Apovincamine

Names

[ Name ]:
Apovincamine

[Synonym ]:
Apo-14,15-dehydrovincamine
14,15-dehydrovincamine
Apovincamina [spanish]
eburnamenine-14-carboxylic acid methyl ester
Apovincaminum [latin]
Apovincaminum
Vinpocetine impurity B
Apovincaminic acid methyl
(3S,16S)-Apovincaminsaeure
Apovincamina
(+)-trans-Cavinton

Biological Activity

[Description]:

Apovincamine (cis-Apovincamine) is an indole alkaloid isolated from the Malaysian Alstonia pneumatophora (Apocynaceae). Apovincamine shows anti-melanogenesis activity[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Others >> Others

[In Vitro]

Apovincamine (cis-Apovincamine; 6.3, 12.5, 25, 50, 100 μM) dose-dependently inhibits cells viability with an IC50 of 49.8 μM and shows anti-melanogenesis in B16 mouse melanoma cells[1].

[References]

[1]. Koichiro Koyama, et al. Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophore. Bioorg Med Chem. 2010 Jun 15;18(12):4415-21.

Chemical & Physical Properties

[ Density]:
1.3g/cm3

[ Boiling Point ]:
405.7ºC at 760mmHg

[ Melting Point ]:
160-162℃

[ Molecular Formula ]:
C₂₁H₂₄N₂O₂

[ Molecular Weight ]:
336.42700

[ Flash Point ]:
199.1ºC

[ Exact Mass ]:
336.18400

[ PSA ]:
34.47000

[ LogP ]:
3.69610

[ Index of Refraction ]:
1.678

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: JW4793000

CHEMICAL NAME :: Eburnamenine-14-carboxylic acid, methyl ester, (3-alpha,16-alpha)-

CAS REGISTRY NUMBER :: 4880-92-6

LAST UPDATED :: 199806

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C21-H24-N2-O2

MOLECULAR WEIGHT :: 336.47

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2200 mg/kg

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

REFERENCE :: FRXXBL French Demande Patent Document. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #2319362

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4140777

Safety Information

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

Effects of aging and vincamine derivatives on pericapillary microenvironment: stereological characterization of the cerebral capillary network.

Neurobiol. Aging 11(1) , 39-46, (1990)

Changes in the pericapillary microenvironment of adult (18-month-old) and senescent (27 1/2-month-old) Fischer-344 rats treated for 6 weeks with daily IP injections of brovincamine or apovincamine (0,...

Alpneumines A-H, new anti-melanogenic indole alkaloids from Alstonia pneumatophora.

Bioorg. Med. Chem. 18(12) , 4415-21, (2010)

Eight new indole alkaloids, alpneumines A-H (1-8) were isolated from the Malaysian Alstonia pneumatophora (Apocynaceae) and their structures were determined by MS and 2D NMR spectroscopic methods. Alp...

Synthesis of vinca alkaloids and related compounds. Part 84. Sulfonamide derivatives of some vinca alkaloids with cardiovascular activity.

Arch. Pharm. (Weinheim) 330(6) , 190-8, (1997)

(+)-Vincamine (1) and (+)-vinpocetine (2) were chlorosulfonylated and the resulting sulfonyl chloride isomers (3-6) were transformed into sulfonamides (7-10). The ester group of sulfonamides was modif...