1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide

Synonym(s):1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phen yl-1H-pyrazole-5-carboxamide;2-Methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)-amide;2-Methyl-2H-pyrazole-3-carboxylic acid-(2-methyl-4- o-tolyl-azophenyl)-amide, CH-223191;2-Methyl-2H-pyrazole-3-carboxylic acid-(2-methyl-4-o-tolyl-azophenyl)-amide, CH-223191;AhR Antagonist - CAS 301326-22-7 - Calbiochem

CAS NO.：301326-22-7
Empirical Formula: C19H19N5O
Molecular Weight: 333.39
MDL number: MFCD00377884
SAFETY DATA SHEET (SDS)
Update Date: 2025-12-29 17:56:15

1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide Structural

What is 1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide?

Description

CH-221391 (CAS 301326-22-7) is an arylhydrocarbon (AhR) receptor antagonist, IC50=30 nM.1 Blocks endogenous AhR agonist-induced differentiation of Th17 cells.2?? Promotes expansion of human hematopoietic stem cells.3 Mitigates cytokine-mediated inflammatory signaling in human fibroblast-like synoviocytes.4 An important tool for probing the involvement of AhR in the toxicity of various environmental toxins such as TCDD and other dioxins.5

The Uses of 1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide

CH-223191 has been used as aryl hydrocarbon receptor (AHR) antagonist in HepaRG cells, TH17-IL-10+ cells and organoids.

What are the applications of Application

CH 223191 is a potent and specific aryl hydrocarbon receptor inhibitor

Definition

ChEBI: 2-methyl-N-[2-methyl-4-(2-methylphenyl)azophenyl]-3-pyrazolecarboxamide is an aromatic amide.

Biochem/physiol Actions

CH-223191 is a potent and specific aryl hydrocarbon receptor (AhR) antagonist. It inhibited TCDD-mediated nuclear translocation and DNA binding of AhR, and inhibited TCDD-induced luciferase activity with an IC50 of 30nM. Unlike some other AhR antagonists which display agonist activity at high concentrations, CH-223191 did not stimulate AhR-dependent transcription even at 100 micromolar. It is also specific for AhR, displaying no affinity for the estrogen receptor, as some other antagonists do.

Storage

Store at +4°C

References

1) Kim et al. (2006), Novel compound 2-methyl-2H-pyrazole-3-carboxylic acid (2-methyl-4-o-tolylazo-phenyl)amide (CH-223191) prevents 2,3,7,8-TCDD-induced toxicity by antagonizing the aryl hydrocarbon receptor; Mol. Pharmacol., 69 1871 2) Veldhoen et al. (2009), Natural agonists for aryl hydrocarbon receptor in culture medium are essential for optimal differentiation of Th17 T cells; J. Exp. Med., 206 43 3) Carlin et al. (2013), T-cell potential of human adult and cord blood hemopoietic stem cells expanded with the use of aryl hydrocarbon receptor antagonists; Cytotherapy, 15 224 4) Lahoti et al. (2013), Aryl hydrocarbon receptor antagonism mitigates cytokine-mediated inflammatory signaling in primary human fibroblast-like synoviocytes; Ann. Rheum. Dis, 72 1708 5) Petroff et al. (2011), The aryl hydrocarbon receptor agonist 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) alters early embryonic development in a rat IVF exposure model; Reprod. Toxicol., 32 286

Properties of 1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide

Melting point:	>164°C (dec.)
Boiling point:	469.4±45.0 °C(Predicted)
Density	1.20±0.1 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: ≥20mg/mL
form	powder
pka	12.98±0.70(Predicted)
color	orange-brown
Stability:	Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

Safety information for 1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral
Precautionary Statement Codes	P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P330:Rinse mouth. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P501:Dispose of contents/container to..…

Computed Descriptors for 1-Methyl-N-[2-methyl-4-[2-(2-methylphenyl)diazenyl]phenyl-1H-pyrazole-5-carboxamide

InChIKey

LKTNEXPODAWWFM-GHVJWSGMSA-N

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