An agonist of α4β2 subunit-containing nAChRs
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(±)-Epibatidine (hydrochloride)

Item No. 31193

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R,2R,4S)-rel-2-(6-chloro-3-pyridinyl)-7-azabicyclo[2.2.1]heptane, dihydrochloride
CAS Number
162885-01-0
Molecular Formula
C11H13ClN2 • 2HCl
Formula Weight
281.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
λmax
215, 270 nm
SMILES
ClC(C=C1)=NC=C1[C@@H]2C[C@H]3CC[C@@H]2N3.Cl.Cl
InChi Code
InChI=1S/C11H13ClN2.2ClH/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;2*1H/t8-,9+,10+;;/m1../s1
InChi Key
DGNNWUINALNROG-YDMPKLSESA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $90

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    5 mg

    $328

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    Product Description

    (±)-Epibatidine is an alkaloid that has been found in Ecuadoran poison frog (E. tricolor) skin extracts and an agonist of α4β2 subunit-containing nicotinic acetylcholine receptors (nAChRs; Ki = 43 pM).1,2 It is selective for α4β2 subunit-containing nAChRs over α7 nAChRs (Ki = 230 nM).1 (±)-Epibatidine enhances 86Rb+ flux in IMR-32 cells (EC50 = 7 nM) and induces dopamine release from rat striatal slices (EC50 = 0.4 nM), effects that can be reduced by the nAChR antagonist mecamylamine (Item No. 14602). In vivo, (±)-epibatidine induces analgesia in the hot plate test and the Straub-tail response in mice (ED50s = 0.005 and 0.02 mg/kg, respectively).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sullivan, J.P., Decker, M.W., Brioni, J.D., et al. (+/-)-Epibatidine elicits a diversity of in vitro and in vivo effects mediated by nicotinic acetylcholine receptors. J. Pharmacol. Exp. Ther. 271(2), 624-631 (1994).

    2. Spande, T.F., Garraffo, H.M., Edwards, M.W., et al. Epibatidine: A novel (chloropyridyl)azabicycloheptane with potent analgesic activity from an Ecuadoran poison frog. J. Am. Chem. Soc. 114(9), 3475-3478 (1992).