3,3,-Diphenylcyclobutanamine is a

psychostimulant Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

which was originally prepared as an

antidepressant Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common side-effects of antidepressants include dry mouth, weight gain, dizziness, hea ...

in the late 1970s. It appears to inhibit the reuptake of

serotonin Serotonin () or 5-hydroxytryptamine (5-HT) is a monoamine neurotransmitter. Its biological function is complex and multifaceted, modulating mood, cognition, reward, learning, memory, and numerous physiological processes such as vomiting and vas ...

norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as both a hormone and neurotransmitter. The name "noradrenaline" (from Latin '' ad'', ...

, and

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic compound, organic chemical of the catecholamine and phenethylamine families. Dopamine const ...

, and may also induce their

release Release may refer to: * Art release, the public distribution of an artistic production, such as a film, album, or song * Legal release, a legal instrument * News release, a communication directed at the news media * Release (ISUP), a code to ident ...

as well. The ''N''-

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...

and ''N'',''N''-dimethyl analogues of the compound are also known and are more potent. All three agents produce

locomotor stimulation Attention deficit hyperactivity disorder (ADHD) is a neurodevelopmental disorder characterised by excessive amounts of inattention, hyperactivity, and impulsivity that are pervasive, impairing in multiple contexts, and otherwise age-inappr ...

in animal studies, with the tertiary amine being the strongest.

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 Diphenylketene is a chemical substance of the ketene family. Diphenylketene, like most disubstituted ketenes, is a red-orange oil at room temperature and pressure. Due to the successive double bonds in the ketene structure R1R2C=C=O, diphenyl kete ...

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 Triethylamine is the chemical compound with the formula N(CH2CH3)3, commonly abbreviated Et3N. It is also abbreviated TEA, yet this abbreviation must be used carefully to avoid confusion with triethanolamine or tetraethylammonium, for which TEA ...

. :

References

{{DEFAULTSORT:Diphenylcyclobutanamine, 3,3- Amines Antidepressants Stimulants Cyclobutanes Benzhydryl compounds

Synthesis

Diphenylketene

See also

References