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145904

Sigma-Aldrich

Quinine

90%

Synonym(s):

6′-Methoxycinchonidine

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About This Item

Empirical Formula (Hill Notation):
C20H24N2O2
CAS Number:
130-95-0
Molecular Weight:
324.42
Beilstein:
91867
EC Number:
205-003-2
MDL number:
MFCD00198096
UNSPSC Code:
12352104
PubChem Substance ID:
24848751
NACRES:
NA.22
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Assay

90%

optical activity

[α]25/D −165°, c = 2 in ethanol

mp

173-175 °C (lit.)

functional group

hydroxyl

SMILES string

COc1ccc2nccc([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4C=C)c2c1

InChI

1S/C20H24N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3/t13-,14-,19-,20+/m0/s1

InChI key

LOUPRKONTZGTKE-WZBLMQSHSA-N

Gene Information

human ... ABCB1(5243) , CYP2C9(1559) , CYP2D6(1565)
rat ... Cyp2d1(266684) , Cyp2d2(25053) , Cyp2d3(24303) , Cyp2d4v1(171522)

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General description

Quinine, a cinchona alkaloid found in the bark of the cinchona tree, is known for its anti-malarial property.[1]

Application

Quinine has been used as a standard during the chemical evaluation of alkaloids in the hydroethanolic extracts of endophytic fungi obtained from the leaves of Costus spiralis by TLC.[2]
Resolving agent for carboxylic acids.[3] Catalyzes the kinetic resolution of furanones.[4]

Biochem/physiol Actions

Potassium channel blocker

Other Notes

remainder hydroquinine

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H317

Hazard Classifications

Acute Tox. 4 Oral - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM6685
BCCL0830
BCCK4568
BCCJ1195
BCCF7206

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Chemical assessment and antimicrobial and antioxidant activities of endophytic fungi extracts isolated from Costus spiralis (Jacq.) Roscoe (Costaceae)
Marson Ascencio PG, et al
Evidence-Based Complementary and Alternative Medicine : ECAM, 2014 (2014)
Tetrahedron, 50, 4775-4775 (1994)
Chirality, 4, 323-323 (1992)
Nicole I Wenzel et al.
Journal of medicinal chemistry, 53(8), 3214-3226 (2010-03-25)
The synthesis and biological evaluation of new organic and organometallic dual drugs designed as potential antimalarial agents are reported. A series of 4-aminoquinoline-based Mannich bases with variations in the aliphatic amino side chain were prepared via a three-steps synthesis. These
Chris de Graaf et al.
Journal of medicinal chemistry, 49(8), 2417-2430 (2006-04-14)
Automated docking strategies successfully applied to binding mode predictions of ligands in Cyt P450 crystal structures in an earlier study (de Graaf et al. J. Med. Chem. 2005, 7, 2308-2318) were used for the catalytic site prediction (CSP) of 65
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. What is the Flinn compatibility storage code and the storage condition for product 145904?

    1 answer

    1. Product 145904 should be stored at ambient temperature in a dark place due to its light sensitivity. The Flinn compatibility storage code (TRGS 510) for this item is 11, indicating it is a combustible solid.

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