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120786-18-7 | (±)-Huperazine A
CAS No: 120786-18-7 Catalog No: AG003BE6 MDL No:MFCD00171439
Product Description
Catalog Number:
AG003BE6
Chemical Name:
(±)-Huperazine A
CAS Number:
120786-18-7
Molecular Formula:
C15H18N2O
Molecular Weight:
242.3162
MDL Number:
MFCD00171439
IUPAC Name:
(13E)-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)/b11-3+
InChI Key:
ZRJBHWIHUMBLCN-QDEBKDIKSA-N
SMILES:
C/C=C/1\C2C=C(CC1(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:
0
Defined Bond Stereocenter Count:
1
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:
2
Undefined Bond Stereocenter Count:
0
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 |
| 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 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| 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 |
| 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 |
| [+]-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 |
| 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 |
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