Tebanicline HCl
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MedKoo CAT#: 526423

CAS#: 203564-54-9 (HCl)

Description: Tebanicline, also known as ABT-594 and Ebanicline, a potent synthetic nicotinic (non-opioid) analgesic drug developed by Abbott. It was developed as a less toxic analogue of the potent poison dart frog-derived compound epibatidine, which is some 200x stronger than morphine as an analgesic but produces extremely dangerous toxic side effects. Like epibatidine, tebanicline showed potent analgesic activity against neuropathic pain in both animal and human trials, but with far less toxicity than its parent compound. It acts as a partial agonist at neuronal nicotinic acetylcholine receptors, binding to both the α3β4 and the α4β2 subtypes.

Chemical Structure

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Tebanicline HCl
CAS# 203564-54-9 (HCl)
Instruction

Theoretical Analysis

MedKoo Cat#: 526423
Name: Tebanicline HCl
CAS#: 203564-54-9 (HCl)
Chemical Formula: C9H12Cl2N2O
Exact Mass: 198.06
Molecular Weight: 235.108
Elemental Analysis: C, 45.98; H, 5.14; Cl, 30.16; N, 11.92; O, 6.80

Price and Availability

Size Price Availability Quantity
25mg USD 350 2 Weeks
50mg USD 550 2 Weeks
100mg USD 950 2 Weeks
200mg USD 1650 2 Weeks
500mg USD 2950 2 Weeks
1g USD 4450 2 Weeks
2g USD 6750 2 Weeks
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Related CAS #: 203564-54-9 (HCl)   209326-19-2 (2HCl)   198283-73-7 (free base)   198283-74-8 (tosylate)   209326-18-1 (benzoate)    

Synonym: Tebanicline HCl; Tebanicline hydrochloride; Tebanicline; ABT-594; ABT 594; ABT594; Ebanicline.

IUPAC/Chemical Name: 5-[[(2R)-azetidin-2-yl]methoxy]-2-chloropyridine hydrochloride

InChi Key: GYVARJONEFSAJB-OGFXRTJISA-N

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

SMILES Code: ClC1=NC=C(OC[C@@H]2NCC2)C=C1.[H]Cl

Appearance: Solid powder

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 235.11 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Ren J, Ding X, Greer JJ. Countering Opioid-induced Respiratory Depression in Male Rats with Nicotinic Acetylcholine Receptor Partial Agonists Varenicline and ABT 594. Anesthesiology. 2020 May;132(5):1197-1211. doi: 10.1097/ALN.0000000000003128. PMID: 32294065.


2: Passlick S, Thapaliya ER, Chen Z, Richers MT, Ellis-Davies GCR. Optical probing of acetylcholine receptors on neurons in the medial habenula with a novel caged nicotine drug analogue. J Physiol. 2018 Nov;596(22):5307-5318. doi: 10.1113/JP276615. Epub 2018 Oct 25. PMID: 30222192; PMCID: PMC6235938.


3: Ding Z, Brown JW, Rueter LE, Mohler EG. Profiling attention and cognition enhancing drugs in a rat touchscreen-based continuous performance test. Psychopharmacology (Berl). 2018 Apr;235(4):1093-1105. doi: 10.1007/s00213-017-4827-y. Epub 2018 Jan 13. PMID: 29332255.


4: Hayashi T, Katsuyama S, Orito T, Suzuki T, Sakurada S. Antinociceptive effect of tebanicline for various noxious stimuli-induced behaviours in mice. Neurosci Lett. 2017 Jan 18;638:46-50. doi: 10.1016/j.neulet.2016.12.013. Epub 2016 Dec 7. PMID: 27939354.


5: Uteshev VV. The therapeutic promise of positive allosteric modulation of nicotinic receptors. Eur J Pharmacol. 2014 Mar 15;727:181-5. doi: 10.1016/j.ejphar.2014.01.072. Epub 2014 Feb 12. PMID: 24530419; PMCID: PMC3982318.


6: Mohler EG, Franklin SR, Rueter LE. Discriminative-stimulus effects of NS9283, a nicotinic α4β2* positive allosteric modulator, in nicotine-discriminating rats. Psychopharmacology (Berl). 2014 Jan;231(1):67-74. doi: 10.1007/s00213-013-3207-5. Epub 2013 Aug 8. PMID: 23925734.


7: Dutta S, Hosmane BS, Awni WM. Population analyses of efficacy and safety of ABT-594 in subjects with diabetic peripheral neuropathic pain. AAPS J. 2012 Jun;14(2):168-75. doi: 10.1208/s12248-012-9328-7. Epub 2012 Feb 11. PMID: 22328206; PMCID: PMC3326158.


8: Dutta S, Awni W. Population pharmacokinetics of ABT-594 in subjects with diabetic peripheral neuropathic pain. J Clin Pharm Ther. 2012 Aug;37(4):475-80. doi: 10.1111/j.1365-2710.2011.01325.x. Epub 2011 Dec 7. PMID: 22145610.


9: Lee CH, Zhu C, Malysz J, Campbell T, Shaughnessy T, Honore P, Polakowski J, Gopalakrishnan M. α4β2 neuronal nicotinic receptor positive allosteric modulation: an approach for improving the therapeutic index of α4β2 nAChR agonists in pain. Biochem Pharmacol. 2011 Oct 15;82(8):959-66. doi: 10.1016/j.bcp.2011.06.044. Epub 2011 Jul 7. PMID: 21763685.


10: Nirogi R, Jabaris SL, Jayarajan P, Abraham R, Shanmuganathan D, Rasheed MA, Royapalley PK, Goura V. Antinociceptive activity of α4β2* neuronal nicotinic receptor agonist A-366833 in experimental models of neuropathic and inflammatory pain. Eur J Pharmacol. 2011 Oct 1;668(1-2):155-62. doi: 10.1016/j.ejphar.2011.06.032. Epub 2011 Jul 3. Erratum in: Eur J Pharmacol. 2011 Dec 30;673(1-3):101. Jabaris, Sugin Lal [added]. PMID: 21756895.


11: Zhu CZ, Chin CL, Rustay NR, Zhong C, Mikusa J, Chandran P, Salyers A, Gomez E, Simler G, Lewis LG, Gauvin D, Baker S, Pai M, Tovcimak A, Brown J, Komater V, Fox GB, Decker MW, Jacobson PB, Gopalakrishnan M, Lee CH, Honore P. Potentiation of analgesic efficacy but not side effects: co-administration of an α4β2 neuronal nicotinic acetylcholine receptor agonist and its positive allosteric modulator in experimental models of pain in rats. Biochem Pharmacol. 2011 Oct 15;82(8):967-76. doi: 10.1016/j.bcp.2011.05.007. Epub 2011 May 17. PMID: 21620806.


12: Munro G, Dyhr H, Grunnet M. Selective potentiation of gabapentin-mediated antinociception in the rat formalin test by the nicotinic acetylcholine receptor agonist ABT-594. Neuropharmacology. 2010 Sep;59(3):208-17. doi: 10.1016/j.neuropharm.2010.05.010. Epub 2010 Jun 1. PMID: 20562022.


13: Mohler EG, Franklin SR, Rueter LE, Fox GB, Decker MW, Browman KE. ABT-594 improves performance in the 5-choice serial reaction time task under conditions of increased difficulty, sub-chronic dosing, and in poorly-performing subjects. Pharmacol Biochem Behav. 2010 Apr;95(2):146-57. doi: 10.1016/j.pbb.2009.12.019. Epub 2010 Jan 11. PMID: 20064548.


14: Sindrup SH. Nicotinic acetylcholine receptor agonism: progress in the management of neuropathic pain? Pain. 2009 Dec;146(3):227-228. doi: 10.1016/j.pain.2009.09.015. Epub 2009 Oct 8. PMID: 19818558.


15: Rowbotham MC, Duan RW, Thomas J, Nothaft W, Backonja MM. A randomized, double-blind, placebo-controlled trial evaluating the efficacy and safety of ABT-594 in patients with diabetic peripheral neuropathic pain. Pain. 2009 Dec;146(3):245-252. doi: 10.1016/j.pain.2009.06.013. Epub 2009 Jul 24. PMID: 19632048.


16: Sippy KB, Anderson DJ, Bunnelle WH, Hutchins CW, Schrimpf MR. Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors. Bioorg Med Chem Lett. 2009 Mar 15;19(6):1682-5. doi: 10.1016/j.bmcl.2009.01.099. Epub 2009 Feb 4. PMID: 19232492.


17: Joshi SK, Mikusa JP, Weaver B, Honore P. Morphine and ABT-594 (a nicotinic acetylcholine agonist) exert centrally mediated antinociception in the rat cyclophosphamide cystitis model of visceral pain. J Pain. 2008 Feb;9(2):146-56. doi: 10.1016/j.jpain.2007.09.004. Epub 2007 Dec 21. PMID: 18088559.


18: Chin CL, Pauly JR, Surber BW, Skoubis PD, McGaraughty S, Hradil VP, Luo Y, Cox BF, Fox GB. Pharmacological MRI in awake rats predicts selective binding of alpha4beta2 nicotinic receptors. Synapse. 2008 Mar;62(3):159-68. doi: 10.1002/syn.20474. PMID: 18081183.


19: Buccafusco JJ, Terry AV Jr, Decker MW, Gopalakrishnan M. Profile of nicotinic acetylcholine receptor agonists ABT-594 and A-582941, with differential subtype selectivity, on delayed matching accuracy by young monkeys. Biochem Pharmacol. 2007 Oct 15;74(8):1202-11. doi: 10.1016/j.bcp.2007.07.010. Epub 2007 Jul 14. PMID: 17706609.


20: Smith JW, Mogg A, Tafi E, Peacey E, Pullar IA, Szekeres P, Tricklebank M. Ligands selective for alpha4beta2 but not alpha3beta4 or alpha7 nicotinic receptors generalise to the nicotine discriminative stimulus in the rat. Psychopharmacology (Berl). 2007 Feb;190(2):157-70. doi: 10.1007/s00213-006-0596-8. Epub 2006 Nov 18. PMID: 17115136.