L-Kynurenine
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Hodoodo CAT#: H597402

CAS#: 2922-83-0

Description: L-Kynurenine is a key intermediate in the breakdown of L-tryptophan and the formation of nicotinamide adenine dinucleotide (NAD+) via the kynurenine pathway. It is involved in a variety of neurological processes and diseases. L-Kynurenine is a substrate for kynureninase/kynurenine hydrolase; kynurenine 3-monooxygenase and kynurenine-oxoglutarate transaminase.


Chemical Structure

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L-Kynurenine
CAS# 2922-83-0

Theoretical Analysis

Hodoodo Cat#: H597402
Name: L-Kynurenine
CAS#: 2922-83-0
Chemical Formula: C10H12N2O3
Exact Mass: 208.08
Molecular Weight: 208.217
Elemental Analysis: C, 57.69; H, 5.81; N, 13.45; O, 23.05

Price and Availability

Size Price Availability Quantity
100mg USD 250 2 Weeks
250mg USD 450 2 Weeks
1g USD 850 2 Weeks
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Synonym: Kynurenine; Kynurenine, L-; CCRIS 4425; L-Kynurenine;

IUPAC/Chemical Name: (S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid

InChi Key: YGPSJZOEDVAXAB-QMMMGPOBSA-N

InChi Code: InChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1

SMILES Code: N[C@@H](CC(C1=CC=CC=C1N)=O)C(O)=O

Appearance: Solid powder

Purity: >95% (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: >3 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).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 208.22 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Pineda-Farias JB, Pérez-Severiano F, González-Esquivel DF, Barragán-Iglesias P, Bravo-Hernández M, Cervantes-Durán C, Aguilera P, Ríos C, Granados-Soto V. The L-kynurenine-probenecid combination reduces neuropathic pain in rats. Eur J Pain. 2013 Oct;17(9):1365-73. doi: 10.1002/j.1532-2149.2013.00305.x. Epub 2013 Mar 25. PubMed PMID: 23529950.

2: Sano M, Ferchaud-Roucher V, Nael C, Aguesse A, Poupeau G, Castellano B, Darmaun D. Simultaneous detection of stable isotope-labeled and unlabeled L-tryptophan and of its main metabolites, L-kynurenine, serotonin and quinolinic acid, by gas chromatography/negative ion chemical ionization mass spectrometry. J Mass Spectrom. 2014 Feb;49(2):128-35. doi: 10.1002/jms.3313. PubMed PMID: 24677305.

3: Mabuchi R, Hara T, Matsumoto T, Shibata Y, Nakamura N, Nakamura H, Kitagawa J, Kanemura N, Goto N, Shimizu M, Ito H, Yamamoto Y, Saito K, Moriwaki H, Tsurumi H. High serum concentration of L-kynurenine predicts unfavorable outcomes in patients with acute myeloid leukemia. Leuk Lymphoma. 2016;57(1):92-8. doi: 10.3109/10428194.2015.1041388. Epub 2015 Jun 18. PubMed PMID: 25907424.

4: Sakakibara K, Feng GG, Li J, Akahori T, Yasuda Y, Nakamura E, Hatakeyama N, Fujiwara Y, Kinoshita H. Kynurenine causes vasodilation and hypotension induced by activation of KCNQ-encoded voltage-dependent K(+) channels. J Pharmacol Sci. 2015 Sep;129(1):31-7. doi: 10.1016/j.jphs.2015.07.042. Epub 2015 Aug 10. PubMed PMID: 26318674.

5: He W, Brumos J, Li H, Ji Y, Ke M, Gong X, Zeng Q, Li W, Zhang X, An F, Wen X, Li P, Chu J, Sun X, Yan C, Yan N, Xie DY, Raikhel N, Yang Z, Stepanova AN, Alonso JM, Guo H. A small-molecule screen identifies L-kynurenine as a competitive inhibitor of TAA1/TAR activity in ethylene-directed auxin biosynthesis and root growth in Arabidopsis. Plant Cell. 2011 Nov;23(11):3944-60. doi: 10.1105/tpc.111.089029. Epub 2011 Nov 22. PubMed PMID: 22108404; PubMed Central PMCID: PMC3246337.

6: Gellért L, Knapp L, Németh K, Herédi J, Varga D, Oláh G, Kocsis K, Menyhárt A, Kis Z, Farkas T, Vécsei L, Toldi J. Post-ischemic treatment with L-kynurenine sulfate exacerbates neuronal damage after transient middle cerebral artery occlusion. Neuroscience. 2013 Sep 5;247:95-101. doi: 10.1016/j.neuroscience.2013.04.063. Epub 2013 May 16. PubMed PMID: 23685169.

7: Mándi Y, Vécsei L. The kynurenine system and immunoregulation. J Neural Transm (Vienna). 2012 Feb;119(2):197-209. doi: 10.1007/s00702-011-0681-y. Epub 2011 Jul 9. Review. PubMed PMID: 21744051.

8: Koshy Cherian A, Gritton H, Johnson DE, Young D, Kozak R, Sarter M. A systemically-available kynurenine aminotransferase II (KAT II) inhibitor restores nicotine-evoked glutamatergic activity in the cortex of rats. Neuropharmacology. 2014 Jul;82:41-8. doi: 10.1016/j.neuropharm.2014.03.004. Epub 2014 Mar 16. PubMed PMID: 24647121; PubMed Central PMCID: PMC4372264.

9: Orsatti L, Speziale R, Orsale MV, Caretti F, Veneziano M, Zini M, Monteagudo E, Lyons K, Beconi M, Chan K, Herbst T, Toledo-Sherman L, Munoz-Sanjuan I, Bonelli F, Dominguez C. A single-run liquid chromatography mass spectrometry method to quantify neuroactive kynurenine pathway metabolites in rat plasma. J Pharm Biomed Anal. 2015 Mar 25;107:426-31. doi: 10.1016/j.jpba.2015.01.030. Epub 2015 Jan 24. PubMed PMID: 25668794.

10: Pérez-de la Cruz V, Amori L, Sathyasaikumar KV, Wang XD, Notarangelo FM, Wu HQ, Schwarcz R. Enzymatic transamination of D-kynurenine generates kynurenic acid in rat and human brain. J Neurochem. 2012 Mar;120(6):1026-35. doi: 10.1111/j.1471-4159.2012.07653.x. Epub 2012 Feb 2. PubMed PMID: 22224417; PubMed Central PMCID: PMC3929305.

11: Tuna D, Došlić N, Mališ M, Sobolewski AL, Domcke W. Mechanisms of photostability in kynurenines: a joint electronic-structure and dynamics study. J Phys Chem B. 2015 Feb 12;119(6):2112-24. doi: 10.1021/jp501782v. Epub 2014 Aug 1. PubMed PMID: 25054917.

12: Song H, Park H, Kim YS, Kim KD, Lee HK, Cho DH, Yang JW, Hur DY. L-kynurenine-induced apoptosis in human NK cells is mediated by reactive oxygen species. Int Immunopharmacol. 2011 Aug;11(8):932-8. doi: 10.1016/j.intimp.2011.02.005. Epub 2011 Feb 23. PubMed PMID: 21352963.

13: Apalset EM, Gjesdal CG, Ueland PM, Midttun Ø, Ulvik A, Eide GE, Meyer K, Tell GS. Interferon (IFN)-γ-mediated inflammation and the kynurenine pathway in relation to bone mineral density: the Hordaland Health Study. Clin Exp Immunol. 2014 Jun;176(3):452-60. doi: 10.1111/cei.12288. PubMed PMID: 24528145; PubMed Central PMCID: PMC4008990.

14: Theofylaktopoulou D, Ulvik A, Midttun Ø, Ueland PM, Vollset SE, Nygård O, Hustad S, Tell GS, Eussen SJ. Vitamins B2 and B6 as determinants of kynurenines and related markers of interferon-γ-mediated immune activation in the community-based Hordaland Health Study. Br J Nutr. 2014 Oct 14;112(7):1065-72. doi: 10.1017/S0007114514001858. Epub 2014 Aug 8. PubMed PMID: 25105221.

15: Chauvel V, Vamos E, Pardutz A, Vecsei L, Schoenen J, Multon S. Effect of systemic kynurenine on cortical spreading depression and its modulation by sex hormones in rat. Exp Neurol. 2012 Aug;236(2):207-14. doi: 10.1016/j.expneurol.2012.05.002. Epub 2012 May 14. PubMed PMID: 22587906.

16: Guo S, Vecsei L, Ashina M. The L-kynurenine signalling pathway in trigeminal pain processing: a potential therapeutic target in migraine? Cephalalgia. 2011 Jul;31(9):1029-38. doi: 10.1177/0333102411404717. Epub 2011 May 18. Review. PubMed PMID: 21593189.

17: Wang XD, Notarangelo FM, Wang JZ, Schwarcz R. Kynurenic acid and 3-hydroxykynurenine production from D-kynurenine in mice. Brain Res. 2012 May 21;1455:1-9. doi: 10.1016/j.brainres.2012.03.026. Epub 2012 Mar 17. PubMed PMID: 22498176; PubMed Central PMCID: PMC3340494.

18: Klockow JL, Glass TE. Development of a fluorescent chemosensor for the detection of kynurenine. Org Lett. 2013 Jan 18;15(2):235-7. doi: 10.1021/ol303025m. Epub 2012 Dec 24. PubMed PMID: 23265271.

19: Liu XC, Holtze M, Powell SB, Terrando N, Larsson MK, Persson A, Olsson SK, Orhan F, Kegel M, Asp L, Goiny M, Schwieler L, Engberg G, Karlsson H, Erhardt S. Behavioral disturbances in adult mice following neonatal virus infection or kynurenine treatment--role of brain kynurenic acid. Brain Behav Immun. 2014 Feb;36:80-9. doi: 10.1016/j.bbi.2013.10.010. Epub 2013 Oct 17. PubMed PMID: 24140727; PubMed Central PMCID: PMC3947209.

20: Maitrani C, Heyes DJ, Hay S, Arumugam S, Popik VV, Phillips RS. Preparation and photophysical properties of a caged kynurenine. Bioorg Med Chem Lett. 2012 Apr 15;22(8):2734-7. doi: 10.1016/j.bmcl.2012.02.097. Epub 2012 Mar 6. PubMed PMID: 22444682.