120447-62-3,MFCD06804635
Catalog No.:AA0075Y8

120447-62-3 | (±)-Vesamicol HCl (AH-5183)

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5mg
≥99%(HPLC)
in stock  
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50mg
≥99%(HPLC)
in stock  
$820.00   $574.00
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100mg
≥99%(HPLC)
in stock  
$1,429.00   $1,000.00
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250mg
≥99%(HPLC)
in stock  
$3,143.00   $2,200.00
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  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
Technical Information
Catalog Number:
AA0075Y8
Chemical Name:
(±)-Vesamicol HCl (AH-5183)
CAS Number:
120447-62-3
Molecular Formula:
C17H26ClNO
Molecular Weight:
295.8474
MDL Number:
MFCD06804635
SMILES:
OC1CCCCC1N1CCC(CC1)c1ccccc1.Cl
NSC Number:
759580
Properties
Computed Properties
 
Complexity:
266  
Covalently-Bonded Unit Count:
2  
Defined Atom Stereocenter Count:
0  
Defined Bond Stereocenter Count:
0  
Formal Charge:
0  
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0  
Rotatable Bond Count:
2  
Undefined Atom Stereocenter Count:
2  
Undefined Bond Stereocenter Count:
0  

Literature

Title: Pyrrolovesamicols--synthesis, structure and VAChT binding of two 4-fluorobenzoyl regioisomers.

Journal: Bioorganic & medicinal chemistry letters 20120315

Title: Role of stored calcium in the regulation of neurotransmitter quantum size.

Journal: Bulletin of experimental biology and medicine 20120201

Title: Effects of acetylcholinesterase inhibitor paraoxon denote the possibility of non-quantal acetylcholine release in myocardium of different vertebrates.

Journal: Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology 20120101

Title: Alpha cells secrete acetylcholine as a non-neuronal paracrine signal priming beta cell function in humans.

Journal: Nature medicine 20110701

Title: Non-quantal release of acetylcholine in guinea-pig airways: role of choline transporter.

Journal: Experimental physiology 20110401

Title: Accessible silanol sites - beneficial for the RP-HPLC separation of constitutional and diastereomeric azaspirovesamicol isomers.

Journal: Journal of chromatography. A 20101210

Title: Search for the acetylcholine and vesamicol binding sites in vesicular acetylcholine transporter: the region around the lumenal end of the transport channel.

Journal: Journal of neurochemistry 20101101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: 3D QSAR study, synthesis, and in vitro evaluation of (+)-5-FBVM as potential PET radioligand for the vesicular acetylcholine transporter (VAChT).

Journal: Bioorganic & medicinal chemistry 20101101

Title: Enantioseparation of vesamicol and novel vesamicol analogs by high-performance liquid chromatography on different chiral stationary phases.

Journal: Journal of chromatography. A 20100611

Title: Possible important pair of acidic residues in vesicular acetylcholine transporter.

Journal: Biochemistry 20100413

Title: Synthesis and in vitro biological evaluation of carbonyl group-containing inhibitors of vesicular acetylcholine transporter.

Journal: Journal of medicinal chemistry 20100408

Title: Equilibrium binding and transport by vesicular acetylcholine transporter.

Journal: Methods in molecular biology (Clifton, N.J.) 20100101

Title: Evaluation of radioiodinated vesamicol analogs for sigma receptor imaging in tumor and radionuclide receptor therapy.

Journal: Cancer science 20091101

Title: Multiple protonation states of vesicular acetylcholine transporter detected by binding of [3H]vesamicol.

Journal: Biochemistry 20090929

Title: The potential of (-)-o-[11C]methylvesamicol for diagnosing cholinergic deficit dementia.

Journal: Synapse (New York, N.Y.) 20090201

Title: First CoMFA characterization of vesamicol analogs as ligands for the vesicular acetylcholine transporter.

Journal: Journal of medicinal chemistry 20080410

Title: Impairment of muscarinic transmission in transgenic APPswe/PS1dE9 mice.

Journal: Neurobiology of aging 20080301

Title: A new 18F-labeled fluoroacetylmorpholino derivative of vesamicol for neuroimaging of the vesicular acetylcholine transporter.

Journal: Nuclear medicine and biology 20080201

Title: Mutational and bioinformatics analysis of proline- and glycine-rich motifs in vesicular acetylcholine transporter.

Journal: Journal of neurochemistry 20060901

Title: Synthesis and evaluation of vesamicol analog (-)-O-[11C]methylvesamicol as a PET ligand for vesicular acetylcholine transporter.

Journal: Annals of nuclear medicine 20060701

Title: Taurine elevates dopamine levels in the rat nucleus accumbens; antagonism by strychnine.

Journal: The European journal of neuroscience 20060601

Title: Evaluation of (+)-p-[11C]methylvesamicol for mapping sigma1 receptors: a comparison with [11C]SA4503.

Journal: Nuclear medicine and biology 20060501

Title: Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor.

Journal: Bioorganic & medicinal chemistry 20060415

Title: Increase of insulin secretion by ginsenoside Rh2 to lower plasma glucose in Wistar rats.

Journal: Clinical and experimental pharmacology & physiology 20060101

Title: Structural changes of benzylether derivatives of vesamicol and their influence on the binding selectivity to the vesicular acetylcholine transporter.

Journal: European journal of medicinal chemistry 20051201

Title: Vesicles in snake motor terminals comprise one functional pool and utilize a single recycling strategy at all stimulus frequencies.

Journal: The Journal of physiology 20051015

Title: New transport assay demonstrates vesicular acetylcholine transporter has many alternative substrates.

Journal: Neurochemistry international 20050901

Title: Mutational and pH analysis of ionic residues in transmembrane domains of vesicular acetylcholine transporter.

Journal: Biochemistry 20050607

Title: Choline is transported by vesicular acetylcholine transporter.

Journal: Journal of neurochemistry 20041101

Title: Methamidophos transiently inhibits neuronal nicotinic receptors of rat substantia nigra dopaminergic neurons via open channel block.

Journal: Neuroscience letters 20041021

Title: Acetylcholine binding site in the vesicular acetylcholine transporter.

Journal: Biochemistry 20040907

Title: Transmembrane reorientation of the substrate-binding site in vesicular acetylcholine transporter.

Journal: Biochemistry 20040713

Title: A validated LC method for the determination of vesamicol enantiomers in human plasma using vancomycin chiral stationary phase and solid phase extraction.

Journal: Journal of pharmaceutical and biomedical analysis 20040528

Title: 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.

Journal: Bioorganic & medicinal chemistry 20040315

Title: Choline acetyltransferase: regulation and coupling with protein kinase and vesicular acetylcholine transporter on synaptic vesicles.

Journal: Neurochemical research 20040101

Title: Evaluation of radioiodinated (-)-o-iodovesamicol as a radiotracer for mapping the vesicular acetylcholine transporter.

Journal: Annals of nuclear medicine 20030901

Title: Specificity of the rat vesicular acetylcholine transporter.

Journal: Neurochemical research 20030401

Title: Effects of the venom of a Mygalomorph spider (Lasiodora sp.) on the isolated rat heart.

Journal: Toxicon : official journal of the International Society on Toxinology 20030101

Title: Equilibrium binding and transport studies.

Journal: Methods in molecular biology (Clifton, N.J.) 20030101

Title: Regulation of vesicular acetylcholine transporter by the activation of excitatory amino acid receptors in the avian retina.

Journal: Cellular and molecular neurobiology 20021201

Title: Enantioseparation of vesamicol in human serum by capillary electrophoresis with solid phase extraction and sulfated-beta-cyclodextrin.

Journal: Journal of pharmaceutical and biomedical analysis 20021015

Title: Release of acetylcholine by Die-Huang-Wan to enhance insulin secretion for lowering plasma glucose in Wistar rats.

Journal: Autonomic neuroscience : basic & clinical 20020930

Title: Characterization of radioiodinated (-)-ortho-iodovesamicol binding in rat brain preparations.

Journal: Life sciences 20020816

Title: Analysis of uptake and release of newly synthesized acetylcholine in PC12 cells overexpressing the rat vesicular acetylcholine transporter (VAChT).

Journal: Brain research. Molecular brain research 20020430

Title: PET and SPET tracers for mapping the cardiac nervous system.

Journal: European journal of nuclear medicine and molecular imaging 20020301

Title: Stable beta-secretase activity and presynaptic cholinergic markers during progressive central nervous system amyloidogenesis in Tg2576 mice.

Journal: The American journal of pathology 20020201

Title: Analysis of point mutants in the Caenorhabditis elegans vesicular acetylcholine transporter reveals domains involved in substrate translocation.

Journal: The Journal of biological chemistry 20011109

Title: Release of non-neuronal acetylcholine from the isolated human placenta is mediated by organic cation transporters.

Journal: British journal of pharmacology 20011101

Title: In vivo assessment of acetylcholine-releasing function at cardiac vagal nerve terminals.

Journal: American journal of physiology. Heart and circulatory physiology 20010701

Title: Selective antibody-induced cholinergic cell and synapse loss produce sustained hippocampal and cortical hypometabolism with correlated cognitive deficits.

Journal: Experimental neurology 20010701

Title: Repetitive nerve stimulation decreases the acetylcholine content of quanta at the frog neuromuscular junction.

Journal: The Journal of physiology 20010501

Title: Neurotrophins differentially enhance acetylcholine release, acetylcholine content and choline acetyltransferase activity in basal forebrain neurons.

Journal: Journal of neurochemistry 20010401

Title: Synthesis and evaluation of radiolabeled piperazine derivatives of vesamicol as SPECT agents for cholinergic neurons.

Journal: Nuclear medicine and biology 20010401

Title: Effect of vagal autotransplantation on quantitative [3H]-vesamicol binding image in rats with unilateral lesions of nucleus baslis magnocellularis.

Journal: Neuroscience letters 20010302

Title: Cholinergic activity of aged rhesus monkeys revealed by positron emission tomography.

Journal: Synapse (New York, N.Y.) 20010101

Title: High 3H-vesamicol binding in ALS motor neurons--autoradiographic visulalization of hyperactivities?

Journal: Acta neurologica Scandinavica 20010101

Title: Active transport of acetylcholine by the human vesicular acetylcholine transporter.

Journal: The Journal of biological chemistry 19961101

Title: Vesamicol analogues as sigma ligands. Molecular determinants of selectivity at the vesamicol receptor.

Journal: Biochemical pharmacology 19950315

Title: S M Efange, et al. N-hydroxyalkyl derivatives of 3 beta-phenyltropane and 1-methylspiroH-indoline-3,4'-piperidine: vesamicol analogues with affinity for monoamine transporters. J Med Chem. 1997 Nov 21;40(24):3905-14.

Title: H Kobayashi, et al. Effects of systemic administration of 2-(4-phenyl-piperidino)-cyclohexanol (vesamicol) and an organophosphate DDVP on the cholinergic system in brain regions of rats. Brain Res Bull. 1997;43(1):17-23.

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SDS
Tags:120447-62-3 Molecular Formula|120447-62-3 MDL|120447-62-3 SMILES|120447-62-3 (±)-Vesamicol HCl (AH-5183)
Catalog No.: AA0075Y8
120447-62-3,MFCD06804635
120447-62-3 | (±)-Vesamicol HCl (AH-5183)
Pack Size: 5mg
Purity: ≥99%(HPLC)
in stock
$199.00 $139.00
Pack Size: 50mg
Purity: ≥99%(HPLC)
in stock
$820.00 $574.00
Pack Size: 100mg
Purity: ≥99%(HPLC)
in stock
$1,429.00 $1,000.00
Pack Size: 250mg
Purity: ≥99%(HPLC)
in stock
$3,143.00 $2,200.00
Quantity
- +
Add to Card
Order Now
bulk Quotation Request
Technical Information
Catalog Number: AA0075Y8
Chemical Name: (±)-Vesamicol HCl (AH-5183)
CAS Number: 120447-62-3
Molecular Formula: C17H26ClNO
Molecular Weight: 295.8474
MDL Number: MFCD06804635
SMILES: OC1CCCCC1N1CCC(CC1)c1ccccc1.Cl
NSC Number: 759580
Properties
Complexity: 266  
Covalently-Bonded Unit Count: 2  
Defined Atom Stereocenter Count: 0  
Defined Bond Stereocenter Count: 0  
Formal Charge: 0  
Heavy Atom Count: 20  
Hydrogen Bond Acceptor Count: 2  
Hydrogen Bond Donor Count: 2  
Isotope Atom Count: 0  
Rotatable Bond Count: 2  
Undefined Atom Stereocenter Count: 2  
Undefined Bond Stereocenter Count: 0  
Literature fold

Title: Pyrrolovesamicols--synthesis, structure and VAChT binding of two 4-fluorobenzoyl regioisomers.

Journal: Bioorganic & medicinal chemistry letters20120315

Title: Role of stored calcium in the regulation of neurotransmitter quantum size.

Journal: Bulletin of experimental biology and medicine20120201

Title: Effects of acetylcholinesterase inhibitor paraoxon denote the possibility of non-quantal acetylcholine release in myocardium of different vertebrates.

Journal: Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology20120101

Title: Alpha cells secrete acetylcholine as a non-neuronal paracrine signal priming beta cell function in humans.

Journal: Nature medicine20110701

Title: Non-quantal release of acetylcholine in guinea-pig airways: role of choline transporter.

Journal: Experimental physiology20110401

Title: Accessible silanol sites - beneficial for the RP-HPLC separation of constitutional and diastereomeric azaspirovesamicol isomers.

Journal: Journal of chromatography. A20101210

Title: Search for the acetylcholine and vesamicol binding sites in vesicular acetylcholine transporter: the region around the lumenal end of the transport channel.

Journal: Journal of neurochemistry20101101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters20101101

Title: 3D QSAR study, synthesis, and in vitro evaluation of (+)-5-FBVM as potential PET radioligand for the vesicular acetylcholine transporter (VAChT).

Journal: Bioorganic & medicinal chemistry20101101

Title: Enantioseparation of vesamicol and novel vesamicol analogs by high-performance liquid chromatography on different chiral stationary phases.

Journal: Journal of chromatography. A20100611

Title: Possible important pair of acidic residues in vesicular acetylcholine transporter.

Journal: Biochemistry20100413

Title: Synthesis and in vitro biological evaluation of carbonyl group-containing inhibitors of vesicular acetylcholine transporter.

Journal: Journal of medicinal chemistry20100408

Title: Equilibrium binding and transport by vesicular acetylcholine transporter.

Journal: Methods in molecular biology (Clifton, N.J.)20100101

Title: Evaluation of radioiodinated vesamicol analogs for sigma receptor imaging in tumor and radionuclide receptor therapy.

Journal: Cancer science20091101

Title: Multiple protonation states of vesicular acetylcholine transporter detected by binding of [3H]vesamicol.

Journal: Biochemistry20090929

Title: The potential of (-)-o-[11C]methylvesamicol for diagnosing cholinergic deficit dementia.

Journal: Synapse (New York, N.Y.)20090201

Title: First CoMFA characterization of vesamicol analogs as ligands for the vesicular acetylcholine transporter.

Journal: Journal of medicinal chemistry20080410

Title: Impairment of muscarinic transmission in transgenic APPswe/PS1dE9 mice.

Journal: Neurobiology of aging20080301

Title: A new 18F-labeled fluoroacetylmorpholino derivative of vesamicol for neuroimaging of the vesicular acetylcholine transporter.

Journal: Nuclear medicine and biology20080201

Title: Mutational and bioinformatics analysis of proline- and glycine-rich motifs in vesicular acetylcholine transporter.

Journal: Journal of neurochemistry20060901

Title: Synthesis and evaluation of vesamicol analog (-)-O-[11C]methylvesamicol as a PET ligand for vesicular acetylcholine transporter.

Journal: Annals of nuclear medicine20060701

Title: Taurine elevates dopamine levels in the rat nucleus accumbens; antagonism by strychnine.

Journal: The European journal of neuroscience20060601

Title: Evaluation of (+)-p-[11C]methylvesamicol for mapping sigma1 receptors: a comparison with [11C]SA4503.

Journal: Nuclear medicine and biology20060501

Title: Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor.

Journal: Bioorganic & medicinal chemistry20060415

Title: Increase of insulin secretion by ginsenoside Rh2 to lower plasma glucose in Wistar rats.

Journal: Clinical and experimental pharmacology & physiology20060101

Title: Structural changes of benzylether derivatives of vesamicol and their influence on the binding selectivity to the vesicular acetylcholine transporter.

Journal: European journal of medicinal chemistry20051201

Title: Vesicles in snake motor terminals comprise one functional pool and utilize a single recycling strategy at all stimulus frequencies.

Journal: The Journal of physiology20051015

Title: New transport assay demonstrates vesicular acetylcholine transporter has many alternative substrates.

Journal: Neurochemistry international20050901

Title: Mutational and pH analysis of ionic residues in transmembrane domains of vesicular acetylcholine transporter.

Journal: Biochemistry20050607

Title: Choline is transported by vesicular acetylcholine transporter.

Journal: Journal of neurochemistry20041101

Title: Methamidophos transiently inhibits neuronal nicotinic receptors of rat substantia nigra dopaminergic neurons via open channel block.

Journal: Neuroscience letters20041021

Title: Acetylcholine binding site in the vesicular acetylcholine transporter.

Journal: Biochemistry20040907

Title: Transmembrane reorientation of the substrate-binding site in vesicular acetylcholine transporter.

Journal: Biochemistry20040713

Title: A validated LC method for the determination of vesamicol enantiomers in human plasma using vancomycin chiral stationary phase and solid phase extraction.

Journal: Journal of pharmaceutical and biomedical analysis20040528

Title: 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.

Journal: Bioorganic & medicinal chemistry20040315

Title: Choline acetyltransferase: regulation and coupling with protein kinase and vesicular acetylcholine transporter on synaptic vesicles.

Journal: Neurochemical research20040101

Title: Evaluation of radioiodinated (-)-o-iodovesamicol as a radiotracer for mapping the vesicular acetylcholine transporter.

Journal: Annals of nuclear medicine20030901

Title: Specificity of the rat vesicular acetylcholine transporter.

Journal: Neurochemical research20030401

Title: Effects of the venom of a Mygalomorph spider (Lasiodora sp.) on the isolated rat heart.

Journal: Toxicon : official journal of the International Society on Toxinology20030101

Title: Equilibrium binding and transport studies.

Journal: Methods in molecular biology (Clifton, N.J.)20030101

Title: Regulation of vesicular acetylcholine transporter by the activation of excitatory amino acid receptors in the avian retina.

Journal: Cellular and molecular neurobiology20021201

Title: Enantioseparation of vesamicol in human serum by capillary electrophoresis with solid phase extraction and sulfated-beta-cyclodextrin.

Journal: Journal of pharmaceutical and biomedical analysis20021015

Title: Release of acetylcholine by Die-Huang-Wan to enhance insulin secretion for lowering plasma glucose in Wistar rats.

Journal: Autonomic neuroscience : basic & clinical20020930

Title: Characterization of radioiodinated (-)-ortho-iodovesamicol binding in rat brain preparations.

Journal: Life sciences20020816

Title: Analysis of uptake and release of newly synthesized acetylcholine in PC12 cells overexpressing the rat vesicular acetylcholine transporter (VAChT).

Journal: Brain research. Molecular brain research20020430

Title: PET and SPET tracers for mapping the cardiac nervous system.

Journal: European journal of nuclear medicine and molecular imaging20020301

Title: Stable beta-secretase activity and presynaptic cholinergic markers during progressive central nervous system amyloidogenesis in Tg2576 mice.

Journal: The American journal of pathology20020201

Title: Analysis of point mutants in the Caenorhabditis elegans vesicular acetylcholine transporter reveals domains involved in substrate translocation.

Journal: The Journal of biological chemistry20011109

Title: Release of non-neuronal acetylcholine from the isolated human placenta is mediated by organic cation transporters.

Journal: British journal of pharmacology20011101

Title: In vivo assessment of acetylcholine-releasing function at cardiac vagal nerve terminals.

Journal: American journal of physiology. Heart and circulatory physiology20010701

Title: Selective antibody-induced cholinergic cell and synapse loss produce sustained hippocampal and cortical hypometabolism with correlated cognitive deficits.

Journal: Experimental neurology20010701

Title: Repetitive nerve stimulation decreases the acetylcholine content of quanta at the frog neuromuscular junction.

Journal: The Journal of physiology20010501

Title: Neurotrophins differentially enhance acetylcholine release, acetylcholine content and choline acetyltransferase activity in basal forebrain neurons.

Journal: Journal of neurochemistry20010401

Title: Synthesis and evaluation of radiolabeled piperazine derivatives of vesamicol as SPECT agents for cholinergic neurons.

Journal: Nuclear medicine and biology20010401

Title: Effect of vagal autotransplantation on quantitative [3H]-vesamicol binding image in rats with unilateral lesions of nucleus baslis magnocellularis.

Journal: Neuroscience letters20010302

Title: Cholinergic activity of aged rhesus monkeys revealed by positron emission tomography.

Journal: Synapse (New York, N.Y.)20010101

Title: High 3H-vesamicol binding in ALS motor neurons--autoradiographic visulalization of hyperactivities?

Journal: Acta neurologica Scandinavica20010101

Title: Active transport of acetylcholine by the human vesicular acetylcholine transporter.

Journal: The Journal of biological chemistry19961101

Title: Vesamicol analogues as sigma ligands. Molecular determinants of selectivity at the vesamicol receptor.

Journal: Biochemical pharmacology19950315

Title: S M Efange, et al. N-hydroxyalkyl derivatives of 3 beta-phenyltropane and 1-methylspiroH-indoline-3,4'-piperidine: vesamicol analogues with affinity for monoamine transporters. J Med Chem. 1997 Nov 21;40(24):3905-14.

Title: H Kobayashi, et al. Effects of systemic administration of 2-(4-phenyl-piperidino)-cyclohexanol (vesamicol) and an organophosphate DDVP on the cholinergic system in brain regions of rats. Brain Res Bull. 1997;43(1):17-23.

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