ABT-418

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 529906

CAS#: 147402-53-7

Description: ABT-418 is a nicotinic acetylcholine receptor (nAchR) agonist potentially for the treatment of attention deficit disorder.


Price and Availability

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ABT-418 is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 529906
Name: ABT-418
CAS#: 147402-53-7
Chemical Formula: C9H14N2O
Exact Mass: 166.11
Molecular Weight: 166.22
Elemental Analysis: C, 65.03; H, 8.49; N, 16.85; O, 9.62


Synonym: A-81418; ABT-418; A81418; ABT418; A 81418; ABT 418;

IUPAC/Chemical Name: Isoxazole, 3-methyl-5-((2S)-1-methyl-2-pyrrolidinyl)-

InChi Key: ILLGYRJAYAAAEW-QMMMGPOBSA-N

InChi Code: InChI=1S/C9H14N2O/c1-7-6-9(12-10-7)8-4-3-5-11(8)2/h6,8H,3-5H2,1-2H3/t8-/m0/s1

SMILES Code: CN1[C@H](C2=CC(C)=NO2)CCC1


Technical Data

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).

Harmonized System Code:
293490


References

1: Guo T, Yang C, Guo L, Liu K. A comparative study of the effects of ABT-418 and methylphenidate on spatial memory in an animal model of ADHD. Neurosci Lett. 2012 Oct 18;528(1):11-5. doi: 10.1016/j.neulet.2012.08.068. PubMed PMID: 22985505.

2: Dallanoce C, Magrone P, Matera C, Lo Presti L, De Amici M, Riganti L, Clementi F, Gotti C, De Micheli C. Synthesis of novel chiral Δ2-isoxazoline derivatives related to ABT-418 and estimation of their affinity at neuronal nicotinic acetylcholine receptor subtypes. Eur J Med Chem. 2010 Dec;45(12):5594-601. doi: 10.1016/j.ejmech.2010.09.009. PubMed PMID: 20932609.

3: Kenney JW, Wilkinson DS, Gould TJ. The enhancement of contextual fear conditioning by ABT-418. Behav Pharmacol. 2010 May;21(3):246-9. doi: 10.1097/FBP.0b013e32833a5b9d. PubMed PMID: 20400893; PubMed Central PMCID: PMC3042125.

4: Reichel CM, Murray JE, Barr JD, Bevins RA. Extinction with varenicline and nornicotine, but not ABT-418, weakens conditioned responding evoked by the interoceptive stimulus effects of nicotine. Neuropharmacology. 2010 Jun;58(8):1237-45. doi: 10.1016/j.neuropharm.2010.03.005. PubMed PMID: 20302882; PubMed Central PMCID: PMC2881947.

5: Takechi K, Suemaru K, Kiyoi T, Tanaka A, Araki H. The α4β2 nicotinic acetylcholine receptor modulates autism-like behavioral and motor abnormalities in pentylenetetrazol-kindled mice. Eur J Pharmacol. 2016 Mar 15;775:57-66. doi: 10.1016/j.ejphar.2016.02.021. PubMed PMID: 26868186.

6: Sihver W, Fasth KJ, Ogren M, Bivehed H, Bergström M, Nordberg A, Watanabe Y, Långström B. In vitro evaluation of 11C-labeled (S)-nicotine, (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole, and (R,S)-1-methyl-2-(3-pyridyl)azetidine as nicotinic receptor ligands for positron emission tomography studies. J Neurochem. 1998 Oct;71(4):1750-60. PubMed PMID: 9751211.

7: Decker MW, Brioni JD, Sullivan JP, Buckley MJ, Radek RJ, Raszkiewicz JL, Kang CH, Kim DJ, Giardina WJ, Wasicak JT, et al. (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl)isoxazole (ABT 418): a novel cholinergic ligand with cognition-enhancing and anxiolytic activities: II. In vivo characterization. J Pharmacol Exp Ther. 1994 Jul;270(1):319-28. PubMed PMID: 7913497.

8: Young JW, Meves JM, Geyer MA. Nicotinic agonist-induced improvement of vigilance in mice in the 5-choice continuous performance test. Behav Brain Res. 2013 Mar 1;240:119-33. doi: 10.1016/j.bbr.2012.11.028. PubMed PMID: 23201359; PubMed Central PMCID: PMC3538919.

9: Arneric SP, Sullivan JP, Briggs CA, Donnelly-Roberts D, Anderson DJ, Raszkiewicz JL, Hughes ML, Cadman ED, Adams P, Garvey DS, et al. (S)-3-methyl-5-(1-methyl-2-pyrrolidinyl) isoxazole (ABT 418): a novel cholinergic ligand with cognition-enhancing and anxiolytic activities: I. In vitro characterization. J Pharmacol Exp Ther. 1994 Jul;270(1):310-8. PubMed PMID: 7518514.

10: Wilens TE, Biederman J, Spencer TJ, Bostic J, Prince J, Monuteaux MC, Soriano J, Fine C, Abrams A, Rater M, Polisner D. A pilot controlled clinical trial of ABT-418, a cholinergic agonist, in the treatment of adults with attention deficit hyperactivity disorder. Am J Psychiatry. 1999 Dec;156(12):1931-7. PubMed PMID: 10588407.

11: Sihver W, Fasth KJ, Ogren M, Lundqvist H, Bergström M, Watanabe Y, Långström B, Nordberg A. In vivo positron emission tomography studies on the novel nicotinic receptor agonist [11C]MPA compared with [11C]ABT-418 and (S)(-)[11C]nicotine in rhesus monkeys. Nucl Med Biol. 1999 Aug;26(6):633-40. PubMed PMID: 10587101.

12: Valette H, Bottlaender M, Dollé F, Dolci L, Syrota A, Crouzel C. An attempt to visualize baboon brain nicotinic receptors with N-[11C]ABT-418 and N-[11C]methyl-cytisine. Nucl Med Commun. 1997 Feb;18(2):164-8. PubMed PMID: 9076773.

13: McGaughy J, Decker MW, Sarter M. Enhancement of sustained attention performance by the nicotinic acetylcholine receptor agonist ABT-418 in intact but not basal forebrain-lesioned rats. Psychopharmacology (Berl). 1999 May;144(2):175-82. PubMed PMID: 10394999.

14: Prendergast MA, Jackson WJ, Terry AV Jr, Decker MW, Arneric SP, Buccafusco JJ. Central nicotinic receptor agonists ABT-418, ABT-089, and (-)-nicotine reduce distractibility in adult monkeys. Psychopharmacology (Berl). 1998 Mar;136(1):50-8. PubMed PMID: 9537682.

15: Potter A, Corwin J, Lang J, Piasecki M, Lenox R, Newhouse PA. Acute effects of the selective cholinergic channel activator (nicotinic agonist) ABT-418 in Alzheimer's disease. Psychopharmacology (Berl). 1999 Mar;142(4):334-42. PubMed PMID: 10229057.

16: Anderson DJ, Williams M, Pauly JR, Raszkiewicz JL, Campbell JE, Rotert G, Surber B, Thomas SB, Wasicak J, Arneric SP, et al. Characterization of [3H]ABT-418: a novel cholinergic channel ligand. J Pharmacol Exp Ther. 1995 Jun;273(3):1434-41. PubMed PMID: 7791118.

17: Prendergast MA, Terry AV Jr, Jackson WJ, Marsh KC, Decker MW, Arneric SP, Buccafusco JJ. Improvement in accuracy of delayed recall in aged and non-aged, mature monkeys after intramuscular or transdermal administration of the CNS nicotinic receptor agonist ABT-418. Psychopharmacology (Berl). 1997 Apr;130(3):276-84. PubMed PMID: 9151363.

18: Papke RL, Thinschmidt JS, Moulton BA, Meyer EM, Poirier A. Activation and inhibition of rat neuronal nicotinic receptors by ABT-418. Br J Pharmacol. 1997 Feb;120(3):429-38. PubMed PMID: 9031746; PubMed Central PMCID: PMC1564486.

19: Brioni JD, Kim DJ, Brodie MS, Decker MW, Arneric SP. ABT-418: discriminative stimulus properties and effect on ventral tegmental cell activity. Psychopharmacology (Berl). 1995 Jun;119(4):368-75. PubMed PMID: 7480515.

20: Donnelly-Roberts DL, Xue IC, Arneric SP, Sullivan JP. In vitro neuroprotective properties of the novel cholinergic channel activator (ChCA), ABT-418. Brain Res. 1996 May 6;719(1-2):36-44. PubMed PMID: 8782861.