U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H21NO6
Molecular Weight 383.3945
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDRASTINE

SMILES

COC1=CC=C2[C@H](OC(=O)C2=C1OC)[C@@H]3N(C)CCC4=CC5=C(OCO5)C=C34

InChI

InChIKey=JZUTXVTYJDCMDU-MOPGFXCFSA-N
InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H21NO6
Molecular Weight 383.3945
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26821251 | https://www.ncbi.nlm.nih.gov/pubmed/25609220 | https://www.ncbi.nlm.nih.gov/pubmed/2163278

Hydrastine is an alkaloid, one of the chief components of goldenseal (Hydrastis canadensis) which was discovered in 1851 by Alfred P. Durand. Goldenseal is unique from other hydrastine containing plants in that (-)-β- hydrastine is the only hydrastine isomer present, while the (+)-enantiomer is found in other hydrastine-containing plants. . While a number of therapeutic activities have been attributed to berberine, the pharmacological effects of hydrastine are less studied and its safety profile is poorly understood and to frame the relevant pharmacological effects of hydrastine within the specific stereochemistry found in goldenseal. Hydrastine has been shown to have several specific biological activities including, inhibition of tyrosine hydroxylase in PC-12 cells, a relaxant effect on guinea pig isolated trachea, and inhibition of several cytochrome P450 (CYP) enzymes. Toxicological studies performed on goldenseal powder in mice and rats indicate that at commonly used doses goldenseal supplements are non-toxic, thus its constituents are likely to be safe for human use when taken at reasonable doses. Despite goldenseal’s widespread usage, the pharmacokinetics of hydrastine in humans has not been adequately described. While it is difficult to determine the proper dosage range for any herbal product, a recent extensive survey of the literature suggests a daily dose of Hydrastis in the range of 0.9 to 3 g per day. Hydrastine has been reported to elicit abortifacient effects and induce preterm labor in pregnant women when taken orally.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
208 ng/mL
1.13 mg/kg single, oral
dose: 1.13 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDRASTINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
495 ng × h/mL
1.13 mg/kg single, oral
dose: 1.13 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDRASTINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.8 h
1.13 mg/kg single, oral
dose: 1.13 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDRASTINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015-01-05
Seasonal variation of biomass and bioactive alkaloid content of goldenseal, Hydrastis canadensis.
2010-10
Toxicology and carcinogenesis studies of goldenseal root powder (Hydrastis Canadensis) in F344/N rats and B6C3F1 mice (feed studies).
2010-08
Problems, artifacts and solutions in the INADEQUATE NMR experiment.
2010-08
BIAdb: a curated database of benzylisoquinoline alkaloids.
2010-03-05
Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species.
2009-08-24
Validation of a liquid chromatography-tandem mass spectrometric assay for the quantitative determination of hydrastine and berberine in human serum.
2009-05-01
Expanding the repertoire of small molecule transcriptional activation domains.
2009-02-01
Determination of hydrastine and berberine in goldenseal raw materials, extracts, and dietary supplements by high-performance liquid chromatography with UV: collaborative study.
2008-08-30
Effects of herbal products and their constituents on human cytochrome P450(2E1) activity.
2007-12
Effects of (1R,9S)-beta-hydrastine on intracellular calcium concentration in PC12 cells.
2007-08
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.) 3: effect on human lens and retinal pigment epithelial cells.
2007-07-25
An in vitro evaluation of cytochrome P450 inhibition and P-glycoprotein interaction with goldenseal, Ginkgo biloba, grape seed, milk thistle, and ginseng extracts and their constituents.
2007-07
Inhibitory effects of (1R,9S)-beta-Hydrastine on calcium transport in PC12 cells.
2007-01
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine.
2006-06
Capillary zone electrophoresis as a tool for the quality control of goldenseal extracts.
2005-06
Enantio-selective inhibition of (1R,9S)- and (1S,9R)-beta-hydrastines on dopamine biosynthesis in PC12 cells.
2004-12
A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis.
2004-11
1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae).
2004-10
Effects of (1R,9S)-beta-hydrastine on l-DOPA-induced cytotoxicity in PC12 cells.
2004-03-19
[Extraction and HPLC analysis of alkaloids in goldenseal].
2004-03
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.
2003-12-03
Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components.
2003-11
Microbial transformation of the phthalideisoquinoline alkaloid, (-)-beta-hydrastine.
2003-08
Method validation for determination of alkaloid content in goldenseal root powder.
2003-07-11
Variations in alkaloid content of herbal products containing goldenseal.
2003-07-03
Individual and combined effect of (+/-)-alpha-hydrastine and (+/-)-beta-hydrastine on spore germination of some fungi.
2003
A validated high performance liquid chromatographic method for the analysis of Goldenseal.
2002-03
Pharmacological properties of nicotinic acetylcholine receptors in isolated Locusta migratoria neurones.
2002-02-15
Differential modulation of respiratory neuronal discharge patterns by GABA(A) receptor and apamin-sensitive K(+) channel antagonism.
2001-11
Effects of hydrastine derivatives on dopamine biosynthesis in PC12 cells.
2001-10
High-performance liquid chromatography determination of hydrastine and berberine in dietary supplements containing goldenseal.
2001-07
Antitubercular natural products: berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2.
1998-10
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991-01-01
Screening for new compounds with antiherpes activity.
1984-10
Patents

Patents

Sample Use Guides

The disposition and metabolism of hydrastine was investigated in 11 healthy subjects following an oral dose of 2.7 g of goldenseal supplement containing 78 mg of hydrastine.
Route of Administration: Oral
A549 cells were incubated with the indicated concentrations of (-)-β-hydrastine for 24 h. The cells were then collected, rinsed with PBS, and suspended in staining buffer (10 μg/ml propidium iodide, 0.5% Tween-20, 0.1% RNase in PBS). The cells were analyzed using a FACS Vantage flow cytometer with Cell Quest acquisition and analysis software program (Becton-Dickinson and Co., San Jose, CA, USA).
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:48:01 GMT 2025
Edited
by admin
on Mon Mar 31 17:48:01 GMT 2025
Record UNII
8890V3217X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HYDRASTINE
MI   USP-RS   WHO-DD  
Common Name English
HYDRASTINE (CONSTITUENT OF GOLDENSEAL) [DSC]
Preferred Name English
NSC-757430
Code English
Hydrastine [WHO-DD]
Common Name English
HYDRASTINE [USP-RS]
Common Name English
HYDRASTINE [MI]
Common Name English
PHTHALIDE (S)-6,7-DIMETHOXY-3-(R)-(5,6,7,8-TETRAHYDRO-6-METHYL-1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)-
Common Name English
(S)-6,7-Dimethoxy-3-(R)-(6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one
Systematic Name English
Classification Tree Code System Code
DSLD 1119 (Number of products:5)
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
NCI_THESAURUS C221
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C76031
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
WIKIPEDIA
Hydrastine
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
CAS
118-08-1
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
FDA UNII
8890V3217X
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
EPA CompTox
DTXSID9025409
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
PUBCHEM
197835
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
RS_ITEM_NUM
1313210
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
NSC
757430
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
ChEMBL
CHEMBL1256919
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-233-0
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
MESH
C013024
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY
MERCK INDEX
m6076
Created by admin on Mon Mar 31 17:48:01 GMT 2025 , Edited by admin on Mon Mar 31 17:48:01 GMT 2025
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY