Absorption, Distribution and Excretion
More than half of the bound dyes in all hepatocyte components are bound to sol proteins; of these, 80% are bound to components that comprise only 15% of the sol proteins. The bile excretion of the azo dye carcinogen N,N-dimethyl-4-aminoazo (C-14)benzene (DAB) was studied in male rats. Following a single intravenous injection of the carcinogen, 20-25% of the injected radioactive material appeared in the bile within one hour, entirely as metabolites. Intraperitoneal injection into Wistar rats revealed a tendency for the carcinogen to bind to liver tissue, cell nuclei, and chromatin, with a specific binding affinity for nuclear non-histone proteins. Metabolism/Metabolites In rats, 4'-dimethylamino-4-hydroxyazobenzene and 4-methylaminoazobenzene are produced. /Excerpt from table/
The metabolic pathways of DAB are as follows: 1) reduction and cleavage of the azo group; 2) demethylation; 3) cyclohydroxylation; 4) N-hydroxylation; 5) N-acetylation and O-binding of metabolites.
In rats and mice, carcinogenic aromatic azo dyes undergo N-hydroxylation; for example, N-hydroxy-N-acetyl-4-aminoazobenzene is a urinary metabolite of the hepatocarcinogen 4-dimethylaminoazobenzene…
This study investigated the azo reduction reaction of dimethylaminoazobenzene (DAB) in vitro using purified rat liver NADPH cytochrome P450 reductase and a partially purified recombinant cytochrome P450 system. Male Wistar rats were induced with clofibrate, naffenoxam, phenobarbital, or β-naphthylflavonoid before isolating liver microsomes. Both purified NADPH cytochrome P450 reductase and the recombinant system reduced dimethylaminoazobenzene, but the latter's reduction rate was more than five times higher. The reduction of dimethylaminoazobenzene was optimal at a 2:1 ratio of azoreductase to cytochrome P450. Clofibrate was the only inducer of azoreductase. The reaction with the suicide inhibitor 10-undecynyl acid distinguished laurate hydroxylase from azoreductase. The recombinant system was active in both air and carbon monoxide, while purified NADPH cytochrome P450 reductase was inhibited in air. In both systems, the presence of flavin adenine dinucleotide or flavin mononucleotide increased the azoreduction rate of dimethylaminoazobenzene by nearly 50 times, but this was observed only under anaerobic conditions, indicating that the promoting effect of electron flow to dimethylaminoazobenzene came solely from NADPH cytochrome P450 reductase, not from cytochrome P450 itself. This was confirmed using cytochrome P450 inhibitors. …A non-essential electron flow appears to exist between cytochrome P450 and dimethylaminoazobenzene, bypassing the oxygen-sensitive step. Dietary riboflavin may attenuate the hepatocarcinogenicity of dimethylaminoazobenzene solely through its effects on gut bacteria. For more complete data on the metabolism/metabolites of 4-(dimethylamino)azobenzene (7 in total), please visit the HSDB record page.

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Biological half-life
No relevant report found; [TDR, page 547]

[1]. Nakano N, et, al. An automatic monitor of formaldehyde in air by a monitoring tape method. J Environ Monit. 1999 Jun;1(3):255-8.

According to an independent committee of scientific and health experts, 4-Dimethylaminoazobenzene is possibly carcinogenic. 4-Dimethylaminoazobenzene is a yellow crystalline flake or orange powder. (NTP, 1992) 4-(Dimethylamino)azobenzene belongs to the azobenzene family of compounds. 4-Dimethylaminoazobenzene is used as a polishing agent, wax, and dye in soaps. Short-term (acute) skin contact with 4-dimethylaminoazobenzene in humans may cause contact dermatitis. Currently, there is no information on the chronic (long-term), reproductive, developmental, or carcinogenic effects of 4-dimethylaminoazobenzene in humans. Animal studies have reported birth defects in the offspring of mice exposed to 4-dimethylaminoazobenzene, and oral administration of 4-dimethylaminoazobenzene can cause lung, liver, and bladder tumors. The U.S. Environmental Protection Agency has not classified 4-dimethylaminoazobenzene as a carcinogen. The International Agency for Research on Cancer (IARC) has classified 4-dimethylaminoazobenzene as a Group 2B carcinogen, possibly carcinogenic to humans. 4-Dimethylaminoazobenzene is a yellow crystalline solid compound. It was once used as a polishing agent, a colorant in waxes, polystyrene, and soaps, and also as a pH indicator, but is no longer used or produced in the United States. Contact with this substance can cause dermatitis. 4-Dimethylaminoazobenzene is a likely human carcinogen. (NCI05) It is a reagent primarily used to induce experimental liver cancer. According to the Fourth Annual Report on Carcinogens published in 1985 (NTP 85-002, page 89), this compound is a likely carcinogen. (Merck, 11th edition) Mechanism of Action 4-Dimethylaminoazobenzene (or Cream Yellow) was used as a laboratory liver carcinogen to study the mechanism of action of such compounds, including structure-activity relationships. Due to its characteristic color change with pH, it was the first carcinogen confirmed to bind to cellular macromolecules. Because of the presence of flavin-dependent azo dye reductases, it was one of the first carcinogens discovered whose activity was significantly regulated by nutrients. Introducing polar groups such as sulfonic acids into simple azo dyes usually eliminates their carcinogenic and mutagenic properties. Therefore, molecules such as FD and C Red No. 2 (amaranth) are not mutagenic or carcinogenic. On the other hand, tetrazo dyes, such as Direct Black 38 or Direct Blue 6, although not inherently mutagenic and highly polar, release benzidine, a mutagenic and carcinogenic substance, upon bacterial reduction of the azo bonds. These dyes are highly carcinogenic.

C14H15N3

225.2890

225.126

60-11-7

N,N-dimethyl-4-(phenyldiazenyl)aniline-d5;1398109-08-4

6053

YELLOW CRYSTALLINE LEAFLETS
Yellow, leaf-shaped crystals.

1.0±0.1 g/cm3

371.0±25.0 °C at 760 mmHg

111 °C (dec.)(lit.)

178.2±23.2 °C

0.0±0.8 mmHg at 25°C

1.567

4.43

27.96

0

3

3

17

236

0

N(C([H])([H])[H])(C([H])([H])[H])C1C([H])=C([H])C(=C([H])C=1[H])/N=N/C1C([H])=C([H])C([H])=C([H])C=1[H]

JCYPECIVGRXBMO-UHFFFAOYSA-N

InChI=1S/C14H15N3/c1-17(2)14-10-8-13(9-11-14)16-15-12-6-4-3-5-7-12/h3-11H,1-2H3

N,N-dimethyl-4-phenyldiazenylaniline

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

注意： 本产品在运输和储存过程中需避光。

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

注意: 如下所列的是一些常用的体内动物实验溶解配方，主要用于溶解难溶或不溶于水的产品（水溶度<1 mg/mL）。 建议您先取少量样品进行尝试，如该配方可行，再根据实验需求增加样品量。

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注射用配方1: DMSO : Tween 80： Saline = 10 : 5 : 85 (如： 100 μL DMSO → 50 μL Tween 80 → 850 μL Saline)
*生理盐水/Saline的制备：将0.9g氯化钠/NaCl溶解在100 mL ddH ₂ O中，得到澄清溶液。
注射用配方 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL DMSO → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)
注射用配方 3: DMSO : Corn oil = 10 : 90 (如： 100 μL DMSO → 900 μL Corn oil)
示例: 以注射用配方 3 (DMSO : Corn oil = 10 : 90) 为例说明, 如果要配制 1 mL 2.5 mg/mL的工作液, 您可以取 100 μL 25 mg/mL 澄清的 DMSO 储备液，加到 900 μL Corn oil/玉米油中, 混合均匀。

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注射用配方 4: DMSO : 20% SBE-β-CD in Saline = 10 : 90 [如：100 μL DMSO → 900 μL (20% SBE-β-CD in Saline)]
*20% SBE-β-CD in Saline的制备（4°C，储存1周）：将2g SBE-β-CD (磺丁基-β-环糊精) 溶解于10mL生理盐水中，得到澄清溶液。
注射用配方 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (如： 500 μL 2-Hydroxypropyl-β-cyclodextrin (羟丙基环胡精)→ 500 μL Saline)
注射用配方 6: DMSO : PEG300 : Castor oil : Saline = 5 : 10 : 20 : 65 (如： 50 μL DMSO → 100 μL PEG300 → 200 μL Castor oil → 650 μL Saline)
注射用配方 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (如： 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
注射用配方 8: 溶解于Cremophor/Ethanol (50 : 50), 然后用生理盐水稀释。
注射用配方 9: EtOH : Corn oil = 10 : 90 (如： 100 μL EtOH → 900 μL Corn oil)
注射用配方 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (如： 100 μL EtOH → 400 μL PEG300 → 50 μL Tween 80 → 450 μL Saline)

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口服配方 1: 悬浮于0.5% CMC Na (羧甲基纤维素钠)
口服配方 2: 悬浮于0.5% Carboxymethyl cellulose (羧甲基纤维素)
示例: 以口服配方 1 (悬浮于 0.5% CMC Na)为例说明, 如果要配制 100 mL 2.5 mg/mL 的工作液, 您可以先取0.5g CMC Na并将其溶解于100mL ddH2O中，得到0.5%CMC-Na澄清溶液；然后将250 mg待测化合物加到100 mL前述 0.5%CMC Na溶液中，得到悬浮液。

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口服配方 3: 溶解于 PEG400 (聚乙二醇400)
口服配方 4: 悬浮于0.2% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 5: 溶解于0.25% Tween 80 and 0.5% Carboxymethyl cellulose (羧甲基纤维素)
口服配方 6: 做成粉末与食物混合

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注意: 以上为较为常见方法，仅供参考， InvivoChem并未独立验证这些配方的准确性。具体溶剂的选择首先应参照文献已报道溶解方法、配方或剂型，对于某些尚未有文献报道溶解方法的化合物，需通过前期实验来确定（建议先取少量样品进行尝试），包括产品的溶解情况、梯度设置、动物的耐受性等。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。