Tricyclic
Encyclopedia
Tricyclics are chemical compound
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

s that contain three interconnected rings of atom
Cyclic compound
In chemistry, a cyclic compound is a compound in which a series of atoms is connected to form a loop or ring.While the vast majority of cyclic compounds are organic, a few inorganic substances form cyclic compounds as well, including sulfur, silanes, phosphanes, phosphoric acid, and triboric acid. ...

s.

Many compounds have a tricyclic structure, but in pharmacology
Pharmacology
Pharmacology is the branch of medicine and biology concerned with the study of drug action. More specifically, it is the study of the interactions that occur between a living organism and chemicals that affect normal or abnormal biochemical function...

, the term has traditionally been reserved to describe heterocyclic drugs. Among these are antidepressant
Antidepressant
An antidepressant is a psychiatric medication used to alleviate mood disorders, such as major depression and dysthymia and anxiety disorders such as social anxiety disorder. According to Gelder, Mayou &*Geddes people with a depressive illness will experience a therapeutic effect to their mood;...

s, antipsychotic
Antipsychotic
An antipsychotic is a tranquilizing psychiatric medication primarily used to manage psychosis , particularly in schizophrenia and bipolar disorder. A first generation of antipsychotics, known as typical antipsychotics, was discovered in the 1950s...

s, and antihistamine
Antihistamine
An H1 antagonist is a histamine antagonist of the H1 receptor that serves to reduce or eliminate effects mediated by histamine, an endogenous chemical mediator released during allergic reactions...

s (as antiallergens, anti-motion sickness
Motion sickness
Motion sickness or kinetosis, also known as travel sickness, is a condition in which a disagreement exists between visually perceived movement and the vestibular system's sense of movement...

 drugs, antipruritic
Antipruritic
Antipruritics, also known as anti-itch drugs, are medications that inhibit the itching that is often associated with sunburns, allergic reactions, eczema, psoriasis, chickenpox, fungal infections, insect bites and stings like those from mosquitoes, fleas, and mites, and contact dermatitis and...

s, and hypnotic
Hypnotic
Hypnotic drugs are a class of psychoactives whose primary function is to induce sleep and to be used in the treatment of insomnia and in surgical anesthesia...

s/sedative
Sedative
A sedative or tranquilizer is a substance that induces sedation by reducing irritability or excitement....

s) of the dibenzazepine
Dibenzazepine
Dibenzazepine is a chemical compound with two benzene rings fused to an azepine group.Dibenzazepine is used as an intermediate for the synthesis of specific analgesic and antipsychotic agents....

, dibenzocycloheptene
Dibenzocycloheptene
Dibenzocycloheptene is a chemical compound featuring two benzene rings bound to a cycloheptene group.Various tricyclic antidepressants contain the dibenzocycloheptene moiety in their chemical structures, including amineptine, amitriptyline, amitriptylinoxide, butriptyline, demexiptiline,...

, dibenzothiazepine
Dibenzothiazepine
Dibenzothiazepines are chemical compounds which are derivatives of thiazepine with two benzo rings.An example is quetiapine. Another is tianeptine....

, dibenzothiepin
Dibenzothiepin
Dibenzothiepins are chemical compounds which are derivatives of thiepin with two benzo rings.Examples include dothiepin, methiothepin, and zotepine....

, phenothiazine
Phenothiazine
Phenothiazine is an organic compound that occurs in various antipsychotic and antihistaminic drugs. It has the formula S2NH. This yellow tricyclic compound is soluble in acetic acid, benzene, and ether. The compound is related to the thiazine-class of heterocyclic compounds...

, and thioxanthene
Thioxanthene
Thioxanthene is a chemical compound in which the oxygen atom in xanthene is replaced with a sulfur atom. It is also related to phenothiazine. Several of its derivatives are used as typical antipsychotics in the treatment of schizophrenia and other psychoses....

 chemical classes, and others.

History

  • Promethazine
    Promethazine
    Promethazine is a first-generation antihistamine of the phenothiazine family. The drug has anti-motion sickness, antiemetic, and anticholinergic effects, as well as a strong sedative effect and in some countries is prescribed for insomnia when benzodiazepines are contraindicated...

     and other first generation antihistamines with a tricyclic structure were discovered in the 1940s.
  • Chlorpromazine
    Chlorpromazine
    Chlorpromazine is a typical antipsychotic...

    , derived from promethazine originally as a sedative, was found to have neuroleptic properties in the early 1950s, and was the first typical antipsychotic
    Typical antipsychotic
    Typical antipsychotics are a class of antipsychotic drugs first developed in the 1950s and used to treat psychosis...

    .
  • Imipramine
    Imipramine
    Imipramine , also known as melipramine, is an antidepressant medication, a tricyclic antidepressant of the dibenzazepine group...

    , originally investigated as an antipsychotic, was discovered in the early 1950s, and was the first tricyclic antidepressant
    Tricyclic antidepressant
    Tricyclic antidepressants are heterocyclic chemical compounds used primarily as antidepressants. The TCAs were first discovered in the early 1950s and were subsequently introduced later in the decade; they are named after their chemical structure, which contains three rings of atoms...

    .
  • Antidepressants with a tetracyclic structure such as mianserin
    Mianserin
    Mianserin is a psychoactive drug of the tetracyclic antidepressant chemical class which is classified as a noradrenergic and specific serotonergic antidepressant and has antidepressant, anxiolytic, hypnotic, antiemetic, orexigenic, and antihistamine effects...

     and maprotiline
    Maprotiline
    Maprotiline is a tetracyclic antidepressant . It is a strong norepinephrine reuptake inhibitor with only weak effects on serotonin and dopamine reuptake....

     were first developed in the 1970s as tetracyclic antidepressant
    Tetracyclic antidepressant
    Tetracyclic antidepressants are a class of drugs used primarily as antidepressants that were first introduced in the 1970s. They are named after their chemical structure which contains four rings of atoms and are closely related to the tricyclic antidepressants which contain three rings of...

    s.
  • Clozapine
    Clozapine
    Clozapine is an antipsychotic medication used in the treatment of schizophrenia, and is also used off-label in the treatment of bipolar disorder. Wyatt. R and Chew...

     was introduced as the first atypical antipsychotic
    Atypical antipsychotic
    The atypical antipsychotics are a group of antipsychotic tranquilizing drugs used to treat psychiatric conditions. Some atypical antipsychotics are FDA approved for use in the treatment of schizophrenia...

     in the 1990s.
  • Loratadine
    Loratadine
    Loratadine is a second-generation H1 histamine antagonist drug used to treat allergies. Structurally, it is closely related to tricyclic antidepressants such as imipramine, and distantly related to the atypical antipsychotic quetiapine. It is marketed by Schering-Plough under several trade names...

     was introduced as a non-sedating second generation antihistamine in the 1990s.

Gallery

Antidepressants

Imipramine
Imipramine
Imipramine , also known as melipramine, is an antidepressant medication, a tricyclic antidepressant of the dibenzazepine group...


Amitriptyline
Amitriptyline
Amitriptyline is a tricyclic antidepressant . It is the most widely used TCA and has at least equal efficacy against depression as the newer class of SSRIs...


Mirtazapine
Mirtazapine
Mirtazapine is a tetracyclic antidepressant used primarily in the treatment of depression. It is also sometimes used as a hypnotic, antiemetic, and appetite stimulant, and for the treatment of anxiety, among other indications...


Iprindole
Iprindole
Iprindole , formerly known as pramindole, is a tricyclic antidepressant used in Europe for the treatment of depression. It was introduced by Wyeth and has been used clinically since 1967...


Tianeptine
Tianeptine
Tianeptine was discovered by The French Society of Medical Research in the 1960s. Under the trade-names it is a drug used for treating major depressive episodes ....

Antipsychotics

Chlorpromazine
Chlorpromazine
Chlorpromazine is a typical antipsychotic...


Thioridazine
Thioridazine
Thioridazine is a piperidine typical antipsychotic drug belonging to the phenothiazine drug group and was previously widely used in the treatment of schizophrenia and psychosis...


Chlorprothixene
Chlorprothixene
Chlorprothixene is a typical antipsychotic drug of the thioxanthene class and was the first of the series to be synthesized...


Loxapine
Loxapine
Loxapine is a typical antipsychotic medication, used primarily in the treatment of schizophrenia. It is a member of the dibenzoxazepine class and as a dibenzazepine derivative, it is structurally related to clozapine...


Clozapine
Clozapine
Clozapine is an antipsychotic medication used in the treatment of schizophrenia, and is also used off-label in the treatment of bipolar disorder. Wyatt. R and Chew...

Antihistamines

Promethazine
Promethazine
Promethazine is a first-generation antihistamine of the phenothiazine family. The drug has anti-motion sickness, antiemetic, and anticholinergic effects, as well as a strong sedative effect and in some countries is prescribed for insomnia when benzodiazepines are contraindicated...


Cyproheptadine
Cyproheptadine
Cyproheptadine , sold under the brand name Periactin, is a first-generation antihistamine with additional anticholinergic, antiserotonergic, and local anesthetic properties.- Indications :...


Latrepirdine

Loratadine
Loratadine
Loratadine is a second-generation H1 histamine antagonist drug used to treat allergies. Structurally, it is closely related to tricyclic antidepressants such as imipramine, and distantly related to the atypical antipsychotic quetiapine. It is marketed by Schering-Plough under several trade names...


Rupatadine
Rupatadine
Rupatadine is a second generation antihistamine and PAF antagonist used to treat allergies. It was discovered and developed by J. Uriach y Cia, S. A...

Others

Carvedilol
Carvedilol
Carvedilol is a non-selective beta blocker/alpha-1 blocker indicated in the treatment of mild to moderate congestive heart failure . It is marketed under various trade names including Carvil , Coreg , Dilatrend , Eucardic , and Carloc as a generic drug ., and as a...


Cyclobenzaprine
Cyclobenzaprine
Cyclobenzaprine is a muscle relaxant medication used to relieve skeletal muscle spasms and associated pain in acute musculoskeletal conditions. It is the most well-studied drug for this application, and it also has been used off-label for fibromyalgia treatment.- Mechanism of action :The mechanism...


Pizotifen
Pizotifen
Pizotifen or pizotyline , trade name Sandomigran, is a benzocycloheptene based drug used as a medicine, primarily as a preventative to reduce the frequency of recurrent migraine headaches.-Uses:...


Monatepil
Monatepil
Monatepil is a calcium channel blocker and α1-adrenergic receptor antagonist used as an antihypertensive.- References :...

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