Dihydrokainic acid

Names

[ Name ]:
Dihydrokainic acid

[Synonym ]:
2-Carboxy-4-isopropyl-3-pyrrolidineacetic acid
MFCD03412037
(2S,3S,4R)-3-(carboxymethyl)-4-propan-2-ylpyrrolidine-2-carboxylic acid
Dihydrokainic acid

Biological Activity

[Description]:

Dihydrokainic acid (DHK) is a glutamate transporter GLT1 (EAAT2) inhibitor. Dihydrokainic acid impairs novel object recognition (NOR) memory performance in mice. Dihydrokainic acid also shows epileptogenic effects[1].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> EAAT2

Research Areas >> Neurological Disease

[Target]

GLT1[1]

[References]

[1]. Tian SW, et al. Glutamate transporter GLT1 inhibitor dihydrokainic acid impairs novel object recognition memory performance in mice. Physiol Behav. 2019 Feb 1;199:28-32.

[2]. Butcher SP, et al. On the epileptogenic effects of kainic acid and dihydrokainic acid in the dentate gyrus of the rat. Neuropharmacology. 1988 Apr;27(4):375-81.

Chemical & Physical Properties

[ Density]:
1.187g/cm3

[ Boiling Point ]:
416.6ºC at 760mmHg

[ Melting Point ]:
285 °C (dec.)

[ Molecular Formula ]:
C₁₀H₁₇NO₄

[ Molecular Weight ]:
215.25

[ Exact Mass ]:
215.11600

[ PSA ]:
86.63000

[ LogP ]:
0.73470

[ Index of Refraction ]:
1.492

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/21/22

[ Safety Phrases ]:
26-36

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

EAAT2 (GLT-1; slc1a2) glutamate transporters reconstituted in liposomes argues against heteroexchange being substantially faster than net uptake.

J. Neurosci. 34(40) , 13472-85, (2014)

The EAAT2 glutamate transporter, accounts for >90% of hippocampal glutamate uptake. Although EAAT2 is predominantly expressed in astrocytes, ∼10% of EAAT2 molecules are found in axon terminals. Despit...

Activation of sodium-dependent glutamate transporters regulates the morphological aspects of oligodendrocyte maturation via signaling through calcium/calmodulin-dependent kinase IIβ's actin-binding/-stabilizing domain.

Glia 62(9) , 1543-58, (2014)

Signaling via the major excitatory amino acid glutamate has been implicated in the regulation of various aspects of the biology of oligodendrocytes, the myelinating cells of the central nervous system...

A functional coupling between extrasynaptic NMDA receptors and A-type K+ channels under astrocyte control regulates hypothalamic neurosecretory neuronal activity.

J. Physiol. 592(Pt 13) , 2813-27, (2014)

Neuronal activity is controlled by a fine-tuned balance between intrinsic properties and extrinsic synaptic inputs. Moreover, neighbouring astrocytes are now recognized to influence a wide spectrum of...