Cinchonidine

Names

[ CAS No. ]:
485-71-2

[ Name ]:
Cinchonidine

[Synonym ]:
(+)-cinchonine
(R)-4-Quinolinyl[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methanol
L-CINCHONIDINE
Cinchonan-9-ol, (8α,9R)-
(R)-4-Chinolinyl[(2S,4S,5R)-5-vinyl-1-azabicyclo[2.2.2]oct-2-yl]methanol
(-)-CINCHONIDINE
(R)-[(2S,4S,5R)-5-éthènyl-1-azabicyclo[2.2.2]oct-2-yl](4-quinoléinyl)méthanol
α-Quinidine
Cinchondine
Cinchovatine
MFCD00006783
Cinchonidine
1-Cinchonidine
EINECS 207-622-3
chinchonidine
a-quinidine
(8α,9R)-Cinchonan-9-ol
(8a,9R)-Cinchonan-9-ol
Cinchovatine (VAN)
TCMDC-123934

Biological Activity

[Description]:

Cinchonidine (α-Quinidine) is a cinchona alkaloid found in Cinchona officinalis and Gongronema latifolium. A building block used in asymmetric synthesis in organic chemistry. Weak inhibitor of serotonin transporter (SERT) with Kis of 330, 4.2, 36, 196, 15 μM for dSERT, hSERT, hSERT I172M, hSERT S438T, hSERT Y95F, respectively. Antimalarial activities[1].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Serotonin Transporter

Natural Products >> Alkaloid

Research Areas >> Infection

[Target]

Ki: 330 μM (dSERT), 4.2 μM (hSERT), 36 μM (hSERT I172M), 196 μM (hSERT S438T), 15 μM (hSERT Y95F) [1]

[In Vitro]

[References]

[1]. Beckman ML, et al. Stereoselective inhibition of serotonin transporters by antimalarial compounds. Neurochem Int. 2014 Jul;73:98-106.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
464.5±30.0 °C at 760 mmHg

[ Melting Point ]:
204-206ºC

[ Molecular Formula ]:
C₁₉H₂₂N₂O

[ Molecular Weight ]:
294.391

[ Flash Point ]:
234.7±24.6 °C

[ Exact Mass ]:
294.173218

[ PSA ]:
36.36000

[ LogP ]:
3.35

[ Vapour Pressure ]:
0.0±1.2 mmHg at 25°C

[ Index of Refraction ]:
1.652

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GD2975000

CHEMICAL NAME :: Cinchonidine

CAS REGISTRY NUMBER :: 485-71-2

LAST UPDATED :: 199701

DATA ITEMS CITED :: 3

MOLECULAR FORMULA :: C19-H22-N2-O

MOLECULAR WEIGHT :: 294.43

WISWESSER LINE NOTATION :: T66 BNJ EYQ- DT66 A B CNTJ A1U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 206 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - muscle contraction or spasticity

REFERENCE :: APTOA6 Acta Pharmacologica et Toxicologica. (Copenhagen, Denmark) V.1-59, 1945-86. For publisher information, see PHTOEH Volume(issue)/page/year: 4,265,1948

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Bird - quail

DOSE/DURATION :: >316 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EESADV Ecotoxicology and Environmental Safety. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1977- Volume(issue)/page/year: 6,149,1982

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H317-H361d-H373

[ Precautionary Statements ]:
P280

[ Target Organs ]:
Heart, Immune system

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn:Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S36/37

[ RIDADR ]:
UN 1544

[ WGK Germany ]:
3

[ RTECS ]:
GD2975000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2939200000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2939200000

Articles

Thousands of chemical starting points for antimalarial lead identification.

Nature 465 , 305-10, (2010)

Malaria is a devastating infection caused by protozoa of the genus Plasmodium. Drug resistance is widespread, no new chemical class of antimalarials has been introduced into clinical practice since 19...

Direct, catalytic, and regioselective synthesis of 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles from N-oxides.

Org. Lett. 16(3) , 864-7, (2014)

A one-step transformation of heterocyclic N-oxides to 2-alkyl-, aryl-, and alkenyl-substituted N-heterocycles is described. The success of this broad-scope methodology hinges on the combination of cop...

Membranes for specific adsorption: immobilizing molecularly imprinted polymer microspheres using electrospun nanofibers.

Chimia 65(3) , 182-6, (2011)

Molecularly imprinted polymer microspheres were immobilized within a polymer nanofiber membrane by electrospinning. Such membranes simplify the handling of functional microspheres and provide specific...

Related Compounds

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.