nitrafudam

{{Short description|Antidepressant compound}}

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{{Infobox drug

| drug_name = Nitrafudam

| image = Nitrafudam.svg

| width = 250px

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| CAS_number = 64743-09-5

| PubChem = 163304

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| ChemSpiderID = 143312

| UNII = 7R3267A08Y

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| ChEMBL = 2111024

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| C=11 | H=9 | N=3 | O=3

| StdInChI=1S/C11H9N3O3/c12-11(13)10-6-5-9(17-10)7-3-1-2-4-8(7)14(15)16/h1-6H,(H3,12,13)

| StdInChIKey = FYUZOMGBPKUZNJ-UHFFFAOYSA-N

| SMILES = C1=CC=C(C(=C1)C2=CC=C(O2)C(=N)N)[N+](=O)[O-]

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Nitrafudam is an antidepressant compound that was developed in the 1970-1980s.{{cite journal | vauthors = Pong SF, Pelosi SS, Wessels FL, Yu CN, Burns RH, White RE, Anthony DR, Ellis KO, Wright GC, White RL | title = 5-phenyl-2-furamidines: a new chemical class of potential antidepressants | journal = Arzneimittel-Forschung | volume = 33 | issue = 10 | pages = 1411–1416 | year = 1983 | pmid = 6140016 }}{{cite patent |country=US |number=3919231 |inventor=Pelosi SS Jr, White RE, White RL Jr, Wright GC, You CN |gdate=1975 |assign=Morton Norwich Products Inc |url=https://patents.google.com/patent/US3919231A/en?oq=US3919231}} It contains three functional groups: a nitrobenzene, a furan ring and an amidine.

Synthesis

File:Nitrafudam synthesis.svg

Azo coupling between 2-nitrophenyldiazonium chloride [119-66-4] (1) and furfural (2) leads to 5-(2-nitrophenyl)furfural [20000-96-8] (3). Treatment of the aldehyde with hydroxylamine gives the corresponding aldoxime (PC789659). Upon dehydration, FGI to the nitrile occurs [57666-58-7] (4). A Pinner reaction with anhydrous methanolic hydrogen chloride gives the corresponding imidate (imino-ether) [62821-40-3] (5). An addition-elimination reaction with ammonia causes FGI to an amidine, thus completing the synthesis of nitrafudam (6).

References

{{Reflist}}

Amidines

Category:Nitrobenzenes

Category:Furans

Category:Antidepressants

{{Antidepressants}}

{{Monoamine reuptake inhibitors}}