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Merck

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

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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

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

Sigma-Aldrich

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Sigma-Aldrich

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p-Aminoclonidine hydrochloride

Aminopterin powder

Sigma-Aldrich

A1784

Aminopterin

Benoxathian hydrochloride solid

Sigma-Aldrich

B016

Benoxathian hydrochloride

form

powder

form

solid

form

powder

form

solid

assay

≥97% (NMR)

assay

-

assay

≥97% (TLC)

assay

-

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

storage condition

desiccated

storage condition

-

storage condition

-

storage condition

-

solubility

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

solubility

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.4 mg/mL (Solutions may be stored for several days at 4 °C), boiling water: 100 mg/mL (Solutions may be stored for several days at 4 °C), 0.1 M HCl: soluble (Solutions may be stored for several days at 4 °C), methanol: soluble (Solutions may be stored for several days at 4 °C)

solubility

2 M NaOH: 50 mg/mL (Solutions may be stored for 1-2 days at 4°C.), DMSO: soluble (Solutions may be stored for 1-2 days at 4°C.)

solubility

H2O: soluble (Aqueous solutions may be stored for several weeks at -20 °C.), ethanol: soluble, isopropanol: soluble

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.[1] 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.[2]

Biochem/physiol Actions

L-BMAA hydrochloride helps to block the addition of heparan sulfate to glypican-1.[3] It possesses unusual glutamate receptor binding properties.[4] It may cause amyotrophic lateral sclerosis/Lou Gehrig′s disease.[5]

General description

L-BMAA hydrochloride/β-N-methylamino-l-alanine (BMAA) is a cyanobacterial neurotoxin.[3]

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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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
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
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)
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)
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)
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