Epibatidine (CHEM002072)

Record Information
Version1.0
Creation Date2009-07-03 22:19:13 UTC
Update Date2026-05-14 18:45:21 UTC
Accession NumberCHEM002072
Identification
Common NameEpibatidine
ClassSmall Molecule
Description
Epibatidine is a toxin found in certain poisonous frogs (Epipedobates tricolour). It is a powerful analgesic and works by activating nicotinic acetylcholine receptors. (2)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Animal Toxin
  • Frog/Toad Toxin
  • Human Neurotoxin
  • Natural Compound
  • Organic Compound
  • Organochloride
Chemical Structure
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC11H13ClN2
Average Molecular Mass208.687 g/mol
Monoisotopic Mass208.077 g/mol
CAS Registry Number140111-52-0
IUPAC Name2-(6-chloropyridin-3-yl)-7-azabicyclo[2.2.1]heptane
Traditional Nameepibatidine
SMILESClC1=CC=C(C=N1)C1CC2CCC1N2
InChI IdentifierInChI=1S/C11H13ClN2/c12-11-4-1-7(6-13-11)9-5-8-2-3-10(9)14-8/h1,4,6,8-10,14H,2-3,5H2
InChI KeyNLPRAJRHRHZCQQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as epibatidine analogues. Epibatidine analogues are compounds containing an epibatidine moiety, with a structure characterized by a 2-chloropyridine moiety connected to an 7-azabicyclo[2.2.1]Heptane in exo position.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassEpibatidine analogues
Sub ClassNot Available
Direct ParentEpibatidine analogues
Alternative Parents
Substituents
  • Epibatidine-skeleton
  • Pyrrolidinylpyridine
  • 2-halopyridine
  • Aralkylamine
  • Aryl chloride
  • Aryl halide
  • Pyridine
  • Heteroaromatic compound
  • Pyrrolidine
  • Azacycle
  • Secondary aliphatic amine
  • Secondary amine
  • Organoheterocyclic compound
  • Amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP1.98ALOGPS
logP1.84ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)10.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity57.39 m³·mol⁻¹ChemAxon
Polarizability22.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureInjection (sting/bite) (1) ; inhalation (smoking) (3)
Mechanism of ToxicityEpibatidine works by binding and activating nicotinic acetylcholine receptors. (2)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesEpibatidine is a toxin found in certain poisonous frogs (Epipedobates tricolour). (2)
Minimum Risk LevelNot Available
Health EffectsEpibatidine is neurotoxic. It may also cause receptor blocks at neuromuscular junctions, causing respiratory paralysis and death. It is also a powerful analgesic. (2)
SymptomsEpibatidine is neurotoxic. It may also cause receptor blocks at neuromuscular junctions, causing respiratory paralysis and death. It is also a powerful analgesic. (2)
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0242582
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00028244
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkEpibatidine
Chemspider ID1167
ChEBI IDNot Available
PubChem Compound ID1204
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Csaba Sz antay, Zsuzsanna B. Kardos, Istv an Moldvai, Eszter T. Major, Csaba Sz antay, Jr., Attila M andi, G abor Blask o, Gyula Simig, Gy orgyi Lax, S andor Drabant, Tamas Sz all asi, M arton Fekete, G abor Gigler, “Process for the preparation of epibatidine.” U.S. Patent US5545741, issued March, 1994.

MSDSNot Available
General References