27370

Cinchonine

crystallized, ≥98.0% (NT)

• Synonym(s): NSC 6176
• Empirical Formula (Hill Notation): C₁₉H₂₂N₂O
• CAS Number: 118-10-5
• Molecular Weight: 294.39
• UNSPSC Code: 12352104
• NACRES: NA.22
• PubChem Substance ID: 57648242
• EC Number: 204-234-6
• Beilstein/REAXYS Number: 89689
• MDL number: MFCD00064372

Properties

• Quality Segment: 100
• assay: ≥98.0% (NT)
• form: powder
• optical activity: [α]20/D +225±5°, c = 0.5% in ethanol
• quality: crystallized
• impurities: ~15% dihydrocinchonine (HPLC)
• mp: 260-263 °C
• functional group: hydroxyl
• SMILES string: O[C@H]([C@H]1C[C@@H]2CCN1C[C@@H]2C=C)c3ccnc4ccccc34
• InChI: 1S/C19H22N2O/c1-2-13-12-21-10-8-14(13)11-18(21)19(22)16-7-9-20-17-6-4-3-5-15(16)17/h2-7,9,13-14,18-19,22H,1,8,10-12H2/t13-,14-,18+,19-/m0/s1
• InChI key: KMPWYEUPVWOPIM-QAMTZSDWSA-N
• Gene Information: human ... CYP2D6(1565)

Description

General description

Cinchonine is a cinchona alkaloid generally found in the bark of Cinchona officinalis plants. It is a pseudoenantiomer that is commonly employed in malaria therapy. Cinchonine is also used as an organocatalyst in many asymmetric reactions.

Application

Cinchonine can be used:

• As a substrate in the study of supercritical fluid chromatography (SFC) parameters in pharmaceutical analysis.[1]
• To prepare possible butyrylcholinesterase inhibitors.[2]

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302,H317
• pcodes: P261 - P264 - P272 - P280 - P301 + P312 - P302 + P352
• Hazard Classifications: Acute Tox. 4 Oral - Skin Sens. 1A
• Storage Class: 11 - Combustible Solids
• wgk: WGK 1
• ppe: dust mask type N95 (US), Eyeshields, Gloves