{{Short description|Chemical compound}} {{Drugbox | IUPAC_name = 5''H''-dibenzo(a,d)cyclohepten-5-one ''O''-(2-(methylamino)ethyl)oxime | image = demexiptiline.png | image_class = skin-invert-image | alt = Skeletal formula of demexiptiline | width = 180 | image2 = Demexiptiline-3D-spacefill.png | image_class2 = bg-transparent | alt2 = Space-filling model of the demexiptiline molecule
<!--Clinical data--> | tradename = Deparon, Tinoran | pregnancy_category = | legal_status = Rx-only | routes_of_administration = Oral
<!--Pharmacokinetic data--> | bioavailability = | metabolism = | elimination_half-life = 35 hours<ref name="Dörwald2013">{{cite book| vauthors = Dörwald FZ |title=Lead Optimization for Medicinal Chemists: Pharmacokinetic Properties of Functional Groups and Organic Compounds|url=https://books.google.com/books?id=YTeY9ZEfNccC&pg=PA313|date=4 February 2013|publisher=John Wiley & Sons|isbn=978-3-527-64565-7|pages=313–}}</ref> | excretion =
<!--Identifiers--> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 24701-51-7 | ATC_prefix = none | ATC_suffix = | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB08998 | PubChem = 28876 | ChEMBL = 2107576 | ChemSpiderID = 26858 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = EYX738UZ5P
<!--Chemical data--> | C=18 | H=18 | N=2 | O=1 | SMILES = O(\N=C3/c1ccccc1\C=C/c2c3cccc2)CCNC }}
'''Demexiptiline''' (brand names '''Deparon''', '''Tinoran''') is a tricyclic antidepressant (TCA) used in France for the treatment of depression.<ref name="isbn3-88763-075-0">{{cite book | author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | page = 301 | isbn = 3-88763-075-0 | url = https://books.google.com/books?id=5GpcTQD_L2oC&q=demexiptiline&pg=PA301}}</ref><ref name="isbn0-412-46630-9">{{cite book | vauthors = Triggle DJ | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | page = 583 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=DeX7jgInYFMC&q=demexiptiline&pg=RA1-PA583}}</ref> It acts primarily as a norepinephrine reuptake inhibitor similarly to desipramine.<ref name="pmid8370568">{{cite journal | vauthors = Teste JF, Pelsy-Johann I, Decelle T, Boulu RG | title = Anti-immobility activity of different antidepressant drugs using the tail suspension test in normal or reserpinized mice | journal = Fundamental & Clinical Pharmacology | volume = 7 | issue = 5 | pages = 219–26 | year = 1993 | pmid = 8370568 | doi = 10.1111/j.1472-8206.1993.tb00235.x| s2cid = 24240307 }}</ref>
==Synthesis== :upright=2|class=skin-invert-image
The ketone dibenzosuberenone (1) is treated with hydroxylamine (2) to give its ketoxime (3). Base-catalyzed alkylation with {{chem2|ClCH2CH2NHCH3}} (4) yields demexiptiline.<ref>{{cite journal | vauthors = Aichinger G, Behner O, Hoffmeister F, Schütz S | title = Basic tricyclic oxyiminoethers and their pharmacological properties | journal = Arzneimittel-Forschung | volume = 19 | pages = Suppl 5a:838+ | date = June 1969 | pmid = 5819763 |language=DE }}</ref><ref>{{cite patent |title=Basic oximes and their preparation | inventor = Schütz S, Behner O, Hoffmeister F | country = US | number = 3963778 | gdate = 1976-06-15 | assign1 = Bayer AG }}</ref>
==References== {{Reflist|2}}
==Further reading== {{refbegin}} * {{cite journal | vauthors = Martin A, Masson JM, Jusseaume P, Beloncle M, Voisinet C | title = [Demexiptiline in the treatment of melancholic states (reflections after 3 years of use)] | language = fr | journal = Annales médico-psychologiques | volume = 139 | issue = 9 | pages = 1023–35 |date=November 1981 | pmid = 7337336}} {{refend}}
{{Antidepressants}} {{Navboxes | title = Pharmacodynamics | titlestyle = background:#ccccff | list1 = {{Adrenergic receptor modulators}} {{Histamine receptor modulators}} {{Monoamine reuptake inhibitors}} {{Muscarinic acetylcholine receptor modulators}} {{Serotonin receptor modulators}} }} {{Tricyclics}} {{Use dmy dates|date=March 2018}}
Category:Dibenzocycloheptenes Category:Ketoxime ethers Category:Tricyclic antidepressants
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