Oxytocin is a naturally occurring small cyclic neuropeptide that regulates the release of hormones during the period of childbirth and breastfeeding in women, and recently it has been shown to play a pivotal role in social recognition and interactions in both genders. Furthermore, it has been suggested that oxytocin offers a potential therapeutic treatment for autism, schizophrenia and other psychiatric disorders. The significant medical applications of Oxytocin has driven efforts to improve its in vivo stability and while some improvement have been made this is often at the expense of biological activity and easy of synthesis. We aimed to develop a new route to access stable (yet biologically active) Oxytocin analogs in a one pot process from commercially available source materials. Through selective modification of the Oxytocin scaffold with perfluoro-heteroaromatics we were able to access analog structures with enhanced in vitro stability (e.g. chymotrypsin and pepsin). Our in vitro stability data and the biological profile of a perfluoro-heteroaromatic tagged Oxytocin will be presented.