3,3,-Diphenylcyclobutanamine is a psychostimulant drug which was originally prepared as an antidepressant in the late 1970s.[1] It appears to inhibit the reuptake of serotonin, norepinephrine, and dopamine, and may also induce their release as well.[1] The N-methyl and N,N-dimethyl analogues of the compound are also known and are more potent.[1] All three agents produce locomotor stimulation in animal studies, with the tertiary amine being the strongest.[1]

Clinical data
ATC code
  • none
Legal status
Legal status
  • In general: uncontrolled
PubChem CID
Chemical and physical data
Molar mass223.31 g/mol g·mol−1
3D model (JSmol)


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.[2] The ketone was prepared in low yield by the reaction of diphenylketene with 2 equiv of diazomethane.[3] The latter synthesis, although low yielding, was used and the desired amines were prepared from 3,3-diphenylcyclobutanone.


Diphenylketene is produced by the elimination of hydrogen chloride from diphenylacetyl chloride in the presence of triethylamine.[4]

See also


  1. Carnmalm B; Rämsby S; Renyi AL; Ross SB; Ogren SO (January 1978). "Antidepressant agents. 9. 3,3-Diphenylcyclobutylamines, a new class of central stimulants". Journal of Medicinal Chemistry. 21 (1): 78–82. doi:10.1021/jm00199a014. PMID 22757.
  2. Wilt, J. W.; Dabek, R. A.; Welzel, K. C. (1972). "Transannular neophyl rearrangement". The Journal of Organic Chemistry. 37 (3): 425–430. doi:10.1021/jo00968a022.
  3. Michejda, C. J.; Comnick, R. W. (1975). "Acetolysis of 3,3-disubstituted cyclobutyl tosylates". The Journal of Organic Chemistry. 40 (8): 1046–1050. doi:10.1021/jo00896a010.
  4. Edward C. Taylor; Alexander McKillop & George H. Hawks. (1972). Checked by C. J. Michejda, D. D. von Riesen, R. W. Comnick, and Henry E. Baumgarten. "DIPHENYLKETENE [Ethenone, diphenyl-]". Organic Syntheses. 52: 36. doi:10.15227/orgsyn.052.0036.
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