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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H21NO6.ClH
Molecular Weight 419.855
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDRASTINE HYDROCHLORIDE

SMILES

Cl.[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]3([H])N(C)CCC4=C3C=C5OCOC5=C4

InChI

InChIKey=URBFHJWLYXILMP-VOMIJIAVSA-N
InChI=1S/C21H21NO6.ClH/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;1H/t18-,19+;/m1./s1

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 for new compounds with antiherpes activity.
1984 Oct
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991 Jan-Feb
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 Oct
Differential modulation of respiratory neuronal discharge patterns by GABA(A) receptor and apamin-sensitive K(+) channel antagonism.
2001 Nov
Pharmacological properties of nicotinic acetylcholine receptors in isolated Locusta migratoria neurones.
2002 Feb 15
A validated high performance liquid chromatographic method for the analysis of Goldenseal.
2002 Mar
Individual and combined effect of (+/-)-alpha-hydrastine and (+/-)-beta-hydrastine on spore germination of some fungi.
2003
Microbial transformation of the phthalideisoquinoline alkaloid, (-)-beta-hydrastine.
2003 Aug
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.
2003 Dec 3
Enantio-selective inhibition of (1R,9S)- and (1S,9R)-beta-hydrastines on dopamine biosynthesis in PC12 cells.
2004 Dec
Effects of (1R,9S)-beta-hydrastine on l-DOPA-induced cytotoxicity in PC12 cells.
2004 Mar 19
A new glucosyl feruloyl quinic acid as a potential marker for roots and rhizomes of goldenseal, Hydrastis canadensis.
2004 Nov
1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae).
2004 Oct
Capillary zone electrophoresis as a tool for the quality control of goldenseal extracts.
2005 Jun
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine.
2006 Jun
Effects of (1R,9S)-beta-hydrastine on intracellular calcium concentration in PC12 cells.
2007 Aug
Effects of herbal products and their constituents on human cytochrome P450(2E1) activity.
2007 Dec
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.) 3: effect on human lens and retinal pigment epithelial cells.
2007 Jul-Aug
Determination of hydrastine and berberine in goldenseal raw materials, extracts, and dietary supplements by high-performance liquid chromatography with UV: collaborative study.
2008 Jul-Aug
Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species.
2009 Aug 24
Expanding the repertoire of small molecule transcriptional activation domains.
2009 Feb 1
Validation of a liquid chromatography-tandem mass spectrometric assay for the quantitative determination of hydrastine and berberine in human serum.
2009 May 1
Toxicology and carcinogenesis studies of goldenseal root powder (Hydrastis Canadensis) in F344/N rats and B6C3F1 mice (feed studies).
2010 Aug
Problems, artifacts and solutions in the INADEQUATE NMR experiment.
2010 Aug
BIAdb: a curated database of benzylisoquinoline alkaloids.
2010 Mar 5
Seasonal variation of biomass and bioactive alkaloid content of goldenseal, Hydrastis canadensis.
2010 Oct
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
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 Fri Dec 15 15:01:13 UTC 2023
Edited
by admin
on Fri Dec 15 15:01:13 UTC 2023
Record UNII
562PDC2I9K
Record Status Validated (UNII)
Record Version
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Name Type Language
HYDRASTINE HYDROCHLORIDE
MART.   MI   WHO-DD  
Common Name English
HYDRASTINE HYDROCHLORIDE [MART.]
Common Name English
HYDRASTINE HYDROCHLORIDE [MI]
Common Name English
Hydrastine hydrochloride [WHO-DD]
Common Name English
HYDRASTINE HCL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C221
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID40974771
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
NCI_THESAURUS
C76032
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
CAS
5936-28-7
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
EVMPD
SUB14127MIG
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
ECHA (EC/EINECS)
227-692-9
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
SMS_ID
100000077614
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
FDA UNII
562PDC2I9K
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
PUBCHEM
197834
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL1256919
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY
MERCK INDEX
m6076
Created by admin on Fri Dec 15 15:01:13 UTC 2023 , Edited by admin on Fri Dec 15 15:01:13 UTC 2023
PRIMARY Merck Index
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ACTIVE MOIETY