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
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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12689850
Curator's Comment: Known to be CNS penetrant in rat. Human data not available
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9771274 |
|||
Target ID: CHEMBL2109234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7476906 |
0.16 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10501548
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.
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854023
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140111-52-0
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m4935
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DTXSID00894067
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DB07720
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M6K314F1XX
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Epibatidine
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)