Cinchonine

HCID 90454CAS 118-10-5

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Grundinformationen

Standard-SMILES: C=C[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](O)c1ccnc2ccccc12
InChIKey: KMPWYEUPVWOPIM-QAMTZSDWSA-N
Summenformel: C19H22N2O
Durchschnittliche Molmasse: 294,4 g/mol
Monoisotopische Masse: 294,17321332

Überblick

Cinchonine is cinchonan in which a hydrogen at position 9 is substituted by hydroxy (S configuration). It occurs in the bark of most varieties of Cinchona shrubs, and is frequently used for directing chirality in asymmetric synthesis. It has a role as a metabolite. It is an (8xi)-cinchonan-9-ol and a cinchona alkaloid. It derives from a hydride of a cinchonan.

Namen und Bezeichner

Bevorzugter Name: Cinchonine
IUPAC: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol

Namen und Synonyme

cinchonine118-10-5D-Cinchonine(9S)-Cinchonan-9-olCinchonan-9-ol, (9S)-(8R,9S)-Cinchonine(+)-CinconineDTXSID6045082NSC-6176V43X79NZCDCHEBI:27509DTXCID801474963

Weitere Namen anzeigen

2-Quinuclidinemethanol, alpha-(5-vinyl-2-quinolyl)-alpha-(5-Vinyl-2-quinuclidinyl)-4-quinolinemethanol(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol(S)-((2R,4S,5R)-5-ethenyl-1-azabicyclo(2.2.2)octan-2-yl)-quinolin-4-ylmethanolLA-40221RefChem:126196204-234-6(+)-Cinchonine

Datenbank-Bezeichner

CAS: 118-10-5
PubChem CID: 90454
DTXSID: DTXSID6045082
ChEMBL: CHEMBL588619
ChEBI: CHEBI:27509
UNII: V43X79NZCD
EC Number: 204-234-6
Nikkaji: J2.475I

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,7
Polarare Oberfläche (TPSA): 36,4 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 3
Schwere Atome: 22
Formalladung: 0
Komplexität: 412

Experimentelle und physikochemische Eigenschaften

SpringerMaterials PropertiesCrystal structure

LogP2.68

Collision Cross Section · 2 Einträge

165.21 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

166.3 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 65 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Cinchonan-9-ol, (9S)-

Status: Active Update: 13-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/16829

Cinchonan-9-ol, (9S)-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological ClassificationAgents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)