CAS 118-10-5 Cinchonine (HCID 90454)

Overview

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.

Names & identifiers

Preferred name: Cinchonine
IUPAC: (S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol
English name: Cinchonine
Molecular formula: C19H22N2O
Molecular weight: 294.39

Names & synonyms

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

Show more names

Cinchonin(S)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methanolNSC 6176LA40221)Xin KeningXin Kenning

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 2.7
Topological polar surface area: 36.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 22
Formal charge: 0
Complexity: 412

Experimental & physicochemical properties

SpringerMaterials PropertiesCrystal structure

LogP2.68

Collision Cross Section · 2 items

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]

Physicochemical properties

Melting point: 260 · 260-263 °C
alpha: 224 · 224 º (c=0.5, alcohol)
Boiling point: 436.16 °C · 436.16°C (rough estimate)
Density: 1.0863 · 1.0863 (rough estimate)
bulk density: 130 kg/m3 · 130kg/m3
vapor pressure: 0 Pa · 0Pa at 25℃
refractive index: 223 ° · 223 ° (C=0.5, EtOH)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: 0.25 g/l · 0.25g/l
form: Micro-Crystalline Powder
pka: 5.85 · 5.85, 9.92(at 25℃)
color: White to light beige
PH: 9 · 9.0 (0.25g/l, H2O, 20℃)(as aqueous solution)
optical activity: 23 · [α]23/D +228°, c = 0.5 in ethanol
Water Solubility: Insoluble
Sensitive: Light Sensitive
Merck: 14 · 14,2287
BRN: 89689 · 89689
Stability: Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
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
InChIKey: KMPWYEUPVWOPIM-QHQSXHFQSA-N
SMILES: N21[C@H](C[C@@H]([C@H](C2)C=C)CC1)[C@@H](O)c3c4c(ncc3)cccc4
LogP: 2.82 at · 2.82 at 25℃
CAS DataBase Reference: 118 · 118-10-5(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 43 X79NZCD · V43X79NZCD
NIST Chemistry Reference: Cinchonine(118-10-5)
EPA Substance Registry System: -9 · Cinchonan-9-ol, (9S)- (118-10-5)
UNSPSC Code: 12352104 · 12352104
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H317
Precautionary statements: 261 · P261-P264-P270-P280-P301+P312-P302+P352
Hazard Codes: Xn
Risk Statements: 20 · 20/22-20/21/22
Safety Statements: 26 · 26-36-36/37
RIDADR: 1544 · 1544
WGK Germany: 3 · 3
RTECS: 3500000 · GD3500000
F: 8 · 8-34
TSCA: TSCA listed
HazardClass: 6.1 · 6.1(b)
PackingGroup: III
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralSkin · Acute Tox. 4 OralSkin Sens. 1
Toxicity: 50 i.p · LD50 i.p. in rats: 152 mg/kg (Johnson, Poe)
REACH Registrations: Active

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Regulatory Information · 3 items

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%)

Safety data

F: 8-34
wgk: 3
tsca: TSCA listed
rtecs: GD3500000
ridadr: 1544
hs_code: 29339900
Toxicity: LD50 i.p. in rats: 152 mg/kg (Johnson, Poe)
risk_code: 20/22-20/21/22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 26-36-36/37
hazard_class: 6.1(b)
Storage Class: 11 - Combustible Solids
packing_group: III
Hazard statements: H302-H317
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralSkin Sens. 1
Precautionary statements: P261-P264-P270-P280-P301+P312-P302+P352

Chemistry & industry

Pharmacology

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)

Uses & manufacturing

General Manufacturing InformationCinchonan-9-ol, (9S)-: ACTIVE

Applications · 4 items

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

Usescardiotonic

UsesStereomeric with Cinchonidine (C441925). Antimalarial.

UsesCinchonine occurs in most varieties of cinchonabark (Cinchona micrantha and Rubiaceae).It is used as an antimalarial agent.

Upstream & downstream products

Upstream raw materials

1-Azabicyclo[3.2.2]nonan-3-ol, 6-ethenyl-2-(4-quinolinyl)-, (1S,2R,3S,5S,6R)-

Downstream products

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]

北京华美互利生物化工010-56205725 · [email protected]

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

山西玉宁生物科技有限公司13623677056

Additional notes

DefinitionChEBI: 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.