| Verifiedrevid: | 477217189 |
| Iupac Name: | 3,3-diphenylcyclobutan-1-amine |
| Legal Status: | Uncontrolled |
| Cas Number: | 64895-45-0 |
| Unii: | CN43PDA78X |
| Atc Prefix: | none |
| Pubchem: | 47486 |
| Chemspiderid: | 43204 |
| C: | 16 |
| H: | 17 |
| N: | 1 |
| Smiles: | c1ccc(cc1)C3(c2ccccc2)CC(N)C3 |
| Stdinchi: | 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 |
| Stdinchikey: | IABBZBVTZRKDFW-UHFFFAOYSA-N |
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]
A number of methods were tried in order to construct the strained four-carbon ring. A synthesis of 3,3-diphenylcyclobutanoneappeared 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]