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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

Quality Level

100

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

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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Nikolaos Dimopoulos et al.
The Biochemical journal, 399(3), 473-481 (2006-07-11)
An increase in circulating levels of specific NEFAs (non-esterified fatty acids) has been implicated in the pathogenesis of insulin resistance and impaired glucose disposal in skeletal muscle. In particular, elevation of SFAs (saturated fatty acids), such as palmitate, has been
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
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)
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
T Z Su et al.
Endocrinology, 139(3), 832-837 (1998-03-10)
System A is one of the most highly regulated transport systems for transport of neutral amino acids into mammalian cells. Stimulation of uptake of alpha-[3H]methylaminoisobutyric acid (MeAIB), a nonmetabolizable system A substrate, by a novel insulin-sensitizing agent, troglitazone, in 3T3-L1
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