hydrastinine

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 447739800

| IUPAC_name = 6-Methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol

| image = Hydrastinine.svg

| 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 = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3512

| ChEMBL = 1623232

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = V1I0L48X6E

| C=11 | H=13 | N=1 | O=3

| smiles = O1c2c(OC1)cc3c(c2)CCN(C3O)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| 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 = {{stdinchicite|correct|chemspider}}

| 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.{{cite journal | vauthors = Freudenmann RW, Oxler F, Bernschneider-Reif S | title = The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents | journal = Addiction | volume = 101 | issue = 9 | pages = 1241–5 | date = September 2006 | pmid = 16911722 | doi = 10.1111/j.1360-0443.2006.01511.x | url = https://zenodo.org/record/894510 | doi-access = free }}

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.{{cite journal | vauthors = Verweij AM | title = [Contamination of illegal amphetamine. Hydrastatinine as a contaminant in 3,4-(methylenedioxy)methylamphetamine] | journal = Archiv für Kriminologie | volume = 188 | issue = 1–2 | pages = 54–7 | year = 1991 | pmid = 1953248 }}