Hydrastinine

Hydrastinine

Systematic (IUPAC) name
6-methyl-5,6,7,8-tetrahydro[1,3]dioxolo[4,5-g]isoquinolin-5-ol
Clinical data
Pregnancy category	?
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
CAS Number	6592-85-4
ATC code	none
PubChem	CID 3638
ChemSpider	3512
UNII	V1I0L48X6E
ChEMBL	CHEMBL1623232
Chemical data
Formula	C11H13NO3
Molar mass	207.226
SMILES 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 Key:YOJQZPVUNUQTDF-UHFFFAOYSA-N
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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 intermediary in the synthesis of hydrastinine. 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. Roland W. Freudenmann, Florian Öxler, and Sabine Bernschneider-Reif (2006). "The origin of MDMA (ecstasy) revisited: the true story reconstructed from the original documents" (PDF). 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.