Hydrastinine

Last updated
Hydrastinine
Hydrastinine.svg
Clinical data
Pregnancy
category
  •  ?
ATC code
  • none
Pharmacokinetic data
Metabolism Hepatic
Excretion Renal
Identifiers
  • 6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.026.849 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C11H13NO3
Molar mass 207.229 g·mol−1
3D model (JSmol)
  • O1c2c(OC1)cc3c(c2)CCN(C3O)C
  • InChI=1S/C11H13NO3/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13/h4-5,11,13H,2-3,6H2,1H3 Yes check.svgY
  • Key:YOJQZPVUNUQTDF-UHFFFAOYSA-N Yes check.svgY
   (verify)

Hydrastinine is a semisynthetic alkaloid made via the nitric acid induced hydrolysis of the alkaloid hydrastine hydrochloride, which is extracted from Hydrastis canadensis L. (Ranunculaceae). The drug was patented by Bayer as a haemostatic drug during the 1910s.

The first known synthesis of methylenedioxymethamphetamine (MDMA) 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. [1]

Hydrastinine has also been found as a unwanted side product in MDMA made by the reductive amination of 3,4-methylenedioxyphenylpropan-2-one with methylamine. [2]

References

  1. ↑ Freudenmann RW, Oxler F, Bernschneider-Reif S (September 2006). "The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents". Addiction. 101 (9): 1241–5. doi: 10.1111/j.1360-0443.2006.01511.x . PMID   16911722.
  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.
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