ABT-724 (free base)

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

MedKoo CAT#: 524122

CAS#: 70006-24-5

Description: ABT-724 acts as a dopamine agonist and is selective for the D4 subtype. It was developed as a possible drug for the treatment of erectile dysfunction. It continues to be used in scientific research into the function of the D4 receptor.


Price and Availability

Size
Price

Size
Price

Size
Price

ABT-724, purity > 98%, is not in stock, may be available through custom synthesis. Minimum 1 gram order is requested. Current shipping out time is about 70 days after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 524122
Name: ABT-724 (free base)
CAS#: 70006-24-5
Chemical Formula: C17H19N5
Exact Mass: 293.16405
Molecular Weight: 293.37
Elemental Analysis: C, 69.60; H, 6.53; N, 23.87


Synonym: ABT-724; ABT 724; ABT724; UNII-4WV2575JWT;

IUPAC/Chemical Name: 1H-Benzimidazole, 2-((4-(2-pyridinyl)-1-piperazinyl)methyl)-

InChi Key: FRPJGTNLZNXQEX-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H19N5/c1-2-6-15-14(5-1)19-16(20-15)13-21-9-11-22(12-10-21)17-7-3-4-8-18-17/h1-8H,9-13H2,(H,19,20)

SMILES Code: C1(CN2CCN(C3=NC=CC=C3)CC2)=NC4=CC=CC=C4N1


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, not in water

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


Additional Information

Related CAS#
474417-17-9 (ABT-724)


References

1: Sanna F, Contini A, Melis MR, Argiolas A. Role of dopamine D4 receptors in copulatory behavior: Studies with selective D4 agonists and antagonists in male rats. Pharmacol Biochem Behav. 2015 Oct;137:110-8. doi: 10.1016/j.pbb.2015.08.012. Epub 2015 Aug 16. PubMed PMID: 26287845.

2: Yin P, Cao AH, Yu L, Guo LJ, Sun RP, Lei GF. ABT-724 alleviated hyperactivity and spatial learning impairment in the spontaneously hypertensive rat model of attention-deficit/hyperactivity disorder. Neurosci Lett. 2014 Sep 19;580:142-6. doi: 10.1016/j.neulet.2014.08.008. Epub 2014 Aug 12. PubMed PMID: 25128216.

3: Koffarnus MN, Newman AH, Grundt P, Rice KC, Woods JH. Effects of selective dopaminergic compounds on a delay-discounting task. Behav Pharmacol. 2011 Aug;22(4):300-11. doi: 10.1097/FBP.0b013e3283473bcb. PubMed PMID: 21694584; PubMed Central PMCID: PMC3135665.

4: Depoortère R, Bardin L, Rodrigues M, Abrial E, Aliaga M, Newman-Tancredi A. Penile erection and yawning induced by dopamine D2-like receptor agonists in rats: influence of strain and contribution of dopamine D2, but not D3 and D4 receptors. Behav Pharmacol. 2009 Jul;20(4):303-11. doi: 10.1097/FBP.0b013e32832ec5aa. PubMed PMID: 19584712.

5: Marona-Lewicka D, Chemel BR, Nichols DE. Dopamine D4 receptor involvement in the discriminative stimulus effects in rats of LSD, but not the phenethylamine hallucinogen DOI. Psychopharmacology (Berl). 2009 Apr;203(2):265-77. doi: 10.1007/s00213-008-1238-0. Epub 2008 Jul 6. PubMed PMID: 18604600.

6: Newman-Tancredi A, Heusler P, Martel JC, Ormière AM, Leduc N, Cussac D. Agonist and antagonist properties of antipsychotics at human dopamine D4.4 receptors: G-protein activation and K+ channel modulation in transfected cells. Int J Neuropsychopharmacol. 2008 May;11(3):293-307. Epub 2007 Sep 26. PubMed PMID: 17897483.

7: Marona-Lewicka D, Nichols DE. Further evidence that the delayed temporal dopaminergic effects of LSD are mediated by a mechanism different than the first temporal phase of action. Pharmacol Biochem Behav. 2007 Oct;87(4):453-61. Epub 2007 Jun 14. PubMed PMID: 17618679.

8: Patel MV, Kolasa T, Mortell K, Matulenko MA, Hakeem AA, Rohde JJ, Nelson SL, Cowart MD, Nakane M, Miller LN, Uchic ME, Terranova MA, El-Kouhen OF, Donnelly-Roberts DL, Namovic MT, Hollingsworth PR, Chang R, Martino BR, Wetter JM, Marsh KC, Martin R, Darbyshire JF, Gintant G, Hsieh GC, Moreland RB, Sullivan JP, Brioni JD, Stewart AO. Discovery of 3-methyl-N-(1-oxy-3',4',5',6'-tetrahydro-2'H-[2,4'-bipyridine]-1'-ylmethyl)benzam ide (ABT-670), an orally bioavailable dopamine D4 agonist for the treatment of erectile dysfunction. J Med Chem. 2006 Dec 14;49(25):7450-65. PubMed PMID: 17149874.

9: Engstrom KM, Daanen JF, Wagaw S, Stewart AO. Gram scale synthesis of the glucuronide metabolite of ABT-724. J Org Chem. 2006 Oct 27;71(22):8378-83. PubMed PMID: 17064008.

10: Boehmler W, Carr T, Thisse C, Thisse B, Canfield VA, Levenson R. D4 Dopamine receptor genes of zebrafish and effects of the antipsychotic clozapine on larval swimming behaviour. Genes Brain Behav. 2007 Mar;6(2):155-66. PubMed PMID: 16764679.

11: Cowart M, Latshaw SP, Bhatia P, Daanen JF, Rohde J, Nelson SL, Patel M, Kolasa T, Nakane M, Uchic ME, Miller LN, Terranova MA, Chang R, Donnelly-Roberts DL, Namovic MT, Hollingsworth PR, Martino BR, Lynch JJ 3rd, Sullivan JP, Hsieh GC, Moreland RB, Brioni JD, Stewart AO. Discovery of 2-(4-pyridin-2-ylpiperazin-1-ylmethyl)-1H-benzimidazole (ABT-724), a dopaminergic agent with a novel mode of action for the potential treatment of erectile dysfunction. J Med Chem. 2004 Jul 15;47(15):3853-64. PubMed PMID: 15239663.

12: Brioni JD, Moreland RB, Cowart M, Hsieh GC, Stewart AO, Hedlund P, Donnelly-Roberts DL, Nakane M, Lynch JJ 3rd, Kolasa T, Polakowski JS, Osinski MA, Marsh K, Andersson KE, Sullivan JP. Activation of dopamine D4 receptors by ABT-724 induces penile erection in rats. Proc Natl Acad Sci U S A. 2004 Apr 27;101(17):6758-63. Epub 2004 Apr 15. PubMed PMID: 15087502; PubMed Central PMCID: PMC404118.