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Hydrastinine

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Hydrastinine
Clinical data
Pregnancy
category
  • ?
ATC code
  • none
Pharmacokinetic data
MetabolismHepatic
ExcretionRenal
Identifiers
  • 6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.026.849Edit this at Wikidata
Chemical and physical data
FormulaC11H13NO3
Molar mass207.229 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 checkY
  • Key:YOJQZPVUNUQTDF-UHFFFAOYSA-N checkY
  (verify)

Hydrastinine is a semisynthetictetrahydroisoquinoline alkaloid made via thenitric acid induced hydrolysis of the alkaloidhydrastine hydrochloride, which is extracted fromHydrastis canadensis L. (Ranunculaceae). The drug was patented byBayer as ahaemostatic drug during the 1910s.

The first known synthesis ofmethylenedioxymethamphetamine (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 major unwanted side product in MDMA made by thereductive amination of 3,4-methylenedioxyphenylpropan-2-one and methylamine.[2]

See also

[edit]

References

[edit]
  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.
Phenethylamines
Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
(and further-extended)
Catecholamines
(and close relatives)
Cyclized
phenethylamines
Phenylalkylpyrrolidines
2-Benzylpiperidines
(phenidates)
Phenylmorpholines
(phenmetrazines)
Phenyloxazolamines
(aminorexes)
Isoquinolines and
tetrahydroisoquinolines
2-Aminoindanes
2-Aminotetralins
Others / unsorted
Related compounds
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