Hemicholinium-3

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Hemicholinium-3
Skeletal formula
Space-filling model of the hemicholinium-3 cation
Clinical data
Synonyms2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol
ATC code
  • None
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
ChEMBL
ECHA InfoCard100.005.663 Edit this at Wikidata
Chemical and physical data
FormulaC24H34N2O42+
Molar mass414.538 g/mol
3D model (JSmol)
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Hemicholinium-3 (HC3), also known as hemicholine, is a drug which blocks the reuptake of choline by the high-affinity choline 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.[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[edit]

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[edit]

References[edit]

  1. ^ Carlson, Neil R. (2007). Physiology of Behavior (9th ed.). Boston: Pearson Education, Inc. p. 117. ISBN 0-205-46724-5.
  2. ^ Freeman, JJ; Kosh, JW; Parrish, JS (October 1982). "Peripheral toxicity of hemicholinium-3 in mice". British Journal of Pharmacology. 77 (2): 239–44. PMC 2044599. PMID 7139185.