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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
Pricing and availability is not currently available.

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

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

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assay

≥97% (NMR)

assay

-

assay

≥97% (TLC)

assay

-

form

powder

form

solid

form

powder

form

solid

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.

-

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

storage condition

desiccated

storage condition

-

storage condition

-

storage condition

-

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

11 - Combustible Solids

wgk_germany

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
    085M4732V
    124M4734V
    104M4721V
    073M4710V
    023M4705V

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    Neurotoxic amino acids and their isomers in desert environments
    Metcalf JS, et al.
    Journal of arid environments, 140-144 (2015)
    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
    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
    2-Amino-β-methylamino-propionc acid, a new amino acid from seeds of Cycas circinali.
    Vega, et al.
    Psychochemistry, 6, 759-762 (1967)
    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
    View All Related Papers

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