CAS 118-10-5

Cinchonine

Description:

Cinchonine is an alkaloid derived from the bark of the cinchona tree, primarily known for its use in traditional medicine and as a precursor in the synthesis of various pharmaceuticals. It is a white to pale yellow crystalline powder with a bitter taste and is sparingly soluble in water but more soluble in organic solvents like ethanol and chloroform. The molecular formula of cinchonine is C18H21N, and it has a complex structure featuring a quinoline ring system. This compound exhibits stereoisomerism, with the natural form being the (S)-enantiomer. Cinchonine has been historically significant as an antimalarial agent and is also used in the synthesis of other compounds, including quinine. Additionally, it has applications in organic chemistry as a chiral ligand in asymmetric synthesis. Its pharmacological properties include antipyretic and analgesic effects, although it is less commonly used today compared to its derivatives. Safety considerations include potential toxicity at high doses, necessitating careful handling and usage in laboratory and medicinal contexts.

Formula: C₁₉H₂₂N₂O

InChI: 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: InChIKey=KMPWYEUPVWOPIM-QAMTZSDWSA-N

SMILES: [C@@H](O)([C@@]1([N@@]2C[C@H](C=C)[C@](C1)(CC2)[H])[H])C=3C4=C(N=CC3)C=CC=C4

Synonyms:

• (3alpha,9R)-cinchonan-9-ol
• (3alpha,9S)-cinchonan-9-ol
• (4beta,9S)-cinchonan-1-ium-9-ol
• (8R,9S)-Cinchonine
• (8alpha,9S)-cinchonan-9-ol
• (9R)-cinchonan-9-ol
• (9S)-9-hydroxycinchonan-1-ium
• (9S)-cinchonan-9-ol
• Alpha-(5-Vinyl-2-Quinuclidinyl)-4-Quinolinemethanol
• Cinchonan-9-Ol
• Cinchonan-9-ol, (9S)-
• Cinchonin
• Cinconina
• Nsc 6176
• d-Cinchonine
• Cinchonine

Cinchonine

CAS: 118-10-5

Formula: C₁₉H₂₂N₂O

Purity: >98.0%(T)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 294.40

Ref: 3B-C0350

(+)-Cinchonine, 98+%, cont. up to 3% quinidine/dihydroquinidine and 3% quinine/dihydroquinine

CAS: 118-10-5

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Sci

Formula: C₁₉H₂₂N₂O

Purity: 98+%

Color and Shape: White to pale cream, Crystals or powder or crystalline powder

Molecular weight: 294.40

Ref: 02-A17523

Cinchonine

CAS: 118-10-5

Cinchonine (LA40221), a potent amide local anesthetic for surface use, is toxic and limited to spinal anesthesia.

Formula: C₁₉H₂₂N₂O

Purity: 99.45%

Color and Shape: White Or Almost White Solid Powder

Molecular weight: 294.39

Ref: TM-T0012

(S)-Quinolin-4-yl((1S,2R,4S,5S)-5-vinylquinuclidin-2-yl)methanol

CAS: 118-10-5

Formula: C₁₉H₂₂N₂O

Purity: 85%

Color and Shape: Solid

Molecular weight: 294.3908

Ref: IN-DA0032AT

Cinchonine

CAS: 118-10-5

Formula: C₁₉H₂₂N₂O

Purity: (Titration) ≥ 99.0%

Color and Shape: White to almost white crystalline powder

Molecular weight: 294.39

Ref: 7W-GK1431

Cinchonine

CAS: 118-10-5

Cinchonine

Purity: ≥80%

Molecular weight: 294.39g/mol

Ref: 54-BUP19783

(5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)(quinolin-4-yl)methanol

CAS: 118-10-5

(5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)(quinolin-4-yl)methanol

Purity: ≥95%

Color and Shape: White Solid

Molecular weight: 294.39g/mol

Ref: 54-OR28810

(+)-cinchonine

CAS: 118-10-5

Cinchona alkaloid

Formula: C₁₉H₂₂N₂O

Purity: ≥ 95.0 % (HPLC)

Color and Shape: Powder

Molecular weight: 294.4

Ref: 5G-80963

Cinchonine

CAS: 118-10-5

Stability Light Sensitive
Applications Stereomeric with Cinchonidine (C441925). Antimalarial.
References Litchfield, J., et al.: J. Pharm. Exp. Ther., 96, 99 (1949), Trager, W., et al.: Science, 193, 673 (1976), Panisko, D., et al.: Drugs, 39, 160 (1990), Karle, J., et al.: Antimicrob. Agents Chemother., 36, 1538 (1992),

Formula: C₁₉H₂₂N₂O

Color and Shape: Neat

Molecular weight: 294.39

Ref: TR-C441935

(+)-Cinchonine

CAS: 118-10-5

Formula: C₁₉H₂₂N₂O

Purity: 85%

Color and Shape: Solid, Crystalline Powder or Powder

Molecular weight: 294.398

Ref: 10-F121600

Quinidine EP Impurity B

CAS: 118-10-5

Formula: C₁₉H₂₂N₂O

Molecular weight: 294.4

Ref: ST-EA-CP-Q9007

Cinchonine

CAS: 118-10-5

Cinchonine is a naturally occurring alkaloid, which is derived from the bark of the Cinchona tree. This compound is known for its antimalarial properties, functioning primarily through the inhibition of the heme polymerase enzyme in Plasmodium parasites. By interfering with the conversion of toxic heme into the non-toxic hemozoin, cinchonine effectively causes an accumulation of toxic heme within the parasite, ultimately leading to its death.

Formula: C₁₉H₂₂N₂O

Purity: Min. 95%

Molecular weight: 294.39 g/mol

Ref: 3D-FC11047