Beta-Methylamino-L-alanine

beta-Methylamino-L-alanine

Names
IUPAC name (2S)-2-Amino-3-(methylamino)propanoic acid
Other names 2-Amino-3-methylaminopropanoic acid
Identifiers
CAS Number	15920-93-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:73169 N
ChemSpider	94816 N
KEGG	C08291 N
MeSH	alpha-amino-beta-methylaminopropionate
PubChem CID	105089
InChI InChI=1S/C4H10N2O2/c1-6-2-3(5)4(7)8/h3,6H,2,5H2,1H3,(H,7,8)/t3-/m0/s1 N Key: UJVHVMNGOZXSOZ-VKHMYHEASA-N N
SMILES CNC[C@@H](C(=O)O)N
Properties
Chemical formula	C4H10N2O2
Molar mass	118.14 g·mol−1
log P	−0.1
Acidity (pKa)	1.883
Basicity (pKb)	12.114
Related compounds
Related alkanoic acids	Sarcosine Dimethylglycine Glycocyamine Creatine N-Methyl-D-aspartic acid Guanidinopropionic acid Arginine
Related compounds	Dimethylacetamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

β-Methylamino-L-alanine, or BMAA, is a non-proteinogenic amino acid produced by cyanobacteria. BMAA is a neurotoxin and its potential role in various neurodegenerative disorders is the subject of scientific research.

BMAA is a derivative of the amino acid alanine with a methylamino group on the side chain. This non-proteinogenic amino acid is classified as a polar base.

BMAA is produced by cyanobacteria in marine, freshwater and terrestrial environments. In cultured non-nitrogen-fixing cyanobacteria, BMAA production increases in nitrogen depleted medium. BMAA has been found in aquatic organisms and in plants with cyanobacterial symbionts such as certain lichens, the floating fern Azolla, the leaf petioles of the tropical flowering plant Gunnera, cycads as well as in animals that eat the fleshy covering of cycad seeds, including flying foxes.

High concentrations of BMAA are present in shark fins. Because BMAA is a neurotoxin, consumption of shark fin soup and cartilage pills may therefore pose a health risk. The toxin can be detected via several laboratory methods, including liquid chromatography, high-performance liquid chromatography, mass spectrometry, amino acid analyzer, capillary electrophoresis and NMR spectroscopy.