MedKoo Cat#: 556180 | Name: 3-Hydroxykynurenamine

Description:

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

3-Hydroxykynurenamine, also known as 3-Hydroxy-L-kynurenamine or 3-HKA, is a biogenic amine produced via an alternative pathway of tryptophan metabolism. In vitro, 3-HKA has an anti-inflammatory profile by inhibiting the IFN-γ mediated STAT1/NF-κΒ pathway in both mouse and human dendritic cells (DCs) with a consequent decrease in the release of pro-inflammatory chemokines and cytokines, most notably TNF, IL-6, and IL12p70. 3-HKA has protective effects in an experimental mouse model of psoriasis by decreasing skin thickness, erythema, scaling and fissuring, reducing TNF, IL-1β, IFN-γ, and IL-17 production, and inhibiting generation of effector CD8+ T cells. Similarly, in a mouse model of nephrotoxic nephritis, besides reducing inflammatory cytokines, 3-HKA improves proteinuria and serum urea nitrogen, overall ameliorating immune-mediated glomerulonephritis and renal dysfunction.

Chemical Structure

3-Hydroxykynurenamine
3-Hydroxykynurenamine
CAS#99362-47-7

Theoretical Analysis

MedKoo Cat#: 556180

Name: 3-Hydroxykynurenamine

CAS#: 99362-47-7

Chemical Formula: C9H12N2O

Exact Mass: 180.0899

Molecular Weight: 180.21

Elemental Analysis: C, 59.99; H, 6.71; N, 15.55; O, 17.76

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
3-Hydroxy-L-kynurenamine; 3-HKA; 3-Hydroxykynurenamine; 3-Hydroxy-kynurenamine;
IUPAC/Chemical Name
3-Amino-1-(2-amino-3-hydroxyphenyl)-1-propanone
InChi Key
ODOPEICAGBYCFH-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H12N2O2/c10-5-4-7(12)6-2-1-3-8(13)9(6)11/h1-3,13H,4-5,10-11H2
SMILES Code
O=C(C1=CC=CC(O)=C1N)CCN
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Tryptophan catabolism is a major metabolic pathway utilized by several professional and non-professional antigen presenting cells to maintain immunological tolerance.

Preparing Stock Solutions

The following data is based on the product molecular weight 180.21 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
1. Clement CC, D'Alessandro A, Thangaswamy S, Chalmers S, Furtado R, Spada S, Mondanelli G, Ianni F, Gehrke S, Gargaro M, Manni G, Cara LCL, Runge P, Tsai WL, Karaman S, Arasa J, Fernandez-Rodriguez R, Beck A, Macchiarulo A, Gadina M, Halin C, Fallarino F, Skobe M, Veldhoen M, Moretti S, Formenti S, Demaria S, Soni RK, Galarini R, Sardella R, Lauvau G, Putterman C, Alitalo K, Grohmann U, Santambrogio L. 3-hydroxy-L-kynurenamine is an immunomodulatory biogenic amine. Nat Commun. 2021 Jul 21;12(1):4447. doi: 10.1038/s41467-021-24785-3. PMID: 34290243; PMCID: PMC8295276. 2. Synthesis of 3-hydroxyquinuramine (2-amino-3-hydroxy-β-aminopropiophenone) https://www.jstage.jst.go.jp/article/nikkashi1948/77/3/77_3_510/_article/-char/ja/