Demexiptiline

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 5H-dibenzo(a,d)cyclohepten-5-one O-(2-(methylamino)ethyl)oxime

| image = demexiptiline.png

| alt = Skeletal formula of demexiptiline

| width = 180

| image2 = Demexiptiline-3D-spacefill.png

| alt2 = Space-filling model of the demexiptiline molecule

| tradename = Deparon, Tinoran

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life = 35 hours{{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–}}

| excretion =

| 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

| 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.{{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}}{{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}} It acts primarily as a norepinephrine reuptake inhibitor similarly to desipramine.{{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 }}

Synthesis

:upright=2

The ketone dibenzosuberenone (1) is treated with hydroxylamine (2) to give its ketoxime (3). Base-catalyzed alkylation with {{chem2|ClCH2CH2NHCH3}} (4) yields demexiptiline.{{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 }}{{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 }}

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}}

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{{Tricyclics}}

{{Use dmy dates|date=March 2018}}

Category:Dibenzocycloheptenes

Category:Ketoxime ethers

Category:Tricyclic antidepressants

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