3,3-diphenylcyclobutanamine 3,3-diphenylcyclobutanamine 3,3,-diphenylcyclobutanamine is a psychostimulant drug which was originally prepared as an antidepressant in the late 1970s. it appears to inhibit the reuptake of serotonin, norepinephrine, and dopamine, and may also induce their release as well. the n-methyl and n,n-dimethyl analogues of the compound are also known and are more potent. all three agents produce locomotor stimulation in animal studies, with the tertiary amine being the strongest. 3,3-diphenylcyclobutanamineclinical dataatc codenonelegal statuslegal status in general: uncontrolled identifiers iupac name 3,3-diphenylcyclobutan-1-amine cas number64895-45-0 ypubchem cid47486chemspider43204 yuniicn43pda78xchemical and physical dataformulac16h17nmolar mass223.319 g·mol−13d model (jsmol)interactive image smiles c1ccc(cc1)c3(c2ccccc2)cc(n)c3 inchi inchi=1s/c16h17n/c17-15-11-16(12-15,13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10,15h,11-12,17h2 ykey:iabbzbvtzrkdfw-uhfffaoysa-n y (verify) synthesis a number of methods were tried in order to construct the strained four-carbon ring. a synthesis of 3,3-diphenylcyclobutanone appeared in the literature. the ketone was prepared in low yield by the reaction of diphenylketene with 2 equiv of diazomethane. the latter synthesis, although low yielding, was used and the desired amines were prepared from 3,3-diphenylcyclobutanone. diphenylketene diphenylketene is produced by the elimination of hydrogen chloride from diphenylacetyl chloride in the presence of triethylamine. preparation of diphenylketene