The ketone dibenzosuberenone (1) is treated with hydroxylamine (2) to give its ketoxime (3). Base-catalyzed alkylation with ClCH2CH2NHCH3 (4) yields demexiptiline.[5][6]
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Tricyclic antidepressants (TCAs) are a class of medications that are used primarily as antidepressants. TCAs were discovered in the early 1950s and were marketed later in the decade. They are named after their chemical structure, which contains three rings of atoms. Tetracyclic antidepressants (TeCAs), which contain four rings of atoms, are a closely related group of antidepressant compounds.
Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. Imipramine is taken by mouth.
Desipramine, sold under the brand name Norpramin among others, is a tricyclic antidepressant (TCA) used in the treatment of depression. It acts as a relatively selective norepinephrine reuptake inhibitor, though it does also have other activities such as weak serotonin reuptake inhibitory, α1-blocking, antihistamine, and anticholinergic effects. The drug is not considered a first-line treatment for depression since the introduction of selective serotonin reuptake inhibitor (SSRI) antidepressants, which have fewer side effects and are safer in overdose.
Dibenzepin, sold under the brand name Noveril among others, is a tricyclic antidepressant (TCA) used widely throughout Europe for the treatment of depression. It has similar efficacy and effects relative to other TCAs like imipramine but with fewer side effects.
Butriptyline, sold under the brand name Evadyne among others, is a tricyclic antidepressant (TCA) that has been used in the United Kingdom and several other European countries for the treatment of depression but appears to no longer be marketed. Along with trimipramine, iprindole, and amoxapine, it has been described as an "atypical" or "second-generation" TCA due to its relatively late introduction and atypical pharmacology. It was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.
Lofepramine, sold under the brand names Gamanil, Lomont, and Tymelyt among others, is a tricyclic antidepressant (TCA) which is used to treat depression. The TCAs are so named as they share the common property of having three rings in their chemical structure. Like most TCAs lofepramine is believed to work in relieving depression by increasing concentrations of the neurotransmitters norepinephrine and serotonin in the synapse, by inhibiting their reuptake. It is usually considered a third-generation TCA, as unlike the first- and second-generation TCAs it is relatively safe in overdose and has milder and less frequent side effects.
Melitracen is a tricyclic antidepressant (TCA), for the treatment of depression and anxiety. In addition to single drug preparations, it is also available as Deanxit, marketed by Lundbeck, a combination product containing both melitracen and flupentixol.
Niaprazine (INN) is a sedative-hypnotic drug of the phenylpiperazine group. It has been used in the treatment of sleep disturbances since the early 1970s in several European countries including France, Italy, and Luxembourg. It is commonly used with children and adolescents on account of its favorable safety and tolerability profile and lack of abuse potential.
Medifoxamine, previously sold under the brand names Clédial and Gerdaxyl, is an atypical antidepressant with additional anxiolytic properties acting via dopaminergic and serotonergic mechanisms which was formerly marketed in France and Spain, as well as Morocco. The drug was first introduced in France sometime around 1990. It was withdrawn from the market in 1999 (Morocco) and 2000 (France) following incidences of hepatotoxicity.
Carpipramine is an atypical antipsychotic used for the treatment of schizophrenia and anxiety in France and Japan. In addition to its neuroleptic and anxiolytic effects, carpipramine also has hypnotic properties. It is structurally related to both tricyclics like imipramine and butyrophenones like haloperidol.
Bifemelane (INN) (Alnert, Celeport), or bifemelane hydrochloride (JAN), also known as 4-(O-benzylphenoxy)-N-methylbutylamine, is an antidepressant and cerebral activator that was widely used in the treatment of cerebral infarction patients with depressive symptoms in Japan, and in the treatment of senile dementia as well. It also appears to be useful in the treatment of glaucoma. It has been discontinued in Japan since 1998, when it was removed from the market reportedly for lack of effectiveness.
Oxaflozane (INN) (brand name Conflictan) is an antidepressant and anxiolytic drug that was introduced by Solvay in France in 1982 for the treatment of depression but has since been discontinued. It is a prodrug of flumexadol (N-dealkyloxaflozane; 2-(3-trifluoromethylphenyl)morpholine; CERM-1841 or 1841-CERM), which is reported to act as an agonist of the serotonin 5-HT1A (pKi = 7.1) and 5-HT2C (pKi = 7.5) receptors and, to a much lesser extent, of the 5-HT2A (pKi = 6.0) receptor. In addition to its serotonergic properties, oxaflozane may also produce anticholinergic side effects at high doses, namely in overdose.
Quinupramine is a tricyclic antidepressant (TCA) used in Europe for the treatment of depression.
Binedaline (also called binodaline or binedaline hydrochloride;) is a drug that was investigated as an antidepressant in the 1980s but was never marketed. It acts as a selective norepinephrine reuptake inhibitor (Ki = 25 nM), with relatively insignificant influence on the serotonin (Ki = 847 nM) and dopamine (Ki >= 2 μM) transporters. It has negligible affinity for the α-adrenergic, mACh, H1, or 5-HT2 receptors.
Noxiptiline, also known as noxiptyline and dibenzoxine, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1970s for the treatment of depression. It has imipramine-like effects, acting as a serotonin and norepinephrine reuptake inhibitor, among other properties. Of the TCAs, noxiptiline has been described as one of the most effective, rivaling amitriptyline in clinical efficacy.
Amitriptylinoxide, or amitriptyline N-oxide, is a tricyclic antidepressant (TCA) which was introduced in Europe in the 1970s for the treatment of depression.
Imipraminoxide, or imipramine N-oxide, is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1960s for the treatment of depression.
Propizepine is a tricyclic antidepressant (TCA) used in France for the treatment of depression which was introduced in the 1970s.
Pipofezine, sold under the brand name Azafen or Azaphen, is a tricyclic antidepressant approved in Russia for the treatment of depression. It was introduced in the late 1960s and is still used today.
Fluotracen (SKF-28,175) is a tricyclic drug which has both antidepressant and antipsychotic activity. This profile of effects is similar to that of related agents like amoxapine, loxapine, and trimipramine which may also be used in the treatment of both depression and psychosis. It was believed that such duality would be advantageous in the treatment of schizophrenia, as depression is often comorbid with the disorder and usual antipsychotics often worsen such symptoms. In any case, however, fluotracen was never marketed.
↑ Teste JF, Pelsy-Johann I, Decelle T, Boulu RG (1993). "Anti-immobility activity of different antidepressant drugs using the tail suspension test in normal or reserpinized mice". Fundamental & Clinical Pharmacology. 7 (5): 219–26. doi:10.1111/j.1472-8206.1993.tb00235.x. PMID8370568. S2CID24240307.
↑ Aichinger G, Behner O, Hoffmeister F, Schütz S (June 1969). "Basic tricyclic oxyiminoethers and their pharmacological properties". Arzneimittel-Forschung (in German). 19: Suppl 5a:838+. PMID5819763.
↑ US 3963778,Schütz S, Behner O, Hoffmeister F,"Basic oximes and their preparation",issued 1976-06-15, assigned to Bayer AG
Further reading
Martin A, Masson JM, Jusseaume P, Beloncle M, Voisinet C (November 1981). "[Demexiptiline in the treatment of melancholic states (reflections after 3 years of use)]". Annales médico-psychologiques (in French). 139 (9): 1023–35. PMID7337336.
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