1. Exposure Data

1.1. Chemical and physical data

1.1.1. Synonyms, structural and molecular data

Magenta I

Chem. Abstr. Serv. Reg. No.: 632-99-5; replaces 8053-09-6

Chem. Abstr. Name: 4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-l-ylidene)methyl]-2-methylbenzenamine, monohydrochloride

Colour Index No.: 42510

Synonyms: Basic fuchsin; basic fuchsine; basic magenta; Basic Violet 14; CI Basic Violet 14; CI Basic Violet 14, monohydrochloride; fuchsin; fuchsine; rosaniline; rosaniline chloride; rosaniline hydrochloride; rosanilinium chloride

Magenta II

Chem. Abstr. Serv. Reg. No.: 26261-57-4

Chem. Abstr. Name: 4-[(4-Aminophenyl)(4-imino-3-methyl-2,5-cyclohexadien-1-ylidene)methyl]-2-methylbenzenamine, monohydrochloride Synonym: Dimethyl fuchsin

Magenta III

Chem. Abstr. Serv. Reg. No.: 3248-91-7; replaces 100359-07-7

Chem. Abstr. Name: 4-[(4-Amino-3-methylphenyl)(4-imino-3-methyl-2,5-cyclohexa-dien-l-ylidene)methyl]-2-methylbenzenamine, monohydrochloride

Colour Index No.: 42520

Synonyms: Basic Violet 2; CI Basic Violet 2; neofuchsine; new fuchsine; new magenta; trimethyl fuchsin; isorubine

CI Basic Red 9

Chem. Abstr. Serv. Reg. No.: 569-61-9; replaces 70426-60-7; 131883-55-1

Chem. Abstr. Name: 4-[(4-Aminophenyl)(4-imino-2,5-cyclohexadien-l-ylidene)methyl]-benzenamine, monohydrochloride

Colour Index No.: 42500

Synonyms: Basic fuchsin; basic parafuchsine; Basic Red 9; basic rubine; CI Basic Red 9, monohydrochloride; para-fuchsin; para-fuchsine; parafuchsin; parafuchsine; para-magenta; pararosaniline; pararosaniline chloride; pararosaniline hydrochloride; para-rosaniline hydrochloride

1.1.2. Chemical and physical properties of the substances

Magenta I (CI 42510)

• (a) Description: Dark-green crystalline powder (Green, 1990)
• (b) Melting-point: 250 °C (decomposes) (Green, 1990)
• (c) Spectroscopy data: Infrared and ultraviolet spectral data have been reported (Sadtler Research Laboratories, 1980; Pouchert, 1981, Green, 1990; Sadtler Research Laboratories, 1991).
• (d) Solubility: Soluble in water (4 mg/ml), ethanol (30 mg/ml), ethylene glycol methyl ether (30 mg/ml) (Green, 1990) and methanol (Sadtler Research Laboratories, 1980)
• (e) Reactivity: Destroyed by strong oxidizing agents; readily reduced to leuco-bases with a variety of reducing reagents; sensitive to photochemical oxidation (Bannister & Elliott, 1983)

CI Basic Red 9 (CI 42500)

• (a) Description: Dark-green crystalline powder (Green, 1990)
• (b) Melting-point: 268–270 °C (decomposes) (Green, 1990)
• (c) Spectroscopy data: Infrared, ultraviolet and nuclear magnetic resonance spectral data have been reported (Sadtler Research Laboratories, 1980; Pouchert, 1981; US National Toxicology Program, 1986; Green, 1990; Sadtler Research Laboratories, 1991).
• (d) Solubility: Soluble in water (2–3 mg/ml), ethanol (2–25 mg/ml), ethylene glycol methyl ether (50–70 mg/ml) (Green, 1990) and methanol (Sadtler Research Laboratories, 1980)
• (e) Reactivity: Destroyed by strong oxidizing agents; readily reduced to leuco-bases with a variety of reducing reagents sensitive to photochemical oxidation (Bannister & Elliott, 1983)

1.1.3. Trade names, technical products and impurities

Magenta I

Some trade names are: Aizen Magenta; Astra Fuchsine B; Basic Magenta E 200; C-WR Violet 8; Calcozine Fuchsine HO; Calcozine Magenta RTN; Calcozine Magenta XX; Cerise B; Diabasic Magenta; Diamond Fuchsine; Fuchsine A; Fuchsine CS; Fuchsine G; Fuchsine HO; Fuchsine N; Fuchsine RTN; Fuchsine SBP; Fuchsine Y; Magenta DP; Magenta E; Magenta G; Magenta PN; Magenta S; Magenta Superfine; Orient Basic Magenta; 12418 Red

Magenta, a cationic triarylmethane dye, is commonly, but not always, a homologous mixture of dyes; in a given lot, any homologue may be dominant. The Biological Stain Commission has determined, however, that for a lot to perform satisfactorily in all the usual applications embraced by the protocol of the Commission, CI Basic Red 9 (CI 42500) must comprise not less than 50% of the total dye present; other components that may be found are magenta I (CI 42510), magenta II and magenta III (CI 42520). Both CI Basic Red 9 and magenta III can be produced directly as pure products; however, to obtain pure magenta I and magenta II, free of the other homologue, chromatographic separation must be used (Green, 1990).

Magenta I is commercially available as a biological stain-grade product (Aldrich Chemical Co., 1992).

CI Basic Red 9

Some trade names are: Calcozine Magenta N; Fuchsine DR 001; Fuchsine SP; Fuchsine SPC; Orient Para Magenta Base

CI Basic Red 9 is available commercially as a certified biological stain at a purity of approximately 95%; it is also available at a purity of at least 88% (Aldrich Chemical Co., 1992).

1.1.4. Analysis

A rapid method for the assay of triarylmethane dyes (Knecht method) is titration with titanium trichloride to a colourless end-point (Bannister & Elliott, 1983).

2. Studies of Cancer in Humans

3. Studies of Cancer in Experimental Animals

3.1. Oral administration

3.1.1. Mouse

Magenta I

Groups of 30 male and 30 female stock mice [strain and age unspecified] were treated intragastrically with 0 or 6 mg magenta I [purity unspecified] in arachis oil twice weekly for 52 weeks [about 600 mg/kg bw per week], to give a total dose of 624 mg per mouse. Controls were given subcutaneous injections of arachis oil. The mice were held as long as possible, and at 90 weeks 21/30 control and 23/30 treated males and 21/30 control and 17/30 treated females were still alive. Only gross lesions were examined microscopically. No treatment-related increase in the incidence of tumours was observed in mice of either sex; one liver-cell tumour was observed in a treated female (Bonser et al., 1956). [The Working Group noted the inadequate study design.]

CI Basic Red 9

Groups of 50 male and 50 female B6C3F₁ mice, 6–10 weeks of age, were administered 0, 500 or 1000 mg/kg of diet (ppm) CI Basic Red 9 in the diet for 103 weeks and were killed at 110–115 weeks of age. Two lots of the test chemical were used, with purities of 93 and 99% (water was the major impurity). Mean body weights of treated mice were lower than those of controls throughout the study. At the end of the experiment, 42/50 control, 32/50 low-dose and 36/50 high-dose males and 31/50 control, 12/50 low-dose and 6/50 high-dose females were alive (p < 0.001). In male mice, CI Basic Red 9 caused a dose-related increase in the incidence of hepatocellular carcinomas (control, 10/50; low-dose, 20/50; high-dose, 27/50;p < 0.001, incidental tumour trend test). The incidence of hepatocellular adenomas was 22/50 (control), 21/50 (low-dose) and 17/50 (high-dose). The combined incidence of liver tumours was 29/50 (control), 37/50 (low-dose) and 41/50 (high-dose) (p = 0.005, incidental tumour trend test). In female mice, the compound caused a dose-related increase in the incidence of hepatocellular carcinomas (control, 3/49; low-dose, 19/50; high-dose, 37/49; p < 0.001, Cochran-Armitage trend test). The incidence of hepatocellular adenomas was 2/49 control, 18/50 low-dose (p < 0.001, Fischer exact test) and 4/49 high-dose. The combined incidence of liver tumours in females was 5/49 control, 35/50 low-dose and 41/49 high-dose (p < 0.001, Cochran-Armitage trend test). An increase in the incidence of benign and malignant adrenal phaeochromocytomas (combined) was found in females (control, 1/48; low-dose, 8/47; high-dose, 8/45;p = 0.015, Cochran-Armitage trend test) (US National Toxicology Program, 1986).

3.1.2. Rat

Magenta I

Groups of 40 male and 40 female Sprague-Dawley rats, 12 weeks old, were treated intragastrically with 0 or 400 mg/kg bw magenta I (CI 42510) [purity unspecified] in 0.9% saline solution twice a week. Controls were given saline only. After two weeks, the dose of 400 mg/kg was found to be toxic, and treatment was discontinued for one week; after a further six weeks, half of the original dose (200 mg/kg bw) was used for the remaining treatment, for life. Average survival times were 104 weeks for control males, 59 weeks for treated males, 92 weeks for control females and 49 weeks for treated females. No treatment-related increase in the incidence of tumours was observed in rats of either sex (Ketkar & Mohr, 1982). [The Working Group noted the poor survival in the treated groups and the inadequate reporting of the study.]

CI Basic Red 9

In the same study, groups of 40 male and 40 female Sprague-Dawley rats, 12 weeks old, were treated intragastrically twice a week with 0 or 600 mg/kg bw CI Basic Red 9 [purity unspecified] in 0.9% saline. The dose of 600 mg/kg was found to be toxic and, after 12 weeks, treatment was discontinued for one week; after a further six weeks, half of the original dose (300 mg/kg bw) was used for the remaining treatment, for life. Average survival times were 104 weeks for control males, 70 weeks for treated males, 92 weeks for control female and 69 weeks for treated females. No treatment-related increase in the incidence of tumours was observed in rats of either sex (Ketkar & Mohr, 1982). [The Working Group noted the poor survival in the treated groups and the inadequate reporting of the study.]

Groups of 50 male and 50 female Fischer 344/N rats, six to seven weeks of age, were administered 0, 1000 or 2000 mg/kg of diet (ppm) (males) and 0, 500 or 1000 ppm (females) CI Basic Red 9 in the diet for 103 weeks and were killed at 110–113 weeks of age. Two lots of the test chemical were used, with purities of 93 and 99% (water was the major impurity). Increased mortality was seen in high-dose males and females, and, at the end of the experiment, 36/50 control, 29/50 low-dose and 0/50 high-dose males and 37/50 control, 35/50 low-dose and 14/50 high-dose females were still alive. CI Basic Red 9 caused significant increases in the incidences of benign and malignant tumours at various sites in both males and females (Table 1) (US National Toxicology Program, 1986).

Table 1

Trends in tumour incidences at specific sites in Fischer 344/N rats fed diets containing CI Basic Red 9.

3.1.3. Hamster

Magenta I

Groups of 40 male and 40 female outbred Syrian golden hamsters, 12 weeks old, were treated intragastrically with 0, 400 or 600 mg/kg bw magenta I (CI 42510) [purity unspecified] in 0.9% saline solution twice a week for life. In the high-dose group, the majority of animals died within the first 10 weeks of treatment; the lower dose was well tolerated, and body weight development and average survival times were similar to those of controls. After 72 weeks of treatment, 17/40 control and 17/40 low-dose males and 3/40 control and 0/40 low-dose females were still alive; by 88 weeks of treatment, all treated and control animals had died. No treatment-related increase in the incidence of tumours was observed in hamsters of either sex (Green et al., 1979). [The Working Group noted the high mortality in the control and treated groups, especially in females.]

CI Basic Red 9

In the same study, similar groups of hamsters were treated intragastrically with 0, 300 or 600 mg/kg bw CI Basic Red 9 [purity unspecified] in 0.9% saline solution twice a week for life. In the high-dose group, the majority of animals died within the first 10 weeks of treatment; the lower dose was well tolerated, and body weight development and average survival times were similar to those of controls. After 72 weeks of treatment, 17/40 control and 15/40 low-dose males and 3/40 control and 3/40 low-dose females were still alive; by 88 weeks of treatment, all treated and control animals had died. No treatment-related increase in the incidence of tumours was observed in hamsters of either sex (Green et al., 1979). [The Working Group noted the high mortality in control and treated animals, especially in females.]

4. Other Relevant Data

4.4. Genetic and related effects

4.4.1. Humans

No data were available to the Working Group.

4.4.2. Experimental systems (see also Table 2 and Appendices 1 and 2)

Table 2

Genetic and related effects of CI Basic Red 9 (para-rosaniline).

No data were available on the genetic and related effects of magenta.

CI Basic Red 9 induced repairable DNA damage in bacterial differential toxicity assays, in the absence of activation. It was generally not mutagenic to Salmonella typhimurium; some activity was observed in the presence of exogenous activating systems, especially those derived from Syrian hamster liver. It induced forward mutation in Escherichia coli in the absence of exogenous metabolism. It did not induce mitotic recombination in Saccharomyces cerevisiae.

Conflicting reports were obtained for induction of unscheduled DNA synthesis in rat hepatocytes in vitro: in a single study, it induced unscheduled DNA synthesis in primary hepatocytes from Syrian hamsters but not from rats. The compound gave inconclusive responses in two tests for mutation at the tk locus in mouse lymphoma L5178Y cells and positive responses in another. CI Basic Red 9 did not induce chromosomal rearrangement or sister chromatid exchange in Chinese hamster ovary cells. It induced morphological transformation of Syrian hamster embryo cells in the presence, but not in the absence, of an exogenous activating system from hamster liver. It also induced transformation of BALBc/3T3 mouse cells and enhanced Rauscher leukaemia virus-induced transformation of Fischer rat embryo cells.

Oral administration of CI Basic Red 9 to mice or rats resulted in urine that was mutagenic to S. typhimurium. The dye did not induce mitotic recombination in S. cerevisiae or mutation in S. typhimurium recovered from the peritoneal cavity of mice, and it did not induce mutation in S. typhimurium after intramuscular administration.

5. Summary of Data Reported and Evaluation

6. References

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