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Hemicholinium-3

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]

Hemicholinium-3
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)
CAS Number
  • 312-45-8 Y
PubChem CID
  • 9399
IUPHAR/BPS
  • 4493
ChemSpider
  • 9029 Y
UNII
  • 65NY3I7ZD0
ChEMBL
  • ChEMBL268697 N
CompTox Dashboard (EPA)
  • DTXSID80883358
ECHA InfoCard100.005.663
Chemical and physical data
FormulaC24H34N2O42+
Molar mass414.546 g·mol−1
3D model (JSmol)
  • Interactive image
  • [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 Y
  • Key:OPYKHUMNFAMIBL-UHFFFAOYSA-L Y
 NY (what is this?)  (verify)

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 NR (2007). Physiology of Behavior (9th ed.). Boston: Pearson Education, Inc. p. 117. ISBN 978-0-205-46724-2.
  2. ^ Freeman JJ, Kosh JW, Parrish JS (October 1982). "Peripheral toxicity of hemicholinium-3 in mice". British Journal of Pharmacology. 77 (2): 239–44. doi:10.1111/j.1476-5381.1982.tb09291.x. PMC 2044599. PMID 7139185.

hemicholinium, also, known, hemicholine, drug, which, blocks, reuptake, choline, high, affinity, choline, transporter, encoded, humans, gene, slc5a7, presynapse, reuptake, choline, rate, limiting, step, synthesis, acetylcholine, hence, hemicholinium, decreases. 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 Hemicholinium 3Clinical dataOther names2 4 4 2 hydroxy 4 4 dimethylmorpholin 4 ium 2 yl phenyl phenyl 4 4 dimethylmorpholin 4 ium 2 olATC codeNoneIdentifiersIUPAC name 2S 2S 2 2 biphenyl 4 4 diylbis 2 hydroxy 4 4 dimethylmorpholin 4 ium CAS Number312 45 8 YPubChem CID9399IUPHAR BPS4493ChemSpider9029 YUNII65NY3I7ZD0ChEMBLChEMBL268697 NCompTox Dashboard EPA DTXSID80883358ECHA InfoCard100 005 663Chemical and physical dataFormulaC 24H 34N 2O 42 Molar mass414 546 g mol 13D model JSmol Interactive imageSMILES Br Br OC1 OCC N C C C1 c2ccc cc2 c3ccc cc3 C4 O OCC N C C C4InChI 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 YKey OPYKHUMNFAMIBL UHFFFAOYSA L Y N Y what is this verify 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 editHemicholinium 3 is highly toxic because it interferes with cholinergic neurotransmission The LD50 of hemicholinium 3 for mice is about 35 mg 2 See also editTriethylcholine VesamicolReferences edit Carlson NR 2007 Physiology of Behavior 9th ed Boston Pearson Education Inc p 117 ISBN 978 0 205 46724 2 Freeman JJ Kosh JW Parrish JS October 1982 Peripheral toxicity of hemicholinium 3 in mice British Journal of Pharmacology 77 2 239 44 doi 10 1111 j 1476 5381 1982 tb09291 x PMC 2044599 PMID 7139185 nbsp Wikimedia Commons has media related to Hemicholinium 3 Retrieved from https en wikipedia org w index php title Hemicholinium 3 amp oldid 1197809671, wikipedia, wiki, book, books, library,

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