A-412,997

A-412,997

Systematic (IUPAC) name
N-(3-methylphenyl)-2-(4-pyridin-2-ylpiperidin-1-yl)acetamide
Identifiers
CAS Number	630116-49-3 1347744-96-0 (di‑hydrochloride)
PubChem	CID 10425450
IUPHAR/BPS	3301
ChemSpider	8600878
ChEMBL	CHEMBL375596
Chemical data
Formula	C19H23N3O
Molar mass	309.405 g/mol
SMILES CC1=CC(NC(CN2CCC(C3=CC=CC=N3)CC2)=O)=CC=C1
InChI InChI=1S/C19H23N3O/c1-15-5-4-6-17(13-15)21-19(23)14-22-11-8-16(9-12-22)18-7-2-3-10-20-18/h2-7,10,13,16H,8-9,11-12,14H2,1H3,(H,21,23) Key:JFCDMGGMCUKHST-UHFFFAOYSA-N
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A-412,997 is a drug which acts as a dopamine agonist that is used in scientific research. It is the first drug developed that is a highly selective agonist for the D₄ subtype, with significantly improved selectivity over older D₄-preferring compounds such as PD-168,077 and CP-226,269.^[1] In animal tests it improved cognitive performance in rats to a similar extent as methylphenidate, but without producing place preference or other signs of abuse liability.^[2][3] Also unlike other dopamine agonists, selective D₄ agonists do not cause side effects such as sedation and nausea, and so might have advantages over older dopamine agonist drugs.^[4]

References

1. Moreland, RB; Patel, M; Hsieh, GC; Wetter, JM; Marsh, K; Brioni, JD (2005). "A-412997 is a selective dopamine D4 receptor agonist in rats". Pharmacology, Biochemistry, and Behavior 82 (1): 140–7. doi:10.1016/j.pbb.2005.08.001. PMID 16153699.
2. Browman, KE; Curzon, P; Pan, JB; Molesky, AL; Komater, VA; Decker, MW; Brioni, JD; Moreland, RB; Fox, GB (2005). "A-412997, a selective dopamine D4 agonist, improves cognitive performance in rats". Pharmacology, Biochemistry, and Behavior 82 (1): 148–55. doi:10.1016/j.pbb.2005.08.002. PMID 16154186.
3. Woolley, Marie L.; Waters, Kerry A.; Reavill, Charlie; Bull, Sharlene; Lacroix, Laurent P.; Martyn, Abbe J.; Hutcheson, Daniel M.; Valerio, Enzo; Bate, Simon; Jones, Declan N.C.; Dawson, Lee A. (December 2008). "Selective dopamine D4 receptor agonist (A-412997) improves cognitive performance and stimulates motor activity without influencing reward-related behaviour in rat". Behavioural Pharmacology 19 (8): 765–76. doi:10.1097/FBP.0b013e32831c3b06. PMID 19020411.
4. Osinski, MA; Uchic, ME; Seifert, T; Shaughnessy, TK; Miller, LN; Nakane, M; Cox, BF; Brioni, JD; Moreland, RB (2005). "Dopamine D2, but not D4, receptor agonists are emetogenic in ferrets". Pharmacology, Biochemistry, and Behavior 81 (1): 211–9. doi:10.1016/j.pbb.2005.03.012. PMID 15894081.