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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=NC=C(C=C1)[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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.16 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
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
Record UNII
M6K314F1XX
Record Status Validated (UNII)
Record Version