U-92,016-A

U-92,016-A
Identifiers
	IUPAC name (8R)-8-(Dipropylamino)-6,7,8,9-tetrahydro-3H-benzindole-2-carbonitrile;
CAS Number	136924-88-4 ; hydrochloride: 149654-41-1 ;
PubChem CID	9904242;
IUPHAR/BPS	30;
ChemSpider	8079896 ;
UNII	9JQ994EAB3; hydrochloride: DSP36A348S ;
ChEMBL	ChEMBL71920 ;
CompTox Dashboard (EPA)	DTXSID00432645 ;
Chemical and physical data
Formula	C19H25N3
Molar mass	295.430 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N#Cc3cc1c(ccc2c1C(N(CCC)CCC)CC2)3;
	InChI InChI=1S/C19H25N3/c1-3-9-22(10-4-2)16-7-5-14-6-8-19-18(17(14)12-16)11-15(13-20)21-19/h6,8,11,16,21H,3-5,7,9-10,12H2,1-2H3/t16-/m1/s1 ; Key:WDDZPZKGLZNGEH-MRXNPFEDSA-N ;
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U-92,016-A is a psychoactive drug and research chemical used in scientific studies. It acts as a potent, high efficacy, and selective 5-HT_1A receptor full agonist with a long duration of action.^[1]^[2] It has been suggested that it could be developed as an anxiolytic or antidepressant drug.^[1]

References

^ ^a ^b Romero AG, Leiby JA, McCall RB, Piercey MF, Smith MW, Han F (1993). "Novel 2-substituted tetrahydro-3H-benzindolamines: highly potent and selective agonists acting at the 5-HT1A receptor as possible anxiolytics and antidepressants". J Med Chem. 36 (15): 2066–2074. doi:10.1021/jm00067a003. PMID 8101876.
^ McCall RB, Romero AG, Bienkowski MJ, Harris DW, McGuire JC, Piercey MF, Shuck ME, Smith MW, Svensson KA, Schreur PJ, et al. (1994). "Characterization of U-92016A as a selective, orally active, high intrinsic activity 5-hydroxytryptamine1A agonist". J Pharmacol Exp Ther. 271 (2): 875–883. PMID 7965808.

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[pmid8101876-1] Romero AG, Leiby JA, McCall RB, Piercey MF, Smith MW, Han F (1993). "Novel 2-substituted tetrahydro-3H-benzindolamines: highly potent and selective agonists acting at the 5-HT1A receptor as possible anxiolytics and antidepressants". J Med Chem. 36 (15): 2066–2074. doi:10.1021/jm00067a003. PMID 8101876.

[pmid7965808-2] McCall RB, Romero AG, Bienkowski MJ, Harris DW, McGuire JC, Piercey MF, Shuck ME, Smith MW, Svensson KA, Schreur PJ, et al. (1994). "Characterization of U-92016A as a selective, orally active, high intrinsic activity 5-hydroxytryptamine1A agonist". J Pharmacol Exp Ther. 271 (2): 875–883. PMID 7965808.

[1]

[2]

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

Identifiers

IUPAC name (8R)-8-(Dipropylamino)-6,7,8,9-tetrahydro-3H-benzindole-2-carbonitrile
CAS Number	136924-88-4^Y hydrochloride: 149654-41-1^Y
PubChem CID	9904242
IUPHAR/BPS	30
ChemSpider	8079896^Y
UNII	9JQ994EAB3 hydrochloride: DSP36A348S^Y
ChEMBL	ChEMBL71920^Y
CompTox Dashboard (EPA)	DTXSID00432645
Chemical and physical data
Formula	C₁₉H₂₅N₃
Molar mass	295.430 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES N#Cc3cc1c(ccc2c1C(N(CCC)CCC)CC2)3
InChI InChI=1S/C19H25N3/c1-3-9-22(10-4-2)16-7-5-14-6-8-19-18(17(14)12-16)11-15(13-20)21-19/h6,8,11,16,21H,3-5,7,9-10,12H2,1-2H3/t16-/m1/s1^Y Key:WDDZPZKGLZNGEH-MRXNPFEDSA-N^Y
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