Hydrastinine

Hydrastinine
Clinical data
Pregnancy; category	?;
ATC code	none;
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
	IUPAC name 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 ;
UNII	V1I0L48X6E;
ChEMBL	ChEMBL1623232;
CompTox Dashboard (EPA)	DTXSID3048073 ;
ECHA InfoCard	100.026.849
Chemical and physical data
Formula	C11H13NO3
Molar mass	207.229 g·mol−1
3D model (JSmol)	Interactive image;
	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 ;
	(verify)

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.

Pregnancy
category

?

ATC code

none

MetabolismHepatic

ExcretionRenal

Quick facts Clinical data, Pregnancycategory ...

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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 a major unwanted side product in MDMA made by the reductive amination of 3,4-methylenedioxyphenylpropan-2-one and methylamine.^[2]

[1]

[2]

Hydrastinine

See also

References

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