Hydrastinine is a semisynthetic alkaloid from the hydrolysis of the alkaloid

hydrastine Hydrastine is an isoquinoline 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. It is present in ''Hydrastis canadensis'' ...

, which was found naturally in small quantities in ''

Hydrastis canadensis ''For the magazine from West Virginia see Goldenseal (magazine)'' Goldenseal (''Hydrastis canadensis''), also called orangeroot or yellow puccoon, is a perennial herb in the buttercup family Ranunculaceae, native to North America. It may be di ...

'' L. (

Ranunculaceae Ranunculaceae (buttercup or crowfoot family; Latin "little frog", from "frog") is a family of over 2,000 known species of flowering plants in 43 genera, distributed worldwide. The largest genera are ''Ranunculus'' (600 species), ''Delphinium' ...

). Hydrastinine was produced by oxidative splitting of hydrastine hydrochloride with nitric acid in good yield. The drug was patented by

Bayer Bayer AG (, commonly pronounced ; ) is a German multinational corporation, multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Headquartered in Leverkusen, Bayer's areas of busi ...

as a

haemostatic An antihemorrhagic (antihæmorrhagic) agent is a substance that promotes hemostasis (stops bleeding). It may also be known as a hemostatic (also spelled haemostatic) agent. Antihemorrhagic agents used in medicine have various mechanisms of action: ...

drug during the 1910s. The first known synthesis of methylenedioxymethamphetamine (

MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in Tablet (pharmacy), tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for Recreational dru ...

) was actually an intermediate in the synthesis of the methylated analogue of hydrastinine, methylhydrastinine. 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.

References

{{reflist Alkaloids 5,6,7,8-Tetrahydro-(1,3)dioxolo(4,5-g)isoquinolines