You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Toxin, Toxin Target Database.
Record Information
Version2.0
Creation Date2009-07-03 22:19:13 UTC
Update Date2014-12-24 20:25:40 UTC
Accession NumberT3D2530
Identification
Common NameEpibatidine
ClassSmall Molecule
DescriptionEpibatidine is a toxin found in certain poisonous frogs (Epipedobates tricolour). It is a powerful analgesic and works by activating nicotinic acetylcholine receptors. (2)
Compound Type
  • Amine
  • Animal Toxin
  • Frog/Toad Toxin
  • Natural Compound
  • Organic Compound
  • Organochloride
Chemical Structure
Thumb
Synonyms
Synonym
(+/-)-epibatidine
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 KeyInChIKey=NLPRAJRHRHZCQQ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as epibatidine analogues. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassAlkaloids and derivatives
Sub ClassEpibatidine analogues
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
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.467 mg/mLALOGPS
logP1.98ALOGPS
logP1.84ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)10.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.92 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity57.39 m3·mol-1ChemAxon
Polarizability22.06 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-046959b515e82db7e6fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3390000000-8f766845caae11ffc884View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsi-8900000000-8bd101dee7036183998dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-8d4deb0cede3f9c09d4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0590000000-9918548508966d5ecabfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-2900000000-26082d9becf367cbadfdView in MoNA
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB07720
HMDB IDNot Available
PubChem Compound ID1204
ChEMBL IDCHEMBL6623
ChemSpider ID1167
KEGG IDC11690
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC082748
Stitch IDEpibatidine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot 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
  1. Chiba K, Trevor A, Castagnoli N Jr: Metabolism of the neurotoxic tertiary amine, MPTP, by brain monoamine oxidase. Biochem Biophys Res Commun. 1984 Apr 30;120(2):574-8. [6428396 ]
  2. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
  3. Wikipedia. Frog. Last Updated 10 August 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Toxic substance binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is blocked by alpha-bungarotoxin.
Gene Name:
CHRNA7
Uniprot ID:
P36544
Molecular Weight:
56448.925 Da
References
  1. Niessen KV, Tattersall JE, Timperley CM, Bird M, Green C, Seeger T, Thiermann H, Worek F: Interaction of bispyridinium compounds with the orthosteric binding site of human alpha7 and Torpedo californica nicotinic acetylcholine receptors (nAChRs). Toxicol Lett. 2011 Sep 25;206(1):100-4. doi: 10.1016/j.toxlet.2011.06.009. Epub 2011 Jun 16. [21703337 ]
  2. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA1
Uniprot ID:
P02708
Molecular Weight:
54545.235 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB1
Uniprot ID:
P11230
Molecular Weight:
56697.9 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Acetylcholine-activated cation-selective channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRND
Uniprot ID:
Q07001
Molecular Weight:
58894.55 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Cation transmembrane transporter activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNE
Uniprot ID:
Q04844
Molecular Weight:
54696.54 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNG
Uniprot ID:
P07510
Molecular Weight:
57882.8 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Extracellular ligand-gated ion channel activity
Specific Function:
Not Available
Gene Name:
CHRFAM7A
Uniprot ID:
Q494W8
Molecular Weight:
46217.335 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
General Function:
Receptor binding
Specific Function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane. In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma.
Gene Name:
CHRNA10
Uniprot ID:
Q9GZZ6
Molecular Weight:
49704.295 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular Weight:
59764.82 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA3
Uniprot ID:
P32297
Molecular Weight:
57479.54 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodium ions.
Gene Name:
CHRNA4
Uniprot ID:
P43681
Molecular Weight:
69956.47 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA5
Uniprot ID:
P30532
Molecular Weight:
53053.965 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Acetylcholine-activated cation-selective channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNA6
Uniprot ID:
Q15825
Molecular Weight:
56897.745 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Calcium channel activity
Specific Function:
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasma membrane (PubMed:11752216, PubMed:25282151). The channel is permeable to a range of divalent cations including calcium, the influx of which may activate a potassium current which hyperpolarizes the cell membrane (PubMed:11752216, PubMed:25282151). In the ear, this may lead to a reduction in basilar membrane motion, altering the activity of auditory nerve fibers and reducing the range of dynamic hearing. This may protect against acoustic trauma. May also regulate keratinocyte adhesion (PubMed:11021840).
Gene Name:
CHRNA9
Uniprot ID:
Q9UGM1
Molecular Weight:
54806.63 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeable to sodiun ions.
Gene Name:
CHRNB2
Uniprot ID:
P17787
Molecular Weight:
57018.575 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Drug binding
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB3
Uniprot ID:
Q05901
Molecular Weight:
52728.215 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]
General Function:
Ligand-gated ion channel activity
Specific Function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name:
CHRNB4
Uniprot ID:
P30926
Molecular Weight:
56378.985 Da
References
  1. Wikipedia. Epibatidine. Last Updated 31 May 2009. [Link]