 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C9H13CL3N2O |
| Molecular Weight | 271.57131934166 |
| Exact Mass | 270.009 |
| CAS # | 209326-19-2 |
| Related CAS # | Tebanicline hydrochloride;203564-54-9 |
| PubChem CID | 146673022 |
| Appearance | White to off-white solid powder |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 15 |
| Complexity | 168 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | ClC1=CC=C(C=N1)OC[C@H]1CCN1.Cl.Cl |
| InChi Key | HZMFFIXATGBQGR-XCUBXKJBSA-N |
| InChi Code | 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 |
| Chemical Name | 5-[[(2R)-azetidin-2-yl]methoxy]-2-chloropyridine;dihydrochloride |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Ki: 37 pM (nAChR)[1] |
| ln Vitro | Tebanicline is a new and powerful cholinergic nAChR ligand that exhibits preferential selectivity for neuronal nAChRs and analgesic effects. With a Ki of 37 pM, it prevents cytisine from binding to α4β2 neuronal nAChRs. Tebanicline functions as an agonist. ABT-594 has an EC50 value of 140 nM at the transfected human α4β2 neuronal nAChR in K177 cells, with increased 86Rb+ efflux as a measure of cation efflux, and an intrinsic activity compared with (−)-nicotine of 130%; an EC50 value of 340 nM at the nAChR subtype expressed in IMR-32 cells; an EC50 value of 1220 nM at the F11 dorsal root ganglion cell line; and an EC50 value of 56,000 nM measured directly by ion currents at the human α7 homo-oligimeric nAChR produced in oocytes[1]. |
| ln Vivo | Tebanicline is a strong antinociceptive drug that works well in models of both acute and chronic pain. Its effects are mostly mediated by activation of central neuronal nAChRs[2]. In mice, tebanicline has strong antinociceptive effects against both acutely painful heat stimulation. Orally administered ABT-594 is active, however it is ten times less effective than it is after intraperitoneal injection. The noncompetitive neuronal nicotinic acetylcholine receptor antagonist ABT-594 blocks the antinociceptive effect but does not reverse it[3]. In rat models of acute thermal pain, persistent chemical pain, and neuropathic pain, temanicol exerts antinociceptive effects. In a heat threshold test, direct tebanicline injection into the nucleus raphe magnus (NRM) is antinociceptive, and the impact of systemic tebanicline is attenuated by the loss of serotonergic neurons in the NRM[4]. |
| References |
[1]. 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]. 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]. Antinociceptive effects of the novel neuronal nicotinic acetylcholine receptor agonist, ABT-594, in mice. Eur J Pharmacol. 1998 Apr 3;346(1):23-33. [4]. The role of neuronal nicotinic acetylcholine receptors in antinociception: effects of ABT-594. J Physiol Paris. 1998 Jun-Aug;92(3-4):221-4. |
Solubility Data
| Solubility (In Vitro) |
H2O: 100 mg/mL (368.23 mM) DMSO: ≥ 34 mg/mL (125.20 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (7.66 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (7.66 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (7.66 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 25 mg/mL (92.06 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6823 mL | 18.4115 mL | 36.8229 mL | |
| 5 mM | 0.7365 mL | 3.6823 mL | 7.3646 mL | |
| 10 mM | 0.3682 mL | 1.8411 mL | 3.6823 mL |