Cinchonine

Catalog Number	ACM118105-1
CAS Number	118-10-5
Description	Cinchonine is a natural compound that has been found to have anti-cancer properties. It has shown to inhibit the growth of xenograft tumors in mice, which may be due to its ability to inhibit P-glycoprotein (P-gp). Cinchonine is metabolized by CYP2D6 and CYP3A4, with tiglic acid being the main metabolite. Cinchonine also has pro-apoptotic effects on HL60 cells and group P2 bowel disease. It has a structural analysis that includes an acetyl group at position 3 and methyl groups at positions 2 and 4. The reaction solution for cinchonine is shown below: Cinchonine can be synthesized from two molecules of pyridine via a condensation reaction with tiglic acid to form the intermediate nitrile followed by hydrolysis of the nitrile group with sodium hydroxide.
Synonyms	4-Quinolyl(5-vinyl-1-azabicyclo[2.2.2]oct-2-yl)methanol(5-Ethenyl-1-azabicyclo[2.2.2]oct-2-yl)(quinolin-4-yl)methanol
IUPAC Name	(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;
Molecular Weight	294.39 g/mol
Molecular Formula	C19H22N2O
Canonical SMILES	C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O
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	KMPWYEUPVWOPIM-QAMTZSDWSA-N
Melting Point	260-263 °C
Purity	98%+
Appearance	Solid
Application	Cinchonine occurs in most varieties of cinchonabark (Cinchona micrantha and Rubiaceae).It is used as an antimalarial agent.
Storage	Store below +30°C.
Complexity	412
Covalently-Bonded Unit Count	1
Defined Atom Stereocenter Count	4
EC Number	204-234-6
Exact Mass	294.17321333
Harmonized Tariff Code	Switzerland: 29392000 - USA: 2939200050 - Slovakia: 2939200000 - UK: 2939200000 - China: 2939200000
Heavy Atom Count	22
Hydrogen Bond Acceptor Count	3
Hydrogen Bond Donor Count	1
Isomeric SMILES	C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=CC=NC4=CC=CC=C34)O
MDL Number	MFCD00064372
Monoisotopic Mass	294.17321333
PhysicalState	Micro-crystalline powder
Rotatable Bond Count	3
Topological Polar Surface Area	36.4 Ų

Custom Q&A

What is the chemical formula of Cinchonine?

The chemical formula of Cinchonine is C19H22N2O.

What is the molecular weight of Cinchonine?

The molecular weight of Cinchonine is 294.39.

What is the melting point of Cinchonine?

The melting point of Cinchonine is 260-263 °C.

What is the solubility of Cinchonine?

The solubility of Cinchonine is 0.25g/l.

What is the optical activity of Cinchonine?

The optical activity of Cinchonine is [α]23/D +228°, c = 0.5 in ethanol.

What are some safety hazards associated with Cinchonine?

Cinchonine is classified as Hazard Code Xn, and it has Risk Statements 20/22-20/21/22. It should be stored away from strong oxidizing agents.

What is the usage of Cinchonine?

Cinchonine is used as a cardiotonic and antimalarial agent. It is also employed in asymmetric reactions as an organocatalyst.

How can Cinchonine be purified?

Cinchonine can be purified by crystallizing it from ethanol or diethyl ether.

What are some synonyms for Cinchonine?

Some synonyms for Cinchonine include (+)-cinconine, D-CINCHONINE, and CINCHONAN-9-OL.

How is Cinchonine structurally related to other compounds?

Cinchonine is a stereoisomer and pseudo-enantiomer of cinchonidine, and it is structurally similar to quinine, an antimalarial drug.

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