3-(isotridecyloxy)propylamine

Endpoint summary

Additional information

Substance:

The common name for the substance 3-(Isotridecyloxy)-1-propane amine also used in this dossier is Etheramine C13i.

 

The substance '3-(Isotridecyloxy)-1-propane amine CAS no 50977-10-1 consists mainly of the ether amine with the carbon chain length of C11-14-iso, C13 rich. The average chain length, based on data from the raw material, is 12.6.

The manufacturing process is a two-step process, where in the first step fatty alcohol is reacted with acrylonitrile at elevated temperature. In the second step the ethernitrile hydrogenated to the corresponding primary amine.

 

Etheramine C13i has a molecular weight of 257, a logP of 4.63, but under environmental and physiological conditions at pH ≤ 8, the logD is about 2.14 (http://www.chemicalize.org) related to the protonation of the primary amine.

The substance is a clear liquid, with a melting point below -30ºC and has a vapour pressure of 0.425 Pa at 20 °C, which represents a concentration in the air of about 45 mg/m3 or 4.2 ppm.

 

 

Toxicological profile

As the substance is used as intermediate, and handling takes place under strictly controlled conditions, only a limited toxicological profile is required.

 

The oral LD50 of Etheramine C13i is within the range of 300-2000 mg/kg bw, with LD50 cut-off value of 500 mg/kg body weight.

Acute toxicity of comparable etheramines show similar levels of acute oral toxicity, although showing aa h a tendency of increased toxicity with shortening of the alkyl chain.

Thein vivodermal corrosion study in rabbits, indicates that Etheramine C13i causes corrosive effects of the skin following 3 minutes exposure, which developed with the course of a week. Also a BCOP test showed corrosive effects for the eyes.

Due to its corrosive properties, further acute in vivo testing via dermal and inhalation route is not justified. This is also applicable for testing for sensitization.

As the substance is corrosive, symptoms of local respiratory irritation are expected, which should limit the systemic uptake of amount needed for systemic toxicity considering the relatively low acute oral toxicity.

Also for acute dermal toxicity, effects will be characterised by local tissue damage. Systemic uptake via skin is likely to be very limited, in view of the use of protective measure related to the handling of corrosive material.

There is no information available from testing. Cross reading with primary alkylamines indicates that the substance would not be sensitising to skin.

There are no concerns for genotoxicity following testing for bacterial mutagenicity. Also various available QSARs for genotoxicity endpoints do not indicate a concern.

 

There is no information available regarding toxicity following repeated dose and on toxicity to reproduction.

 

Toxicokinetics, metabolism and distribution

Etheramine C13i is mainly protonated under environmental conditions. The protonated fraction will behave as salt in water. Etheramine C13i is surface active and has a low solubility in the form of CMC. Similarly to other cationic fatty nitrile derivatives, Etheramine C13i is expected to sorb strongly to sorbents. As a consequence, absorption from gastro-intestinal system is likely to be slow.

 

The mode of action of Etheramine follows from its structure, consisting of an apolar fatty acid chain and a polar end of a primary amine from the ether part with primary amine. The structure can disrupt the cytoplasmatic membrane, leading to lyses of the cell content and consequently the death of the cell.

Etheramine C13i is corrosive to skin, and toxicity following dermal exposure is characterised by local tissue damage, rather than the result of percutaneously absorbed material.

 

With a vapour pressure of 0.425 Pa at 20 °C, potential for inhalation is limited.