(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,3S,4R)-2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid;(2S,3R,4R)-2-Carboxy-4-iospropyl-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
- Molecular Weight:
- 215.25
- MDL Number:
- MFCD03412037
- MOL File:
- 52497-36-6.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| FDA UNII | MQ4LMC2HN5 |
| UNSPSC Code | 12352106 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H312-H332-H302 | |||||||||
| Precautionary statements | P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501 | |||||||||
| PPE | dust mask type N95 (US), Eyeshields, Gloves | |||||||||
| Hazard Codes | Xn | |||||||||
| Risk Statements | 20/21/22 | |||||||||
| Safety Statements | 26-36 | |||||||||
| WGK Germany | 3 | |||||||||
| Storage Class | 11 - Combustible Solids | |||||||||
| NFPA 704 |
|
(2S,3S,4R)-2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid price More Price(33)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | D1064 | Dihydrokainic acid ≥98% (HPLC), powder | 52497-36-6 | 10mg | $299 | 2026-04-30 | Buy |
| Sigma-Aldrich | D1064 | Dihydrokainic acid ≥98% (HPLC), powder | 52497-36-6 | 50mg | $1010 | 2026-04-30 | Buy |
| Cayman Chemical | 28478 | Dihydrokainic Acid ≥95% | 52497-36-6 | 1mg | $41 | 2026-04-30 | Buy |
| Cayman Chemical | 28478 | Dihydrokainic Acid ≥95% | 52497-36-6 | 5mg | $140 | 2026-04-30 | Buy |
| Cayman Chemical | 28478 | Dihydrokainic Acid ≥95% | 52497-36-6 | 10mg | $235 | 2026-04-30 | Buy |
(2S,3S,4R)-2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid Chemical Properties, Uses, 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
Preparation Products
(2S,3S,4R)-2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid Suppliers
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| 3B Pharmachem (Wuhan) International Co.,Ltd. | 18930552037 | 3bsc@sina.com | China | 15813 | 69 |
| Ascent Scientific | 4401179829988 | customerservice@ascentscientific.co.uk | United Kingdom | 279 | 60 |
| Shanghai Macklin Biochemical Co.,Ltd. | 15221275939 15221275939 | shenlinxing@macklin.cn | China | 15775 | 55 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| EMMX Biotechnology LLC | 888-539-0666 | info@emmx.com | United States | 8435 | 60 |
| Shanghai EFE Biological Technology Co., Ltd. | 021-65675885 18964387627 | info@efebio.com | China | 9799 | 58 |
| Amadis Chemical Company Limited | 571-89925085 | sales@amadischem.com | China | 131885 | 58 |
| BOC Sciences | 16314854226; +8616314854226 | inquiry@bocsci.com | United States | 19852 | 58 |
| TargetMol Chemicals Inc. | +1-781-999-5354; +1-00000000000 | marketing@targetmol.com | United States | 32431 | 58 |
| Nextpeptide Inc | +86-0571-81612335 +8613336028439 | sales@nextpeptide.com | China | 19904 | 58 |
View Latest Price from (2S,3S,4R)-2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-04-20 | Dihydrokainic acid
52497-36-6
|
$185.00-1070.00 | 10g | TargetMol Chemicals Inc. |
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- Dihydrokainic acid
52497-36-6
- $185.00-1070.00
- TargetMol Chemicals Inc.
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