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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:
Molecular Weight:
154.60
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32

Quality Level

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

General description

L-BMAA hydrochloride/β-N-methylamino-l-alanine (BMAA) is a cyanobacterial neurotoxin.[1]

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.[2] 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.[3]

Biochem/physiol Actions

L-BMAA hydrochloride helps to block the addition of heparan sulfate to glypican-1.[1] It possesses unusual glutamate receptor binding properties.[4] It may cause amyotrophic lateral sclerosis/Lou Gehrig′s disease.[5]

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

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    David A Davis et al.
    Journal of neuropathology and experimental neurology, 79(4), 393-406 (2020-02-23)
    The early neuropathological features of amyotrophic lateral sclerosis/motor neuron disease (ALS/MND) are protein aggregates in motor neurons and microglial activation. Similar pathology characterizes Guamanian ALS/Parkinsonism dementia complex, which may be triggered by the cyanotoxin β-N-methylamino-l-alanine (BMAA). We report here the
    Neurotoxic amino acids and their isomers in desert environments
    Metcalf JS, et al.
    Journal of arid environments, 140-144 (2015)
    Olga A Koksharova et al.
    Toxins, 12(6) (2020-06-10)
    All cyanobacteria produce a neurotoxic non-protein amino acid β-N-methylamino-L-alanine (BMAA). However, the biological function of BMAA in the regulation of cyanobacteria metabolism still remains undetermined. It is known that BMAA suppresses the formation of heterocysts in diazotrophic cyanobacteria under nitrogen
    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)
    Aifeng Li et al.
    Aquatic toxicology (Amsterdam, Netherlands), 221, 105425-105425 (2020-02-15)
    Neurotoxin β-N-methylamino-L-alanine (BMAA) has been widely detected in diverse aquatic organisms and hypothesized as an environmental risk to neurodegenerative diseases in humans. However, the knowledge of its toxicity to marine organisms requires attention. In the present study, embryos and sperm

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