Hemicholinium-3: Difference between revisions

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Revision as of 11:00, 2 December 2010 editBeetstra (talk \| contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit		Revision as of 11:10, 2 December 2010 edit undoCheMoBot (talk \| contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per Chem/Drugbox validation (report [[Misplaced Pages talk:WiNext edit →
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	{{Drugbox		{{Drugbox
			\| verifiedrevid = 400103507
	\| IUPAC_name = (2''S'',2'''S'')-2,2'-biphenyl-4,4'-diyl''bis''(2-hydroxy-4,4-dimethylmorpholin-4-ium)		\| IUPAC_name = (2''S'',2'''S'')-2,2'-biphenyl-4,4'-diyl''bis''(2-hydroxy-4,4-dimethylmorpholin-4-ium)
	\| image = Hemicholinium-3.svg		\| image = Hemicholinium-3.svg
	\| InChI = 1/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 = 1/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
	\| InChIKey = OPYKHUMNFAMIBL-NUQVWONBAD		\| InChIKey = OPYKHUMNFAMIBL-NUQVWONBAD
			\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 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		\| StdInChI = 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
			\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = OPYKHUMNFAMIBL-UHFFFAOYSA-L		\| StdInChIKey = OPYKHUMNFAMIBL-UHFFFAOYSA-L
	\| CAS_number = 312-45-8		\| CAS_number = 312-45-8
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	\| ATC_suffix =		\| ATC_suffix =
	\| PubChem = 9399		\| PubChem = 9399
			\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 9029		\| ChemSpiderID = 9029
	\| C = 24 \| H = 34 \| N = 2 \| O = 4 <sup>+2</sup>		\| C = 24 \| H = 34 \| N = 2 \| O = 4 <sup>+2</sup>

Revision as of 11:10, 2 December 2010

Pharmaceutical compound

Hemicholinium-3
Clinical data

Other names	2-phenyl]-4,4-dimethylmorpholin-4-ium-2-ol
ATC code	None
Identifiers
IUPAC name (2S,2'S)-2,2'-biphenyl-4,4'-diylbis(2-hydroxy-4,4-dimethylmorpholin-4-ium)
CAS Number	312-45-8
PubChem CID	9399
ChemSpider	9029
CompTox Dashboard (EPA)	DTXSID80883358
ECHA InfoCard	100.005.663
Chemical and physical data
Formula	C₂₄H₃₄N₂O₄
Molar mass	Expression error: Unexpected < operator414.538 g/molExpression error: Unexpected < operator
3D model (JSmol)	Interactive image
SMILES ..OC1(OCC(C)(C)C1)c2ccc(cc2)c3ccc(cc3)C4(O)OCC(C)(C)C4
InChI 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 Key:OPYKHUMNFAMIBL-UHFFFAOYSA-L
(verify)

Hemicholinium-3 (HC3), also known as hemicholine, is a drug which blocks the reuptake of choline by the high affinity transporter ChT (encoded in humans by the gene SLC5A7) at the presynapse. The reuptake of choline is the rate limiting step in the synthesis of acetylcholine; hence, hemicholinium-3 decreases the synthesis of acetylcholine. It is therefore classified as an indirect acetylcholine antagonist.

Acetylcholine is synthesized from choline and a donated acetyl group from acetyl-CoA, by the action of choline acetyltransferase (ChAT). Thus, decreasing the amount of choline available to a neuron will decrease the amount of acetylcholine produced. Neurons affected by hemicholinium-3 must rely on the transport of choline from the soma (cell body), rather than relying on reuptake of choline from the synaptic cleft.

Hemicholinium-3 is frequently used as a research tool in animal and in vitro experiments.