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	207.226 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 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 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 an impurity or side product in MDMA synthesis performed by low pressure amination of 3,4-methylenedioxyphenylpropan-2-one with methylamine.[2]

References

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.
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.

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[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.