A neurotoxic non-proteinogenic amino acid
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β-Methylamino-L-Alanine (hydrochloride)

Item No. 23287

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-(methylamino)-L-alanine, monohydrochloride
CAS Number
16012-55-8
Synonyms
  • BMAA
  • L-BMAA
Molecular Formula
C4H10N2O2 • HCl
Formula Weight
154.6
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Slightly solubleWater: Slightly soluble
SMILES
N[C@H](C(O)=O)CNC.Cl
InChi Code
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
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    10 mg

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    Cayman Chemical
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    Product Description

    β-Methylamino-L-alanine (BMAA) is a neurotoxic non-proteinogenic amino acid that has been found in cyanobacteria.1,2 It is cytotoxic to mouse primary cortical neurons when used at a concentration of 3 mM in the presence of bicarbonate, an effect that can be blocked by the NMDA receptor antagonist MK-801 or the mGluR5 receptor antagonist MPEP (Item No. 14536).3 BMAA (3 mM) stimulates release of glutamate and induces oxidative stress in the same cells.4 It also enhances neuronal cell death induced by amyloid-β (25-35) in mouse primary cortical neurons when used at a concentration of 0.1 mM.3 Intracerebroventricular administration of BMAA (500 µg/animal) induces wet-dog shakes, rigidity, and clonic convulsions in rats.5 It induces parkinsonism in cynomolgus monkeys.6 BMAA has been found in commercial seafood.7

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Holtcamp, W. The emerging science of BMAA: Do cyanobacteria contribute to neurodegenerative disease? Environ. Health Perspect. 120(3), A110-A116 (2012).

    2. Chiu, A.S., Gehringer, M.M., Welch, J.H., et al. Does α-amino-β-methylaminopropionic acid (BMAA) play a role in neurodegeneration? Int. J. Environ. Res. Public Health 8(9), 3728-3746 (2011).

    3. Lobner, D., Piana, P.M.T., Salous, A.K., et al. β-N-methylamino-L-alanine enhances neurotoxicity through multiple mechanisms. Neurobiol. Dis. 25(2), 360-366 (2007).

    4. Liu, X., Rush, T., Zapata, J., et al. β-N-methylamino-L-alanine induces oxidative stress and glutamate release through action on system Xc¯. Exp. Neurol. 217(2), 429-433 (2009).

    5. Matsuoka, Y., Rakonczay, Z., Giacobini, E., et al. L-β-methylamino-alanine-induced behavioral changes in rats. Pharmacol. Biochem. Behav. 44(3), 727-734 (1993).

    6. Spencer, P.S., Nunn, P.B., Hugon, J., et al. Guam amyotrophic lateral sclerosis-parkinsonism-dementia linked to a plant excitant neurotoxin. Science 237(4814), 517-522 (1987).

    7. Jiang, L., Kiselova, N., Rosén, J., et al. Quantification of neurotoxin BMAA (β-N-methylamino-L-alanine) in seafood from Swedish markets. Sci. Rep. 4, 6931 (2014).