AR-A000002

AR-A000002
Clinical data
ATC code	none;
Identifiers
	IUPAC name (R)-N-[5-methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide;
PubChem CID	9846516;
ChemSpider	8022230;
CompTox Dashboard (EPA)	DTXSID801027304 ;
Chemical and physical data
Formula	C27H36N4O2
Molar mass	448.599 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C5COCCN5c(cc4)ccc4C(=O)NC2CCc1c(C2)c(ccc1C)N3CCN(C)CC3;
	InChI InChI=1S/C27H36N4O2/c1-20-3-10-26(31-13-11-29(2)12-14-31)25-19-22(6-9-24(20)25)28-27(32)21-4-7-23(8-5-21)30-15-17-33-18-16-30/h3-5,7-8,10,22H,6,9,11-19H2,1-2H3,(H,28,32)/t22-/m1/s1; Key:IHDRUIHIJWCTIY-JOCHJYFZSA-N;
	(verify)

AR-A000002 is a drug which is one of the first compounds developed to act as a selective antagonist for the serotonin receptor 5-HT_1B,^[1] with approximately 10x selectivity for 5-HT_1B over the closely related 5-HT_1D receptor.^[2] It has been shown to produce sustained increases in levels of serotonin in the brain, and has anxiolytic effects in animal studies.^[3]^[4]

References

^ Hudzik TJ, Yanek M, Porrey T, Evenden J, Paronis C, Mastrangelo M, Ryan C, Ross S, Stenfors C. Behavioral pharmacology of AR-A000002, a novel, selective 5-hydroxytryptamine(1B) antagonist. Journal of Pharmacology and Experimental Therapeutics. 2003 Mar;304(3):1072-84. PMID 12604684
^ Ahlgren C, Eriksson A, Tellefors P, Ross SB, Stenfors C, Malmberg A. In vitro characterization of AR-A000002, a novel 5-hydroxytryptamine(1B) autoreceptor antagonist. European Journal of Pharmacology. 2004 Sep 19;499(1-2):67-75. PMID 15363952
^ Stenfors C, Ahlgren C, Yu H, Wedén M, Larsson LG, Ross SB. Effects of long-term administration of the 5-hydroxytryptamine1B receptor antagonist AR-A000002 to guinea pigs. Psychopharmacology. 2004 Mar;172(3):333-40. PMID 14652708
^ Stenfors C, Hallerbäck T, Larsson LG, Wallsten C, Ross SB. Pharmacology of a novel selective 5-hydroxytryptamine1B receptor antagonist, AR-A000002. Naunyn Schmiedebergs Archives of Pharmacology. 2004 Mar;369(3):330-7. PMID 14758468

[1] Hudzik TJ, Yanek M, Porrey T, Evenden J, Paronis C, Mastrangelo M, Ryan C, Ross S, Stenfors C. Behavioral pharmacology of AR-A000002, a novel, selective 5-hydroxytryptamine(1B) antagonist. Journal of Pharmacology and Experimental Therapeutics. 2003 Mar;304(3):1072-84. PMID 12604684

[2] Ahlgren C, Eriksson A, Tellefors P, Ross SB, Stenfors C, Malmberg A. In vitro characterization of AR-A000002, a novel 5-hydroxytryptamine(1B) autoreceptor antagonist. European Journal of Pharmacology. 2004 Sep 19;499(1-2):67-75. PMID 15363952

[3] Stenfors C, Ahlgren C, Yu H, Wedén M, Larsson LG, Ross SB. Effects of long-term administration of the 5-hydroxytryptamine1B receptor antagonist AR-A000002 to guinea pigs. Psychopharmacology. 2004 Mar;172(3):333-40. PMID 14652708

[4] Stenfors C, Hallerbäck T, Larsson LG, Wallsten C, Ross SB. Pharmacology of a novel selective 5-hydroxytryptamine1B receptor antagonist, AR-A000002. Naunyn Schmiedebergs Archives of Pharmacology. 2004 Mar;369(3):330-7. PMID 14758468

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v t e Anxiolytics (N05B)
5-HT_1ARTooltip 5-HT1A receptor agonists	Buspirone Gepirone Tandospirone
GABA_ARTooltip GABAA receptor PAMsTooltip positive allosteric modulators	Benzodiazepines: Adinazolam Alprazolam Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl loflazepate Etizolam Fludiazepam Halazepam Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam; Others: Alpidem^‡ Barbiturates (e.g., phenobarbital) Carbamates (e.g., meprobamate) Carisoprodol Chlormezanone^‡ Ethanol (alcohol) Etifoxine
Hypnotics	Zopiclone
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIsTooltip Selective serotonin reuptake inhibitors (e.g., escitalopram) SNRIsTooltip Serotonin-norepinephrine reuptake inhibitors (e.g., duloxetine) SARIsTooltip Serotonin antagonist and reuptake inhibitors (e.g., trazodone) TCAsTooltip Tricyclic antidepressants (e.g., clomipramine^#) TeCAsTooltip Tetracyclic antidepressants (e.g., mirtazapine) MAOIsTooltip Monoamine oxidase inhibitors (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Antipsychotics	Quetiapine Flupentixol
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cycloserine Fabomotizole Hydroxyzine Lorpiprazole Mebicar Mepiprazole Nicotine Opipramol Oxaflozane^‡ Phenaglycodol Phenibut Picamilon Selank Tiagabine Tofisopam Validolum
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III