Hemicholinium-3
Clinical data
ATC code
None
Identifiers
(2S ,2'S )-2,2'-biphenyl-4,4'-diylbis (2-hydroxy-4,4-dimethylmorpholin-4-ium)
Synonyms
2-[4-[4-(2-hydroxy-4,4-dimethylmorpholin-4-ium-2-yl)phenyl]phenyl]-4,4-dimethylmorpholin-4-ium-2-ol
CAS Number
312-45-8 Y
PubChem (CID)
9399
IUPHAR/BPS
4493
ChemSpider
9029 Y
ChEMBL
CHEMBL268697 N
ECHA InfoCard
100.005.663
Chemical and physical data
Formula
C 24 H 34 N 2 O 4 2+
Molar mass
414.538 g/mol
3D model (Jmol )
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
N Y (what is this?) (verify)
"HC-3" redirects here. For the United States Navy helicopter squadron designated HC-3 from 1967 to 2005, see
HCS-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]
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 [ edit ]
Hemicholinium-3 has no clinical use, but is frequently used as a research tool in animal and in vitro experiments. The clinical use is limited since it prevents uptake into the cell which is not a rate limiting factor under normal, physiological frequencies of activation. This type of inhibition only becomes apparent at excessively high firing rates, whereby the uptake of choline into the nerve terminal as a rate limiting factor becomes apparent.
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 [ edit ]
References [ edit ]
^ Carlson, Neil R. (2007). Physiology of Behavior (9th ed.). Boston: Pearson Education, Inc. p. 117. ISBN 0-205-46724-5 .
mACh
Muscarinic antagonists : 3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide
Anisodamine
Anisodine
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BIBN 99
Biperiden
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CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
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CS-27349
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EA-3167
EA-3443
EA-3580
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HL-031,120
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J-104,129
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Mamba toxin 3
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PD-102,807
PD-0298029
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Pirenzepine
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RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
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WIN-2299
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nACh
Nicotinic agonists : 5-HIAA
A-84,543
A-366,833
A-582,941
A-867,744
ABT-202
ABT-418
ABT-560
ABT-894
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Altinicline
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Anatoxin-a
AR-R17779
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Butyrylcholine
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EVP-4473
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GTS-21
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NS-1738
PHA-543,613
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RJR-2429
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SB-206553
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SIB-1508Y
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SSR-180,711
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TC-1698
TC-1734
TC-1827
TC-2216
TC-5214
TC-5619
TC-6683
Tebanicline
Tropisetron
UB-165
Varenicline
WAY-317,538
XY-4083