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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 Latest revision as of 19:56, 23 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,111 edits removed Category:Phenylmorpholines; added Category:Morpholines using HotCat 
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{{Short description|Chemical compound}}
{{Drugbox {{Drugbox
| Verifiedfields = changed
⚫ | IUPAC_name = (2''S'',2'''S'')-2,2'-biphenyl-4,4'-diyl''bis''(2-hydroxy-4,4-dimethylmorpholin-4-ium)
| Watchedfields = changed
⚫ | image = Hemicholinium-3.svg
| verifiedrevid = 400103507
⚫ | 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
⚫ | IUPAC_name = (2''S'',2''S'')-2,2'-biphenyl-4,4'-diyl''bis''(2-hydroxy-4,4-dimethylmorpholin-4-ium)
⚫ | InChIKey = OPYKHUMNFAMIBL-NUQVWONBAD
⚫ | image = Hemicholinium-3.svg
| 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
| alt = Skeletal formula
| StdInChIKey = OPYKHUMNFAMIBL-UHFFFAOYSA-L
| width = 260
⚫ | CAS_number = 312-45-8
| image2 = Hemicholinium-3 cation spacefill.png
⚫ | ATC_prefix = None
| alt2 = Space-filling model of the hemicholinium-3 cation
⚫ | ATC_suffix =

<!--Clinical data-->
| tradename =
⚫ | legal_status =
⚫ | routes_of_administration =

<!--Pharmacokinetic data-->
⚫ | bioavailability =
⚫ | metabolism =
⚫ | elimination_half-life =
⚫ | excretion =

<!--Identifiers-->
| IUPHAR_ligand = 4493
| CAS_number_Ref = {{cascite|correct|??}}
⚫ | CAS_number = 312-45-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 65NY3I7ZD0
⚫ | ATC_prefix = None
⚫ | ATC_suffix =
| PubChem = 9399 | PubChem = 9399
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9029 | ChemSpiderID = 9029
| ChEMBL_Ref = {{ebicite|changed|EBI}}
⚫ | C = 24 | H = 34 | N = 2 | O = 4 <sup>+2</sup>
| ChEMBL = 268697
| molecular_weight = 414.538 g/mol

<!--Chemical data-->
⚫ | C=24 | H=34 | N=2 | O=4 |charge=2+
| smiles = ..OC1(OCC(C)(C)C1)c2ccc(cc2)c3ccc(cc3)C4(O)OCC(C)(C)C4 | smiles = ..OC1(OCC(C)(C)C1)c2ccc(cc2)c3ccc(cc3)C4(O)OCC(C)(C)C4
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | synonyms = <small>2-phenyl]-4,4-dimethylmorpholin-4-ium-2-ol</small>
⚫ | 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
⚫ | bioavailability =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | metabolism =
⚫ | StdInChIKey = OPYKHUMNFAMIBL-UHFFFAOYSA-L
⚫ | elimination_half-life =
⚫ | synonyms = <small>2-phenyl]-4,4-dimethylmorpholin-4-ium-2-ol</small>
⚫ | excretion =
⚫ | legal_status =
⚫ | routes_of_administration =
}} }}


'''Hemicholinium-3''' ('''HC3'''), also known as '''hemicholine''', is a ] which blocks the ] of ] by the high affinity transporter ChT (encoded in humans by the gene ]) at the ]. The reuptake of choline is the ] in the synthesis of ]; hence, hemicholinium-3 decreases the synthesis of acetylcholine. It is therefore classified as an ] ].<ref name="Carlson">{{cite book | first= Neil R. | last= Carlson | year= 2007 | title= Physiology of Behavior, 9th ed. | location= Boston | publisher=Pearson Education, Inc. | isbn= 0-205-46724-5 | page= 117}}</ref> '''Hemicholinium-3''' ('''HC3'''), also known as '''hemicholine''', is a ] which blocks the ] of ] by the high-affinity ] (ChT; encoded in humans by the gene ''SLC5A7'') at the ]. The reuptake of choline is the ] in the synthesis of ]; hence, hemicholinium-3 decreases the synthesis of acetylcholine. It is therefore classified as an ] ].<ref name="Carlson">{{cite book | first= Neil R. | last= Carlson | name-list-style = vanc | year= 2007 | title= Physiology of Behavior | edition=9th | location= Boston | publisher=Pearson Education, Inc. | isbn= 978-0-205-46724-2 | page= 117}}</ref>


Acetylcholine is synthesized from choline and a donated ] group from ], by the action of ] (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 ] (cell body), rather than relying on reuptake of choline from the synaptic cleft. Acetylcholine is synthesized from choline and a donated ] group from ], by the action of ] (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 ] (cell body), rather than relying on reuptake of choline from the synaptic cleft.


==Toxicity==
Hemicholinium-3 is frequently used as a research tool in animal and ] experiments.
Hemicholinium-3 is highly toxic because it interferes with cholinergic neurotransmission. The LD50 of hemicholinium-3 for mice is about 35 μg.<ref>{{cite journal | vauthors = Freeman JJ, Kosh JW, Parrish JS | title = Peripheral toxicity of hemicholinium-3 in mice | journal = British Journal of Pharmacology | volume = 77 | issue = 2 | pages = 239–44 | date = October 1982 | pmid = 7139185 | pmc = 2044599 | doi = 10.1111/j.1476-5381.1982.tb09291.x }}</ref>


== See also == == See also ==
* ] *]
*]


== References == == References ==
{{Reflist}} {{Reflist}}
{{Commons cat}}
{{Acetylcholine metabolism and transport modulators}}


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{{Cholinergics}}

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