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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
Structure of HYDRASTININE HYDROCHLORIDE

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

HIDE SMILES / InChI

Description
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
weak
weak
yes [IC50 82 uM]
yes [IC50 95 uM]
yes [Ki 37 uM]
PubMed

PubMed

TitleDatePubMed
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.
2003 Dec 3
[Extraction and HPLC analysis of alkaloids in goldenseal].
2004 Mar
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine.
2006 Jun
Thin-layer chromatography/desorption electrospray ionization mass spectrometry: investigation of goldenseal alkaloids.
2007 Apr 1
Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species.
2009 Aug 24
Patents

Patents

Sample Use Guides

Rat LD50=104 mg/kg
Route of Administration: Intraperitoneal
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.
Name Type Language
HYDRASTININE HYDROCHLORIDE
MART.   WHO-DD  
Common Name English
HYDRASTININE HCL
Common Name English
HYDRASTININUM MURIATICUM
HPUS  
Common Name English
5,6,7,8-TETRAHYDRO-6-METHYL-1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-OL, HYDROCHLORIDE
Systematic Name English
1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-OL, 5,6,7,8-TETRAHYDRO-6-METHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
HYDRASTININE HYDROCHLORIDE [MART.]
Common Name English
Hydrastinine hydrochloride [WHO-DD]
Common Name English
NSC-93766
Code English
HYDRASTININUM MURIATICUM [HPUS]
Common Name English
1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-OL, HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C78311
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
Code System Code Type Description
PUBCHEM
71833
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
PRIMARY
FDA UNII
S8253P6A1G
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
PRIMARY
EVMPD
SUB14128MIG
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL1623232
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
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MESH
C024595
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
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CAS
4884-68-8
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
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NSC
93766
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
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SMS_ID
100000077595
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
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ECHA (EC/EINECS)
225-497-3
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
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NCI_THESAURUS
C90856
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
PRIMARY
EPA CompTox
DTXSID0047878
Created by admin on Fri Dec 15 16:05:20 GMT 2023 , Edited by admin on Fri Dec 15 16:05:20 GMT 2023
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