Structure via PubChem · Public domain (PubChem)
hemicholinium-3 dibromide
Sign in to saveAlso known as hemicholinium-3 bromide, HC3, HC-3, hemicholine
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.
In the Vinony graph
Vinony's link graph records 258 inbound references to hemicholinium-3 dibromide, and connects out to botulinum toxin group, chlorpyrifos and metrifonate.
Vinony files it under Acetylcholine synthesis inhibitors, Biphenyls and Chemical pages without DrugBank identifier.
Vinony links it to 4 Wikipedia language editions.
Chemical data
- Formula
- C24H34Br2N2O4
- Molecular weight
- 574.3 g/mol
- IUPAC name
- 2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol dibromide
- SMILES
- C[N+]1(CCOC(C1)(C2=CC=C(C=C2)C3=CC=C(C=C3)C4(C[N+](CCO4)(C)C)O)O)C.[Br-].[Br-]
- InChIKey
- OPYKHUMNFAMIBL-UHFFFAOYSA-L
- Polar surface area
- 58.9 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2 papers- Pre- and postjunctional neuromuscular blockade by carbachol.Naunyn-Schmiedeberg's archives of pharmacology · 1975
- The effect of cholinesterase inhibitors on the antimuscarinic effect of hemicholinium-3 (HC-3) in the rat.The Journal of pharmacy and pharmacology · 1976
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 572.0885317679999
Show 3 more facts
- canonical SMILES
- C[N+]1(CCOC(C1)(C2=CC=C(C=C2)C3=CC=C(C=C3)C4(C[N+](CCO4)(C)C)O)O)C.[Br-].[Br-]
- chemical formula
- C₂₄H₃₄Br₂N₂O₄
- Commons category
- Hemicholinium-3
Sources (1)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Toxicity
- See also
- References
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.
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.
Excerpted from Wikipedia’s “hemicholinium-3 dibromide” article, available under the CC BY-SA 4.0 licence.