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15920-93-1 | L-Alanine, 3-(methylamino)-
CAS No: 15920-93-1 Catalog No: AG001QK9 MDL No:MFCD00055227
Product Description
Catalog Number:
AG001QK9
Chemical Name:
L-Alanine, 3-(methylamino)-
CAS Number:
15920-93-1
Molecular Formula:
C4H10N2O2
Molecular Weight:
118.1344
MDL Number:
MFCD00055227
IUPAC Name:
(2S)-2-amino-3-(methylamino)propanoic acid
InChI:
InChI=1S/C4H10N2O2/c1-6-2-3(5)4(7)8/h3,6H,2,5H2,1H3,(H,7,8)/t3-/m0/s1
InChI Key:
UJVHVMNGOZXSOZ-VKHMYHEASA-N
SMILES:
CNC[C@@H](C(=O)O)N
UNII:
108SA6URTV
Properties
Complexity:
84.1
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
1
Defined Bond Stereocenter Count:
0
Exact Mass:
118.074g/mol
Formal Charge:
0
Heavy Atom Count:
8
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
118.136g/mol
Monoisotopic Mass:
118.074g/mol
Rotatable Bond Count:
3
Topological Polar Surface Area:
75.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.8
Literature
| Title | Journal |
|---|---|
| Excitotoxic potential of the cyanotoxin β-methyl-amino-L-alanine (BMAA) in primary human neurons. | Toxicon : official journal of the International Society on Toxinology 20121101 |
| Reactivity of β-methylamino-L-alanine in complex sample matrixes complicating detection and quantification by mass spectrometry. | Analytical chemistry 20120918 |
| Weak BMAA toxicity compares with that of the dietary supplement β-alanine. | Neurobiology of aging 20120701 |
| The non-protein amino acid β-N-methylamino-L-alanine in Portuguese cyanobacterial isolates. | Amino acids 20120601 |
| Selective LC-MS/MS method for the identification of BMAA from its isomers in biological samples. | Analytical and bioanalytical chemistry 20120601 |
| Analytical techniques for the detection of α-amino-β-methylaminopropionic acid. | The Analyst 20120507 |
| Shark fin consumption may expose people to neurotoxic BMAA. | Environmental health perspectives 20120501 |
| Elucidation of matrix effects and performance of solid-phase extraction for LC-MS/MS analysis of β-N-methylamino-L-alanine (BMAA) and 2,4-diaminobutyric acid (DAB) neurotoxins in cyanobacteria. | The Analyst 20120307 |
| Synergistic toxicity of the environmental neurotoxins methylmercury and β-N-methylamino-L-alanine. | Neuroreport 20120307 |
| Reversed-phase HPLC/FD method for the quantitative analysis of the neurotoxin BMAA (β-N-methylamino-L-alanine) in cyanobacteria. | Toxicon : official journal of the International Society on Toxinology 20120301 |
| The emerging science of BMAA: do cyanobacteria contribute to neurodegenerative disease? | Environmental health perspectives 20120301 |
| Cyanobacterial neurotoxin β-N-methylamino-L-alanine (BMAA) in shark fins. | Marine drugs 20120201 |
| The effect of exogenous β-N-methylamino-L: -alanine on the growth of Synechocystis PCC6803. | Microbial ecology 20120101 |
| Spatial clustering of amyotrophic lateral sclerosis and the potential role of BMAA. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20120101 |
| A comparative study on three analytical methods for the determination of the neurotoxin BMAA in cyanobacteria. | PloS one 20120101 |
| Determination of the non protein amino acid β-N-methylamino-l-alanine in estuarine cyanobacteria by capillary electrophoresis. | Toxicon : official journal of the International Society on Toxinology 20111001 |
| Does α-amino-β-methylaminopropionic acid (BMAA) play a role in neurodegeneration? | International journal of environmental research and public health 20110901 |
| Nitrogen starvation of cyanobacteria results in the production of β-N-methylamino-L-alanine. | Toxicon : official journal of the International Society on Toxinology 20110801 |
| Amyotrophic lateral sclerosis: one or multiple causes? | Neurology international 20110406 |
| The effect of β-N-methylamino-L-alanine (BMAA) on oxidative stress response enzymes of the macrophyte Ceratophyllum demersum. | Toxicon : official journal of the International Society on Toxinology 20110401 |
| Washed cycad flour contains β-N-methyl amino-L-alanine and may explain parkinsonism symptoms. | Annals of neurology 20110201 |
| β-N-Methylamino-L-alanine (BMAA) uptake by the aquatic macrophyte Ceratophyllum demersum. | Ecotoxicology and environmental safety 20110101 |
| The cyanobacteria derived toxin Beta-N-methylamino-L-alanine and amyotrophic lateral sclerosis. | Toxins 20101201 |
| Distinguishing the cyanobacterial neurotoxin beta-N-methylamino-L-alanine (BMAA) from its structural isomer 2,4-diaminobutyric acid (2,4-DAB). | Toxicon : official journal of the International Society on Toxinology 20101101 |
| β-N-methylamino-L-alanine induces neurological deficits and shortened life span in Drosophila. | Toxins 20101101 |
| Cycas micronesica (Cycadales) plants devoid of endophytic cyanobacteria increase in beta-methylamino-L-alanine. | Toxicon : official journal of the International Society on Toxinology 20100915 |
| Development and application of a comprehensive two-dimensional gas chromatography with time-of-flight mass spectrometry method for the analysis of L-beta-methylamino-alanine in human tissue. | Journal of chromatography. A 20100702 |
| Detection of the neurotoxin BMAA within cyanobacteria isolated from freshwater in China. | Toxicon : official journal of the International Society on Toxinology 20100501 |
| Metabotropic glutamate receptor 1 mediates the electrophysiological and toxic actions of the cycad derivative beta-N-Methylamino-L-alanine on substantia nigra pars compacta DAergic neurons. | The Journal of neuroscience : the official journal of the Society for Neuroscience 20100414 |
| Selective death of cholinergic neurons induced by beta-methylamino-L-alanine. | Neuroreport 20100106 |
| LC-MS/MS determination of the isomeric neurotoxins BMAA (beta-N-methylamino-L-alanine) and DAB (2,4-diaminobutyric acid) in cyanobacteria and seeds of Cycas revoluta and Lathyrus latifolius. | Toxicon : official journal of the International Society on Toxinology 20100101 |
| Analytical protocol for identification of BMAA and DAB in biological samples. | The Analyst 20100101 |
| Effects of the cyanobacterial neurotoxin beta-N-methylamino-L-alanine on the early-life stage development of zebrafish (Danio rerio). | Aquatic toxicology (Amsterdam, Netherlands) 20091213 |
| Long-term cognitive impairments in adult rats treated neonatally with beta-N-Methylamino-L-Alanine. | Toxicological sciences : an official journal of the Society of Toxicology 20091101 |
| Parkinson-dementia complex and development of a new stable isotope dilution assay for BMAA detection in tissue. | Toxicology and applied pharmacology 20091015 |
| Cyanobacterial neurotoxin BMAA in ALS and Alzheimer's disease. | Acta neurologica Scandinavica 20091001 |
| Liquid chromatographic determination of the cyanobacterial toxin beta-n-methylamino-L-alanine in algae food supplements, freshwater fish, and bottled water. | Journal of food protection 20090801 |
| Augmentation and ionic mechanism of effect of beta-N-methylamino-L-alanine in presence of bicarbonate on membrane potential of Retzius nerve cells of the leech Haemopis sanguisuga. | Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20090701 |
| A mutation in the Proteosomal Regulatory Particle AAA-ATPase-3 in Arabidopsis impairs the light-specific hypocotyl elongation response elicited by a glutamate receptor agonist, BMAA. | Plant molecular biology 20090701 |
| Selective brain uptake and behavioral effects of the cyanobacterial toxin BMAA (beta-N-methylamino-L-alanine) following neonatal administration to rodents. | Toxicological sciences : an official journal of the Society of Toxicology 20090601 |
| beta-N-methylamino-l-alanine induces oxidative stress and glutamate release through action on system Xc(-). | Experimental neurology 20090601 |
| Cycad seeds and chronic neurologic disease (Cycas species). | Disease-a-month : DM 20090601 |
| beta-N-methylamino-L-alanine induced in vivo retinal cell death. | Journal of neurochemistry 20090501 |
| Lack of cerebral bmaa in human cerebral cortex. | Neurology 20090414 |
| 1H NMR determination of beta-N-methylamino-L-alanine (L-BMAA) in environmental and biological samples. | Toxicon : official journal of the International Society on Toxinology 20090401 |
| The ALS/PDC syndrome of Guam and the cycad hypothesis. | Neurology 20090203 |
| The ALS/PDC syndrome of Guam and the cycad hypothesis. | Neurology 20090203 |
| The ALS/PDC syndrome of Guam and the cycad hypothesis. | Neurology 20090203 |
| Retention of the cyanobacterial neurotoxin beta-N-methylamino-l-alanine in melanin and neuromelanin-containing cells--a possible link between Parkinson-dementia complex and pigmentary retinopathy. | Pigment cell & melanoma research 20090201 |
| Improving derivatization efficiency of BMAA utilizing AccQ-Tag in a complex cyanobacterial matrix. | Amino acids 20090101 |
| Beta-methylamino-L-alanine analysis by liquid chromatography tandem mass spectrometry with iTRAQ as the derivative. | European journal of mass spectrometry (Chichester, England) 20090101 |
| Beyond Guam: the cyanobacteria/BMAA hypothesis of the cause of ALS and other neurodegenerative diseases. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| Three phases of research on beta-N-methylamino-L-alanine (BMAA)--a neurotoxic amino acid. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| Previous studies underestimate BMAA concentrations in cycad flour. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| Consumption of fa cai Nostoc soup: a potential for BMAA exposure from Nostoc cyanobacteria in China? | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| Mechanisms of beta-N-methylamino-L-alanine induced neurotoxicity. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| BMAA neurotoxicity in Drosophila. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| Toxicity of the cyanobacterial neurotoxin beta-N-methylamino-L-alanine to three aquatic animal species. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| Cyanobacteria, neurotoxins and water resources: are there implications for human neurodegenerative disease? | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| Determination of the neurotoxins BMAA (beta-N-methylamino-L-alanine) and DAB (alpha-,gamma-diaminobutyric acid) by LC-MSMS in Dutch urban waters with cyanobacterial blooms. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| A cluster of amyotrophic lateral sclerosis in New Hampshire: a possible role for toxic cyanobacteria blooms. | Amyotrophic lateral sclerosis : official publication of the World Federation of Neurology Research Group on Motor Neuron Diseases 20090101 |
| Determination of the neurotoxin BMAA (beta-N-methylamino-L-alanine) in cycad seed and cyanobacteria by LC-MS/MS (liquid chromatography tandem mass spectrometry). | The Analyst 20081201 |
| Beta-N-methylamino-L-alanine (BMAA) in novel South African cyanobacterial isolates. | Ecotoxicology and environmental safety 20081001 |
| Cyanobacteria (Nostoc commune) used as a dietary item in the Peruvian highlands produce the neurotoxic amino acid BMAA. | Journal of ethnopharmacology 20080619 |
| Effective determination method for a cyanobacterial neurotoxin, beta-N-methylamino-L-alanine. | Toxicon : official journal of the International Society on Toxinology 20080601 |
| Co-occurrence of beta-N-methylamino-L-alanine, a neurotoxic amino acid with other cyanobacterial toxins in British waterbodies, 1990-2004. | Environmental microbiology 20080301 |
| Animal models of BMAA neurotoxicity: a critical review. | Life sciences 20080130 |
| Toxin types, toxicokinetics and toxicodynamics. | Advances in experimental medicine and biology 20080101 |
| Conventional laboratory methods for cyanotoxins. | Advances in experimental medicine and biology 20080101 |
| [Revisit to Kii ALS--the innovated concept of ALS-Parkinsonism-dementia complex, clinicopathological features, epidemiology and etiology]. | Brain and nerve = Shinkei kenkyu no shinpo 20071001 |
| Is there a role for naturally occurring cyanobacterial toxins in neurodegeneration? The beta-N-methylamino-L-alanine (BMAA) paradigm. | Neurochemistry international 20070601 |
| Characterization of ethyl chloroformate derivative of beta-methylamino-L-alanine. | Journal of the American Society for Mass Spectrometry 20070501 |
| Beta-methylamino-alanine (BMAA) injures hippocampal neurons in vivo. | Neurotoxicology 20070501 |
| Beta-N-methylamino-L-alanine enhances neurotoxicity through multiple mechanisms. | Neurobiology of disease 20070201 |
| Commentary on: Return of the cycad hypothesis--does the amyotrophic lateral sclerosis/Parkinsonism dementia complex (ALS/PDC) of Guam have new implications for global health? | Neuropathology and applied neurobiology 20061201 |
| A nonprotein amino acid and neurodegeneration. | Science (New York, N.Y.) 20061124 |
| Acute perfusion of BMAA in the rat's striatum by in vivo microdialysis. | Toxicology letters 20061101 |
| Geographic isolates of atypical Parkinsonism and tauopathy in the tropics: possible synergy of neurotoxins. | Movement disorders : official journal of the Movement Disorder Society 20061001 |
| Debating the cause of a neurological disorder. | Science (New York, N.Y.) 20060922 |
| BMAA selectively injures motor neurons via AMPA/kainate receptor activation. | Experimental neurology 20060901 |
| Neurodegenerative disease. Guam's deadly stalker: on the loose worldwide? | Science (New York, N.Y.) 20060728 |
| Neurotoxic flying foxes as dietary items for the Chamorro people, Marianas Islands. | Journal of ethnopharmacology 20060615 |
| Lack of behavioral and neuropathological effects of dietary beta-methylamino-L-alanine (BMAA) in mice. | Pharmacology, biochemistry, and behavior 20060601 |
| Sporadic amyotrophic lateral sclerosis as an infectious disease: a possible role of cyanobacteria? | Medical hypotheses 20060101 |
| Lack of beta-methylamino-l-alanine in brain from controls, AD, or Chamorros with PDC. | Neurology 20050913 |
| Putative neurotoxin ecologically widespread. | The Lancet. Neurology 20050601 |
| Electrophysiological effect of beta-N-methylamino-L-alanine on retzius nerve cells of the leech Haemopis sanguisuga. | Annals of the New York Academy of Sciences 20050601 |
| Environmental neurotoxin may pose health threat. | JAMA 20050525 |
| The Lathyrus excitotoxin beta-N-oxalyl-L-alpha,beta-diaminopropionic acid is a substrate of the L-cystine/L-glutamate exchanger system xc-. | Toxicology and applied pharmacology 20041015 |
| Occurrence of beta-methylamino-l-alanine (BMAA) in ALS/PDC patients from Guam. | Acta neurologica Scandinavica 20041001 |
| Food chain of evidence points to brain toxin. | JAMA 20031203 |
| Western Pacific ALS/PDC and flying foxes: What's next? | Neurology 20030812 |
| Biomagnification of cycad neurotoxins in flying foxes: implications for ALS-PDC in Guam. | Neurology 20030812 |
| Expressed sequence tag analysis in Cycas, the most primitive living seed plant. | Genome biology 20030101 |
| The cycad neurotoxic amino acid, beta-N-methylamino-L-alanine (BMAA), elevates intracellular calcium levels in dissociated rat brain cells. | Journal of ethnopharmacology 20021001 |
| Cycad neurotoxins, consumption of flying foxes, and ALS-PDC disease in Guam. | Neurology 20020326 |
| A pharmacological characterization of the mGluR1 alpha subtype of the metabotropic glutamate receptor expressed in a cloned baby hamster kidney cell line. | Brain research 19930813 |
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