Introduction：Basic information about (-)-EBURNAMONINE CAS 4880-88-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
(-)-EBURNAMONINE Basic information
| Product Name: | (-)-EBURNAMONINE |
| Synonyms: | (-)-eburnamonina;(-)-EBURNAMONINE;EBURNAMONINE, (-)-;VINCAMONE;(3alpha,16alpha)-eburnamenin-14(15H)-one;(-)-EBURNAMONINE 98+%;3α,16α-Eburnamonine;EBURNAMONINE, (-)-(RG) |
| CAS: | 4880-88-0 |
| MF: | C19H22N2O |
| MW: | 294.39 |
| EINECS: | 225-490-5 |
| Product Categories: | Inhibitors;Alkaloids;Complex Molecules;Asymmetric Synthesis;Chiral Building Blocks |
| Mol File: | 4880-88-0.mol |
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(-)-EBURNAMONINE Chemical Properties
| 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) |
| pka | 8.13±0.40(Predicted) |
| form | White to slightly yellow crystalline powder. |
| color | White |
| Merck | 13,3520 |
| InChI | InChI=1/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/s3 |
| InChIKey | WYJAPUKIYAZSEM-ZUMOKTPVNA-N |
| SMILES | [C@]12([H])N3CCC[C@@]1(CC)CC(=O)N1C4C(=CC=CC=4)C(CC3)=C21 |&1:0,6,r| |
| LogP | 3.790 (est) |
| CAS DataBase Reference | 4880-88-0(CAS DataBase Reference) |
Safety Information
| Safety Statements | 22-24/25 |
| WGK Germany | 2 |
| RTECS | YY8575570 |
| F | 8-10 |
(-)-EBURNAMONINE Usage And Synthesis
| Chemical Properties | white to slightly yellow crystalline powder |
| Originator | Euburnamonine ,Shanghai LanshengCorporation |
| Uses | Cerebral vasodilatator |
| Uses | (-)-Eburnamonine shows protective effects on mice from the lethal consequences of hypoxia. |
| 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 100ml of xylene. 12 g of supported silver carbonate (a silver carbonate-Celitereagent, containing 50% of silver carbonate) were added to the suspension,and the system was boiled for 8 hours under a nitrogen atmosphere, withconstant stirring. Thereafter the hot solution was filtered, washed with 3 x 30ml to 5% sodium carbonate solution, dried over magnesium sulfate, andevaporated under reduced pressure. 1.05 g of a solid residue, which was amixture of racemic vincamone and racemic vincanol, was obtained. 40 ml ofethyl ether were added to the mixture, and the insoluble crystals were filteredoff. The crystals were recrystallized from methanol, to yield 0.5 g of (+/-)-eburnamonine (vincamone). Yield: 29.5%. MP: 201°-202°C. The value wasidentical with the literature value (J. Mokry et aI.: CoII. Czech, Chem. Comm.28, 1309, 1963). The etheral mother liquor was processed by preparativelayer chromatography (adsorbent: Kieselgel PF 254+366 , developing agent: a14:2 mixture of benzene and methanol). The obtained substance wasrecrystallized from ether to yield 0.2 g (16%) of (+/-)-vincanol (eburnamine).MP: 163-164°C, under decomposition. The IR spectrum of the obtainedsubstance 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, thesolution 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 withwater, 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 hadMP: 173°-176°C.; α D 20 = +96°. |
| Therapeutic Function | Cerebrotonic |
(-)-EBURNAMONINE Preparation Products And Raw materials
| Raw materials | DIBENZOATE-->Dibenzoyltartaric acid |
