Hydrastinine

Chemical compound
  • ?
ATC code
  • none
Pharmacokinetic dataMetabolismHepaticExcretionRenalIdentifiers
  • 6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol
CAS Number
  • 6592-85-4
PubChem CID
  • 3638
ChemSpider
  • 3512 checkY
UNII
  • V1I0L48X6E
ChEMBL
  • ChEMBL1623232
CompTox Dashboard (EPA)
  • DTXSID3048073 Edit this at Wikidata
ECHA InfoCard100.026.849 Edit this at WikidataChemical and physical dataFormulaC11H13NO3Molar mass207.229 g·mol−13D model (JSmol)
  • Interactive image
  • O1c2c(OC1)cc3c(c2)CCN(C3O)C
InChI
  • 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 checkY
  • Key:YOJQZPVUNUQTDF-UHFFFAOYSA-N checkY
  (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 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 an impurity or side product in MDMA synthesis performed by low pressure 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.