Structure via PubChem · Public domain (PubChem)
L-hydrastine
Sign in to saveAlso known as (3S)-6,7-dimethoxy-3-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one, hydrastine
Hydrastine is an isoquinoline alkaloid which was discovered in 1851 by Alfred P. Durand. Nitric acid induced hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug in the early 1900s. It is present in Hydrastis canadensis (thus the name) and other plants of the family Ranunculaceae.
In the Vinony graph
Vinony's link graph records 201 inbound references to L-hydrastine, and connects out to picrotoxin, tetrahydrodeoxycorticosterone and (RS)-baclofen.
It sits within the topics 3-(5,6,7,8-tetrahydro-(1,3)dioxolo(4,5-g)isoquinolin-5-yl)-3H-2-benzofuran-1-ones, Benzylisoquinoline alkaloids and Chemical pages without DrugBank identifier.
Vinony links it to 10 Wikipedia language editions.
Chemical data
- Formula
- C21H21NO6
- Molecular weight
- 383.4 g/mol
- IUPAC name
- (3S)-6,7-dimethoxy-3-[(5R)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one
- SMILES
- CN1CCC2=CC3=C(C=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
- InChIKey
- JZUTXVTYJDCMDU-MOPGFXCFSA-N
- XLogP
- 2.7
- Polar surface area
- 66.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 383.136887
Show 5 more facts
- found in taxon
- Artemisia maritima
- isomeric SMILES
- CN1CCC2=CC3=C(C=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
- chemical formula
- C₂₁H₂₁NO₆
- canonical SMILES
- CN1CCC2=CC3=C(C=C2C1C4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OCO3
- described by source
- Encyclopædia Britannica 11th edition
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Total synthesis
- Biological action
- See also
- References
- External links
Hydrastine is an isoquinoline alkaloid which was discovered in 1851 by Alfred P. Durand. Nitric acid induced hydrolysis of hydrastine yields hydrastinine, which was patented by Bayer as a haemostatic drug in the early 1900s. It is present in Hydrastis canadensis (thus the name) and other plants of the family Ranunculaceae.
==Total synthesis==
Excerpted from Wikipedia’s “L-hydrastine” article, available under the CC BY-SA 4.0 licence.
Gallery (2)
Available in 10 languages
via Wikidata sitelinks · CC0