Binospirone

Binospirone
Clinical data
ATC code	none;
Identifiers
	IUPAC name 8-[2-(2,3-dihydro-1,4-benzodioxin-2-ylmethylamino)ethyl]-8-azaspiro[4.5]decane-7,9-dione;
CAS Number	102908-59-8 ; mesylate: 124756-23-6 ;
PubChem CID	60769;
ChemSpider	54766;
UNII	T3M5D109V5; mesylate: 155R3B9K8H ;
ChEMBL	ChEMBL1487115;
Chemical and physical data
Formula	C20H26N2O4
Molar mass	358.438 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1N(C(=O)CC2(C1)CCCC2)CCNCC3Oc4ccccc4OC3;
	InChI InChI=1S/C20H26N2O4/c23-18-11-20(7-3-4-8-20)12-19(24)22(18)10-9-21-13-15-14-25-16-5-1-2-6-17(16)26-15/h1-2,5-6,15,21H,3-4,7-14H2; Key:BVMYCHKQPGEOSI-UHFFFAOYSA-N;

Binospirone (MDL-73,005-EF) is a drug which acts as a partial agonist at 5-HT_1A somatodendritic autoreceptors but as an antagonist at postsynaptic 5-HT_1A receptors.^[1] It has anxiolytic effects.^[2]

References[]

^ Bertrand F, Lehmann O, Galani R, Lazarus C, Jeltsch H, Cassel JC (April 2001). "Effects of MDL 73005 on water-maze performances and locomotor activity in scopolamine-treated rats". Pharmacology, Biochemistry, and Behavior. 68 (4): 647–60. doi:10.1016/S0091-3057(01)00448-8. PMID 11526961. S2CID 8595441.
^ Moser PC, Tricklebank MD, Middlemiss DN, Mir AK, Hibert MF, Fozard JR (February 1990). "Characterization of MDL 73005EF as a 5-HT1A selective ligand and its effects in animal models of anxiety: comparison with buspirone, 8-OH-DPAT and diazepam". British Journal of Pharmacology. 99 (2): 343–9. doi:10.1111/j.1476-5381.1990.tb14706.x. PMC 1917389. PMID 1970269.

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[1] Bertrand F, Lehmann O, Galani R, Lazarus C, Jeltsch H, Cassel JC (April 2001). "Effects of MDL 73005 on water-maze performances and locomotor activity in scopolamine-treated rats". Pharmacology, Biochemistry, and Behavior. 68 (4): 647–60. doi:10.1016/S0091-3057(01)00448-8. PMID 11526961. S2CID 8595441.

[2] Moser PC, Tricklebank MD, Middlemiss DN, Mir AK, Hibert MF, Fozard JR (February 1990). "Characterization of MDL 73005EF as a 5-HT1A selective ligand and its effects in animal models of anxiety: comparison with buspirone, 8-OH-DPAT and diazepam". British Journal of Pharmacology. 99 (2): 343–9. doi:10.1111/j.1476-5381.1990.tb14706.x. PMC 1917389. PMID 1970269.

[1]

[2]

v t 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) Carisoprodol 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

v t Piperazines
Simple piperazines (no additional rings)	Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	2C-B-PP 3,4-CFP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,935 Hydroxyzine Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine
Benzo(iso)thiazolylpiperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Flupentixol Fluphenazine Loxapine Metitepine Olanzapine Opipramol Oxyprothepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol

Clinical data


ATC code	none
Identifiers
IUPAC name 8-[2-(2,3-dihydro-1,4-benzodioxin-2-ylmethylamino)ethyl]-8-azaspiro[4.5]decane-7,9-dione
CAS Number	102908-59-8^Y mesylate: 124756-23-6^Y
PubChem CID	60769
ChemSpider	54766
UNII	T3M5D109V5 mesylate: 155R3B9K8H^Y
ChEMBL	ChEMBL1487115
Chemical and physical data
Formula	C₂₀H₂₆N₂O₄
Molar mass	358.438 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C1N(C(=O)CC2(C1)CCCC2)CCNCC3Oc4ccccc4OC3
InChI InChI=1S/C20H26N2O4/c23-18-11-20(7-3-4-8-20)12-19(24)22(18)10-9-21-13-15-14-25-16-5-1-2-6-17(16)26-15/h1-2,5-6,15,21H,3-4,7-14H2 Key:BVMYCHKQPGEOSI-UHFFFAOYSA-N

Binospirone

See also[]

References[]