ABT-594 - CAS 198283-73-7
Catalog number:
198283-73-7
Category:
Inhibitor
Not Intended for Therapeutic Use. For research use only.
Molecular Formula:
C9H11ClN2O
Molecular Weight:
198.65
COA:
Inquire
Targets:
nAChR
Description:
ABT-594, also called as Tebanicline, the (R)-enantiomer of A-98593, is a potent synthetic non-opioid nicotinic analgesic drug. ABT-594 is a novel nAChR ligan which is shown to exert potent analgesic action in models of nociceptive and persistent pain and to possess substantially reduced activity at peripheral nAChRs.
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Brife Description:
An analgesic agent
Appearance:
Solid powder
Synonyms:
5-[[(2R)-azetidin-2-yl]methoxy]-2-chloropyridine; Tebanicline; ABT-594; ABT 594; ABT594; Ebanicline
Solubility:
Soluble in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -42℃ for long term (months to years).
MSDS:
Inquire
Shelf Life:
2 years
Boiling Point:
321.1±22.0 °C | Condition: Press: 760 Torr
Melting Point:
116-117 °C
Density:
1.228±0.06 g/cm3
InChIKey:
MKTAGSRKQIGEBH-SSDOTTSWSA-N
InChI:
1S/C9H11ClN2O/c10-9-2-1-8(5-12-9)13-6-7-3-4-11-7/h1-2,5,7,11H,3-4,6H2/t7-/m1/s1
Canonical SMILES:
C1CNC1COC2=CN=C(C=C2)Cl
1.Antinociceptive activity of α4β2* neuronal nicotinic receptor agonist A-366833 in experimental models of neuropathic and inflammatory pain.
Nirogi R1, Jabaris SL, Jayarajan P, Abraham R, Shanmuganathan D, Rasheed MA, Royapalley PK, Goura V. Eur J Pharmacol. 2011 Oct 1;668(1-2):155-62. doi: 10.1016/j.ejphar.2011.06.032. Epub 2011 Jul 3.
Nerve injury, diabetes and cancer therapies are often associated with painful neuropathy. The mechanism underlying neuropathic pain remains poorly understood. The current therapies have limited efficacy and are associated with dose-limiting side effects. Compounds which act at nicotinic acetylcholine receptors have also been reported to show antinociceptive activity. Among those, tebanicline (ABT-594) a potent nicotinic acetylcholine receptor agonist demonstrated analgesic effects across a broad range of preclinical models of nociceptive and neuropathic pain. Another nicotinic acetylcholine receptor agonist, 5-[(1R,5S)-3,6-Diazabicyclo[3.2.0]heptan-6-yl]nicotinonitrile (A-366833) from the same group produced significant antinociceptive effects in writhing pain (abdominal constriction), acute thermal pain (hot box), persistent chemical pain (formalin induced) and neuropathic pain. In the present study, we have demonstrated the efficacy of A-366833 in rat models of chronic constriction injury, partial sciatic nerve ligation, spinal nerve ligation, diabetes, chemotherapy induced neuropathic pain and complete Freund's adjuvant induced inflammatory pain.
2.Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors.
Sippy KB1, Anderson DJ, Bunnelle WH, Hutchins CW, Schrimpf MR. Bioorg Med Chem Lett. 2009 Mar 15;19(6):1682-5. doi: 10.1016/j.bmcl.2009.01.099. Epub 2009 Feb 4.
Several N-pyridin-3-yl spirobicyclic diamines, designed as conformationally restricted analogs of tebanicline (ABT-594), were synthesized as novel ligands for nicotinic acetylcholine receptors (nAChR). The spirocyclic compounds exhibited weaker binding affinity, than other constrained analogs in accord with a pharmacophore model. Nevertheless, some (1a, 1b) possessed (partial) agonist potencies comparable to nicotine at the alpha4beta2 subtype, but with greatly improved selectivity relative to the alpha3beta4* nAChR.
3.3-(2,5-Dihydro-1H-pyrrol-2-ylmethoxy)pyridines: synthesis and analgesic activity.
Baraznenok IL1, Jonsson E, Claesson A. Bioorg Med Chem Lett. 2005 Mar 15;15(6):1637-40.
We disclose an efficient procedure for the preparation of ethers of 2-substituted 2-hydroxymethylpyrroline and of 2-aminomethyl-3-pyrrolines, involving, as a key step, formation and nucleophilic ring opening of a cyclic sulfamidate. Several new analogs of epibatidine (1) and tebanicline (ABT-594, 2) were prepared and tested for analgesic activity in the mouse formalin model.
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CAS 198283-73-7 ABT-594

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