カイニン酸
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/05/28 22:52:20」(JST)
[Wiki en表示]
Kainic acid |
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IUPAC name
(2S,3S,4S)-3-(Carboxymethyl)-4-prop-1-en-2-ylpyrrolidine-2-carboxylic acid[1]
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Other names
(3S,4S)-3-(Carboxymethyl)-4-prop-1-en-2-yl-L-proline; 2-Carboxy-3-carboxymethyl-4-isopropenyl-pyrrolidine[citation needed]
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Identifiers |
CAS number |
487-79-6 Y |
PubChem |
10255 |
ChemSpider |
9837 Y |
UNII |
SIV03811UC Y |
KEGG |
C12819 N |
MeSH |
Kainic+acid |
ChEBI |
CHEBI:31746 Y |
ChEMBL |
CHEMBL27527 N |
Beilstein Reference |
86660 |
Jmol-3D images |
Image 1 |
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CC(=C)[C@H]1CN[C@@H]([C@H]1CC(=O)O)C(=O)O
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InChI=1S/C10H15NO4/c1-5(2)7-4-11-9(10(14)15)6(7)3-8(12)13/h6-7,9,11H,1,3-4H2,2H3,(H,12,13)(H,14,15) N
Key: VLSMHEGGTFMBBZ-UHFFFAOYSA-N N
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Properties |
Molecular formula |
C10H15NO4 |
Molar mass |
213.23 g mol−1 |
Melting point |
215 °C, 488 K, 419 °F (decomposes)
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log P |
0.635 |
Acidity (pKa) |
2.031 |
Basicity (pKb) |
11.966 |
Structure |
Crystal structure |
Monoclinic |
N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
Infobox references |
Kainic acid is a natural marine acid present in some seaweed. It is a specific agonist for the kainate receptor used as an ionotropic glutamate receptor which mimics the effect of glutamate. Along with quisqualate, it is used in experiments to distinguish a receptor from the other ionotropic receptors for glutamate such as NMDA and AMPA.
Contents
- 1 Occurrence
- 2 Applications
- 3 See also
- 4 References
- 5 External links
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Occurrence
In 1953, kainic acid was originally isolated from the seaweed[2] called "Kainin-sou"(海人草) or "Makuri" (Digenea simplex) in Japan. "Kainin-sou" is used as an anthelmintic in Japan.
Kainic acid is a potent central nervous system stimulant, and has been developed as the prototype neuroexcitatory amino acid for the induction of seizures in experimental animals, at a typical dose of 10-30 mg/kg in mice. Kainic acid is neuroexcitotoxic and epileptogenic, acting through specific kainate receptors. Because of the supply shortage in 2000, the price of kainic acid has risen significantly.
Applications
- antiworming agent
- neuroscience research
- neurodegenerative agent
- modeling of epilepsy
- modeling of Alzheimer's disease
See also
- Domoic acid
- Kainate receptor
References
- ^ PubChem 10255
- ^ Moloney, Mark G. (1998). "Excitatory amino acids". Natural Product Reports 15 (2): 205–219. doi:10.1039/a815205y. PMID 9586226.
External links
Glutamatergics
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Ionotropic |
AMPA
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- Agonists: 5-Fluorowillardiine
- AMPA
- Domoic acid
- Quisqualic acid; Positive allosteric modulators: Aniracetam
- Cyclothiazide
- CX-516
- CX-546
- CX-614
- CX-691
- CX-717
- Diazoxide
- HCTZ
- IDRA-21
- LY-392,098
- LY-404,187
- LY-451,395
- LY-451,646
- LY-503,430
- Org 26576
- Oxiracetam
- PEPA
- Piracetam
- Pramiracetam
- S-18986
- Sunifiram
- Unifiram
Antagonists: ATPO
- Barbiturates
- BGG492
- Caroverine
- CNQX
- DNQX
- GYKI-52466
- NBQX
- Perampanel
- Talampanel
- Tezampanel
- Topiramate; Negative allosteric modulators: GYKI-53,655
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NMDA
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- Agonists: Glutamate/acite site competitive agonists: Aspartate
- Glutamate
- Homoquinolinic acid
- Ibotenic acid
- NMDA
- Quinolinic acid
- Tetrazolylglycine; Glycine site agonists: ACBD
- ACPC
- ACPD
- Alanine
- CCG
- Cycloserine
- DHPG
- Fluoroalanine
- Glycine
- HA-966
- L-687,414
- Milacemide
- Sarcosine
- Serine
- Tetrazolylglycine; Polyamine site agonists: Acamprosate
- Spermidine
- Spermine
Antagonists: Competitive antagonists: AP5 (APV)
- AP7
- CGP-37849
- CGP-39551
- CGP-39653
- CGP-40116
- CGS-19755
- CPP
- LY-233,053
- LY-235,959
- LY-274,614
- MDL-100,453
- Midafotel (d-CPPene)
- NPC-12,626
- NPC-17,742
- PBPD
- PEAQX
- Perzinfotel
- PPDA
- SDZ-220581
- Selfotel; Noncompetitive antagonists: ARR-15,896
- Caroverine
- Dexanabinol
- FPL-12495
- FR-115,427
- Hodgkinsine
- Magnesium
- MDL-27,266
- NPS-1506
- Psychotridine
- Zinc; Uncompetitive pore blockers: 2-MDP
- 3-MeO-PCP
- 8A-PDHQ
- Alaproclate
- Amantadine
- Aptiganel
- ARL-12,495
- ARL-15,896-AR
- ARL-16,247
- Budipine
- Delucemine
- Dexoxadrol
- Dextrallorphan
- Dieticyclidine
- Dizocilpine
- Endopsychosin
- Esketamine
- Etoxadrol
- Eticyclidine
- Gacyclidine
- Ibogaine
- Indantadol
- Ketamine
- Ketobemidone
- Loperamide
- Memantine
- Meperidine (Pethidine)
- Methadone (Levomethadone)
- Methorphan (Dextromethorphan
- Levomethorphan)
- Methoxetamine
- Milnacipran
- Morphanol (Dextrorphan
- Levorphanol)
- NEFA
- Neramexane
- Nitrous oxide
- Noribogaine
- Orphenadrine
- PCPr
- Phencyclamine
- Phencyclidine
- Propoxyphene
- Remacemide
- Rhynchophylline
- Riluzole
- Rimantadine
- Rolicyclidine
- Sabeluzole
- Tenocyclidine
- Tiletamine
- Tramadol
- Xenon; Glycine site antagonists: ACEA-1021
- ACEA-1328
- ACPC
- Carisoprodol
- CGP-39653
- CKA
- DCKA
- Felbamate
- Gavestinel
- GV-196,771
- Kynurenic acid
- L-689,560
- L-701,324
- Lacosamide
- Licostinel
- LU-73,068
- MDL-105,519
- Meprobamate
- MRZ 2/576
- PNQX
- ZD-9379; NR2B subunit antagonists: Besonprodil
- CO-101,244 (PD-174,494)
- CP-101,606
- Eliprodil
- Haloperidol
- Ifenprodil
- Isoxsuprine
- Nylidrin
- Ro8-4304
- Ro25-6981
- Traxoprodil; Polyamine site antagonists: Arcaine
- Co 101676
- Diaminopropane
- Acamprosate
- Diethylenetriamine
- Huperzine A
- Putrescine
- Ro 25-6981; Unclassified/unsorted antagonists: Chloroform
- Diethyl ether
- Enflurane
- Ethanol (Alcohol)
- Halothane
- Isoflurane
- Methoxyflurane
- Toluene
- Trichloroethane
- Trichloroethanol
- Trichloroethylene
- Xylene
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Kainate
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- Agonists: 5-Iodowillardiine
- ATPA
- Domoic acid
- Kainic acid
- LY-339,434
- SYM-2081
Antagonists: BGG492
- CNQX
- DNQX
- LY-382,884
- NBQX
- NS102
- Tezampanel
- Topiramate
- UBP-302; Negative allosteric modulators: NS-3763
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Metabotropic |
Group I
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- Agonists: Non-selective: ACPD
- DHPG
- Quisqualic acid; mGlu1-selective: Ro01-6128
- Ro67-4853
- Ro67-7476
- VU-71; mGlu5-selective: ADX-47273
- CDPPB
- CHPG
- DFB
- VU-1545
Antagonists: Non-selective: MCPG
- NPS-2390; mGlu1-selective: BAY 36-7620
- CPCCOEt
- LY-367,385
- LY-456,236; mGlu5-selective: CTEP
- Dipraglurant
- DMeOB
- LY-344,545
- SIB-1757
- SIB-1893; Negative allosteric modulators: Fenobam
- MPEP
- MTEP
- GRN-529
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Group II
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- Agonists: Non-selective: CBiPES
- DCG-IV
- Eglumegad
- LY-379,268
- LY-404,039
- LY-487,379
- MGS-0028; mGlu2-selective: BINA
- LY-566,332
Antagonists: Non-selective: APICA
- EGLU
- HYDIA
- LY-307,452
- LY-341,495
- MCPG
- MGS-0039: mGlu2-selective: PCCG-4; mGlu3-selective: CECXG; Negative allosteric modulators: RO4491533
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Group III
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- Agonists: Non-selective: L-AP4; mGlu4-selective: PHCCC
- VU-001,171
- VU-0155,041; mGlu7-selective: AMN082; mGlu8-selective: DCPG
Antagonists: Non-selective: CPPG
- MAP4
- MSOP
- MPPG
- MTPG
- UBP-1112; mGlu7-selective: MMPIP
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Transporter
inhibitors |
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Others |
Precursors
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Cofactors
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- α-Ketoglutaric acid
- Iron
- Sulfur
- Vitamin B2 (as FAD and FMN)
- Vitamin B3 (as NADPH)
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Others
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UpToDate Contents
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English Journal
- Ketone bodies attenuate excitotoxic cell injury in the rat hippocampal slice under conditions of reduced glucose availability.
- Youssef FF.
- Neurological research.Neurol Res.2015 Mar;37(3):211-6. doi: 10.1179/1743132814Y.0000000430. Epub 2014 Aug 1.
- Calorie restriction and the ketogenic diet have been successfully used in models of neuroprotection. However, there are limitations in clinical application of these diets and attention has turned to understanding their mechanism of action. Ketone bodies are produced in both diets and maybe involved
- PMID 25082548
- Increased levels and activity of cathepsins B and D in kainate-induced toxicity.
- Banerjee M1, Sasse VA2, Wang Y2, Maulik M3, Kar S4.
- Neuroscience.Neuroscience.2015 Jan 22;284:360-73. doi: 10.1016/j.neuroscience.2014.10.003. Epub 2014 Oct 13.
- Administration of kainic acid induces acute seizures that result in the loss of neurons, gliosis and reorganization of mossy fiber pathways in the hippocampus resembling those observed in human temporal lobe epilepsy. Although these structural changes have been well characterized, the mechanisms und
- PMID 25307300
- Cholesterol metabolite cholestane-3β,5α,6β-triol suppresses epileptic seizures by negative modulation of voltage-gated sodium channels.
- Tang L1, Wang Y1, Leng T1, Sun H1, Zhou Y2, Zhu W1, Qiu P1, Zhang J3, Lu B1, Yan M1, Chen W1, Su X1, Yin W4, Huang Y1, Hu H5, Yan G6.
- Steroids.Steroids.2015 Jan 8. pii: S0039-128X(15)00005-7. doi: 10.1016/j.steroids.2014.12.025. [Epub ahead of print]
- Imbalance of excitation and inhibition in neurons is implicated in the pathogenesis of epilepsy. Voltage-gated sodium channels, which play a vital role in regulating neuronal excitability, are one of the major targets for developing anti-epileptic drugs. Here we provide evidence that cholestane-3β,
- PMID 25578735
Japanese Journal
- Acupuncture suppresses kainic acid-induced neuronal death and inflammatory events in mouse hippocampus
- Kim Seung-Tae,Doo Ah-Reum,Kim Seung-Nam [他]
- The journal of physiological sciences 62(5), 377-383, 2012-09
- NAID 40019399908
- Protection of Apigenin against Kainate-Induced Excitotoxicity by Anti-oxidative Effects
- Han Jin-Yi,Ahn Sun-Young,Kim Chung-Soo [他]
- Biological & pharmaceutical bulletin 35(9), 1440-1446, 2012-09
- NAID 40019391458
Related Links
- Kainic acid (kainate) is a natural marine acid present in some seaweed. Kainic acid is a potent neuroexcitatory amino acid that acts by activating glutamate, the principal excitatory neurotransmitter in the central nervous system.
- 和光純薬工業株式会社は、試験研究用試薬・抗体の製造販売および各種受託サービスを行っています。先端技術の研究から、ライフサイエンス関連、有機合成用や環境測定用試薬まで、幅広い分野で多種多様なニーズに応えています。
★リンクテーブル★
[★]
- 英
- kainic acid, kainate, digenic acid
- ラ
- acidum kainicum
- 関
- カイニン酸受容体
[★]
カイニン酸受容体、カイニン酸レセプター
- 関
- kainate receptor