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Hemicholinium-3
Systematic (IUPAC) name
(2S,2'S)-2,2'-biphenyl-4,4'-diyl bis(2-hydroxy-4,4-dimethylmorpholin-4-ium)
Identifiers
CAS number 312-45-8
ATC code none
PubChem 3585
Chemical data
Formula C 24H34N2O4 +2 
Mol. mass 414.538 g/mol
Synonyms 2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status
Routes IM, IV

Hemicholinium-3, 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.[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.

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

References

  1. ^ Carlson, Neil R. (2007). Physiology of Behavior, 9th ed.. Boston: Pearson Education, Inc.. p. 117. ISBN 0-205-46724-5.  
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