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Substance Name: Vincamine [INN:BAN:DCF]
RN: 1617-90-9
UNII: 996XVD0JHT
InChIKey: RXPRRQLKFXBCSJ-GIVPXCGWSA-N

Note

  • A major alkaloid of Vinca minor L., Apocynaceae. It has been used therapeutically as a vasodilator and antihypertensive agent, particularly in cerebrovascular disorders.

Molecular Formula

  • C21-H26-N2-O3

Molecular Weight

  • 354.4474
 

Classification Codes

  • Antihypertensive Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Natural Product
  • Vasodilator Agents
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Names and Synonyms

Name of Substance

  • Vincamine
  • Vincamine [INN:BAN:DCF]

MeSH Heading

  • Vincamine

Synonyms

  • (+)-Vincamine
  • 14,15-Dihydro-14-hydroxyeburnamenine-14-carboxylic acid methyl ester
  • Anasclerol
  • Anasclerol (base)
  • Angiopac
  • Arteriovinca
  • Decincan
  • Devincan
  • Devinkan
  • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16.)
  • EINECS 216-576-3
  • Equipur
  • HSDB 7150
  • Methyl vincaminate
  • Minorin
  • Minorine
  • Monorin
  • Novicet
  • NSC 91998
  • Ocu-vinc
  • Oxygeron
  • Perval
  • Pervincamine
  • Pervone
  • Tripervan
  • UNII-996XVD0JHT
  • Vinca
  • Vinca-Ecobi
  • Vinca-Minor
  • Vincachron
  • Vincadar
  • Vincafolina
  • Vincafor
  • Vincagil
  • Vincamidol
  • Vincamin
  • Vincamina
  • Vincamina [DCIT]
  • Vincamine
  • Vincaminum
  • Vincaminum [INN-Latin]
  • Vincapan
  • Vincapront
  • Vincasaunier
  • Vincimax
  • Vinkametrin
  • Vinodrel retard

Systematic Names

  • Alkaloid obtained from Vinca minor
  • Eburnamenine-14-carboxylic acid, 14,15-dihydro-14-hydroxy-, methyl ester, (3alpha,14beta,16alpha)-
  • Vincamine

Registry Numbers

CAS Registry Number

  • 1617-90-9

FDA UNII

  • 996XVD0JHT

System Generated Number

  • 0001617909

Structure Descriptors

InChI

1S/C21H26N2O3/c1-3-20-10-6-11-22-12-9-15-14-7-4-5-8-16(14)23(17(15)18(20)22)21(25,13-20)19(24)26-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+/m1/s1

InChIKey

RXPRRQLKFXBCSJ-GIVPXCGWSA-N

Smiles

CC[C@@]12CCCN3[C@@H]1c4c(c5ccccc5n4[C@](C2)(C(=O)OC)O)CC3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 195mg/kg (195mg/kg)   European Patent Application. Vol. #0052238,
mouse LD50 intravenous 47740ug/kg (47.74mg/kg)   Agressologie. Revue Internationale de Physio-Biologie et de Pharmacologie Appliquees aux Effets de l'Agression. Vol. 19, Pg. 211, 1978.
mouse LD50 oral 460mg/kg (460mg/kg)   United States Patent Document. Vol. #4011330,
rabbit LD50 intravenous 33mg/kg (33mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 236, Pg. 296, 1959.
rat LD50 intraperitoneal 253mg/kg (253mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 32, Pg. 601, 1982.
rat LD50 oral 1200mg/kg (1200mg/kg)   United States Patent Document. Vol. #3852453,

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 231.5 deg C   EXP
log P (octanol-water) 3.490 (none)   EST
Atmospheric OH Rate Constant 2.60E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.