Hydrastinine

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Chemical compound

title: "Hydrastinine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["methylenedioxyphenethylamines", "tetrahydroisoquinolines"] description: "Chemical compound" topic_path: "general/methylenedioxyphenethylamines" source: "https://en.wikipedia.org/wiki/Hydrastinine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| verifiedrevid = 447739800 | IUPAC_name = 6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol | image = Hydrastinine.svg | image_class = skin-invert-image | width = 200px

| tradename = | pregnancy_category = ? | legal_status = | routes_of_administration =

| bioavailability = | metabolism = Hepatic | elimination_half-life = | excretion = Renal

| CAS_number = 6592-85-4 | ATC_prefix = none | ATC_suffix = | ATC_supplemental = | PubChem = 3638 | DrugBank_Ref = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 3512 | ChEMBL = 1623232 | UNII_Ref = | UNII = V1I0L48X6E

| C=11 | H=13 | N=1 | O=3 | smiles = O1c2c(OC1)cc3c(c2)CCN(C3O)C | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = YOJQZPVUNUQTDF-UHFFFAOYSA-N

Hydrastinine is a semisynthetic tetrahydroisoquinoline 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.

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

References

References

  1. (September 2006). "The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents". Addiction.
  2. (1991). "[Contamination of illegal amphetamine. Hydrastatinine as a contaminant in 3,4-(methylenedioxy)methylamphetamine]". Archiv für Kriminologie.

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methylenedioxyphenethylaminestetrahydroisoquinolines