(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID
- Product Name
- (2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID
- CAS No.
- 52497-36-6
- Chemical Name
- (2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID
- Synonyms
- DHK;DIHYDROKAINIC ACID;Dihydrokainic acid, EAAT2 (GLT-1) inhibitor;2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid;(2S,3S,4R)-3-(carboxymethyl)-4-isopropyl-proline;(2S,3R,4R)-2-Carboxy-4-iospropyl-3-pyrrolidineacetic acid;(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID;3-Pyrrolidineacetic acid, 2-carboxy-4-(1-methylethyl)-, (2S,3S,4R)-;(2S,3S,4R)-3-(Carboxymethyl)-4-isopropylpyrrolidine-2-carboxylic acid;(2S,3S,4R)-3-(carboxymethyl)-4-propan-2-yl-2-pyrrolidinecarboxylic acid
- CBNumber
- CB7153569
- Molecular Formula
- C10H17NO4
- Formula Weight
- 215.25
- MOL File
- 52497-36-6.mol
(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID Property
- Melting point:
- 285 °C (decomp)
- Boiling point:
- 416.6±30.0 °C(Predicted)
- Density
- 1.187±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- H2O: >10 mg/mL
- form
- solid
- pka
- 2.11±0.60(Predicted)
- color
- White
- Water Solubility
- Soluble to 25 mM in water
- 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
- InChIKey
- JQPDCKOQOOQUSC-OOZYFLPDSA-N
- SMILES
- CC(C)[C@H]1CN[C@@H]([C@H]1CC(O)=O)C(O)=O
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H312Harmful in contact with skin
H332Harmful if inhaled
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P312Call a POISON CENTER or doctor/physician if you feel unwell.
P322Specific measures (see …on this label).
P330Rinse mouth.
P363Wash contaminated clothing before reuse.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- D1064
- Product name
- Dihydrokainic acid
- Purity
- ≥98% (HPLC), powder
- Packaging
- 10mg
- Price
- $279
- Updated
- 2025/07/31
- Product number
- D1064
- Product name
- Dihydrokainic acid
- Purity
- ≥98% (HPLC), powder
- Packaging
- 50mg
- Price
- $938
- Updated
- 2025/07/31
- Product number
- 28478
- Product name
- Dihydrokainic Acid
- Packaging
- 1mg
- Price
- $37
- Updated
- 2024/03/01
- Product number
- 28478
- Product name
- Dihydrokainic Acid
- Packaging
- 25mg
- Price
- $442
- Updated
- 2024/03/01
- Product number
- 28478
- Product name
- Dihydrokainic Acid
- Packaging
- 5mg
- Price
- $127
- Updated
- 2024/03/01
(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID Chemical Properties,Usage,Production
Description
Dihydrokainic acid (DHK) is an inhibitor of excitatory amino acid transporter 2 (EAAT2; Ki = 23 μM for glutamate uptake by COS cells expressing EAAT2). It is selective for EEAT2 over EAAT1 and EAAT3 (Ki = >3 mM for both). DHK microinfusion (5 nmol) into the rat infralimbic cortex reduces the time spent immobile in the forced swim test, indicating antidepressant-like behavior, an effect that is blocked by the AMPA receptor antagonist NBQX and the serotonin (5-HT) receptor subtype 5-HT1A antagonist WAY-100635 . It also increases glutamate and serotonin levels and the expression of c-Fos in the dorsal raphe nucleus. In contrast, DHK microinjection (6.25 nmol) into the rat prefrontal cortex (PFC) increases the latency to drink sucrose in a sucrose intake test, indicating anhedonia-like behavior. It also impairs memory acquisition, consolidation, and retrieval in mice in the novel object recognition test.
Uses
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).
Definition
ChEBI: Dihydrokainic acid is a dicarboxylic acid. It is functionally related to a kainic acid.
Biological Activity
EAAT2(GLT1)-selective non-transportable inhibitor of L-glutamate and L-aspartate uptake (K i = 23 μ M). 130-fold selective over EAAT1 and EAAT3 (K i > 3 mM). Also available as part of the Excitatory Amino Acid Transporter Inhibitor Tocriset™ .
Biochem/physiol Actions
Dihydrokainic favors neuronal cell death. It modulates anxiety and depression behaviors.
storage
Room temperature
References
[1] J. ARRIZA. Functional comparisons of three glutamate transporter subtypes cloned from human motor cortex[J]. Journal of Neuroscience, 1994, 42 1: 5559-5569. DOI: 10.1523/jneurosci.14-09-05559.1994
[2] J GASULL-CAMóS. Glial GLT-1 blockade in infralimbic cortex as a new strategy to evoke rapid antidepressant-like effects in rats[J]. Translational Psychiatry, 2017, 7 2: e1038-e1038. DOI: 10.1038/tp.2017.7
[3] JúLIA GASULL-CAMóS . Serotonergic mechanisms involved in antidepressant-like responses evoked by GLT-1 blockade in rat infralimbic cortex[J]. Neuropharmacology, 2018, 139: Pages 41-51. DOI: 10.1016/j.neuropharm.2018.06.029
[4] CATHERINE S JOHN. Blockade of Astrocytic Glutamate Uptake in the Prefrontal Cortex Induces Anhedonia[J]. Neuropsychopharmacology, 2012, 37 11: 2467-2475. DOI: 10.1038/npp.2012.105
[5] SHAO-WEN TIAN . Glutamate transporter GLT1 inhibitor dihydrokainic acid impairs novel object recognition memory performance in mice[J]. Physiology & Behavior, 2019, 199: Pages 28-32. DOI: 10.1016/j.physbeh.2018.10.019
(2S,3S,4R)-2-CARBOXY-4-ISOPROPYL-3-PYRROLIDINEACETIC ACID Preparation Products And Raw materials
Raw materials
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