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Key Documents

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D1064

Sigma-Aldrich

Dihydrokainic acid

≥98% (HPLC), powder

Sinónimos:

2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid

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About This Item

Fórmula empírica (notación de Hill):
C10H17NO4
Número de CAS:
52497-36-6
Peso molecular:
215.25
MDL number:
MFCD03412037
UNSPSC Code:
12352106
PubChem Substance ID:
24277981
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

solubility

H2O: >10 mg/mL

storage temp.

2-8°C

SMILES string

CC(C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O

InChI

1S/C10H17NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h5-7,9,11H,3-4H2,1-2H3,(H,12,13)(H,14,15)/t6-,7+,9-/m0/s1

InChI key

JQPDCKOQOOQUSC-OOZYFLPDSA-N

Gene Information

human ... SLC1A1(6505) , SLC1A2(6506) , SLC1A3(6507)
rat ... Slc1a2(29482) , Slc1a3(29483)

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Application

Dihydrokainic acid has been used as a glutamate transporter (GLT-1) inhibitor in the glutamate uptake assay of astrocytes and glial cells. It may be used as a GLT-1 inhibitor in Lateral habenula (LHb).

Biochem/physiol Actions

Dihydrokainic acid is a selective inhibitor of the GLT-1 glutamate transporter. At higher concentrations, dihydrokainate is a weak inhibitor of AMPA/kainate glutamic acid receptors.
Dihydrokainic favors neuronal cell death. It modulates anxiety and depression behaviors.

Features and Benefits

This compound is featured on the Excitatory Amino Acid Transporters page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Catherine S John et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 37(11), 2467-2475 (2012-06-29)
Major depression is associated with both dysregulated glutamatergic neurotransmission and fewer astrocytes in limbic areas including the prefrontal cortex (PFC). These deficits may be functionally related. Notably, astrocytes regulate glutamate levels by removing glutamate from the synapse via the glutamate
Rescue of glutamate transport in the lateral habenula alleviates depression-and anxiety-like behaviors in ethanol-withdrawn rats
Kang S, et al.
Neuropharmacology, 129(11), 47-56 (2018)
Anita J Bechtholt-Gompf et al.
Neuropsychopharmacology : official publication of the American College of Neuropsychopharmacology, 35(10), 2049-2059 (2010-06-10)
Mood disorders are associated with regional brain abnormalities, including reductions in glial cell and neuron number, glutamatergic irregularities, and differential patterns of brain activation. Because astrocytes are modulators of neuronal activity and are important in trafficking the excitatory neurotransmitter glutamate
Scott M Rawls et al.
Drug and alcohol dependence, 107(2-3), 261-263 (2009-12-17)
Glutamate transporter subtype 1 (GLT-1) activation is a promising - and understudied - approach for managing aspects of morphine tolerance caused by increased glutamatergic transmission. Identification of beta-lactam antibiotics as pharmaceuticals which activate GLT-1 transporters prompted us to hypothesize that
Judy-Fay Ferron et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 29(31), 9850-9860 (2009-08-07)
Isoflurane is a widely used anesthetic which safely and reversibly induces deep coma and associated burst suppression (BS) electroencephalographic patterns. Here we investigate possible underlying causes for the state of cortical hyperexcitability which was recently shown to be one of
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