Tricyclic antidepressants

Amitriptyline, formerly sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat major depressive disorder, and a variety of pain syndromes such as neuropathic pain, fibromyalgia, migraine and tension headaches. Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications.

Clomipramine, sold under the brand name Anafranil among others, is a tricyclic antidepressant (TCA). It is used in the treatment of various conditions, most notably obsessive–compulsive disorder but also many other disorders, including hyperacusis, panic disorder, major depressive disorder, trichotillomania, body dysmorphic disorder and chronic pain. It has also been notably used to treat premature ejaculation and the cataplexy associated with narcolepsy.

chemical compounds used primarily as antidepressants

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.

Maprotiline, sold under the brand name Ludiomil among others, is a tetracyclic antidepressant (TeCA) that is used in the treatment of depression. It may alternatively be classified as a tricyclic antidepressant (TCA), specifically a secondary amine. In terms of its chemistry and pharmacology, maprotiline is closely related to such-other secondary-amine TCAs as nortriptyline and protriptyline and has similar effects to them, albeit with more distinct anxiolytic effects. Additionally, whereas protriptyline tends to be somewhat more stimulating and in any case is distinctly more-or-less non-sedat

Doxepin is a medication belonging to the tricyclic antidepressant (TCA) class of drugs used to treat major depressive disorder, anxiety disorders, difficult-to-treat chronic urticaria, and insomnia. For hives it is a less preferred alternative to antihistamines. It has a mild to moderate benefit for sleeping problems. It is used as a cream for itchiness due to atopic dermatitis or lichen simplex chronicus.

Nortriptyline, sold under the brand name Aventyl, among others, is a tricyclic antidepressant. This medicine is also sometimes used for neuropathic pain, attention deficit hyperactivity disorder (ADHD), smoking cessation and anxiety. Its use for young people with depression and other psychiatric disorders may be limited due to increased suicidality in the 18–24 population initiating treatment. Nortriptyline is not a preferred treatment for attention deficit hyperactivity disorder or smoking cessation. It is taken by mouth.

Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.

Trimipramine, sold under the brand name Surmontil among others, is a tricyclic antidepressant (TCA) which is used to treat depression. It has also been used for its sedative, anxiolytic, and weak antipsychotic effects in the treatment of insomnia, anxiety disorders, and psychosis, respectively. The drug is described as an atypical or "second-generation" TCA because, unlike other TCAs, it seems to be a fairly weak monoamine reuptake inhibitor. Similarly to other TCAs, however, trimipramine does have antihistamine, antiserotonergic, antiadrenergic, antidopaminergic, and anticholinergic activitie

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 has not been 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.

Amoxapine, sold under the brand name Asendin among others, is a tricyclic antidepressant (TCA). It is the N-demethylated metabolite of loxapine. Amoxapine first received marketing approval in the United States in 1980, approximately 10 to 20 years after most of the other TCAs were introduced in the United States.

Dibenzazepine (iminostilbene) is a chemical compound with two benzene rings fused to an azepine ring. Many pharmaceuticals, such as carbamazepine, oxcarbazepine, and depramine, are based on a dibenzazepine structure.

Amineptine, formerly sold under the brand name Survector among others, is an atypical antidepressant of the tricyclic antidepressant (TCA) family. It acts as a selective and mixed dopamine reuptake inhibitor and releasing agent, and to a lesser extent as a norepinephrine reuptake inhibitor.

Protriptyline, sold under the brand name Vivactil among others, is a tricyclic antidepressant (TCA), specifically a secondary amine. Uniquely among most of the TCAs, protriptyline tends to be energizing instead of sedating, and is sometimes used for narcolepsy to achieve a wakefulness-promoting effect.

Opipramol, sold under the brand name Insidon among others, is an anxiolytic and tricyclic antidepressant that is used throughout Europe. Despite chemically being a tricyclic dibenzazepine (iminostilbene) derivative similar to imipramine, opipramol is not a monoamine reuptake inhibitor like most other tricyclic antidepressants, and instead acts primarily as a sigma-1 receptor agonist. It was developed by Schindler and Blattner in 1961.

Dosulepin, also known as dothiepin and sold under the brand name Prothiaden among others, is a tricyclic antidepressant (TCA) which is used in the treatment of depression. Dosulepin was once the most frequently prescribed antidepressant in the United Kingdom, but it is no longer widely used due to its relatively high toxicity in overdose without therapeutic advantages over other TCAs. It acts as a serotonin–norepinephrine reuptake inhibitor (SNRI) and also has other activities including antihistamine, antiadrenergic, antiserotonergic, anticholinergic, and sodium channel-blocking effects.

Melitracen (brand names Melixeran, Trausabun) 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.

Iprindole, sold under the brand names Prondol, Galatur, and Tertran, is an atypical tricyclic antidepressant (TCA) that has been used in the United Kingdom and Ireland for the treatment of depression but appears to no longer be marketed. It was developed by Wyeth and was marketed in 1967. The drug has been described by some as the first "second-generation" antidepressant to be introduced. However, it was very little-used compared to other TCAs, with the number of prescriptions dispensed only in the thousands.

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.

Dimetacrine (also known as dimethacrine and acripramine; brand names Istonil, Istonyl, Linostil, and Miroistonil) is a tricyclic antidepressant (TCA) used in Europe and formerly in Japan for the treatment of depression. It has imipramine-like effects; though, in a double-blind clinical trial against imipramine, dimetacrine was found to have lower efficacy in comparison and produced more weight loss and abnormal liver tests.

Dibenzocycloheptene (also known as dibenzosuberane and dibenzocycloheptadiene) is a tricyclic chemical compound featuring two benzene rings bound to a cycloheptene group. It is an occasional motif in synthetic organic chemistry. Various tricyclic antidepressants (TCAs) contain the dibenzocycloheptene moiety in their chemical structures, including amineptine, amitriptyline, amitriptylinoxide, butriptyline, demexiptiline, nortriptyline, noxiptiline, and protriptyline. Cyclobenzaprine, a skeletal muscle relaxant, also contains this functional group.

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.

Imipraminoxide (brand names Imiprex, Elepsin), or 'imipramine N-oxide', is a tricyclic antidepressant (TCA) that was introduced in Europe in the 1960s for the treatment of depression.

Cianopramine (INN; development code Ro 11-2465; also known as 3-cyanoimipramine) is a tricyclic antidepressant related to imipramine that acts as a serotonin reuptake inhibitor and weak serotonin receptor antagonist. It was investigated for the treatment of depression but was never marketed.

Noxiptiline (brand names Agedal, Elronon, Nogedal), 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.

Demexiptiline (brand names Deparon, Tinoran) is a tricyclic antidepressant (TCA) used in France for the treatment of depression. It acts primarily as a norepinephrine reuptake inhibitor similarly to desipramine.

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

Amezepine is a tricyclic antidepressant (TCA) which was never marketed.

Depramine (INN; GP-31,406), also known as balipramine (BAN) and as 10,11-dehydroimipramine, is a tricyclic antidepressant (TCA) which was never marketed.

Amitriptylinoxide (brand names Amioxid, Ambivalon, Equilibrin), or 'amitriptyline N-oxide', is a tricyclic antidepressant (TCA) which was introduced in Europe in the 1970s for the treatment of depression.

Intriptyline is a tricyclic antidepressant (TCA) that was never marketed.

Metapramine (brand names Prodastene, Timaxel) is a tricyclic antidepressant (TCA) developed by Rhone Poulenc that was introduced for the treatment of depression in France in 1984. In addition to its efficacy against affective disorders, it also has analgesic properties, and may be useful in the treatment of pain.

Octriptyline (SC-27,123) is a tricyclic antidepressant (TCA) that was never marketed.

Propizepine (brand names Depressin, Vagran) is a tricyclic antidepressant (TCA) used in France for the treatment of depression which was introduced in the 1970s.

Cotriptyline (SD-2203-01) is a tricyclic antidepressant (TCA) which was never marketed.

Azepindole (McN-2453) is a tricyclic compound with antidepressant and antihypertensive effects that was developed in the late 1960s but was never marketed.

7-Hydroxyamoxapine is an active metabolite of the antidepressant drug amoxapine (Asendin). It contributes to amoxapine's pharmacology. It is a dopamine receptor antagonist and contributes to amoxapine's antipsychotic properties.

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.

Hepzidine (INN) is a tricyclic antidepressant which was never marketed. It was first described by 1966. ==Synthesis== The synthesis has been described in the chemical literature: 700px|center| The reduction of dibenzosuberone (1) gives dibenzosuberol [1210-34-0] (2). This alcohol forms ethers exceedingly easily, probably via the carbonium ion. Treatment with N-methyl-4-piperidinol [106-52-5] (3) in the presence of acid gives hepzidine (4).

Tampramine (AHR-9,377) is a tricyclic antidepressant (TCA) which was developed in the 1980s but was never marketed. Despite being a TCA, it acts as a selective norepinephrine reuptake inhibitor and has negligible affinity for adrenergic, histaminergic, and muscarinic receptors. It was found to be effective in the forced swim test (FST) model of depression in animal studies but is not known to have ever been trialed in humans.

Losindole (BI-27,062) is an antidepressant with a tricyclic structure. It was never marketed.

Quinupramine (brand names Kevopril, Kinupril, Adeprim, Quinuprine) is a tricyclic antidepressant (TCA) used in Europe for the treatment of depression.

Enprazepine is a tricyclic antidepressant (TCA) which was never marketed.

Ketipramine (G-35,259), also known as ketimipramine or ketoimipramine, is a tricyclic antidepressant (TCA) that was tested in clinical trials for the treatment of depression in the 1960s but was never marketed. It differs from imipramine in terms of chemical structure only by a single ketone group, and is approximately equivalent in effectiveness as an antidepressant in comparison.