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

MedKoo CAT#: 556102

CAS#: 77500-04-0

Description: MeIQx, also known as 8-Methyl-IQX, is a synthetic, pale orange to brown crystalline solid that is soluble in dimethylsulfoxide and methanol. It is produced in small quantities for research purposes. 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline is formed naturally during the cooking of muscle-derived foods (meat and fish). Levels of this chemical produced in this manner are dependent on cooking temperature, cooking time and method of cooking (direct or indirect). It is one of the most abundant heterocyclic amines in a typical Western diet. 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline has also been detected in processed food flavorings, beer, wine, and cigarette smoke. It is reasonably anticipated to be a human carcinogen.


Chemical Structure

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MeIQx
CAS# 77500-04-0

Theoretical Analysis

MedKoo Cat#: 556102
Name: MeIQx
CAS#: 77500-04-0
Chemical Formula: C11H11N5
Exact Mass: 213.1014
Molecular Weight: 213.244
Elemental Analysis: C, 61.96; H, 5.20; N, 32.84

Price and Availability

Size Price Availability Quantity
25.0mg USD 450.0 2 Weeks
50.0mg USD 750.0 2 Weeks
100.0mg USD 1250.0 2 Weeks
200.0mg USD 1950.0 2 Weeks
500.0mg USD 2950.0 2 Weeks
1.0g USD 4250.0 2 Weeks
2.0g USD 6850.0 2 Weeks
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Synonym: 8-Methyl-IQX; MeIQx;

IUPAC/Chemical Name: 3,8-Dimethyl-3H-imidazo(4,5-f)quinoxalin-2-amine

InChi Key: DVCCCQNKIYNAKB-UHFFFAOYSA-N

InChi Code: InChI=1S/C11H11N5/c1-6-5-13-7-3-4-8-10(9(7)14-6)15-11(12)16(8)2/h3-5H,1-2H3,(H2,12,15)

SMILES Code: NC1=NC2=C3N=C(C)C=NC3=CC=C2N1C

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: 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

Preparing Stock Solutions

The following data is based on the product molecular weight 213.244 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

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1: Jiang Y, Jiang Q, Fan D, Wang M, Zhao Y. Effect of Acrolein, a Lipid Oxidation Product, on the Formation of the Heterocyclic Aromatic Amine 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in Model Systems and Roast Salmon Patties. J Agric Food Chem. 2022 May 18;70(19):5887-5895. doi: 10.1021/acs.jafc.2c00970. Epub 2022 May 3. PMID: 35504016.

2: Kocaoğlu Cenkci S, Kaya B. Effects of Chlorophyll a and b in Reducing Genotoxicity of 2-Amino-3,8-dimethylimidazo[4,5-F]quinoxaline (MeIQx). Biology (Basel). 2022 Apr 15;11(4):602. doi: 10.3390/biology11040602. PMID: 35453801; PMCID: PMC9028374.

3: Hidalgo FJ, Lavado-Tena CM, Zamora R. Identification of acrolein as the reactive carbonyl responsible for the formation of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx). Food Chem. 2021 May 1;343:128478. doi: 10.1016/j.foodchem.2020.128478. Epub 2020 Oct 27. PMID: 33158682.

4: Montes C, Contento AM, Villaseñor MJ, Ríos Á. A screen-printed electrode modified with silver nanoparticles and carbon nanofibers in a nafion matrix for ionic liquid-based dispersive liquid-liquid microextraction and voltammetric assay of heterocyclic amine 8-MeIQx in food. Mikrochim Acta. 2020 Feb 26;187(3):190. doi: 10.1007/s00604-020-4138-6. PMID: 32103341.

5: Zhang J, Empl MT, Schneider M, Schröder B, Stadnicka-Michalak J, Breves G, Steinberg P, Sturla SJ. Gut microbial transformation of the dietary mutagen MeIQx may reduce exposure levels without altering intestinal transport. Toxicol In Vitro. 2019 Sep;59:238-245. doi: 10.1016/j.tiv.2019.04.004. Epub 2019 Apr 4. PMID: 30954653.

6: Delannée V, Langouët S, Théret N, Siegel A. A modeling approach to evaluate the balance between bioactivation and detoxification of MeIQx in human hepatocytes. PeerJ. 2017 Sep 1;5:e3703. doi: 10.7717/peerj.3703. PMID: 28879062; PMCID: PMC5582613.

7: Kuroda K, Kijima A, Ishii Y, Takasu S, Jin M, Matsushita K, Kodama Y, Umemura T. Flumequine enhances the in vivo mutagenicity of MeIQx in the mouse liver. Arch Toxicol. 2013 Aug;87(8):1609-19. doi: 10.1007/s00204-013-1064-y. Epub 2013 May 17. PMID: 23681119.

8: Viegas O, Zegura B, Pezdric M, Novak M, Ferreira IM, Pinho O, Filipič M. Protective effects of xanthohumol against the genotoxicity of heterocyclic aromatic amines MeIQx and PhIP in bacteria and in human hepatoma (HepG2) cells. Food Chem Toxicol. 2012 Mar;50(3-4):949-55. doi: 10.1016/j.fct.2011.11.031. Epub 2011 Nov 26. PMID: 22138251.

9: Okamura T, Ishii Y, Suzuki Y, Inoue T, Tasaki M, Kodama Y, Nohmi T, Mitsumori K, Umemura T, Nishikawa A. Effects of co-treatment of dextran sulfate sodium and MeIQx on genotoxicity and possible carcinogenicity in the colon of p53-deficient mice. J Toxicol Sci. 2010 Oct;35(5):731-41. doi: 10.2131/jts.35.731. PMID: 20930467.

10: Okamura T, Ishii Y, Suzuki Y, Inoue T, Tasaki M, Kodama Y, Nohmi T, Mitsumori K, Umemura T, Nishikawa A. Enhancing effects of carbon tetrachloride on in vivo mutagenicity in the liver of mice fed 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx). J Toxicol Sci. 2010 Oct;35(5):709-20. doi: 10.2131/jts.35.709. PMID: 20930465.

11: Suzuki S, Takeshita K, Doi Y, Asamoto M, Takahashi S, Naiki-Ito A, Shirai T. 2-Amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx)-induced hepatocarcinogenesis is not enhanced by CYP1A inducers, alpha- and beta- naphthoflavone: relationship to intralobular distribution of CYP1A expression. Toxicol Pathol. 2010 Jun;38(4):583-91. doi: 10.1177/0192623310367808. Epub 2010 May 6. PMID: 20448087.

12: Takeuchi H, Saoo K, Yamakawa K, Matsuda Y, Yokohira M, Zeng Y, Kuno T, Totsuka Y, Takahashi M, Wakabayashi K, Imaida K. Tumorigenesis of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx), but not enhancing effects of concomitant high-fat diet, on lung carcinogenesis in female A/J mice. Oncol Lett. 2010 Jan;1(1):137-142. doi: 10.3892/ol_00000025. Epub 2010 Jan 1. PMID: 22966271; PMCID: PMC3436480.

13: Metry KJ, Neale JR, Doll MA, Howarth AL, States JC, McGregor WG, Pierce WM Jr, Hein DW. Effect of rapid human N-acetyltransferase 2 haplotype on DNA damage and mutagenesis induced by 2-amino-3-methylimidazo-[4,5-f]quinoline (IQ) and 2-amino-3,8-dimethylimidazo-[4,5-f]quinoxaline (MeIQx). Mutat Res. 2010 Feb 3;684(1-2):66-73. doi: 10.1016/j.mrfmmm.2009.12.001. Epub 2009 Dec 11. PMID: 20004212; PMCID: PMC2820402.

14: Kushida M, Wanibuchi H, Wei M, Kakehashi A, Ozaki K, Sukata T, Miyata K, Ogata K, Uwagawa S, Fukushima S. Ethanol Does Not Promote MeIQx-initiated Rat Colon Carcinogenesis Based on Evidence from Analysis of a Colon Cancer Surrogate Marker. J Toxicol Pathol. 2009 Mar;22(1):65-70. doi: 10.1293/tox.22.65. Epub 2009 Apr 6. PMID: 22271977; PMCID: PMC3246019.

15: Kawabe M, Futakuchi M, Tamano S, Shirai T, Hirose M. Modifying effects of chitin, chitosan and their related compounds on 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) in a rat medium-term hepatocarcinogenesis model, and their post-initiation effects in a female rat 2-stage multi-organ carcinogenesis model. Food Chem Toxicol. 2008 Aug;46(8):2758-63. doi: 10.1016/j.fct.2008.04.032. Epub 2008 Apr 29. PMID: 18547703.

16: Kang JS, Wanibuchi H, Murai T, Morimura K, Kinoshita A, Fukushima S. Analysis of gene expression in different stages of MeIQx-induced rat hepatocarcinogenesis. Oncol Rep. 2007 Apr;17(4):747-52. PMID: 17342310.

17: Takahashi E, Arimoto S, Okamoto K, Negishi T. Enhancement of phase II enzyme activity by purpurin resulting in the suppression of MeIQx-DNA-adduct formation in mice. Mutat Res. 2007 Jan 10;626(1-2):128-34. doi: 10.1016/j.mrgentox.2006.09.011. Epub 2006 Nov 29. PMID: 17137831.

18: Kang JS, Wanibuchi H, Morimura K, Totsuka Y, Yoshimura I, Fukushima S. Existence of a no effect level for MeIQx hepatocarcinogenicity on a background of thioacetamide-induced liver damage in rats. Cancer Sci. 2006 Jun;97(6):453-8. doi: 10.1111/j.1349-7006.2006.00201.x. PMID: 16734722.

19: Kuribayashi M, Asamoto M, Suzuki S, Hokaiwado N, Ogawa K, Shirai T. Lack of modification of 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) rat hepatocarcinogenesis by caffeine, a CYP1A2 inducer, points to complex counteracting influences. Cancer Lett. 2006 Feb 8;232(2):289-99. doi: 10.1016/j.canlet.2005.02.041. Epub 2005 Apr 22. PMID: 16458123.

20: Nishikawa-Ogawa M, Wanibuchi H, Morimura K, Kinoshita A, Nishikawa T, Hayashi S, Yano Y, Fukushima S. N-acetylcysteine and S-methylcysteine inhibit MeIQx rat hepatocarcinogenesis in the post-initiation stage. Carcinogenesis. 2006 May;27(5):982-8. doi: 10.1093/carcin/bgi277. Epub 2005 Dec 7. PMID: 16338951.

MeIQx

25.0mg / USD 450.0