200,000+ products from a single source!

sales@angenechem.com

Home > Amines > 102518-79-6

102518-79-6

102518-79-6 | 5,9-Methanocycloocta[b]pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5R,9R,11E)-

CAS No: 102518-79-6 Catalog No: AG0007MO MDL No:MFCD01714949

Product Description

Catalog Number:
AG0007MO
Chemical Name:
5,9-Methanocycloocta[b]pyridin-2(1H)-one, 5-amino-11-ethylidene-5,6,9,10-tetrahydro-7-methyl-, (5R,9R,11E)-
CAS Number:
102518-79-6
Molecular Formula:
C15H18N2O
Molecular Weight:
242.3162
MDL Number:
MFCD01714949
IUPAC Name:
(1R,9R)-1-amino-13-ethylidene-11-methyl-6-azatricyclo[7.3.1.02,7]trideca-2(7),3,10-trien-5-one
InChI:
InChI=1S/C15H18N2O/c1-3-11-10-6-9(2)8-15(11,16)12-4-5-14(18)17-13(12)7-10/h3-6,10H,7-8,16H2,1-2H3,(H,17,18)/t10-,15+/m0/s1
InChI Key:
ZRJBHWIHUMBLCN-ZUZCIYMTSA-N
SMILES:
C/C=C/1\[C@H]2C=C(C[C@]1(N)c1c(C2)[nH]c(=O)cc1)C
EC Number:
600-320-6

Properties

Complexity:
551  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
0
Exact Mass:
242.142g/mol
Formal Charge:
0
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
242.322g/mol
Monoisotopic Mass:
242.142g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
55.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
1  
XLogP3:
0

Literature

Title Journal
Abcb1a but not Abcg2 played a predominant role in limiting the brain distribution of Huperzine A in mice. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20170901
Zebrafish is a predictive model for identifying compounds that protect against brain toxicity in severe acute organophosphorus intoxication. Archives of toxicology 20170101
Design and synthesis of N-substituted-2-hydroxyiminoacetamides and interactions with cholinesterases. Chemico-biological interactions 20161125
Human serum albumin reduces the potency of acetylcholinesterase inhibitor based drugs for Alzheimer's disease. Chemico-biological interactions 20160405
The role of cholinergic anti-inflammatory pathway in acetic acid-induced colonic inflammation in the rat. Chemico-biological interactions 20130905
Development and validation of a simple assay for the determination of cholinesterase activity in whole blood of laboratory animals. Journal of applied toxicology : JAT 20130401
A combination of [+] and [-]-Huperzine A improves protection against soman toxicity compared to [+]-Huperzine A in guinea pigs. Chemico-biological interactions 20130325
Acetylcholinesterase deficiency decreases apoptosis in dopaminergic neurons in the neurotoxin model of Parkinson's disease. The international journal of biochemistry & cell biology 20130201
An efficient total synthesis of (-)-huperzine A. Organic letters 20120907
Huperzine A ameliorates cognitive deficits and oxidative stress in the hippocampus of rats exposed to acute hypobaric hypoxia. Neurochemical research 20120901
Simultaneously preparative purification of Huperzine A and Huperzine B from Huperzia serrata by macroporous resin and preparative high performance liquid chromatography. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120901
Microemulsion-based patch for transdermal delivery of huperzine A and ligustrazine phosphate in treatment of Alzheimer's disease. Drug development and industrial pharmacy 20120601
Toxicological scoring of Alzheimer's disease drug huperzine in a guinea pig model. Toxicology mechanisms and methods 20120401
Symptomatic and nonamyloid/tau based pharmacologic treatment for Alzheimer disease. Cold Spring Harbor perspectives in medicine 20120301
Chiral separation of Huperzine A using CE - method validation and application in pharmaceutical formulations. Electrophoresis 20120201
Treatment with Huperzine A improves cognition in vascular dementia patients. Cell biochemistry and biophysics 20120101
Huperzine A derivative M3 protects PC12 cells against sodium nitroprusside-induced apoptosis. Acta pharmacologica Sinica 20120101
Examining the interactome of huperzine A by magnetic biopanning. PloS one 20120101
[+]-Huperzine A protects against soman toxicity in guinea pigs. Neurochemical research 20111201
Isolation and characterization of endophytic huperzine A-producing fungi from Huperzia serrata. Journal of industrial microbiology & biotechnology 20110901
An overview on natural cholinesterase inhibitors--a multi-targeted drug class--and their mass production. Mini reviews in medicinal chemistry 20110901
Bis(12)-hupyridone, a novel multifunctional dimer, promotes neuronal differentiation more potently than its monomeric natural analog huperzine A possibly through α7 nAChR. Brain research 20110715
The effects of huperzine A and IDRA 21 on visual recognition memory in young macaques. Neuropharmacology 20110601
Huperzine A activates Wnt/β-catenin signaling and enhances the nonamyloidogenic pathway in an Alzheimer transgenic mouse model. Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology 20110401
Binding of huperzine A and galanthamine to acetylcholinesterase, based on ONIOM method. Nanomedicine : nanotechnology, biology, and medicine 20110201
Improved thin-layer chromatography bioautographic assay for the detection of actylcholinesterase inhibitors in plants. Phytochemical analysis : PCA 20110101
Huperzine induces alteration in oxidative balance and antioxidants in a guinea pig model. Neuro endocrinology letters 20110101
Coadministration of huperzine A and ligustrazine phosphate effectively reverses scopolamine-induced amnesia in rats. Pharmacology, biochemistry, and behavior 20101001
Photohuperzine A-A new photoisomer of huperzine A: structure elucidation, formation kinetics and activity assessment. Journal of pharmaceutical and biomedical analysis 20100605
Preparation, optimization and characteristic of huperzine a loaded nanostructured lipid carriers. Chemical & pharmaceutical bulletin 20100501
Huperzine a improves chronic inflammation and cognitive decline in rats with cerebral hypoperfusion. Journal of neuroscience research 20100301
Intrathecal huperzine A increases thermal escape latency and decreases flinching behavior in the formalin test in rats. Neuroscience letters 20100205
Systemic administration of the potential countermeasure huperzine reversibly inhibits central and peripheral acetylcholinesterase activity without adverse cognitive-behavioral effects. Pharmacology, biochemistry, and behavior 20100101
Effectiveness of donepezil, rivastigmine, and (+/-)huperzine A in counteracting the acute toxicity of organophosphorus nerve agents: comparison with galantamine. The Journal of pharmacology and experimental therapeutics 20091201
Rational design and synthesis of highly potent anti-acetylcholinesterase activity huperzine A derivatives. Bioorganic & medicinal chemistry 20091001
Matrine determination and pharmacokinetics in human plasma using LC/MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20091001
Clinical use of an herbal-derived compound (Huperzine A) to treat putative complex partial seizures in a dog. Epilepsy & behavior : E&B 20090801
Green tea polyphenol (-)-epigallocatechin-3-gallate enhances the inhibitory effect of huperzine A on acetylcholinesterase by increasing the affinity with serum albumin. Nutritional neuroscience 20090801
Cholinergic deficiency involved in vascular dementia: possible mechanism and strategy of treatment. Acta pharmacologica Sinica 20090701
[Release mechanism of huperzine-A swelling sustained-release tablets]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090701
BZYX, a novel acetylcholinesterase inhibitor, significantly improved chemicals-induced learning and memory impairments on rodents and protected PC12 cells from apoptosis induced by hydrogen peroxide. European journal of pharmacology 20090624
Huperzine A protects isolated rat brain mitochondria against beta-amyloid peptide. Free radical biology & medicine 20090601
Two-dimensional turbulent flow chromatography coupled on-line to liquid chromatography-mass spectrometry for solution-based ligand screening against multiple proteins. Journal of chromatography. A 20090320
Lycojapodine A, a novel alkaloid from Lycopodium japonicum. Organic letters 20090319
Brain acetylcholinesterase activity controls systemic cytokine levels through the cholinergic anti-inflammatory pathway. Brain, behavior, and immunity 20090101
Huperzine A for vascular dementia. The Cochrane database of systematic reviews 20090101
Development of a sensitive high-performance liquid chromatographic method with simple extraction for simultaneous determination of huperzine A and huperzine B in the species containing lycopodium alkaloids. Journal of AOAC International 20090101
Protection of red blood cell acetylcholinesterase by oral huperzine A against ex vivo soman exposure: next generation prophylaxis and sequestering of acetylcholinesterase over butyrylcholinesterase. Chemico-biological interactions 20080925
Anti-acetylcholinesterase activities of traditional Chinese medicine for treating Alzheimer's disease. Chemico-biological interactions 20080925
[+]-Huperzine A treatment protects against N-methyl-D-aspartate-induced seizure/status epilepticus in rats. Chemico-biological interactions 20080925
The combination of huperzine A and imidazenil is an effective strategy to prevent diisopropyl fluorophosphate toxicity in mice. Proceedings of the National Academy of Sciences of the United States of America 20080916
Huperzine A attenuates mitochondrial dysfunction after middle cerebral artery occlusion in rats. Journal of neuroscience research 20080815
Huperzine A exhibits anti-inflammatory and neuroprotective effects in a rat model of transient focal cerebral ischemia. Journal of neurochemistry 20080801
Huperzine A for Alzheimer's disease. The Cochrane database of systematic reviews 20080416
Determination of huperzine A in human plasma by liquid chromatography-electrospray tandem mass spectrometry: application to a bioequivalence study on Chinese volunteers. Biomedical chromatography : BMC 20080401
Investigation of the mechanism of enhanced effect of EGCG on huperzine A's inhibition of acetylcholinesterase activity in rats by a multispectroscopic method. Journal of agricultural and food chemistry 20080213
Non-cholinergic effects of huperzine A: beyond inhibition of acetylcholinesterase. Cellular and molecular neurobiology 20080201
[Effects of huperzine A on cognitive function of rats recovering from general anesthesia]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20080201
Huperzine A reverses cholinergic and monoaminergic dysfunction induced by bilateral nucleus basalis magnocellularis injection of beta-amyloid peptide (1-40) in rats. Cellular and molecular neurobiology 20080101
Huperzine A provides neuroprotection against several cell death inducers using in vitro model systems of motor neuron cell death. Neurotoxicity research 20080101
Huperzine A regulates amyloid precursor protein processing via protein kinase C and mitogen-activated protein kinase pathways in neuroblastoma SK-N-SH cells over-expressing wild type human amyloid precursor protein 695. Neuroscience 20071205
East meets West in the search for Alzheimer's therapeutics - novel dimeric inhibitors from tacrine and huperzine A. Current Alzheimer research 20070901
Determination of Huperzine A in rat plasma by high-performance liquid chromatography with a fluorescence detector. Journal of pharmaceutical and biomedical analysis 20070509
Involvement of M1-muscarinic acetylcholine receptors, protein kinase C and mitogen-activated protein kinase in the effect of huperzine A on secretory amyloid precursor protein-alpha. Neuroreport 20070507
Huperzine A as add-on therapy in patients with treatment-resistant schizophrenia: an open-labeled trial. Schizophrenia research 20070501
Reversible inhibition of acetylcholinesterase by carbamates or huperzine A increases residual activity of the enzyme upon soman challenge. Toxicology 20070420
Sensitivity of butyrylcholinesterase knockout mice to (--)-huperzine A and donepezil suggests humans with butyrylcholinesterase deficiency may not tolerate these Alzheimer's disease drugs and indicates butyrylcholinesterase function in neurotransmission. Toxicology 20070420
The effects of Liuwei Dihuang decoction on the gene expression in the hippocampus of senescence-accelerated mouse. Fitoterapia 20070401
Prolonged effects of poly(lactic-co-glycolic acid) microsphere-containing huperzine A on mouse memory dysfunction induced by scopolamine. Basic & clinical pharmacology & toxicology 20070301
Huperzine A protects C6 rat glioma cells against oxygen-glucose deprivation-induced injury. FEBS letters 20070220
Preparative isolation of huperzines A and B from Huperzia serrata by displacement centrifugal partition chromatography. Journal of chromatography. A 20070126
Simple determination of huperzine A in human plasma by liquid chromatographic-tandem mass spectrometric method. Biomedical chromatography : BMC 20070101
Bivalent ligands derived from Huperzine A as acetylcholinesterase inhibitors. Current topics in medicinal chemistry 20070101
Binding of 13-amidohuprines to acetylcholinesterase: exploring the ligand-induced conformational change of the gly117-gly118 peptide bond in the oxyanion hole. Journal of medicinal chemistry 20061116
[Effect of huperzine A on cerebral cholinesterase and acetylcholine in elderly patients during recovery from general anesthesia]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University 20061101
Editorial: natural products chemistry in China. Natural product reports 20061001
Effects of huperzine A on amyloid precursor protein processing and beta-amyloid generation in human embryonic kidney 293 APP Swedish mutant cells. Journal of neuroscience research 20060901
Comparative studies of huperzine A, donepezil, and rivastigmine on brain acetylcholine, dopamine, norepinephrine, and 5-hydroxytryptamine levels in freely-moving rats. Acta pharmacologica Sinica 20060901
Harmless herbs? Think again: merits of a complete medication history. Journal of the American Medical Directors Association 20060901
Effective countermeasure against poisoning by organophosphorus insecticides and nerve agents. Proceedings of the National Academy of Sciences of the United States of America 20060829
Kinetic analysis of the protection afforded by reversible inhibitors against irreversible inhibition of acetylcholinesterase by highly toxic organophosphorus compounds. Biochemical pharmacology 20060728
Acetylcholinesterase triggers the aggregation of PrP 106-126. Biochemical and biophysical research communications 20060721
Position statement of the American Association for Geriatric Psychiatry regarding principles of care for patients with dementia resulting from Alzheimer disease. The American journal of geriatric psychiatry : official journal of the American Association for Geriatric Psychiatry 20060701
Discovery of huperzine A-tacrine hybrids as potent inhibitors of human cholinesterases targeting their midgorge recognition sites. Journal of medicinal chemistry 20060601
[Experimental study on protective effects of HupA in the treatment of isocarbophos poisoning]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases 20060601
Huperzine A attenuates mitochondrial dysfunction in beta-amyloid-treated PC12 cells by reducing oxygen free radicals accumulation and improving mitochondrial energy metabolism. Journal of neuroscience research 20060501
[Effect of HuperzineA on neurophathologic change of mouse exposed by isocarbophos and phoxim]. Wei sheng yan jiu = Journal of hygiene research 20060501
Molecular lipophilicity determination of a huperzine series by HPLC: comparison of C18 and IAM stationary phases. Journal of pharmaceutical and biomedical analysis 20060411
Quantification of huperzine A in Huperzia serrata by HPLC-UV and identification of the major constituents in its alkaloid extracts by HPLC-DAD-MS-MS. Journal of pharmaceutical and biomedical analysis 20060303
Simultaneous determination of ZT-1 and its metabolite Huperzine A in plasma by high-performance liquid chromatography with ultraviolet detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060102
Effects of a memory enhancing peptide on cognitive abilities of brain-lesioned mice: additivity with huperzine A and relative potency to tacrine. Journal of peptide science : an official publication of the European Peptide Society 20060101
Progress in studies of huperzine A, a natural cholinesterase inhibitor from Chinese herbal medicine. Acta pharmacologica Sinica 20060101
In vitro and in vivo characterization of huperzine a loaded microspheres made from end-group uncapped poly(d,l-lactide acid) and poly(d,l-lactide-co-glycolide acid). Chemical & pharmaceutical bulletin 20060101
Herbal medicine in the treatment of Alzheimer's disease. American journal of Alzheimer's disease and other dementias 20060101
Towards a unifying hypothesis of Alzheimer's disease: cholinergic system linked to plaques, tangles and neuroinflammation. Current medicinal chemistry 20060101
Oral administration of pyridostigmine bromide and huperzine A protects human whole blood cholinesterases from ex vivo exposure to soman. Chemico-biological interactions 20051215
Molecular and pharmacological characterization of muscarinic receptors in retinal pigment epithelium: role in light-adaptive pigment movements. Journal of neurochemistry 20051201
Nicotinic-receptor potentiator drugs, huprine X and galantamine, increase ACh release by blocking AChE activity but not acting on nicotinic receptors. Brain research 20051109
A cyanopropyl reversed phase chromatography enables resolution of huperzine A and B on analytical and preparative scales. Journal of separation science 20051101
Huperzine A protects SHSY5Y neuroblastoma cells against oxidative stress damage via nerve growth factor production. European journal of pharmacology 20050905
Optimization of the capillary zone electrophoresis method for Huperzine A determination using experimental design and artificial neural networks. Journal of chromatography. A 20050819
Huperzine A--human serum albumin association: chromatographic and thermodynamic approach. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050625
Effects of huperzine A on secretion of nerve growth factor in cultured rat cortical astrocytes and neurite outgrowth in rat PC12 cells. Acta pharmacologica Sinica 20050601
Ion-pair reverse-phase high performance liquid chromatography method for determination of Huperzine-A in beagle dog serum. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050325
Effect of acidic oligosaccharide sugar chain on scopolamine-induced memory impairment in rats and its related mechanisms. Neuroscience letters 20050221
Effects of acetylcholinesterase and butyrylcholinesterase inhibition on breathing in mice adapted or not to reduced acetylcholinesterase. Pharmacology, biochemistry, and behavior 20050101
Neuroprotective effects of huperzine A. A natural cholinesterase inhibitor for the treatment of Alzheimer's disease. Neuro-Signals 20050101
The Lycopodium alkaloids. Natural product reports 20041201
(+/-)-huprine Y, (-)-huperzine A and tacrine do not show neuroprotective properties in an apoptotic model of neuronal cytoskeletal alteration. Journal of Alzheimer's disease : JAD 20041201
Recent pharmacological studies on natural products in China. European journal of pharmacology 20041001
Comparative effects of huperzine A, donepezil and rivastigmine on cortical acetylcholine level and acetylcholinesterase activity in rats. Neuroscience letters 20040506
Apoptosis induced by beta-amyloid25-35 in acetylcholinesterase-overexpressing neuroblastoma cells. Acta pharmacologica Sinica 20030901
A convergent approach to huperzine A and analogues. Organic & biomolecular chemistry 20030821
Effects of huperzine A on liver cytochrome P-450 in rats. Acta pharmacologica Sinica 20030801
[Studies on analogues of huperzine A for treatment of senile dementia. VI. Asymmetric total synthesis of 14-nor-huperzine A and its inhibitory activity of acetylcholinesterase]. Yao xue xue bao = Acta pharmaceutica Sinica 20030501
Huperzine A attenuates the neurotoxic effect of staurosporine in primary rat cortical neurons. Neuroscience letters 20030410
Potentiation of acetylcholine action by huperzine-A and physostigmine on some vertebrate effectors, including human iris sphincter muscle. Journal of ocular pharmacology and therapeutics : the official journal of the Association for Ocular Pharmacology and Therapeutics 20030401
Acute effects of huperzine A and tacrine on rat liver. Acta pharmacologica Sinica 20030301
Determination of huperzine A in formulated products by reversed-phase-liquid chromatography using diode array and electrospray ionization mass spectrometric detection. Phytomedicine : international journal of phytotherapy and phytopharmacology 20030301
Identification of cytochrome P450 1A2 as enzyme involved in the microsomal metabolism of Huperzine A. European journal of pharmacology 20030214
Enantiomer effects of huperzine A on the aryl acylamidase activity of human cholinesterases. Cellular and molecular neurobiology 20030201
Plants with traditional uses and activities, relevant to the management of Alzheimer's disease and other cognitive disorders. Phytotherapy research : PTR 20030101
Effects of huperzine A on acetylcholinesterase isoforms in vitro: comparison with tacrine, donepezil, rivastigmine and physostigmine. European journal of pharmacology 20021129
Ginkgolide A, B, and huperzine A inhibit nitric oxide-induced neurotoxicity. International immunopharmacology 20021001
X-ray structures of Torpedo californica acetylcholinesterase complexed with (+)-huperzine A and (-)-huperzine B: structural evidence for an active site rearrangement. Biochemistry 20020903
[Advances in search for acetylcholinesterase inhibitor based on the double active sites hypothesis]. Yao xue xue bao = Acta pharmaceutica Sinica 20020901
Subchronic administration of pyridostigmine or huperzine to primates: compared efficacy against soman toxicity. Drug and chemical toxicology 20020801
Huperzine A, a nootropic agent, inhibits fast transient potassium current in rat dissociated hippocampal neurons. Neuroscience letters 20020510
Review of the value of huperzine as pretreatment of organophosphate poisoning. Neurotoxicology 20020501
3D structure of Torpedo californica acetylcholinesterase complexed with huprine X at 2.1 A resolution: kinetic and molecular dynamic correlates. Biochemistry 20020305
Spermidine antagonizes the inhibitory effect of huperzine A on [3H]dizocilpine (MK-801) binding in synaptic membrane of rat cerebral cortex. Neuroscience letters 20020215
Stereoselectivities of enantiomers of huperzine A in protection against beta-amyloid(25-35)-induced injury in PC12 and NG108-15 cells and cholinesterase inhibition in mice. Neuroscience letters 20020114
Huperzine A attenuates amyloid beta-peptide fragment 25-35-induced apoptosis in rat cortical neurons via inhibiting reactive oxygen species formation and caspase-3 activation. Journal of neuroscience research 20020101
Effect of huperzine A on working memory in reserpine- or yohimbine-treated monkeys. European journal of pharmacology 20011221
The NMDA receptor ion channel: a site for binding of Huperzine A. Journal of applied toxicology : JAT 20011201
Huperzine A attenuates cognitive deficits and hippocampal neuronal damage after transient global ischemia in gerbils. Neuroscience letters 20011109
Tacrine-huperzine A hybrids (huprines): a new class of highly potent and selective acetylcholinesterase inhibitors of interest for the treatment of Alzheimer's disease. Mini reviews in medicinal chemistry 20010701
Huperzine A and donepezil protect rat pheochromocytoma cells against oxygen-glucose deprivation. Neuroscience letters 20010622
Subchronic administration of various pretreatments of nerve agent poisoning. I. Protection of blood and central cholinesterases, innocuousness towards blood-brain barrier permeability. Drug and chemical toxicology 20010501
Subchronic administration of various pretreatments of nerve agent poisoning. II. Compared efficacy against soman toxicity. Drug and chemical toxicology 20010501
Long-term potentiation in hippocampus of rats is enhanced by endogenous acetylcholine in a way that is independent of N-methyl-D-aspartate receptors. Neuroscience letters 20010316
Effects of Huperzine used as pre-treatment against soman-induced seizures. Neurotoxicology 20010201
Huperzine A, a nootropic alkaloid, inhibits N-methyl-D-aspartate-induced current in rat dissociated hippocampal neurons. Neuroscience 20010101
Reversal of scopolamine-induced deficits in radial maze performance by (-)-huperzine A: comparison with E2020 and tacrine. European journal of pharmacology 19980522
Effect of huperzine A, a novel acetylcholinesterase inhibitor, on radial maze performance in rats. Pharmacology, biochemistry, and behavior 19950101

© 2019 Angene International Limited. All rights Reserved.