Chemistry:U-92,016-A

U-92,016-A
Identifiers
	IUPAC name (8R)-8-(Dipropylamino)-6,7,8,9-tetrahydro-3H-benz[e]indole-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 ;
Chemical and physical data
Formula	C19H25N3
Molar mass	295.430 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES N#Cc3cc1c(ccc2c1C[C@H](N(CCC)CCC)CC2)[nH]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 ;
	(verify)

Short description: Psychoactive drug

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

↑ ^1.0 ^1.1 "Novel 2-substituted tetrahydro-3H-benz[e]indolamines: highly potent and selective agonists acting at the 5-HT1A receptor as possible anxiolytics and antidepressants.". J Med Chem 36 (15): 2066–2074. 1993. doi:10.1021/jm00067a003. PMID 8101876.
↑ "Characterization of U-92016A as a selective, orally active, high intrinsic activity 5-hydroxytryptamine1A agonist.". J Pharmacol Exp Ther 271 (2): 875–883. 1994. PMID 7965808.

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Original source: https://en.wikipedia.org/wiki/U-92,016-A. Read more

[pmid8101876-1] 1.0 ^1.1 "Novel 2-substituted tetrahydro-3H-benz[e]indolamines: highly potent and selective agonists acting at the 5-HT1A receptor as possible anxiolytics and antidepressants.". J Med Chem 36 (15): 2066–2074. 1993. doi:10.1021/jm00067a003. PMID 8101876.

[pmid7965808-2] "Characterization of U-92016A as a selective, orally active, high intrinsic activity 5-hydroxytryptamine1A agonist.". J Pharmacol Exp Ther 271 (2): 875–883. 1994. PMID 7965808.

[1]

[2]

v t e Anxiolytics (N05B)
5-HT_1AR agonists	Buspirone Gepirone^† Tandospirone
GABA_AR PAMs	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) Chlormezanone^‡ Ethanol (alcohol) Etifoxine Imepitoin; Herbs: Kava Skullcap Valerian
Gabapentinoids (α₂δ VDCC blockers)	Gabapentin Gabapentin enacarbil Phenibut Pregabalin
Antidepressants	SSRIs (e.g., escitalopram) SNRIs (e.g., duloxetine) SARIs (e.g., trazodone) TCAs (e.g., clomipramine^#) TeCAs (e.g., mirtazapine) MAOIs (e.g., phenelzine); Others: Agomelatine Bupropion Tianeptine Vilazodone Vortioxetine
Sympatholytics (Antiadrenergics)	Alpha-1 blockers (e.g., prazosin) Alpha-2 agonists (e.g., clonidine, dexmedetomidine, guanfacine) Beta blockers (e.g., propranolol)
Others	Benzoctamine Cannabidiol Cycloserine Fabomotizole Hydroxyzine Kanna Lavender 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

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Identifiers

IUPAC name (8R)-8-(Dipropylamino)-6,7,8,9-tetrahydro-3H-benz[e]indole-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
Chemical and physical data
Formula	C₁₉H₂₅N₃
Molar mass	295.430 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES N#Cc3cc1c(ccc2c1C[C@H](N(CCC)CCC)CC2)[nH]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
(verify)

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