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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.)

Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine.

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

Variations in alkaloid content of herbal products containing goldenseal.

David J Edwards et al.

Journal of the American Pharmacists Association : JAPhA, 43(3), 419-423 (2003-07-03)

To determine the concentration of hydrastine and berberine, the primary alkaloids in herbal products containing goldenseal. Descriptive comparison of 20 products purchased at local pharmacies or health food stores; 17 products were labeled as containing goldenseal root and 3 products

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