2,5-Dimethoxybenzylamine (1C-H) also known under the putative brand name Zilain, is a drug that was intended for use in obstetrics; it was developed by Soviet scientists in the 1970s.
Use
Pharmacology Little is known about the biological activity of 2,5-dimethoxybenzylamine, but it is known to stimulate uterine contractions.
Synthesis 2,5-Dimethoxybenzylamine reacts with ethyl bromoacetate to form the ethyl ester of N-(2,5-dimethoxy)benzylglycine; 1C-H is also used in the synthesis of pyrrolo[2,3-b]pyrazine-7-carboxamide derivatives.
To obtain 1C-H, a Delépine reaction is used to alkylate hexamethylenetetramine with 2,5-dimethoxybenzyl bromide, followed by acid hydrolysis of the resulting quaternary ammonium salt, and finally neutralization with a base.
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