Hemicholinium-3

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Hemicholinium-3
Skeletal formula
Space-filling model of the hemicholinium-3 cation
Clinical data
Other names2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol
ATC code
  • None
Identifiers
  • (2S,2S)-2,2'-biphenyl-4,4'-diylbis(2-hydroxy-4,4-dimethylmorpholin-4-ium)
JSmol)
  • [Br-].[Br-].OC1(OCC[N+](C)(C)C1)c2ccc(cc2)c3ccc(cc3)C4(O)OCC[N+](C)(C)C4
  • 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 checkY
  • Key:OPYKHUMNFAMIBL-UHFFFAOYSA-L checkY
 ☒NcheckY (what is this?)  (verify)

Hemicholinium-3 (HC3), also known as hemicholine, is a

acetylcholine antagonist.[1]

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.

Toxicity

Hemicholinium-3 is highly toxic because it interferes with cholinergic neurotransmission. The LD50 of hemicholinium-3 for mice is about 35 μg.[2]

See also

References