A cell-permeant glutamate derivative
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Dimethyl DL-Glutamate (hydrochloride)

Item No. 18602

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,5-dimethyl ester glutamic acid, monohydrochloride
Synonyms
  • Glutamic Acid dimethyl ester
  • Dimethyl 2-aminopentanedioate
Molecular Formula
C7H13NO4 • HCl
Formula Weight
211.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMSO: 10 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
COC(C(N)CCC(OC)=O)=O.Cl
InChi Code
InChI=1S/C7H13NO4.ClH/c1-11-6(9)4-3-5(8)7(10)12-2;/h5H,3-4,8H2,1-2H3;1H
InChi Key
MFUPLHQOVIUESQ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 g

    $75

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    10 g

    $143

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    25 g

    $333

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    50 g

    $589

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    Cayman Chemical
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Dimethyl DL-glutamate is a cell-permeant glutamic acid derivative that enhances insulin release in response to glucose in isolated islets and in animal models of diabetes.1,2 It also potentiates the insulinotropic potential of glyburide (Item No. 15009) and glucagon-like peptide 1.1,2 Dimethyl DL-glutamate is used as a cell-permeable form of glutamate in studies of glutamate action in β-cells.3,4 However, it can be cytotoxic to myeloid cells and act as an antagonist of glutamate-mediated neurosignaling.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sener, A., Conget, I., Rasschaert, J., et al. Insulinotropic action of glutamic acid dimethyl ester. Am. J. Physiol. 267(4 Pt 1), E573-E584 (1994).

    2. Cancelas, J., Villaneuva-Peñacarrillo, M.L., Valverde, I., et al. Potentiation and prolongation of the insulinotropic action of glucagon-like peptide 1 by methyl pyruvate or dimethyl ester of L-glutamic acid in a type 2 diabetes animal model. Endocrine 16(2), 113-116 (2001).

    3. Casimir, M., Lasorsa, F.M., Rubi, B., et al. Mitochondrial glutamate carrier GC1 as a newly identified player in the control of glucose-stimulated insulin secretion. The Journal of Biological Chemisty 284(37), 25004-25014 (2009).

    4. Vetterli, L., Carobbio, S., Pournourmohammadi, S., et al. Delineation of glutamate pathways and secretory responses in pancreatic islets with β-cell-specific abrogation of the glutamate dehydrogenase. Mol. Biol. Cell 23(19), 3851-3862 (2012).

    5. Thiele, D.L., and Lipsky, P.E. Spectrum of toxicities of amino acid methyl esters for myeloid cells is determined by distinct metabolic pathways. Blood 79(4), 964-971 (1992).

    6. Segal, M. Glutamate antagonists in rat hippocampus. Br. J. Pharmacol. 58(3), 341-345 (1976).