Hydrastinine

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Hydrastinine
Hydrastinine.png
Clinical data
Pregnancy
category
  •  ?
ATC code
  • none
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
ECHA InfoCard 100.026.849
Chemical and physical data
Formula C11H13NO3
Molar mass 207.226
3D model (JSmol)
  (verify)

Hydrastinine is a semisynthetic alkaloid from the hydrolysis of the alkaloid hydrastine, which was found naturally in small quantities in Hydrastis canadensis L. (Ranunculaceae). Hydrastinine was produced by oxidative splitting of hydrastine hydrochloride with nitric acid in good yield. The drug was patented by Bayer 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.[1]

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.[2]

References[edit]

  1. ^ Roland W. Freudenmann; Florian Öxler; Sabine Bernschneider-Reif (2006). "The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents" (PDF). Addiction. 101 (9): 1241–5. PMID 16911722. doi:10.1111/j.1360-0443.2006.01511.x. 
  2. ^ Verweij, AM (1991). "Contamination of illegal amphetamine. Hydrastatinine as a contaminant in 3,4-(methylenedioxy)methylamphetamine". Archiv für Kriminologie. 188 (1–2): 54–7. PMID 1953248.