Page last updated: 2024-12-07

beta-n-methylamino-l-alanine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Beta-N-methylamino-L-alanine (BMAA) is a non-protein amino acid found in cyanobacteria and some other organisms. It is thought to be produced by cyanobacteria as a byproduct of nitrogen fixation. BMAA is a potent neurotoxin and has been linked to neurodegenerative diseases, such as amyotrophic lateral sclerosis (ALS), Alzheimer's disease, and Parkinson's disease. BMAA is thought to contribute to neurotoxicity by causing misfolding of proteins, leading to the formation of toxic aggregates. BMAA has been found in high concentrations in some marine species, including shellfish, fish, and algae. Its presence in these species has raised concerns about potential human health risks from consuming contaminated seafood. Research on BMAA is ongoing to understand its role in neurodegenerative diseases, its mechanisms of action, and potential strategies for prevention or treatment.'

beta-N-methylamino-L-alanine: glutamate agonist [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

L-BMAA : A non-proteinogenic L-alpha-amino acid that is L-alanine in which one of the methyl hydrogens is replaced by a methylamino group. A non-proteinogenic amino acid produced by cyanobacteria, it is a neurotoxin that has been postulated as a possible cause of neurodegenerative disorders of aging such as Alzheimer's disease, amyotrophic lateral sclerosis, and the amyotrophic lateral sclerosis/parkinsonism-dementia complex (ALS-PDC) syndrome of Guam. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID105089
CHEMBL ID11488
CHEBI ID73169
SCHEMBL ID43839
MeSH IDM0042194

Synonyms (48)

Synonym
C08291 ,
3-methylamino-l-alanine
15920-93-1
chebi:73169 ,
CHEMBL11488
(2s)-2-amino-3-(methylamino)propanoic acid
A3518
2-amino-3-methylamino-propionic acid
AKOS006272382
(s)-2-amino-3-(methylamino)propanoicacid
l-alpha-amino-beta-(methylamino)propanoic acid
bmaa
unii-108sa6urtv
108sa6urtv ,
propionic acid, alpha-amino-beta-methylamino-, l-
beta-(n-methylamino)-l-alanine
l-bmaa
l-alanine, 3-(methylamino)-
l-alpha-amino-beta-(methylamino)propionic acid
3-(methylamino)-l-alanine
beta-n-methylamino-l-alanine
beta-n-methylamino-l-ala
3-(n-methylamino)-l-alanine
(s)-2-amino-3-(methylamino)propanoic acid
AKOS015854057
l-.alpha.-amino-.beta.-(methylamino)propionic acid
(s)-2-amino-3-methylaminopropanoic acid
s(+)-.beta.-methyl-.alpha.,.beta.-diaminopropionic acid
.beta.-(n-methylamino)-l-alanine
l-(.beta.-methylamino)alanine
propionic acid, 2-amino-3-(methylamino)-, l-
.beta.-methylamino-l-alanine
SCHEMBL43839
DTXSID60166611
(s)-2-amino-3-(methylamino)propanoic acid (h-l-dap(me)-oh)
mfcd08063270
|?-n-methylamino-l-ala
beta-n-methylaminoalanine
l-bmaa hcl
EX-A1666
UJVHVMNGOZXSOZ-VKHMYHEASA-N
AMY22064
(s)-2-amino-3-(methylamino)-propanoic acid
PS-12000
?-methylamino-l-alanine dihydrochloride
-n-methylamino-l-alanine
l-|a-(n-methylamino) alanine
bmaa (hydrochloride)

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" We have investigated the toxicity of these amino acids on cultured mouse cortical neurons in the presence of physiological concentrations of bicarbonate (a required toxic cofactor for BMAA neurotoxicity)."( Neurotoxicity of beta-N-methylamino-L-alanine (BMAA) and beta-N-oxalylamino-L-alanine (BOAA) on cultured cortical neurons.
Choi, DW; Koh, JY; Weiss, JH, 1989
)
0.62
" In the late 1960's it was reported to be a toxic component of the cycad flour consumed by Chamorros on Guam which caused the high incidence of amyotrophic lateral sclerosis (ALS) in Guam, that was associated with a Parkinson's disease-like dementia complex (ALS-PDC)."( Animal models of BMAA neurotoxicity: a critical review.
Karamyan, VT; Speth, RC, 2008
)
0.35
"We report the establishment of an in vivo model using the fruit fly Drosophila melanogaster to investigate the toxic effects of L-BMAA."( BMAA neurotoxicity in Drosophila.
Bradley, WG; Escala, W; Papapetropoulos, S; Zhai, RG; Zhou, X, 2009
)
0.35
" The results indicate a synergistic toxic effect of the environmental neurotoxins BMAA and methylmercury, and that the interaction is at the level of glutathione depletion."( Synergistic toxicity of the environmental neurotoxins methylmercury and β-N-methylamino-L-alanine.
Liu, X; Lobner, D; Rush, T, 2012
)
0.38
"Cyanobacteria are some of the oldest organisms on earth, and have evolved to produce a battery of toxic metabolites, including hepatotoxins, dermatoxins, and neurotoxins."( Cyanobacterial Neurotoxins: Their Occurrence and Mechanisms of Toxicity.
Main, BJ; Rodgers, KJ; Samardzic, K, 2018
)
0.48

Bioavailability

ExcerptReferenceRelevance
" We employed stable isotopic forms of BMAA to assess the oral bioavailability of this compound in cynomolgous monkeys (n = 3)."( 2-Amino-3-(methylamino)propanoic acid (BMAA) bioavailability in the primate.
Duncan, MW; Hu, Y; Kopin, IJ; Markey, SP; Pearson, PG; Weick, BG; Ziffer, H,
)
0.13
" We have studied BMAA pharmacokinetics, oral bioavailability and blood-brain barrier permeability in the rat in an attempt to better define the possible role for BMAA in this disease."( 2-amino-3-(methylamino)-propanoic acid (BMAA) pharmacokinetics and blood-brain barrier permeability in the rat.
Duncan, MW; Kopin, IJ; Markey, SP; Pearson, PG; Rapoport, SI; Smith, QR; Villacreses, NE; Wyatt, L, 1991
)
0.28
" To test for BMAA bioavailability in ecosystems where abundant phytoplanktonic blooms regularly occur, samples of filter-feeding shellfish were collected in two Portuguese transitional water bodies."( BMAA in shellfish from two Portuguese transitional water bodies suggests the marine dinoflagellate Gymnodinium catenatum as a potential BMAA source.
Costa, PR; Eriksson, J; Lage, S; Moita, T; Rasmussen, U; Rydberg, SJ, 2014
)
0.4
" The findings might add to the understanding of conflicting data in the literature regarding the occurrence of BMAA, and have implications for studies on possible biomagnification of BMAA in the food chain and bioavailability from food."( BMAA detected as neither free nor protein bound amino acid in blue mussels.
Hellenäs, KE; Rosén, J; Schmiedt, S; Westerberg, E, 2016
)
0.43

Dosage Studied

ExcerptRelevanceReference
" By contrast, comparable oral dosing with BMAA precipitates tremor and weakness, bradykinesia and behavioural changes, with conduction deficits in the principal motor pathway."( Discovery and partial characterization of primate motor-system toxins.
Hugon, J; Ludolph, A; Nunn, PB; Ross, SM; Roy, DN; Schaumburg, HH; Spencer, PS, 1987
)
0.27
" BMAA perfusion produced a dose-response increase in the extracellular output of dopamine."( Acute perfusion of BMAA in the rat's striatum by in vivo microdialysis.
Cano, J; Machado, A; Matarredona, ER; Santiago, M, 2006
)
0.33
" Macaques dosed via oral gavage with BMAA developed marked neurological signs in the absence of cell death."( Do vervets and macaques respond differently to BMAA?
Banack, SA; Cox, PA; Davis, DA; Mash, DC; Metcalf, JS, 2016
)
0.43
" As a first step, we analysed both BMAA enantiomers in cyanobacteria, cycads, and in mammals orally dosed with L-BMAA, to determine if enantiomeric changes could occur in vivo."( Analysis of BMAA enantiomers in cycads, cyanobacteria, and mammals: in vivo formation and toxicity of D-BMAA.
Banack, SA; Cox, GA; Cox, PA; Lobner, D; Metcalf, JS; Nunn, PB; Wyatt, PB, 2017
)
0.46
" UHPLC-MS/MS was used to confirm BMAA exposures in dosed vervets."( l-Serine Reduces Spinal Cord Pathology in a Vervet Model of Preclinical ALS/MND.
Banack, SA; Beierschmitt, A; Bradley, WG; Cox, PA; Davis, DA; Garamszegi, SP; Hagan, MJ; Lecusay, PD; Mash, DC; Metcalf, JS; Palmour, RM; Powell, JT, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
neurotoxinA poison that interferes with the functions of the nervous system.
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (4)

ClassDescription
secondary amino compoundA compound formally derived from ammonia by replacing two hydrogen atoms by organyl groups.
non-proteinogenic L-alpha-amino acidAny L-alpha-amino acid which is not a member of the group of 23 proteinogenic amino acids.
L-alanine derivativeA proteinogenic amino acid derivative resulting from reaction of L-alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of L-alanine by a heteroatom.
diamino acidAny amino acid carrying two amino groups.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (1)

Assay IDTitleYearJournalArticle
AID224503Effect on rate of GTP hydrolysis in the GTP binding protein ras p211998Bioorganic & medicinal chemistry letters, May-05, Volume: 8, Issue:9
Prediction of the GTPase activities by using the semiempirical molecular orbital theory.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (383)

TimeframeStudies, This Drug (%)All Drugs %
pre-199024 (6.27)18.7374
1990's39 (10.18)18.2507
2000's68 (17.75)29.6817
2010's205 (53.52)24.3611
2020's47 (12.27)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.72

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index25.72 (24.57)
Research Supply Index5.97 (2.92)
Research Growth Index5.08 (4.65)
Search Engine Demand Index22.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews39 (9.97%)6.00%
Case Studies1 (0.26%)4.05%
Observational0 (0.00%)0.25%
Other351 (89.77%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]