Hemicholinium-3

Hemicholinium-3

Systematic (IUPAC) name
(2S,2'S)-2,2'-biphenyl-4,4'-diylbis(2-hydroxy-4,4-dimethylmorpholin-4-ium)
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	312-45-8 Y
ATC code	None
PubChem	CID 9399
ChemSpider	9029 Y
ChEMBL	CHEMBL268697 N
Synonyms	2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol
Chemical data
Formula	C24H34N2O4 +2
Mol. mass	414.538 g/mol
SMILES	eMolecules & PubChem
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 Y Key:OPYKHUMNFAMIBL-UHFFFAOYSA-L Y
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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.

Effects

Hemicholinium-3 has no clinical use, but is frequently used as a research tool in animal and in vitro experiments.

Hemoicholinium-3 produces a decrease in acetylcholine content in the nerve terminal and as a consequence results in a decrease in acetylcholine transmission. Since acetylcholine normally binds to nicotinic and muscarinic receptors in synapses, a decrease in acetylcholine would cause a decrease in nicotinic and muscarinic pharmacology.

See also

• Triethylcholine