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Merck
CN

B107

L-BMAA hydrochloride

≥97% (NMR), neurotoxin, 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
UNSPSC Code:
12352209
PubChem Substance ID:
329773160
NACRES:
NA.32
MDL number:
MFCD00055227

Key Documents

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Product Name

L-BMAA hydrochloride, ≥97% (NMR), powder

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

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

Quality Level

100

Related Categories

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000450088
0000450088
0000440271
0000440272
0000440272

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2-Amino-β-methylamino-propionc acid, a new amino acid from seeds of Cycas circinali.
Vega, et al.
Psychochemistry, 6, 759-762 (1967)
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
Johan Eriksson et al.
Amino acids, 36(1), 43-48 (2008-01-12)
Two different assays have been developed and used in order to investigate the optimal conditions for derivatization and detection of acid beta-N-methyl-amino-L-alanine (BMAA) in a cyanobacterial sample. BMAA was extracted from cyanobacterial cultures both from the cytosolic ("free") fraction and
Beta-N-methylamino-L-alanine (L-BMAA) is a potent agonist of 'metabolotropic' glutamate receptors.
A Copani et al.
European journal of pharmacology, 181(3), 327-328 (1990-06-08)
Selective degeneration of cerebellar cortical neurons caused by cycad neurotoxin, L-beta-methylaminoalanine (L-BMAA), in rats
SEAWRIGHT AA, et al.
Neuropathology and Applied Neurobiology, 16(2), 153-169 (1990)
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