Hydrastinine
Encyclopedia
Hydrastinine is a semisynthetic alkaloid from the hydrolysis of the alkaloid hydrastine
Hydrastine
Hydrastine is a natural alkaloid which was discovered in 1851 by Alfred P. Durand. Hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug during the 1910s....

, which was found naturally in small quantities in Hydrastis canadensis L. (Ranunculaceae
Ranunculaceae
Ranunculaceae are a family of about 1700 species of flowering plants in about 60 genera, distributed worldwide....

). Hydrastinine was produced by oxidative splitting of hydrastine hydrochloride with nitric acid in good yield. The drug was patented by Bayer
Bayer
Bayer AG is a chemical and pharmaceutical company founded in Barmen , Germany in 1863. It is headquartered in Leverkusen, North Rhine-Westphalia, Germany and well known for its original brand of aspirin.-History:...

 as a haemostatic drug during the 1910s.

The first known synthesis of methylenedioxymethamphetamine (MDMA) was actually an intermediary in the synthesis of hydrastinine. It was only reviewed for its activity many years after its original synthesis.

Hydrastinine has also been found as an impurity or side product in MDMA synthesis performed by low pressure amination of 3,4-methylenedioxyphenylpropan-2-one with methylamine.
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