HEMICHOLINIUM

Details

Stereochemistry	MIXED
Molecular Formula	C24H34N2O4
Molecular Weight	414.5378
Optical Activity	UNSPECIFIED
Defined Stereocenters	0 / 4
E/Z Centers	0
Charge	2

SHOW SMILES / InChI

Structure Search

SMILES

C[N+]1(C)CCOC(O)(C1)C2=CC=C(C=C2)C3=CC=C(C=C3)C4(O)C[N+](C)(C)CCO4

InChI

InChIKey=JIWUESGGKYLPPG-UHFFFAOYSA-N

InChI=1S/C24H34N2O4/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/q+2

HIDE SMILES / InChI

Molecular Formula	C24H32N2O4
Molecular Weight	412.5219
Charge	0
Count

Stereochemistry	MIXED
Additional Stereochemistry	No
Defined Stereocenters	0 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Choline uptake 2 Target ID: Choline uptake Sources: https://www.ncbi.nlm.nih.gov/pubmed/3409952 \| https://www.ncbi.nlm.nih.gov/pubmed/8075137	Inhibitor 8504		18.0 nM [IC50]
Adenosine A3 receptor 24 Target ID: CHEMBL256 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16250647	Antagonist 2849		12.0 nM [IC50]

PubMed

Title	Date	PubMed
Control of choline oxidation in rat kidney mitochondria.	2009-09	19426704
Characterization of choline uptake in prostate cancer cells following bicalutamide and docetaxel treatment.	2009-09	19352653
The solute carrier 44A1 is a mitochondrial protein and mediates choline transport.	2009-08	19357133
Consumption of a high-fat diet in adulthood ameliorates the effects of neonatal parathion exposure on acetylcholine systems in rat brain regions.	2009-06	19590683
Fat chance? A high-fat diet may offset the effects of developmental neurotoxicity.	2009-06	19590672
Molecular and functional characterization of choline transporter in rat renal tubule epithelial NRK-52E cells.	2009-05-01	19236841
Modulation of choline kinase activity in human cancer cells observed by dynamic 31P NMR.	2009-05	19156696
Choline transport via choline transporter-like protein 1 in conditionally immortalized rat syncytiotrophoblast cell lines TR-TBT.	2009-04	19246089
Mutant SOD1 impairs axonal transport of choline acetyltransferase and acetylcholine release by sequestering KAP3.	2009-03-01	19088126
Estrogen effects on high-affinity choline uptake in primary cultures of rat basal forebrain.	2009-02	18483854
Exposure of neonatal rats to parathion elicits sex-selective impairment of acetylcholine systems in brain regions during adolescence and adulthood.	2008-10	18941570
The epithelial cholinergic system of the airways.	2008-08	18566825
Choline, CDP-choline or phosphocholine increases plasma glucagon in rats: involvement of the peripheral autonomic nervous system.	2008-07-28	18561911
Loss of muscarinic autoreceptor function impairs long-term depression but not long-term potentiation in the striatum.	2008-06-11	18550768
Adolescent nicotine treatment changes the response of acetylcholine systems to subsequent nicotine administration in adulthood.	2008-05-15	18395624
Choline availability and acetylcholine synthesis in the hippocampus of acetylcholinesterase-deficient mice.	2008-05	18023504
Release of acetylcholine by syringin, an active principle of Eleutherococcus senticosus, to raise insulin secretion in Wistar rats.	2008-03-28	18304730
Neonatal exposure to low doses of diazinon: long-term effects on neural cell development and acetylcholine systems.	2008-03	18335101
Complex of amyloid beta peptides with 24-hydroxycholesterol and its effect on hemicholinium-3 sensitive carriers.	2008-03	17717740
Decreased biosynthesis of lung surfactant constituent phosphatidylcholine due to inhibition of choline transporter by gefitinib in lung alveolar cells.	2008-02	17624579
Peripheral administration of CDP-choline and its cholinergic metabolites increases serum insulin: muscarinic and nicotinic acetylcholine receptors are both involved in their actions.	2008-01-24	18162319
Developmental neurotoxic effects of chlorpyrifos on acetylcholine and serotonin pathways in an avian model.	2008-01-07	18436430
Characterization of ouabain-induced noradrenaline and acetylcholine release from in situ cardiac autonomic nerve endings.	2007-12	17995575
Separate or sequential exposure to nicotine prenatally and in adulthood: persistent effects on acetylcholine systems in rat brain regions.	2007-09-14	17683794
Comparative effects of aluminum and ouabain on synaptosomal choline uptake, acetylcholine release and (Na+/K+)ATPase.	2007-07-17	17560001
Deficits in acetylcholine homeostasis, receptors and behaviors in choline transporter heterozygous mice.	2007-07	17010154
Permanent, sex-selective effects of prenatal or adolescent nicotine exposure, separately or sequentially, in rat brain regions: indices of cholinergic and serotonergic synaptic function, cell signaling, and neural cell number and size at 6 months of age.	2007-05	17047666
The involvement of the central cholinergic system in the pressor and bradycardic effects of centrally administrated melittin in normotensive conscious rats.	2007-04	17222905
Increase of acetylcholine release by Panax ginseng root enhances insulin secretion in Wistar rats.	2007-01-29	17123721
Na+, Cl-, and pH dependence of the human choline transporter (hCHT) in Xenopus oocytes: the proton inactivation hypothesis of hCHT in synaptic vesicles.	2006-09-27	17005849
Inhibitory effect of hemicholinium-3 on presynaptic nicotinic acetylcholine receptors located on the terminal region of myenteric motoneurons.	2006-09	16621160
Release of acetylcholine by Hon-Chi to raise insulin secretion in Wistar rats.	2006-08-14	16762503
Release of acetylcholine to raise insulin secretion in Wistar rats by oleanolic acid, one of the active principles contained in Cornus officinalis.	2006-08-14	16759806
Acetyl-L-carnitine protects striatal neurons against in vitro ischemia: the role of endogenous acetylcholine.	2006-06	16500685
Comparative developmental neurotoxicity of organophosphate insecticides: effects on brain development are separable from systemic toxicity.	2006-05	16675431
Choline transport for phospholipid synthesis.	2006-05	16636297
Cortical choline transporter function measured in vivo using choline-sensitive microelectrodes: clearance of endogenous and exogenous choline and effects of removal of cholinergic terminals.	2006-04	16539662
Sex-dependent actions of amyloid beta peptides on hippocampal choline carriers of postnatal rats.	2006-03	16733811
Increase of insulin secretion by ginsenoside Rh2 to lower plasma glucose in Wistar rats.	2006-02-01	16445695
Functional characterization of Na+-independent choline transport in primary cultures of neurons from mouse cerebral cortex.	2006-01-30	16239069
Lasting effects of developmental dexamethasone treatment on neural cell number and size, synaptic activity, and cell signaling: critical periods of vulnerability, dose-effect relationships, regional targets, and sex selectivity.	2006-01	15920497
The Ras/Raf-1/MEK1/ERK signaling pathway coupled to integrin expression mediates cholinergic regulation of keratinocyte directional migration.	2005-11-25	16150734
Chronic treatment with amyloid beta(1-42) inhibits non-cholinergic high-affinity choline transport in NG108-15 cells through protein kinase C signaling.	2005-11-16	16256077
Molecular and functional characterization of an Na+-independent choline transporter in rat astrocytes.	2005-09	16000150
The lateral septal area is involved in the pressor pathway activated by microinjection of norepinephrine into the rat brain cingulate cortex.	2005-09	15963537
3D-QSAR study of bis-azaaromatic quaternary ammonium analogs at the blood-brain barrier choline transporter.	2005-07-01	15878282
Donepezil, tacrine and alpha-phenyl-n-tert-butyl nitrone (PBN) inhibit choline transport by conditionally immortalized rat brain capillary endothelial cell lines (TR-BBB).	2005-04	15918518
Extracellular protons differentially potentiate the responses of native AMPA receptor subtypes regulating neurotransmitter release.	2005-01	15665865
Molecular cloning and functional characterization of a neuronal choline transporter from Trichoplusia ni.	2005-01	15607656
CDP-choline increases plasma ACTH and potentiates the stimulated release of GH, TSH and LH: the cholinergic involvement.	2004-10	15482372

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:55:40 GMT 2025` Edited by `admin` on `Mon Mar 31 21:55:40 GMT 2025`
Record UNII	ZK7JX4771P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HEMICHOLINIUM

Common Name

English

HEMICHOLINIUM [MI]

Preferred Name

English

MORPHOLINIUM, 2,2'-(1,1'-BIPHENYL)-4,4'-DIYLBIS(2-HYDROXY-4,4-DIMETHYL-

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

Hemicholinium