemical Structure

Hemicholinium-3
Hemicholinium-3
CAS#312-45-8 (bromide)

Theoretical Analysis

MedKoo Cat#: 564739

Name: Hemicholinium-3

CAS#: 312-45-8 (bromide)

Chemical Formula: C24H34Br2N2O4

Exact Mass: 0.0000

Molecular Weight: 574.35

Elemental Analysis: C, 50.19; H, 5.97; Br, 27.82; N, 4.88; O, 11.14

Price and Availability

Size Price Availability Quantity
100mg USD 350.00 2 Weeks
500mg USD 1,050.00 2 Weeks
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Related CAS #
16478-59-4 (cation) 312-45-8 (bromide)
Synonym
HC3; HC 3; HC-3; Hemicholinium bromide; Hemicholinium dibromide; Hemicholine; Hemicholinium-3 bromide; Hemicholinium 3 dibromide; Hemicholinium-3 dibromide
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

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.

Recalculate based on batch purity %
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
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.