Nitrafudam

Nitrafudam
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC11H9N3O3
Molar mass231.211 g·mol−1
3D model (JSmol)
  • C1=CC=C(C(=C1)C2=CC=C(O2)C(=N)N)[N+](=O)[O-]
  • InChI=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)
  • Key:FYUZOMGBPKUZNJ-UHFFFAOYSA-N

Nitrafudam is an antidepressant compound that was developed in the 1970-1980s.[1][2] It contains three functional groups: a nitrobenzene, a furan ring and an amidine.

Synthesis

Nitrafudam synthesis
Nitrafudam synthesis

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

  1. ^ Pong SF, Pelosi SS, Wessels FL, Yu CN, Burns RH, White RE, et al. (1983). "5-phenyl-2-furamidines: a new chemical class of potential antidepressants". Arzneimittel-Forschung. 33 (10): 1411–1416. PMID 6140016.
  2. ^ US 3919231, Pelosi SS Jr, White RE, White RL Jr, Wright GC, You CN, issued 1975, assigned to Morton Norwich Products Inc 

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.