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IARC Working Group on the Evaluation of Carcinogenic Risks to Humans. Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide. Lyon (FR): International Agency for Research on Cancer; 1999. (IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, No. 71.)

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Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen Peroxide.

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Dimethylcarbamoyl chloride

Data were last reviewed in IARC (1976) and the compound was classified in IARC Monographs Supplement 7 (1987).

1. Exposure Data

1.1. Chemical and physical data

1.1.1. Nomenclature

  • Chem. Abstr. Serv. Reg. No.: 79-44-7
  • Chem. Abstr. Name: Dimethylcarbamic chloride

1.1.2. Structural and molecular formulae and relative molecular mass

Image 531a

1.1.3. Physical properties (for details, see IARC, 1976)

  • (a) Boiling point: 64°C at 27 kPa
  • (b) Melting point: −33°C
  • (c) Conversion factor: mg/m3 = 4.40 × ppm

1.2. Production and use

Dimethylcarbamoyl chloride has been produced since 1961. It has been used as an intermediate in the manufacture of a number of pharmaceuticals and pesticides (IARC, 1976).

2. Studies of Cancer in Humans

No death from cancer was reported in an investigation of 39 dimethylcarbamoyl chloride production workers, 26 processing workers and 42 ex-workers aged 17–65 years, who were exposed for periods ranging from six months to 12 years (IARC, 1976).

3. Studies of Cancer in Experimental Animals

Dimethylcarbamoyl chloride was tested for carcinogenicity by skin application and by subcutaneous and intraperitoneal injection in female mice of one strain; it induced local tumours (IARC, 1976).

3.1. Inhalation exposure

3.1.1. Rat

A group of 50 male Sprague-Dawley rats was treated by whole-body exposure to an atmosphere of 1 ppm [4.4 mg/m3] dimethylcarbamoyl chloride for 6 h per day on five days per week for six weeks (i.e., 30 exposures). The experiment included two chamber control groups, each of 150 rats. The incidence of nasal cancer corrected for mortality at 480 and 600 days in the exposed group was 12% and 17%, respectively (Snyder et al., 1986). [This experiment was not fully reported.]

3.1.2. Hamster

A group of 100 male Syrian golden hamsters, eight weeks of age, was exposed by inhalation to 1 ppm [4.4 mg/m3] dimethylcarbamoyl chloride for 6 h per day on five days per week for life. Two groups of 50 and 120 male hamsters served as sham-exposed and untreated controls, respectively. Neoplastic lesions of the nasal cavity were observed from 406 to 770 days. Squamous-cell carcinomas of the nasal cavity occurred in 50/99 hamsters in the treated group. No such tumour occurred in controls (Sellakumar et al., 1980).

3.2. Skin application

Mouse: A group of 50 female ICR/Ha Swiss mice was treated by topical application with 2 mg dimethylcarbamoyl chloride in 0.1 mL acetone three times per week for up to 615 days. Three control groups, each of 50 mice, received acetone only for 575–665 days. No skin tumours arose in the control groups, whereas 32/50 mice in the treatment group developed tumours at the site of administration. Time to first tumour was 350 days and the tumours were identified as 1 papilloma, 27 squamous carcinomas and 4 keratoacanthomas (Van Duuren et al., 1987).

In the same study, two groups of 30 female ICR/Ha Swiss mice were injected subcutaneously with 0.43 or 4.3 mg dimethylcarbamoyl chloride in 0.1 mL tricaprylin once per week for 365 days and then observed for the remainder of their lifespan. An additional group of 50 mice received a subcutaneous dose of 4.3 mg per week for 365 days and were then killed. Three control groups consisting of either 30 or 50 (two groups) mice received tricaprylin alone once per week for up to 560–660 days. Two injection-site haemangiomas arose in one of the control groups. Injection-site tumours arose in 9/30, 22/30 and 42/50 of the treated groups, respectively (Van Duuren et al., 1987).

In the same study as the previous skin application experiment, 50 female ICR/Ha Swiss mice were treated by topical application with 5 mg dimethylcarbamoyl chloride in 0.1 mL acetone on a single occasion, followed by three times weekly applications of phorbol myristyl acetate in 0.1 mL acetone [either 0.0025 or 0.005 mg per administration]. Two phorbol myristyl acetate control groups were available. Tumour incidences were: phorbol myristyl acetate, 0.0025 mg dose group, 0/50; 0.005 mg dose group, 3/30, which included 2 papillomas and 1 sarcoma; dimethylcarbamoyl chloride–phorbol myristyl acetate group 10/50, which included 2 papillomas, 7 squamous carcinomas and 1 keratoacanthoma (Van Duuren et al., 1987).

4. Other Data Relevant to an Evaluation of Carcinogenicity and its Mechanisms

4.1. Absorption, distribution, metabolism and excretion

No data were available to the Working Group. However, dimethylcarbamoyl chloride is rapidly hydrolysed on contact with water to dimethylamine, HCl and CO2.

4.2. Toxic effects

4.2.1. Humans

As previously summarized, one case of eye irritation and one of liver disturbances have been observed in workers exposed to dimethylcarbamoyl chloride. No other data were available to the Working Group (IARC, 1976).

4.2.2. Experimental systems

As previously summarized, dimethylcarbamoyl chloride when inhaled by rats damages the nasal mucous membrane, throat and lungs and causes breathing difficulties. It is irritant to the skin of rats and to skin and eye in rabbits. No evidence for sensitizing potential has been shown in guinea-pigs (IARC, 1976).

4.3. Reproductive and developmental effects

No data were available to the Working Group.

4.4. Genetic and related effects

4.4.1. Humans

Chromosomal analysis of peripheral lymphocytes from 10 people who had been occupationally exposed to dimethylcarbamoyl chloride (and diethylcarbamoyl chloride) for periods ranging from 4 to 17 years showed differences in the frequency of chromosomal aberrations (inclusive and exclusive gaps), when compared with a control group of 10 people matched for age, although statistical evaluation revealed no significant increase (Fleig & Thiess, 1978).

4.4.2. Experimental systems (see Table 1 for references)

Table 1. Genetic and related effects of dimethylcarbamoyl chloride.

Table 1

Genetic and related effects of dimethylcarbamoyl chloride.

Dimethylcarbamoyl chloride induced DNA damage and mutation in bacteria. In fungi, it induced aneuploidy, mutation, gene conversion and DNA damage. Dimethylcarbamoyl chloride induced sex-linked recessive lethal mutations in Drosophila melanogaster in two studies, but not in a single feeding (aqueous solution) study, in which it would have been rapidly hydrolysed; it did not induce heritable translocations in two studies using administration by injection. Unscheduled DNA synthesis was not induced in primary cultures of rat hepatocytes. In other cultured mammalian cells, dimethylcarbamoyl chloride induced DNA strand breaks, chromosomal aberrations (in Chinese hamster ovary CHO cells, but not in rat hepatocytes), mutation at the tk locus of mouse lymphoma L5178Y cells and transformation in Syrian hamster embryo cells; conflicting results were obtained in studies of sister-chromatid exchange induction in vitro. In vivo, dimethylcarbamoyl chloride induced micronuclei but not sister chromatid exchanges in bone marrow cells of treated mice.

In conjunction with a carcinogenicity study (described in Section 3.1), male rats were exposed by inhalation to [3H]dimethylcarbamoyl chloride (2.8–7.8 mCi inhaled). The association of radioactivity with DNA purified from the nasal mucosa was 11.0 ± 5.1 dpm/µg DNA per mCi inhaled (Snyder et al., 1986). In vitro reaction of dimethylcarbamoyl chloride with calf thymus DNA resulted in the formation of 6-dimethylcarbamyloxy-2′-deoxyguanosine and 4-dimethylaminothymidine (Segal et al., 1982).

DNA from both rat nasal squamous carcinomas (2) and mouse skin squamous carcinomas (4) and fibrosarcomas (4) arising in dimethylcarbamoyl chloride-treated animals failed to transform NIH 3T3 cells by DNA transfection (Garte et al., 1985).

5. Summary of Data Reported and Evaluation

5.1. Exposure data

Exposure to dimethylcarbamoyl chloride may occur during its manufacture and its use as an intermediate in the manufacture of a number of pharmaceuticals and pesticides.

5.2. Human carcinogenicity data

No deaths from cancer were reported in a small study of workers exposed for periods ranging from six months to 12 years.

5.3. Animal carcinogenicity data

Dimethylcarbamoyl chloride was tested for carcinogenicity in rats and hamsters by inhalation exposure, producing malignant tumours of the nasal cavity. It was also tested in mice by skin application and by subcutaneous and intraperitoneal injection, producing local tumours.

5.4. Other relevant data

No data were available on the metabolism of dimethylcarbamoyl chloride, but it rapidly decomposes on contact with water to dimethylamine, hydrochloric acid and carbon dioxide.

Dimethylcarbamoyl chloride when inhaled by rats damages the nasal mucous membrane, throat and lung.

It has a wide spectrum of genotoxic activity, which is expressed as a result of its direct alkylating activity.

5.5. Evaluation

There is inadequate evidence in humans for the carcinogenicity of dimethylcarbamoyl chloride.

There is sufficient evidence in experimental animals for the carcinogenicity of dimethylcarbamoyl chloride.

Overall evaluation

Dimethylcarbamoyl chloride is probably carcinogenic to humans (Group 2A).

In making the overall evaluation, the Working Group took into consideration that dimethylcarbamoyl chloride is a direct-acting alkylating agent with a wide spectrum of genotoxic activity, including activity in somatic cells in vivo.

6. References

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©International Agency for Research on Cancer, 1999.
Bookshelf ID: NBK499361
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