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M2383

Sigma-Aldrich

α-(Methylamino)isobutyric acid

≥97% (titration)

Synonym(s):

2,N-Dimethylalanine, 2-(Methylamino)-2-methylpropionic acid

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About This Item

Linear Formula:
CH3NHC(CH3)2COOH
CAS Number:
2566-34-9
Molecular Weight:
117.15
Beilstein/REAXYS Number:
1746984
EC Number:
219-898-2
MDL number:
MFCD00004191
UNSPSC Code:
12352209
PubChem Substance ID:
24896726
NACRES:
NA.26

assay

≥97% (titration)

form

powder

technique(s)

ligand binding assay: suitable

color

white

mp

>300 °C (lit.)

storage temp.

−20°C

SMILES string

CNC(C)(C)C(O)=O

InChI

1S/C5H11NO2/c1-5(2,6-3)4(7)8/h6H,1-3H3,(H,7,8)

InChI key

DLAMVQGYEVKIRE-UHFFFAOYSA-N

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Application

α-(Methylamino)isobutyric acid (MeAIB) has been used:
  • as a system A transport system inhibitor to perform inhibition experiments
  • as a system A transport system inhibitor to study its effect on the generation of epileptiform field potentials (EFPs) in the acutely disinhibited cortical slices
  • as an N-acetyltransferase (SNAT) inhibitor in Hank′s balanced salt solution (HBSS) to study its influence on the uptake of 14C-cysteine/ radioactive-labeled cysteine

Biochem/physiol Actions

α-(Methylamino)isobutyric acid (MeAIB), a competitive inhibitor of the neutral amino acid transport A system, is an N-methylated substrate. It is capable of decreasing the amplitude of the miniature excitatory postsynaptic current (mEPSC) in hippocampus neurons developing on top of astrocytes. MeAIB can block the alanine-proline (AP) pathway.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J R Bading et al.
Nuclear medicine and biology, 23(6), 779-786 (1996-08-01)
The A system of amino acid transport is concentrative and thought to be a regulator of cell growth. The [11C]methyl alpha-aminoisobutyric acid (MeAIB) is prospectively an ideal tracer for transport measurements with PET, as it is not metabolized and concentrates
Differentiation of tumour and inflammation: characterisation of [methyl-3H]methionine (MET) and O-(2-[18F]fluoroethyl)-L-tyrosine (FET) uptake in human tumour and inflammatory cells
Barbara Stober et al.
European Journal of Nuclear Medicine, 33, 932-939 (2006)
Nora Sandow et al.
Epilepsia, 50(4), 849-858 (2009-01-30)
Glutamine (GLN) is a precursor for synthesis of glutamate and gamma-aminobutyric acid (GABA) and has been found in the cerebrospinal fluid (CSF) at mean concentrations of 0.6 mM. Experiments on slices are usually performed in artificial CSF (aCSF) kept free
1500368
Meira W, et al.
Cancers, 13(6), 1434-1434 (2021)
A M Pajor et al.
The Journal of membrane biology, 107(3), 237-247 (1989-03-01)
Brush border membrane vesicles (BBMV) were prepared from the gills of the marine mussel, Mytilus edulis. These membranes contained two distinct pathways for cotransport of Na+ and alpha-neutral amino acids. The major pathway in mussel gill BBMV was the alanine-lysine
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