ChemicalBook > CAS DataBase List > (-)-EBURNAMONINE

(-)-EBURNAMONINE

Product Name: (-)-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
Formula Weight: 294.39
MOL File: 4880-88-0.mol

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(-)-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
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)

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Safety

Safety Statements: 22-24/25
WGK Germany: 2
RTECS: YY8575570
F: 8-10

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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.

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N-Bromosuccinimide Price

TRC

Product number: E320600
Product name: (-)-Eburnamonine
Packaging: 50mg
Price: $50
Updated: 2021/12/16

TRC

Product number: E320600
Product name: (-)-Eburnamonine
Packaging: 250mg
Price: $210
Updated: 2021/12/16

TRC

Product number: E320600
Product name: (-)-Eburnamonine
Packaging: 1g
Price: $720
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FE65898
Product name: (-)-Eburnamonine
Packaging: 50mg
Price: $52.5
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FE65898
Product name: (-)-Eburnamonine
Packaging: 100mg
Price: $85
Updated: 2021/12/16

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(-)-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

(-)-EBURNAMONINE Preparation Products And Raw materials

Raw materials

Preparation Products

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(-)-EBURNAMONINE Suppliers

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View Lastest Price from (-)-EBURNAMONINE manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: (-)-EBURNAMONINE 4880-88-0
Price: US $1.00-2.10/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20000KG
Release date: 2024-08-08

NanJing Spring & Autumn Biological Engineering CO., LTD.

Product: (-)-Eburnamonine 4880-88-0 4880-88-0
Price: US $25.00/mg
Min. Order: 20mg
Purity: ≥98%
Supply Ability: 1000.00 kgs
Release date: 2019-07-10

Qiuxian Baitai New Material Co., LTD

Product: High purity vinburnine 4880-88-0
Price: US $210.00-160.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 20 tons
Release date: 2021-03-10

4880-88-0, (-)-EBURNAMONINERelated Search:

(1-METHYL-1H-PYRROL-2-YL)METHYLAMINE 1-Ethyl-2-methylindole 3,3-DIMETHYLPIPERIDINE 1-Butyl-2-methylindole N,N-DIPROPYLTRYPTAMINE 1-METHYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE 3-Methylpiperidine 1-ACETYLINDOLE 2,3-DIMETHYLPIPERIDINE 1,2-Dimethylindole (R)-3,3-DIMETHYL-2-AMINOBUTANE (-)-EBURNAMONINE DIMETHYL-(1-METHYL-1H-PYRROL-2-YLMETHYL)-AMINE 1-ETHYL-2,3,4,9-TETRAHYDRO-1H-BETA-CARBOLINE 2,3,4,9-Tetrahydro-1-isopropyl-1H-pyrido[3,4-b]indole 1-METHYLTRYPTAMINE 2-[1-(Methylamino)ethyl]indole 3-METHYL-INDOLE-1-CARBALDEHYDE

(-)-eburnamonina

(-)-EBURNAMONINE

EBURNAMONINE, (-)-

VINCAMONE

(3alpha,16alpha)-eburnamenin-14(15H)-one

(-)-EBURNAMONINE 98+%

3α,16α-Eburnamonine

EBURNAMONINE, (-)-(RG)

vinburnine

(-)-cis-Eburnamonine

Cervoxan

(41S,13aS)-13a-Ethyl-41-Methyl-2,3,5,6,13,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12(41H)-one

EBURNAMONINE(VINBURNINE), (-)-(P)

(-)-Vi

(3α,16α)-14,15-Dihydroeburnamenin-14-one

3a-Ethyl-2,3,3a,4,10,11b-hexahydro-1H,11H-5a,11a-diaza-benzo[cd]fluoranthen-5-one

EBURNAMONINE(VINBURNINE), (-)-(RG)

Vinburnine base

(3-alpha,16-alpha)-eburnamin-14(15h)-on

3-alpha,16-alpha-eburnamonine

ch-846

cis-vincamone

eburnal

eburnalritardo

l-eburnamonine

(-)-Eburnamonine 4880-88-0

Vinpocetine Impurity 3 ((-)-Vincamone))

Vinpocetine Impurity 25

Eburnamenin-14(15H)-one, (3α,16α)-

High purity vinburnine

(41S,13aS)-13a-Ethyl-2,3,5,6,13,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12(41H)-one

(-)-Vincamone

Vinburnine, 10 mM in DMSO

4880-88-0

C19H22N2O

Cl9H22N20

Complex Molecules

Asymmetric Synthesis

Chiral Building Blocks

Inhibitors

Alkaloids

Complex Molecules

Asymmetric Synthesis

Chiral Building Blocks