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B107

Sigma-Aldrich

L-BMAA hydrochloride

≥97% (NMR), powder

Synonym(s):

S(+)-2-Amino-3-(methylamino)propionic acid hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C4H10N2O2 · HCl
CAS Number:
16012-55-8
Molecular Weight:
154.60
MDL number:
MFCD00055227
UNSPSC Code:
12352209
PubChem Substance ID:
329773160
NACRES:
NA.32

Quality Level

100

Assay

≥97% (NMR)

form

powder

optical activity

[α]/D +21 to +31°, c = 0.5 M in 0.1 M HCl(lit.)

storage condition

desiccated

color

white to beige

solubility

H2O: soluble (solutions may be stored for several days at 4 °C)

storage temp.

−20°C

SMILES string

Cl.CNC[C@H](N)C(O)=O

InChI

1S/C4H10N2O2.ClH/c1-6-2-3(5)4(7)8;/h3,6H,2,5H2,1H3,(H,7,8);1H/t3-;/m0./s1

InChI key

VDXYGASOGLSIDM-DFWYDOINSA-N

General description

L-BMAA hydrochloride/β-N-methylamino-l-alanine (BMAA) is a cyanobacterial neurotoxin.

Application

L-BMAA hydrochloride has been used as a standard to compare all the samples in the analysis of β-N-methylamino-l-alanine (BMAA) isomers in desert crust material. It has also been used as an additive with f/2+Si medium to treat the cells of Phaeodactylum tricornutum and Thalassiosira weissflogii to study its effect on them.

Biochem/physiol Actions

L-BMAA hydrochloride helps to block the addition of heparan sulfate to glypican-1. It possesses unusual glutamate receptor binding properties. It may cause amyotrophic lateral sclerosis/Lou Gehrig′s disease.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The cyanobacterial neurotoxin beta-N-methylamino-l-alanine prevents addition of heparan sulfate to glypican-1 and increases processing of amyloid precursor protein in dividing neuronal cells
Cheng F, et al.
Experimental Cell Research (2019)
Boyin Yan et al.
Chemosphere, 243, 125355-125355 (2019-11-24)
Cyanobacteria produce a series of secondary metabolites, one of which is beta-N-methylamino-l-alanine (BMAA). BMAA is considered to be the cause of human neurodegeneration. Compared with other cyanotoxins, the role of BMAA in cyanobacteria remains unclear. To investigate this question, six
2-Amino-β-methylamino-propionc acid, a new amino acid from seeds of Cycas circinali.
Vega, et al.
Psychochemistry, 6, 759-762 (1967)
The effect of exogenous beta-N-methylamino-l-alanine (BMAA) on the diatoms Phaeodactylum tricornutum and Thalassiosira weissflogii
Lage S, et al.
Harmful Algae, 85-92 (2016)
Alexandra Lepoutre et al.
Toxins, 12(2) (2020-01-25)
The environmental neurotoxin β-methylamino-l-alanine (BMAA) may represent a risk for human health. BMAA accumulates in freshwater and marine organisms consumed by humans. However, few data are available about the kinetics of BMAA accumulation and detoxification in exposed organisms, as well
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