Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Gelsemine
RN: 509-15-9
UNII: 5Y13A78Z72
InChIKey: NFYYATWFXNPTRM-QJICHLCESA-N

Note

  • From Gelsemium sempervirens.

Classification Codes

  • Drug / Therapeutic Agent
  • Natural Product

Molecular Formula

  • C20-H22-N2-O2

Molecular Weight

  • 322.4058
 
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Gelsemine

Synonyms

  • (3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methylspiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1',H)-one
  • 4-27-00-07526 (Beilstein Handbook Reference)
  • BRN 5406576
  • EINECS 208-095-2
  • Gelsemin
  • HSDB 3488
  • NSC 21729
  • Spiro(3,5,8-ethanylylidene-1H-pyrano(3,4-c)pyridine-10,3'-(3H)indol)-2'(1'H)-one, 5-ethenyl-3,4,4a,5,6,7,8,8a-octahydro-7-methyl-, (3R-(3alpha,4abeta,5alpha,8alpha,8abeta,9S*,10S*))-
  • UNII-5Y13A78Z72

Systematic Name

  • Gelsemine

Registry Numbers

CAS Registry Number

  • 509-15-9

FDA UNII

  • 5Y13A78Z72

Other Registry Numbers

  • 1413-63-4
  • 791726-87-9

System Generated Number

  • 0000509159

Structure Descriptors

InChI

1S/C20H22N2O2/c1-3-19-10-22(2)16-11-9-24-15(8-13(11)19)20(17(16)19)12-6-4-5-7-14(12)21-18(20)23/h3-7,11,13,15-17H,1,8-10H2,2H3,(H,21,23)/t11-,13+,15+,16+,17-,19-,20-/m0/s1

InChIKey

NFYYATWFXNPTRM-QJICHLCESA-N

Smiles

CN1C[C@@]2(C=C)[C@@H]3C[C@H]4OC[C@@H]3[C@@H]1[C@@H]2[C@@]45C(=O)Nc6ccccc56

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 49mg/kg (49mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Arzneimittel-Forschung. Drug Research. Vol. 7, Pg. 349, 1957.
rat LDLo unreported 60ug/kg (0.06mg/kg)   "Dispensatory of the United States of America," 24th ed., Osol, A. and G.E. Farrar, Philadelphia, J.B. Lippincott Co., 1947Vol. 24, Pg. 497, 1947.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 178 deg C   EXP
log P (octanol-water) 1.360 (none)   EST
Atmospheric OH Rate Constant 1.36E-10 cm3/molecule-sec 25 EST

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