Kainic acid
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 540253

CAS#: 487-79-6

Description: Kainic acid is an excitatory amino acid and AMPA and kainate receptor agonist found in seaweed. It increases glutamate release and stimulates Na channels, inducing seizures.


Price and Availability

Size
Price

5mg
USD 215
Size
Price

25mg
USD 525
Size
Price

Kainic acid purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 540253
Name: Kainic acid
CAS#: 487-79-6
Chemical Formula: C10H15NO4
Exact Mass: 213.1001
Molecular Weight: 213.23
Elemental Analysis: C, 56.33; H, 7.09; N, 6.57; O, 30.01


Synonym: Digenin; Helminal; Digenic acid; Kainic acid

IUPAC/Chemical Name: (2S,3S,4S)-3-(carboxymethyl)-4-(prop-1-en-2-yl)pyrrolidine-2-carboxylic acid

InChi Key: VLSMHEGGTFMBBZ-OOZYFLPDSA-N

InChi Code: 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)/t6-,7+,9-/m0/s1

SMILES Code: O=C(O)C[C@@H]1[C@@H](C(O)=O)NC[C@@H]1C(C)=C


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Oe K, Ohfune Y, Shinada T. Short total synthesis of (-)-kainic acid. Org Lett. 2014 May 2;16(9):2550-3. doi: 10.1021/ol5009526. Epub 2014 Apr 17. PubMed PMID: 24742128.

2: Liu H, Song Z, Liao D, Zhang T, Liu F, Zhuang K, Luo K, Yang L. Neuroprotective effects of trans-caryophyllene against kainic acid induced seizure activity and oxidative stress in mice. Neurochem Res. 2015 Jan;40(1):118-23. doi: 10.1007/s11064-014-1474-0. Epub 2014 Nov 23. PubMed PMID: 25417010.

3: Mollica A, Costante R, Stefanucci A, Novellino E. New Insight on the Synthesis of Neurotoxins Domoic Acid and Kainic Acid. Protein Pept Lett. 2015;22(8):696-711. PubMed PMID: 25658114.

4: Gynther M, Petsalo A, Hansen SH, Bunch L, Pickering DS. Blood-brain barrier permeability and brain uptake mechanism of kainic acid and dihydrokainic acid. Neurochem Res. 2015 Mar;40(3):542-9. doi: 10.1007/s11064-014-1499-4. Epub 2014 Dec 9. PubMed PMID: 25488153.

5: Zhang M, Watanabe K, Tsukamoto M, Shibuya R, Morimoto H, Ohshima T. A short scalable route to (-)-α-kainic acid using Pt-catalyzed direct allylic amination. Chemistry. 2015 Mar 2;21(10):3937-41. doi: 10.1002/chem.201406557. Epub 2015 Jan 21. PubMed PMID: 25604395.

6: Zanato C, Watson S, Bewick GS, Harrison WT, Zanda M. Synthesis and biological evaluation of (-)-kainic acid analogues as phospholipase D-coupled metabotropic glutamate receptor ligands. Org Biomol Chem. 2014 Dec 21;12(47):9638-43. doi: 10.1039/c4ob02002b. Epub 2014 Oct 27. PubMed PMID: 25347058.

7: Riljak V, Marešová D, Pokorný J, Jandová K. Subconvulsive dose of kainic acid transiently increases the locomotor activity of adult Wistar rats. Physiol Res. 2015;64(2):263-7. Epub 2014 Oct 15. PubMed PMID: 25317690.

8: Orellana A, Pandey SK, Carret S, Greene AE, Poisson JF. A Diels-Alder-based total synthesis of (-)-kainic acid. J Org Chem. 2012 Jun 15;77(12):5286-96. doi: 10.1021/jo300608g. Epub 2012 May 29. PubMed PMID: 22551444.

9: Davis RE, Wilmot GR, Cha JH. Glutamic acid-insensitive [3H]kainic acid binding in goldfish brain. Brain Res. 1992 Jan 31;571(1):73-8. PubMed PMID: 1377085.

10: Kesava Reddy N, Chandrasekhar S. Total synthesis of (-)-α-kainic acid via chirality transfer through Ireland-Claisen rearrangement. J Org Chem. 2013 Apr 5;78(7):3355-60. doi: 10.1021/jo400001t. Epub 2013 Mar 15. PubMed PMID: 23470056.

11: Ramsey UP, Bird CJ, Shacklock PF, Laycock MV, Wright JL. Kainic acid and 1'-hydroxykainic acid from Palmariales. Nat Toxins. 1994;2(5):286-92. PubMed PMID: 7866664.

12: Hampson DR, Huang XP, Wells JW, Walter JA, Wright JL. Interaction of domoic acid and several derivatives with kainic acid and AMPA binding sites in rat brain. Eur J Pharmacol. 1992 Jul 21;218(1):1-8. PubMed PMID: 1383007.

13: Alvarez-Fischer D, Grundmann M, Lu L, Samans B, Fritsch B, Möller JC, Schaefer MK, Hartmann A, Oertel WH, Bandmann O. Prolonged generalized dystonia after chronic cerebellar application of kainic acid. Brain Res. 2012 Jun 29;1464:82-8. doi: 10.1016/j.brainres.2012.05.007. Epub 2012 May 15. PubMed PMID: 22595488.

14: Arena G, Chen CC, Leonori D, Aggarwal VK. Concise synthesis of (+)-allo-kainic acid via MgI2-mediated tandem aziridine ring opening-formal [3 + 2] cycloaddition. Org Lett. 2013 Aug 16;15(16):4250-3. doi: 10.1021/ol4020333. Epub 2013 Aug 2. PubMed PMID: 23909824.

15: Turunc E, Kanit L, Yalcin A. Effect of gamma-glutamylcysteine ethylester on the levels of c-fos mRNA expression, glutathione and reactive oxygen species formation in kainic acid excitotoxicity. J Pharm Pharmacol. 2010 Aug;62(8):1010-7. doi: 10.1111/j.2042-7158.2010.01122.x. PubMed PMID: 20663035.

16: Brown-Croyts LM, Caton PW, Radecki DT, McPherson SL. Phenobarbital pre-treatment prevents kainic acid-induced impairments in acquisition learning. Life Sci. 2000 Jun 30;67(6):643-50. PubMed PMID: 12659170.

17: Luo Z, Zhou B, Li Y. Total synthesis of (-)-(α)-kainic acid via a diastereoselective intramolecular [3 + 2] cycloaddition reaction of an aryl cyclopropyl ketone with an alkyne. Org Lett. 2012 May 18;14(10):2540-3. doi: 10.1021/ol3008414. Epub 2012 May 3. PubMed PMID: 22554402.

18: Matsuoka Y, Kitamura Y, Okazaki M, Kakimura J, Tooyama I, Kimura H, Taniguchi T. Kainic acid induction of heme oxygenase in vivo and in vitro. Neuroscience. 1998 Aug;85(4):1223-33. PubMed PMID: 9681959.

19: Wei G, Chalker JM, Cohen T. Synthesis of (-)-α-kainic acid via TMSCl-promoted Pd-catalyzed zinc-ene cyclization of an allyl acetate. J Org Chem. 2011 Oct 7;76(19):7912-7. doi: 10.1021/jo201341q. Epub 2011 Aug 25. PubMed PMID: 21866925.

20: Jiang S, Kuwano K, Ishikawa N, Yano M, Takatani T, Arakawa O. Production of domoic acid by laboratory culture of the red alga Chondria armata. Toxicon. 2014 Dec 15;92:1-5. doi: 10.1016/j.toxicon.2014.09.003. Epub 2014 Sep 18. PubMed PMID: 25240296.