Azepindole

Chemical compound

Pharmaceutical compound

Azepindole
Clinical data

ATC code	none
Identifiers
IUPAC name 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole
CAS Number	26304-61-0 ^☒N
PubChem CID	33471
ChemSpider	30893 ^checkY
UNII	6BB6FW9T8J
KEGG	D03035 ^checkY
ChEMBL	ChEMBL10758 ^checkY
CompTox Dashboard (EPA)	DTXSID40180916 Edit this at Wikidata
Chemical and physical data
Formula	C₁₂H₁₄N₂
Molar mass	186.258 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES c13c(cc2n1CCCNC2)cccc3
InChI InChI=1S/C12H14N2/c1-2-5-12-10(4-1)8-11-9-13-6-3-7-14(11)12/h1-2,4-5,8,13H,3,6-7,9H2^checkY Key:FEJCIXJKPISCJV-UHFFFAOYSA-N^checkY
^☒NcheckY (what is this?) (verify)

Azepindole (McN-2453) is a tricyclic compound with antidepressant and antihypertensive effects that was developed in the late 1960s but was never marketed.^[1]

References

[edit ]

^ Ganellin CR, Triggle DJ (21 November 1996). Dictionary of pharmacological agents - Google Books. CRC Press. ISBN 9780412466304.

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Antidepressants (N06A)

Specific reuptake inhibitors and/or receptor modulators

SSRIs Tooltip Selective serotonin reuptake inhibitors	Citalopram Escitalopram Fluoxetine ^# Fluvoxamine Indalpine ^‡ Paroxetine Sertraline Zimelidine ^‡
SNRIs Tooltip Serotonin–norepinephrine reuptake inhibitors	Desvenlafaxine Duloxetine Levomilnacipran Milnacipran Tofenacin Venlafaxine
NRIs Tooltip Norepinephrine reuptake inhibitors	Atomoxetine Reboxetine Viloxazine
NDRIs Tooltip Norepinephrine–dopamine reuptake inhibitors	Amineptine ^‡ Bupropion Nomifensine ^‡
NaSSAs Tooltip Noradrenergic and specific serotonergic antidepressants	Mianserin Mirtazapine Setiptiline
SARIs Tooltip Serotonin antagonist and reuptake inhibitors	Etoperidone Nefazodone Trazodone
SMS Tooltip Serotonin modulator and stimulators	Vilazodone Vortioxetine
Others	Agomelatine Amisulpride Dextromethorphan/bupropion Esketamine Etryptamine ^‡ Gepirone Indeloxazine Flupentixol Ketamine ^§ Medifoxamine ^‡ Metryptamine ^‡ Oxaflozane ^‡ Pivagabine ^‡ Tandospirone Teniloxazine Tianeptine

Tricyclic and tetracyclic antidepressants

TCAs Tooltip Tricyclic antidepressants	Amineptine ^‡ Amitriptyline ^# Amitriptylinoxide Amoxapine Butriptyline ^‡ Clomipramine ^# Demexiptiline ^‡ Desipramine Dibenzepin Dimetacrine ^‡ Dosulepin Doxepin Imipramine Imipraminoxide ^‡ Iprindole ^‡ Lofepramine Melitracen Metapramine ^‡ Nitroxazepine Nortriptyline Noxiptiline Opipramol Pipofezine Propizepine ^‡ Protriptyline Quinupramine ^‡ Tianeptine Trimipramine
TeCAs Tooltip Tetracyclic antidepressants	Maprotiline Mianserin Mirtazapine Setiptiline
Others	Tiazesim

Monoamine oxidase inhibitors

Non-selective	Irreversible: Benmoxin ^‡ Iproclozide ^‡ Iproniazid ^‡ Isocarboxazid Isoniazid ^# Linezolid ^# Mebanazine ^‡ Nialamide ^‡ Octamoxin ^‡ Phenelzine Pheniprazine ^‡ Phenoxypropazine ^‡ Pivhydrazine ^‡ Safrazine ^‡ Tedizolid Tranylcypromine Reversible: Caroxazone ^‡ Mixed: Bifemelane
MAO_A Tooltip Monoamine oxidase A-selective	Reversible: Eprobemide Metralindole Minaprine ^‡ Moclobemide Pirlindole Tetrindole Toloxatone
MAO_B Tooltip Monoamine oxidase B-selective	Irreversible: Selegiline

Adjunctive therapies
Atypical antipsychotics (aripiprazole, brexpiprazole, lurasidone, olanzapine, quetiapine, risperidone) Buspirone Lithium (lithium carbonate, lithium citrate) Thyroid hormones (triiodothyronine (T₃), levothyroxine (T₄))

Miscellaneous
Ademetionine (SAMe) GABAkine neurosteroids (brexanolone, zuranolone) Hypericum perforatum (St. John's Wort) Oxitriptan (5-HTP) Rubidium chloride (RbCl) Tryptophan

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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Sympatholytic (and closely related) antihypertensives (C02)

Sympatholytics
(antagonize α-adrenergic
vasoconstriction)

Central

α₂-Adrenergic receptor agonists	Clonidine Guanabenz Guanfacine Guanoxabenz Methyldopa ^# Tiamenidine ^‡
Adrenergic release inhibitors	Bethanidine Bretylium Debrisoquine Guanadrel Guanazodine Guancydine Guanethidine Guanoclor Guanoxan
Imidazoline receptor agonists	Moxonidine Rilmenidine Tolonidine
Ganglion-blocking/nicotinic antagonists	Hexamethonium ^‡ Mecamylamine Pentolinium Trimethaphan

Peripheral

Indirect

Monoamine oxidase inhibitors	Pargyline ^‡
VMAT inhibitors	Bietaserpine Deserpidine Methoserpidine Reserpine Syrosingopine
Tyrosine hydroxylase inhibitors	Metirosine

Direct

α₁-Adrenergic receptor blockers	Doxazosin Ketanserin Indoramin Prazosin Trimazosin Urapidil
Non-selective α-adrenergic receptor blockers	Phentolamine

Other antagonists

Serotonin receptor antagonists	Ketanserin Lidanserin
Endothelin receptor antagonists (for PH Tooltip Pulmonary hypertension)	dual (Aprocitentan, Bosentan, Macitentan (+tadalafil), Riociguat) selective (Ambrisentan (+tadalafil), Sitaxentan, Sotatercept)

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

v t e Tricyclics
Classes	Acridine Anthracene Dibenzazepine Dibenzocycloheptene Dibenzodiazepine Dibenzothiazepine Dibenzothiepin Dibenzoxazepine Dibenzoxepin Phenothiazine Pyridazinobenzoxazine Pyridinobenzodiazepine Thioxanthene
Antidepressants (Tricyclic antidepressants (TCAs))	Amoxapine Amezepine Amineptine Amitriptyline Amitriptylinoxide Amoxapine Aptazapine Azepindole Batelapine Beloxepin Butriptyline Cianopramine Ciclazindol Cidoxepin Clomipramine Cotriptyline Cyanodothiepin Demexiptiline Depramine (balipramine) Desipramine (desmethylimipramine) Desmethylclomipramine Desmethyltrimipramine Dibenzepin Dimetacrine Dosulepin (dothiepin) Doxepin Enprazepine Fantridone Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Loxapine Maprotiline Mariptiline Mazindol Melitracen Metapramine Mezepine Mirtazapine Monometacrine Nitroxazepine Norbutriptyline Nordoxepin Northiaden (nordosulepin) Nortriptyline (noramitriptyline) Noxiptiline Octriptyline Opipramol Pipofezine Pirandamine Propizepine Protriptyline Quinupramine Spiroxepin Tandamine Tampramine Tianeptine Tienopramine Trimipramine
Antihistamines	Azatadine Bisulepin Cidoxepin Clobenzepam Cyproheptadine Dacemazine Deptropine Desloratadine Epinastine Etymemazine Fenethazine Hydroxyethylpromethazine Isopromethazine Isothipendyl Ketotifen Latrepirdine Loratadine Mebhydrolin Mequitazine Methdilazine Olopatadine Oxomemazine Perlapine Phenindamine Pimethixene Pirolate Promethazine Propiomazine Rupatadine Thiazinamium
Antipsychotics	Acetophenazine Alimemazine Amoxapine Asenapine Butaclamol Butaperazine Carfenazine (carphenazine) Carpipramine Chlorpromazine Chlorprothixene Ciclindole Citatepine Clocapramine Clomacran Clorotepine Clotiapine Clozapine Cyanothepin Doclothepin Docloxythepin Erizepine Flucindole Flumezapine Fluotracen Flupentixol Fluphenazine Gevotroline Homopipramol Isofloxythepin Levomepromazine/Methotrimeprazine Loxapine Maroxepin Meperathiepin Mesoridazine Metiapine Metitepine Metoxepin Mosapramine Naranol Octomethothepin Olanzapine Oxyclothepin Oxyprothepin Pentiapine Peradithiepin Perathiepin Perazine Perphenazine Periciazine Pinoxepin Piperacetazine Pipotiazine Piquindone Prochlorperazine Promazine Prothipendyl Quetiapine Savoxepin/Cipazoxapine Sulforidazine Tenilapine Thiethylperazine Thiopropazate Thioridazine Thiothixene Tilozepine Traboxopine Trifluoperazine Triflupromazine Trifluthepin Zotepine Zuclopenthixol
Anticonvulsants	Carbamazepine Dizocilpine Eslicarbazepine Eslicarbazepine acetate Etazepine Licarbazepine Oxcarbazepine Oxitriptyline
Anticholinergics	Darenzepine Dipitramine Nuvenzepine Pirenzepine Profenamine Rispenzepine Siltenzepine Telenzepine Tripitramine Tropatepine Zolenzepine
Others	Adosopine Aminopromazine Atiprosin Benzoctamine Botiacrine Carvedilol Cyclobenzaprine Damotepine Elanzepine Fluradoline Methylene blue Monatepil Oxetorone Pipazethate P7C3 Pinadoline Pitrazepin Pizotifen Serazapine Tipindole

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See also

References