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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H13ClN2
Molecular Weight 208.687
Optical Activity ( + )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPIBATIDINE

SMILES

ClC1=CC=C(C=N1)[C@H]2C[C@@H]3CC[C@H]2N3

InChI

InChIKey=NLPRAJRHRHZCQQ-IVZWLZJFSA-N
InChI=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/t8-,9+,10+/m0/s1

HIDE SMILES / InChI

Molecular Formula C11H13ClN2
Molecular Weight 208.687
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Epibatidine is a piperidine alkaloid that is secreted by the Ecuadoran frog Epipedobates anthonyi. Many laboratories began to synthesize epibatidine and after studying it, scientists realized it was too toxic to be used as a pain-relieving drug. Epibatine is the exo-isomer of the two possible geometric isomers and can exist as two enantiomers (+) – or R- Epibatidine and (-) or S- Epibatidine. The natural compound is the (+) isomer, although there is a little difference in pharmacological activity between (+) and (-) isomers. Epibatidine binds to nicotinic acetylcholine receptors (nAChR) rather than opiate receptors, which is common of most analgesics such as morphine. Epibatidine and both its isomers are extremely potent full agonists for neuronal acetylcholine receptors: alpha4/beta2 and alpha3/beta2. Epibatidine binds not only to nAChR in the brain but also at other neuro-muscular junctions throughout the body. This is not desired as it caused seizures and respiratory and digestive problems. Currently only rudimentary research into epibatidine's effects has been performed.

CNS Activity

Curator's Comment: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Epibatidine, a potent analgetic and nicotinic agonist.
1994 Apr
Comparative pharmacology of epibatidine: a potent agonist for neuronal nicotinic acetylcholine receptors.
1995 Oct
Differential agonist inhibition identifies multiple epibatidine binding sites in mouse brain.
1998 Apr
Epibatidine and pain.
1998 Jul
Patents

Patents

Sample Use Guides

in rats: epibatidine (5 nmol/animal, i.c.v.)-induced elevation of catecholamines; epibatidine (2.5 microg/kg, s.c.) decreased the extracellular concentrations of DA in the brain of naive rats
Route of Administration: Other
It was demonstrated that (+/-)-[3H]epibatidine (1-500 pM) binds to a single population of sites in rat brain with KD of 8 +/- 2 pM. This affinity was confirmed in both kinetic experiments and competition assays with (+/-)-[3H]epibatidine and (-)-[3H]cytisine, which was performed under experimental conditions developed specifically for ligands with subnanomolar affinities.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:18:28 GMT 2023
Edited
by admin
on Sat Dec 16 08:18:28 GMT 2023
Record UNII
M6K314F1XX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPIBATIDINE
MI  
Common Name English
2-(6-CHLOROPYRIDIN-3-YL)-7-AZABICYCLO(2.2.1)HEPTANE
Systematic Name English
7-AZABICYCLO(2.2.1)HEPTANE, 2-(6-CHLORO-3-PYRIDINYL)-, (1R,2R,4S)-
Systematic Name English
CMI-488
Code English
(1R-EXO)-2-(6-CHLORO-3-PYRIDINYL)-7-AZABICYCLO(2.2.1)HEPTANE
Common Name English
(1R,2R,4S)-EPIBATIDINE
Common Name English
ALKALOID 208/210 FROM DENDROBATES
Common Name English
(+)-EPIBATIDINE
Common Name English
EPIBATIDINE [MI]
Common Name English
7-AZABICYCLO(2.2.1)HEPTANE, 2-(6-CHLORO-3-PYRIDINYL)-, (1R-EXO)-
Systematic Name English
Code System Code Type Description
PUBCHEM
854023
Created by admin on Sat Dec 16 08:18:28 GMT 2023 , Edited by admin on Sat Dec 16 08:18:28 GMT 2023
PRIMARY
CAS
140111-52-0
Created by admin on Sat Dec 16 08:18:28 GMT 2023 , Edited by admin on Sat Dec 16 08:18:28 GMT 2023
PRIMARY
MERCK INDEX
m4935
Created by admin on Sat Dec 16 08:18:28 GMT 2023 , Edited by admin on Sat Dec 16 08:18:28 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID00894067
Created by admin on Sat Dec 16 08:18:28 GMT 2023 , Edited by admin on Sat Dec 16 08:18:28 GMT 2023
PRIMARY
DRUG BANK
DB07720
Created by admin on Sat Dec 16 08:18:28 GMT 2023 , Edited by admin on Sat Dec 16 08:18:28 GMT 2023
PRIMARY
FDA UNII
M6K314F1XX
Created by admin on Sat Dec 16 08:18:28 GMT 2023 , Edited by admin on Sat Dec 16 08:18:28 GMT 2023
PRIMARY
WIKIPEDIA
Epibatidine
Created by admin on Sat Dec 16 08:18:28 GMT 2023 , Edited by admin on Sat Dec 16 08:18:28 GMT 2023
PRIMARY
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