H8645
(1S,9R)-(+)-β-Hydrastine
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About This Item
Empirical Formula (Hill Notation):
C21H21NO6
CAS Number:
Molecular Weight:
383.39
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
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+/m0/s1
SMILES string
[H][C@]1(OC(=O)c2c(OC)c(OC)ccc12)[C@@]3([H])N(C)CCc4cc5OCOc5cc34
InChI key
JZUTXVTYJDCMDU-RBUKOAKNSA-N
storage temp.
−20°C
Gene Information
Biochem/physiol Actions
Potent competitive GABAA receptor antagonist which is more potent than bicuculline; isolated from Corydalis stricta.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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J H Huang et al.
British journal of pharmacology, 99(4), 727-730 (1990-04-01)
1. (+)-Hydrastine is a phthalide isoquinoline alkaloid, isolated from Corydalis stricta. It has the same 1S,9R configuration as the competitive GABAA receptor antagonist bicuculline and is the enantiomer of the commercially available (-)-hydrastine. 2. (+)-Hydrastine (CD50 0.16 mg kg-1, i.v.)
Matthias Unger et al.
Electrophoresis, 26(12), 2430-2436 (2005-05-25)
The root extracts of goldenseal (Hydrastis canadensis L.) are popular phytomedicines for the treatment of gastrointestinal disorders and upper respiratory tract infections. Here we describe a simple and fast capillary zone electrophoresis (CZE) method with ultraviolet detection at 225 nm
Shou Yu Yin et al.
Neuropharmacology, 47(7), 1045-1052 (2004-11-24)
The inhibitory effects of (1R,9S)- and (1S,9R)-enantiomers of beta-hydrastine (BHS) on dopamine biosynthesis in PC12 cells were investigated. (1R,9S)-BHS decreased the intracellular dopamine content with the IC50 value of 14.3 microM at 24 h, but (1S,9R)-BHS did not. (1R,9S)-BHS was
James A Douglas et al.
Fitoterapia, 81(7), 925-928 (2010-06-17)
Seasonal variations in biomass and alkaloid contents of goldenseal (Hydrastis canadensis) were investigated. Five-year-old plants gave 5x the yield of roots and rhizomes of two-year-old plants, and summer growth gave significant increases in root biomass but not rhizomes. Berberine contents
J J Inbaraj et al.
Chemical research in toxicology, 19(6), 739-744 (2006-06-20)
Goldenseal is an herb that is widely used in dietary supplements, eye washes, and skin lotions. The presence of Goldenseal root powder in dietary supplements and the topical application of Goldenseal preparations raise the possibility that an adverse phototoxic reaction
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