Azabon
{{Short description|Chemical compound}}
{{Drugbox
| IUPAC_name = 4-(3-Azabicyclo[3.2.2]non-3-ylsulfonyl)aniline
| image = Azabon.svg
| CAS_number = 1150-20-5
| PubChem = 14380
| ChemSpiderID = 13739
| UNII = 4IYS7OKE05
| ChEMBL = 2103973
| KEGG = D03019
| chemical_formula = C14H20N2O2S
| molecular_weight = 280.386
| smiles = c1cc(ccc1N)S(=O)(=O)N2CC3CCC(C2)CC3
| StdInChI2 = 1/C14H20N2O2S/c15-13-5-7-14(8-6-13)19(17,18)16-9-11-1-2-12(10-16)4-3-11/h5-8,11-12H,1-4,9-10,15H2
| StdInChIKey2 = RQBNXPJPWKUTOG-UHFFFAOYAL
| StdInChI = 1S/C14H20N2O2S/c15-13-5-7-14(8-6-13)19(17,18)16-9-11-1-2-12(10-16)4-3-11/h5-8,11-12H,1-4,9-10,15H2
| StdInChIKey = RQBNXPJPWKUTOG-UHFFFAOYSA-N
}}
Azabon is a central nervous system stimulant of the sulfonamide class{{Cite patent | country = WO | number = 2011089215 | inventor = Vetter D, Rau H | assign1 = Ascendis Pharma AS | pubdate = 28 July 2011 | title = Dipeptide-based prodrug linkers for aromatic amine-containing drugs |url=https://patents.google.com/patent/WO2011089215A1/en}} that is also used as a nootropic.{{cite journal | vauthors = Mao F, Ni W, Xu X, Wang H, Wang J, Ji M, Li J | title = Chemical Structure-Related Drug-Like Criteria of Global Approved Drugs | journal = Molecules | volume = 21 | issue = 1 | pages = 75 | date = January 2016 | pmid = 26771590 | doi = 10.3390/molecules21010075 | pmc = 6273477 | doi-access = free }} It has poor antibacterial potency, as is common in benzenesulfonamides with two substituents on N1. It is synthesized from 3-azabicyclo-[2.2.2]nonane, itself prepared by pyrolysis of aliphatic diamine.{{Cite book|title=The Organic Chemistry of Drug Synthesis| vauthors = Lednicer D, Mitscher LA|volume=2|page=115|publisher=Wiley Interscience|year=1980|isbn=0-471-04392-3|url=https://www.mobt3ath.com/uplode/book/book-19950.pdf}}