Tebanicline dihydrochloride

Tebanicline dihydrochloride (Ebanicline dihydrochloride) is a nAChR modulator with potent, orally effective analgesic activity. It inhibits the binding of cytisine to α4β2 neuronal nAChRs with a Ki of 37 pM.

Product information

CAS Number: 209326-19-2

Molecular Weight: 271.57

Formula: C9H13Cl3N2O

Synonym:

Ebanicline dihydrochloride

ABT-594 dihydrochloride

Chemical Name: 5-{[(2R)-azetidin-2-yl]methoxy}-2-chloropyridine; bis(chlorohydrogen)

Smiles: Cl.Cl.ClC1=CC=C(C=N1)OC[C@H]1CCN1

InChiKey: HZMFFIXATGBQGR-XCUBXKJBSA-N

InChi: InChI=1S/C9H11ClN2O.2ClH/c10-9-2-1-8(5-12-9)13-6-7-3-4-11-7;;/h1-2,5,7,11H,3-4,6H2;2*1H/t7-;;/m1../s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : ≥ 34 mg/mL (125.20 mM).

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Tebanicline is a novel, potent cholinergic nAChR ligand with analgesic properties that shows preferential selectivity for neuronal nAChRs. It inhibits the binding of cytisine to α4β2 neuronal nAChRs with a Ki of 37 pM. Functionally, tebanicline is an agonist. At the transfected human α4β2 neuronal nAChR in K177 cells, with increased 86Rb+ efflux as a measure of cation efflux, ABT-594 has an EC50 value of 140 nM with an intrinsic activitycompared with (−)-nicotine of 130%; at the nAChR subtype expressed in IMR-32 cells, an EC50 of 340 nM; at the F11 dorsal root ganglion cell line, an EC50 of 1220 nM; and via direct measurement of ion currents, an EC50 value of 56,000 nM at the human α7 homo-oligimeric nAChR produced in oocytes

In Vivo:

Tebanicline is a potent antinociceptive agent with full efficacy in models of acute and persistent pain and that these effects are mediated predominately by an action at central neuronal nAChRs. Tebanicline produces significant antinociceptive effects in mice against both acute noxious thermal stimulation. ABT-594 is orally active, but 10-fold less potent by this route than after i.p. administration. The antinociceptive effect of ABT-594 is prevented, but not reversed, by the noncompetitive neuronal nicotinic acetylcholine receptor antagonist. Tebanicline has antinociceptive effects in rat models of acute thermal, persistent chemical, and neuropathic pain. Direct injection of tebanicline into the nucleus raphe magnus (NRM) is antinociceptive in a thermal threshold test and destruction of serotonergic neurons in the NRM attenuates the effect of systemic tebanicline.

References:

1. Donnelly-Roberts DL, et al. ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine]: a novel, orally effective analgesic acting via neuronal nicotinic acetylcholine receptors: I. In vitro characterization.J Pharmacol Exp Ther. 1998 May;285(2):777-86.
2. Bannon AW, et al. ABT-594 [(R)-5-(2-azetidinylmethoxy)-2-chloropyridine]: a novel, orally effective antinociceptive agent acting via neuronal nicotinic acetylcholine receptors: II. In vivo characterization. J Pharmacol Exp Ther. 1998 May;285(2):787-94.
3. Decker MW, et al. Antinociceptive effects of the novel neuronal nicotinic acetylcholine receptor agonist, ABT-594, in mice. Eur J Pharmacol. 1998 Apr 3;346(1):23-33.

Products are for research use only. Not for human use.