(-)-EBURNAMONINE Property

Melting point:

174-177 °C(lit.)

alpha 

D25 -102° (chloroform) (Clauder); D -100° (c = 0.783 in chloroform) (Cartier)

Boiling point:

436.16°C (rough estimate)

Density 

1.34

refractive index 

1.5600 (estimate)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

form 

White to slightly yellow crystalline powder.

pka

8.13±0.40(Predicted)

color 

White

Merck 

13,3520

LogP

3.790 (est)

CAS DataBase Reference

4880-88-0(CAS DataBase Reference)

Safety

Safety Statements 

22-24/25

WGK Germany 

2

RTECS 

YY8575570

F 

8-10

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

(-)-EBURNAMONINE Chemical Properties,Usage,Production

Chemical Properties

white to slightly yellow crystalline powder

Originator

Euburnamonine ,Shanghai Lansheng Corporation

Uses

(-)-Eburnamonine shows protective effects on mice from the lethal consequences of hypoxia.

Uses

Cerebral vasodilatator

Definition

ChEBI: Eburnamonine is an alkaloid.

Manufacturing Process

200 g (0.087 moles) of cis-1-ethyl-1-(2'-hydroxy-2'-carboxyethyl)- 1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizine were suspended in 100 ml of xylene. 12 g of supported silver carbonate (a silver carbonate-Celite reagent, containing 50% of silver carbonate) were added to the suspension, and the system was boiled for 8 hours under a nitrogen atmosphere, with constant stirring. Thereafter the hot solution was filtered, washed with 3 x 30 ml to 5% sodium carbonate solution, dried over magnesium sulfate, and evaporated under reduced pressure. 1.05 g of a solid residue, which was a mixture of racemic vincamone and racemic vincanol, was obtained. 40 ml of ethyl ether were added to the mixture, and the insoluble crystals were filtered off. The crystals were recrystallized from methanol, to yield 0.5 g of (+/-)- eburnamonine (vincamone). Yield: 29.5%. MP: 201°-202°C. The value was identical with the literature value (J. Mokry et aI.: CoII. Czech, Chem. Comm. 28, 1309, 1963). The etheral mother liquor was processed by preparative layer chromatography (adsorbent: Kieselgel PF 254+366 , developing agent: a 14:2 mixture of benzene and methanol). The obtained substance was recrystallized from ether to yield 0.2 g (16%) of (+/-)-vincanol (eburnamine). MP: 163-164°C, under decomposition. The IR spectrum of the obtained substance was identical with that of the authentic sample.
Resolution of (+/-)-vincamone:
10.0 g (0.0342 moles) of (+/-)-vincamone and 12.2 g (0.0342 moles) of (-)- dibenzoyl tartaric acid were dissolved in 150 ml of dichloromethane, the solution was seeded with crystalline (-)-vincamone-(-)-dibenzoyl-tartarate, and the mixture was left to stand. The separated crystals were filtered off, dissolved in dimethylformamide, and the pH of the solution was adjusted to 9 with aqueous ammonia. The separated substance was filtered off, washed with water, and dried. This way 4.2 g (84%) of (-)-vincamone were obtained; MP: -176°C; α D 20 = -96°. The mother liquor of resolution was evaporated and (+)- vincamone was separeted as described above. The obtained substance had MP: 173°-176°C.; α D 20 = +96°.

Therapeutic Function

Cerebrotonic