Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H25NO |
| Molecular Weight | 259.3865 |
| Optical Activity | ( - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1CCCC[C@H]1N2CCC(CC2)C3=CC=CC=C3
InChI
InChIKey=YSSBJODGIYRAMI-IAGOWNOFSA-N
InChI=1S/C17H25NO/c19-17-9-5-4-8-16(17)18-12-10-15(11-13-18)14-6-2-1-3-7-14/h1-3,6-7,15-17,19H,4-5,8-13H2/t16-,17-/m1/s1
| Molecular Formula | C17H25NO |
| Molecular Weight | 259.3865 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
(-)-vesamicol is an active enantiomer of vesamicol (AH5183 or [(-)-trans-2-(4-phenylpiperidino)cyclohexanol]). It inhibits the uptake of acetylcholine into cholinergic neuronal storage vesicles. Vesicular acetylcholine transporter (VAChT) is inhibited by (-)-vesamicol, which binds tightly to an allosteric site.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8619013 | https://www.ncbi.nlm.nih.gov/pubmed/9205789 | https://www.ncbi.nlm.nih.gov/pubmed/1925971https://www.ncbi.nlm.nih.gov/pubmed/26138195 | https://www.ncbi.nlm.nih.gov/pubmed/26872437 | https://www.ncbi.nlm.nih.gov/pubmed/24687885
Curator's Comment: (-)-vesamicol is CNS active in animals. No human data available.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Accessible silanol sites - beneficial for the RP-HPLC separation of constitutional and diastereomeric azaspirovesamicol isomers. | 2010-12-10 |
|
| 3D QSAR study, synthesis, and in vitro evaluation of (+)-5-FBVM as potential PET radioligand for the vesicular acetylcholine transporter (VAChT). | 2010-11-01 |
|
| Search for the acetylcholine and vesamicol binding sites in vesicular acetylcholine transporter: the region around the lumenal end of the transport channel. | 2010-11 |
|
| Enantioseparation of vesamicol and novel vesamicol analogs by high-performance liquid chromatography on different chiral stationary phases. | 2010-06-11 |
|
| Possible important pair of acidic residues in vesicular acetylcholine transporter. | 2010-04-13 |
|
| Synthesis and in vitro biological evaluation of carbonyl group-containing inhibitors of vesicular acetylcholine transporter. | 2010-04-08 |
|
| PET radioligands for the vesicular acetylcholine transporter (VAChT). | 2010 |
|
| Equilibrium binding and transport by vesicular acetylcholine transporter. | 2010 |
|
| Evaluation of radioiodinated vesamicol analogs for sigma receptor imaging in tumor and radionuclide receptor therapy. | 2009-11 |
|
| Multiple protonation states of vesicular acetylcholine transporter detected by binding of [3H]vesamicol. | 2009-09-29 |
|
| The potential of (-)-o-[11C]methylvesamicol for diagnosing cholinergic deficit dementia. | 2009-02 |
|
| Neuroimaging of the vesicular acetylcholine transporter by a novel 4-[18F]fluoro-benzoyl derivative of 7-hydroxy-6-(4-phenyl-piperidin-1-yl)-octahydro-benzo[1,4]oxazines. | 2009-01 |
|
| The epithelial cholinergic system of the airways. | 2008-08 |
|
| First CoMFA characterization of vesamicol analogs as ligands for the vesicular acetylcholine transporter. | 2008-04-10 |
|
| Release of acetylcholine by syringin, an active principle of Eleutherococcus senticosus, to raise insulin secretion in Wistar rats. | 2008-03-28 |
|
| Impairment of muscarinic transmission in transgenic APPswe/PS1dE9 mice. | 2008-03 |
|
| A new 18F-labeled fluoroacetylmorpholino derivative of vesamicol for neuroimaging of the vesicular acetylcholine transporter. | 2008-02 |
|
| Characterization of ouabain-induced noradrenaline and acetylcholine release from in situ cardiac autonomic nerve endings. | 2007-12 |
|
| (E)-[125I]-5-AOIBV: a SPECT radioligand for the vesicular acetylcholine transporter. | 2007-11 |
|
| Increase of acetylcholine release by Panax ginseng root enhances insulin secretion in Wistar rats. | 2007-01-29 |
|
| Mutational and bioinformatics analysis of proline- and glycine-rich motifs in vesicular acetylcholine transporter. | 2006-09 |
|
| Release of acetylcholine by Hon-Chi to raise insulin secretion in Wistar rats. | 2006-08-14 |
|
| 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 |
|
| Optically active trans-2-aminocyclopentanols: chemoenzymatic preparation and application as chiral ligands. | 2006-08-10 |
|
| Synthesis and evaluation of vesamicol analog (-)-O-[11C]methylvesamicol as a PET ligand for vesicular acetylcholine transporter. | 2006-07 |
|
| Taurine elevates dopamine levels in the rat nucleus accumbens; antagonism by strychnine. | 2006-06 |
|
| Evaluation of (+)-p-[11C]methylvesamicol for mapping sigma1 receptors: a comparison with [11C]SA4503. | 2006-05 |
|
| Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor. | 2006-04-15 |
|
| Increase of insulin secretion by ginsenoside Rh2 to lower plasma glucose in Wistar rats. | 2006-02-01 |
|
| Structural changes of benzylether derivatives of vesamicol and their influence on the binding selectivity to the vesicular acetylcholine transporter. | 2005-12 |
|
| Vesicles in snake motor terminals comprise one functional pool and utilize a single recycling strategy at all stimulus frequencies. | 2005-10-15 |
|
| New transport assay demonstrates vesicular acetylcholine transporter has many alternative substrates. | 2005-09 |
|
| Mutational and pH analysis of ionic residues in transmembrane domains of vesicular acetylcholine transporter. | 2005-06-07 |
|
| Synthesis and in vitro evaluation of new benzovesamicol analogues as potential imaging probes for the vesicular acetylcholine transporter. | 2005-02-01 |
|
| Choline is transported by vesicular acetylcholine transporter. | 2004-11 |
|
| Methamidophos transiently inhibits neuronal nicotinic receptors of rat substantia nigra dopaminergic neurons via open channel block. | 2004-10-21 |
|
| Acetylcholine binding site in the vesicular acetylcholine transporter. | 2004-09-07 |
|
| Transmembrane reorientation of the substrate-binding site in vesicular acetylcholine transporter. | 2004-07-13 |
|
| A validated LC method for the determination of vesamicol enantiomers in human plasma using vancomycin chiral stationary phase and solid phase extraction. | 2004-05-28 |
|
| Synthesis of novel 4- and 5-substituted benzyl ether derivatives of vesamicol and in vitro evaluation of their binding properties to the vesicular acetylcholine transporter site. | 2004-03-15 |
|
| Donepezil modulates nicotinic receptors of substantia nigra dopaminergic neurones. | 2004-02 |
|
| Choline acetyltransferase: regulation and coupling with protein kinase and vesicular acetylcholine transporter on synaptic vesicles. | 2004-01 |
|
| Exocytotic release of [3H]-acetylcholine by ouabain involves intracellular Ca2+ stores in rat brain cortical slices. | 2003-12 |
|
| Evaluation of radioiodinated (-)-o-iodovesamicol as a radiotracer for mapping the vesicular acetylcholine transporter. | 2003-09 |
|
| Ethanol elevates accumbal dopamine levels via indirect activation of ventral tegmental nicotinic acetylcholine receptors. | 2003-04-25 |
|
| Diffusion pathways to critical cysteines in the vesicular acetylcholine transporter of Torpedo. | 2003-04 |
|
| Specificity of the rat vesicular acetylcholine transporter. | 2003-04 |
|
| Equilibrium binding and transport studies. | 2003 |
|
| Regulation of vesicular acetylcholine transporter by the activation of excitatory amino acid receptors in the avian retina. | 2002-12 |
|
| Vesamicol analogues as sigma ligands. Molecular determinants of selectivity at the vesamicol receptor. | 1995-03-15 |
Sample Use Guides
In Vivo Use Guide
Curator's Comment: I.p route in rats was used: to assess the effect of vesamicol in vivo, we examined cholinergic parameters, such as the subcellular distribution of ACh, activities of enzymes, uptake of choline, and muscarinic receptor binding in the striatum, hippocampus, and cerebral cortex of rats 30 and 60 min after intraperitoneal injection of vesamicol (3 mg/kg) or of vesamicol in combination with DDVP (5 mg/kg), which was administered 10 min before vasamicol.
https://www.ncbi.nlm.nih.gov/pubmed/9205789
Mice: male nude mice were fed a diet
containing 50 mg vesamicol/kg food (10 mg vesamicol/kg
body weight) per day. The administration of vesamicol decreased the tumor growth rate of A549 human BAC tumors. The administration of 50 mg vesamicol/kg food in
the diet was well tolerated and caused no discomfort or weight loss in mice.
Route of Administration:
Oral
The effects of vesamicol (AH5183), a blocker of acetylcholine transport, on the voltage-clamped neuromuscular junction of the frog were studied. Vesamicol (15-30 uM) reduced the peak height of the ionophoretically applied acetylcholine-induced current. The amplitude of the evoked endplate current was also decreased in the presence of vesamicol (30 uM).
| Substance Class |
Chemical
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| Record UNII |
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RACEMATE -> ACTIVE ENANTIOMER |
IN-VITRO
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