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Substance Name: Bicuculline
RN: 485-49-4
UNII: Y37615DVKC
InChIKey: IYGYMKDQCDOMRE-ZWKOTPCHSA-N

Note

  • An isoquinoline alkaloid obtained from Dicentra cucullaria and other plants. It is a competitive antagonist for GABA-A receptors.

Molecular Formula

  • C20-H17-N-O6

Molecular Weight

  • 367.3553
 

Classification Codes

  • Agricultural Chemical
  • Central Nervous System Agents
  • Central Nervous System Stimulants
  • Convulsants
  • Experimental Pesticide
  • GABA Agents
  • GABA Antagonists
  • GABA-A Receptor Antagonists
  • Natural Product
  • Neurotransmitter Agents
  • Unspecified / Unclassified Pesticide
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Names and Synonyms

Name of Substance

  • Bicuculline

MeSH Heading

  • Bicuculline

Synonyms

  • 4-27-00-06900 (Beilstein Handbook Reference)
  • Bicculine
  • Bicucullin
  • Bicuculline
  • BRN 0098786
  • d-Bicuculline
  • EINECS 207-619-7
  • NSC 32192
  • UNII-Y37615DVKC

Systematic Names

  • Bicuculline
  • Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-((5S)-5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (6R)-
  • Furo(3,4-e)-1,3-benzodioxol-8(6H)-one, 6-(5,6,7,8-tetrahydro-6-methyl-1,3-dioxolo(4,5-g)isoquinolin-5-yl)-, (R-(R*,S*))-

Registry Numbers

CAS Registry Number

  • 485-49-4

FDA UNII

  • Y37615DVKC

System Generated Number

  • 0000485494

Structure Descriptors

InChI

1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1

InChIKey

IYGYMKDQCDOMRE-ZWKOTPCHSA-N

Smiles

CN1CCc2cc3c(cc2[C@H]1[C@H]4c5ccc6c(c5C(=O)O4)OCO6)OCO3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 8480ug/kg (8.48mg/kg)   Current Toxicology. Vol. 1, Pg. 199, 1993.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 194 deg C   EXP
pKa Dissociation Constant 4.84 (none)   EXP

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