(-)-EBURNAMONINE
- CAS No.
- 4880-88-0
- Chemical Name:
- (-)-EBURNAMONINE
- Synonyms
- vinburnine;VINCAMONE;eburnalritardo;(-)-Vi;ch-846;eburnal;Cervoxan;cis-vincamone;(-)-Vincamone;l-eburnamonine
- CBNumber:
- CB9130995
- Molecular Formula:
- C19H22N2O
- Molecular Weight:
- 294.39
- MDL Number:
- MFCD00064309
- MOL File:
- 4880-88-0.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| 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 |
| 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) |
| EWG's Food Scores | 1 |
| FDA UNII | G54D0HMY25 |
| ATC code | C04AX17 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|---|---|
| Signal word | Warning |
| Hazard statements | H315-H319 |
| Precautionary statements | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 |
| Safety Statements | 22-24/25 |
| WGK Germany | 2 |
| RTECS | YY8575570 |
| F | 8-10 |
(-)-EBURNAMONINE price More Price(38)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Cayman Chemical | 37569 | (−)-Eburnamonine ≥98% | 4880-88-0 | 50mg | $63 | 2026-04-30 | Buy |
| Cayman Chemical | 37569 | (−)-Eburnamonine ≥98% | 4880-88-0 | 100mg | $112 | 2026-04-30 | Buy |
| Cayman Chemical | 37569 | (−)-Eburnamonine ≥98% | 4880-88-0 | 250mg | $211 | 2026-04-30 | Buy |
| Cayman Chemical | 37569 | (−)-Eburnamonine ≥98% | 4880-88-0 | 500mg | $494 | 2026-04-30 | Buy |
| TRC | TRC-E320600-50MG | (-)-Eburnamonine | 4880-88-0 | 50mg | $64 | 2026-06-03 | Buy |
(-)-EBURNAMONINE Chemical Properties, Uses, Production
Synthesis
Currently, the synthesis of (-)-EBURNAMONINE is mainly divided into two methods: semi-synthetic and total synthesis. Semi-synthetic (-)-EBURNAMONINE is mainly synthesized using taponin extracted from potato as the starting material, while the total chemical synthesis method uses the reduction of intermediates. The total chemical synthesis method is more suitable for industrialization. The fully chemical synthesis method is as follows: (+)-15a-ethyl-2,3,6,11,15,15a-hexahydro-1H,5H-indolo[2,3-a]pyran[3,2-i]quinazine-14,14-(13H)-dicarboxylic acid diethyl ester is an intermediate structure in the chemical synthesis of vinblastine. After chiral resolution and reduction, the optically active (+)-15a-ethyl-2,3,6,11,15,15a-hexahydro-1H,5H-indolo[2,3-a]pyran[3,2-i]quinazine-14,14-(13H)-dicarboxylic acid diethyl ester (compound I) is obtained. Subsequent Pd-C reaction yields the effective structure of the vinblastine product (compound II). src="/NewsImg/2017-04-17/201741711512212247.jpg" alt="Synthesis Route" />
Image: Synthesis Route
Chemical Properties
white to slightly yellow crystalline powder
Originator
Euburnamonine ,Shanghai Lansheng Corporation
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 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
(-)-EBURNAMONINE Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Chemleader Biomedical Co., Limited. | 021-58180488 | sales@MedChemLeader.com | China | 1004 | 58 |
| Chembest Research Laboratories Limited | 021-20908456 | sales@BioChemBest.com | China | 5996 | 61 |
| Shanghai T&W Pharmaceutical Co., Ltd. | +86 21 61551611 | China | 9874 | 58 | |
| China Kouting Group Limited | +86 (21) 5811-6473 5811-6475 | sales@koutingchina.com | China | 494 | 60 |
| UHN Shanghai Research & Development Co., Ltd. | 021-58958002 18930822973 | sales@uhnshanghai.com | China | 997 | 58 |
| MedChemexpress LLC | 021-58955995 | sales@medchemexpress.cn | United States | 4853 | 58 |
| Shanghai Tauto Biotech Co., Ltd. | 021-51320588 | tauto@tautobiotech.com | China | 3984 | 66 |
| Guangzhou Isun Pharmaceutical Co., Ltd | 020-39119399 18927568969 | isunpharm@qq.com | China | 4773 | 55 |
| TargetMol Chemicals Inc. | 021-021-33632979 15002134094 | marketing@targetmol.com | China | 7993 | 58 |
| Bide Pharmatech Ltd. | 400-164-7117 18317119277 | product02@bidepharm.com | China | 40000 | 60 |
View Latest Price from (-)-EBURNAMONINE manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-08-07 | (-)-EBURNAMONINE
4880-88-0
|
$1.00-2.10 | 1KG | 99% | 20000KG | Shaanxi Dideu Medichem Co. Ltd | |
 |
2026-07-14 | Vinburnine
4880-88-0
|
$39.00-80.00 | 99.71% | 10g | TargetMol Chemicals Inc. | ||
 |
2022-02-14 | (-)-Eburnamonine 4880-88-0
4880-88-0
|
$25.00 | 20mg | ≥98% | 1000.00 kgs | NanJing Spring & Autumn Biological Engineering CO., LTD. |
-
- (-)-EBURNAMONINE
4880-88-0
- $1.00-2.10
- 99%
- Shaanxi Dideu Medichem Co. Ltd
-
- Vinburnine
4880-88-0
- $39.00-80.00
- 99.71%
- TargetMol Chemicals Inc.
-
- (-)-Eburnamonine 4880-88-0
4880-88-0
- $25.00
- ≥98%
- NanJing Spring & Autumn Biological Engineering CO., LTD.
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