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H8645

(1S,9R)-(+)-β-Hydrastine

Name: (1S,9R)-(+)-β-Hydrastine
Brand: SIGMA

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About This Item

Empirical Formula (Hill Notation):

C₂₁H₂₁NO₆

CAS Number:

29617-43-4

Molecular Weight:

383.39

UNSPSC Code:

12352200

PubChem Substance ID:

24278171

MDL number:

MFCD00132881

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Properties

storage temp.

−20°C

SMILES string

[H][C@]1(OC(=O)c2c(OC)c(OC)ccc12)[C@@]3([H])N(C)CCc4cc5OCOc5cc34

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

InChI key

JZUTXVTYJDCMDU-RBUKOAKNSA-N

Gene Information

human ... GABRA1(2554), GABRA2(2555), GABRA3(2556), GABRA4(2557), GABRA5(2558), GABRA6(2559), GABRB1(2560), GABRB2(2561), GABRB3(2562)

Description

Biochem/physiol Actions

Potent competitive GABA_A 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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Certificates of Analysis (COA)

Lot/Batch Number

110H0191

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(+)-Hydrastine, a potent competitive antagonist at mammalian GABAA receptors.

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.)

Capillary zone electrophoresis as a tool for the quality control of goldenseal extracts.

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

Enantio-selective inhibition of (1R,9S)- and (1S,9R)-beta-hydrastines on dopamine biosynthesis in PC12 cells.

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

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