Azabon

Azabon
Identifiers
	IUPAC name 4-(3-Azabicyclo[3.2.2]non-3-ylsulfonyl)aniline;
CAS Number	1150-20-5;
PubChem CID	14380;
ChemSpider	13739;
UNII	4IYS7OKE05;
KEGG	D03019;
ChEMBL	ChEMBL2103973;
CompTox Dashboard (EPA)	DTXSID70150925 ;
Chemical and physical data
Formula	C14H20N2O2S
Molar mass	280.386
3D model (JSmol)	Interactive image;
	SMILES c1cc(ccc1N)S(=O)(=O)N2CC3CCC(C2)CC3;
	InChI InChI=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; Key:RQBNXPJPWKUTOG-UHFFFAOYSA-N; ; InChI=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; Key:RQBNXPJPWKUTOG-UHFFFAOYAL;

Azabon is a central nervous system stimulant^[1] of the sulfonamide class^[2] that is also used as a nootropic.^[3] As it is a sulpha drug, care must be taken during administration, and certain individuals must avoid azabon altogether to prevent an allergic reaction. Despite being a sulfonamide, azabon has poor antibacterial potency, although this decreased activity is common among other benzenesulfonamides with two substituents on N₁. Azabon is synthesized from 3-azabicyclo-[2.2.2]nonane, which is itself prepared by pyrolysis of aliphatic diamine.^[4]

References

^ Mathews SM, Jiju V, Thomas I, Panicker JT, Kuriakose LS (2015-07-28). "Sulfa drugs and the skin" (PDF). World Journal of Pharmaceutical Research. 4 (10): 382–390. ISSN 2277-7105.
^ WO 2011089215, Vetter D, Rau H, "Dipeptide-based prodrug linkers for aromatic amine-containing drugs", published 28 July 2011, assigned to Ascendis Pharma AS
^ Mao F, Ni W, Xu X, Wang H, Wang J, Ji M, Li J (January 2016). "Chemical Structure-Related Drug-Like Criteria of Global Approved Drugs". Molecules. 21 (1): 75. doi:10.3390/molecules21010075. PMC 6273477. PMID 26771590.{{cite journal}}: CS1 maint: unflagged free DOI (link)
^ Lednicer D, Mitscher LA (1980). The Organic Chemistry of Drug Synthesis (PDF). Vol. 2. Wiley Interscience. p. 115. ISBN 0-471-04392-3.