Dimethylaminopropylamine

Dimethylaminopropylamine (DMAPA) is a diamine used in the preparation of some surfactants, such as cocamidopropyl betaine which is an ingredient in many personal care products including soaps, shampoos, and cosmetics.

BASF, a major producer, claims that DMAPA-derivatives do not sting the eyes and makes a fine-bubble foam, making it appropriate in shampoos.

[1] DMAPA is commonly produced commercially via the reaction between dimethylamine and acrylonitrile (a Michael reaction) to produce dimethylaminopropionitrile.

A subsequent hydrogenation step yields DMAPA:[2] DMAPA is readily converted to the mustard dimethylaminopropyl-3-chloride, a powerful alkylating agent.

[3] Dimethylaminopropylamine is a known skin irritant and its presence as an impurity in cocamidopropyl betaine is thought to be the cause of irritation experienced by some individuals.

Skeletal formula of dimethylaminopropylamine
Skeletal formula of dimethylaminopropylamine