Details
Stereochemistry | RACEMIC |
Molecular Formula | C11H13NO3.ClH |
Molecular Weight | 243.687 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1CCC2=C(C=C3OCOC3=C2)C1O
InChI
InChIKey=DLNQCQJCIITVHC-UHFFFAOYSA-N
InChI=1S/C11H13NO3.ClH/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;1H
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/14398297Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11582536 | https://www.ncbi.nlm.nih.gov/pubmed/16911722
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14398297
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11582536 | https://www.ncbi.nlm.nih.gov/pubmed/16911722
Hydrastinine is a synthetic alkaloid prepared by various processes from either hydrastine, berberine, or narcotine. It exerts a strong stimulating action on the uterus of all species studied, including human. Hydrastinine and the closely related alkaloid cotarnine have been employed as hemostatics, particularly in abnormal uterine conditions. In the non-pregnant animal, hydrastinine in doses of 10 mg. depressed both tonus and activity, even after the section of the hypogastric. In the pregnant cat, it caused the uterus to contract. A stimulant action was also noted in the non-pregnant animal if nicotine were administered prior to hydrastinine. The rabbit uterus in situ was strongly contracted. Laidlaw believed that hydrastinine acted on the uterus both directly on the smooth muscle and also through its sympathetic innervation. Repeated administration of large doses for a period of time resulted in greatly increased amplitude of contractions which persisted after removal of the drug. The drug was patented by Bayer as a haemostatic drug during the 1910s.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415 |
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Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers. | 2003 Dec 3 |
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[Extraction and HPLC analysis of alkaloids in goldenseal]. | 2004 Mar |
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Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine. | 2006 Jun |
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Thin-layer chromatography/desorption electrospray ionization mass spectrometry: investigation of goldenseal alkaloids. | 2007 Apr 1 |
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Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species. | 2009 Aug 24 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14398297
Rat LD50=104 mg/kg
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11582536
PC12 cells were maintained routinely in RPMI 1640 medium supplemented with 10 % heat-inactivated horse serum and 5 % fetal calf serum plus 100 units/ml penicillin and 100 μg/ml streptomycin at 37 °C. PC12 cells (ca. 1 × 10^5 cells/cm2) were treated with hydrastine derivatives (5 - 40 μM) into the medium and then were incubated for 6 (-48) h in the presence of the hydrastine derivatives. The cells (ca. 1.5 - 2 × 10^5cells/cm2) were harvested with phosphate buffered saline and then were centrifuged. The cell pellets were used for the measurement of dopamine content, and the intracellular TH and AADC activities.
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NCI_THESAURUS |
C78311
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C024595
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DTXSID0047878
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ACTIVE MOIETY
SUBSTANCE RECORD