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D1064

Sigma-Aldrich

Dihydrokainic acid

≥98% (HPLC), GLT-1 glutamate transporter inhibitor, powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H17NO4
CAS Number:
52497-36-6
Molecular Weight:
215.25
MDL number:
MFCD03412037
UNSPSC Code:
12352106
PubChem Substance ID:
24277981
NACRES:
NA.77

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Product Name

Dihydrokainic acid, ≥98% (HPLC), powder

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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Show Differences

1 of 4

This Item
K2389SML0075K0250
Dihydrokainic acid ≥98% (HPLC), powder

Sigma-Aldrich

D1064

Dihydrokainic acid

Kainic acid monohydrate ≥98% (HPLC), from Digenea simplex

Sigma-Aldrich

K2389

Kainic acid monohydrate

OBAA ≥98% (HPLC)

Sigma-Aldrich

SML0075

OBAA

Kainic acid monohydrate ≥99% (TLC)

Sigma-Aldrich

K0250

Kainic acid monohydrate

form

powder

form

powder

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥99% (TLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

solubility

H2O: >10 mg/mL

solubility

H2O: >10 mg/mL

solubility

DMSO: ≥5 mg/mL at 60 °C

solubility

H2O: soluble

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

human ... GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK4(2900), GRIK5(2901), SLC1A1(6505), SLC1A2(6506), SLC1A3(6507)
mouse ... Gria1(14799)
rat ... Gria1(50592), Grik1(29559), Grik4(24406), Grin2a(24409)

Application

Dihydrokainic acid has been used as a glutamate transporter (GLT-1) inhibitor in the glutamate uptake assay of astrocytes[1] and glial cells.[2] It may be used as a GLT-1 inhibitor in Lateral habenula (LHb).[3]

Biochem/physiol Actions

Dihydrokainic acid is a selective GLT-1 glutamate transporter inhibitor; weak inhibitor of AMPA/kainate glutamic acid receptors at high concentrations.
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.[4] It modulates anxiety and depression behaviors.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000483154
0000483154
0000382368
0000382367
0000374645

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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
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
Azar Omrani et al.
The Journal of physiology, 587(Pt 19), 4575-4588 (2009-08-05)
Glutamate transporters are responsible for clearing synaptically released glutamate from the extracellular space. By this action, they maintain low levels of ambient glutamate, thus preventing excitotoxic damage, and contribute to shaping synaptic currents. We show that up-regulation of the glutamate
View All Related Papers

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