Benzocycloheptenes are cycloheptenes with additional benzene rings attached. Most have two benzene rings, and are called dibenzocycloheptenes.
Some benzocycloheptenes and substituted benzocycloheptenes have medical uses as antihistamines, anticholinergics, antidepressants, and antiserotonergics.
Examples include:
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.
Tetracyclic antidepressants (TeCAs) are a class of antidepressants that were first introduced in the 1970s. They are named after their tetracyclic chemical structure, containing four rings of atoms, and are closely related to the tricyclic antidepressants (TCAs), which contain three rings of atoms.
H1 antagonists, also called H1 blockers, are a class of medications that block the action of histamine at the H1 receptor, helping to relieve allergic reactions. Agents where the main therapeutic effect is mediated by negative modulation of histamine receptors are termed antihistamines; other agents may have antihistaminergic action but are not true antihistamines.
Brompheniramine, sold under the brand name Dimetapp among others, is a first-generation antihistamine drug of the propylamine (alkylamine) class. It is indicated for the treatment of the symptoms of the common cold and allergic rhinitis, such as runny nose, itchy eyes, watery eyes, and sneezing. Like the other first-generation drugs of its class, it is considered a sedating antihistamine.
Chlorphenamine, also known as chlorpheniramine, is an antihistamine used to treat the symptoms of allergic conditions such as allergic rhinitis. It is taken orally. The medication takes effect within two hours and lasts for about 4-6 hours.
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.
Doxepin is a medication belonging to the tricyclic antidepressant (TCA) class of drugs used to treat major depressive disorder, anxiety disorders, chronic hives, 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.
Zimelidine was one of the first selective serotonin reuptake inhibitor (SSRI) antidepressants to be marketed. It is a pyridylallylamine, and is structurally different from other antidepressants.
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 activities.
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.
Pizotifen (INN) or pizotyline (USAN), trade name Sandomigran, is a benzocycloheptene-based drug used as a medicine, primarily as a preventive to reduce the frequency of recurrent migraine headaches.
Chlorcyclizine is a first-generation antihistamine of the diphenylmethylpiperazine group marketed in the United States and certain other countries. It is used primarily to treat allergy symptoms such as rhinitis, urticaria, and pruritus, and may also be used as an antiemetic. In addition to its antihistamine effects, chlorcyclizine has some anticholinergic, antiserotonergic, and local anesthetic properties. It has been studied as a potential treatment for various flaviviruses like hepatitis C and Zika virus.
Antihistamines are drugs which treat allergic rhinitis, common cold, influenza, and other allergies. Typically, people take antihistamines as an inexpensive, generic drug that can be bought without a prescription and provides relief from nasal congestion, sneezing, or hives caused by pollen, dust mites, or animal allergy with few side effects. Antihistamines are usually for short-term treatment. Chronic allergies increase the risk of health problems which antihistamines might not treat, including asthma, sinusitis, and lower respiratory tract infection. Consultation of a medical professional is recommended for those who intend to take antihistamines for longer-term use.
Antazoline is a 1st generation antihistamine with anticholinergic properties used to relieve nasal congestion and in eye drops, usually in combination with naphazoline, to relieve the symptoms of allergic conjunctivitis. To treat allergic conjunctivitis, antazoline can be combined in a solution with tetryzoline. The drug is a Histamine H1 receptor antagonist: selectively binding to but not activating the receptor, thereby blocking the actions of endogenous histamine and subsequently leading to the temporary relief of the negative symptoms brought on by histamine.
Bromazine, sold under the brand names Ambodryl, Ambrodil, and Deserol among others, also known as bromodiphenhydramine, is an antihistamine and anticholinergic medication of the ethanolamine class. It is an analogue of diphenhydramine with a bromine substitution on one of the phenyl rings.
Homochlorcyclizine (INN) is an antihistamine of the diphenylmethylpiperazine group which has been marketed in Japan since 1965. It is used in the treatment of allergies and other conditions. It also has some anticholinergic, antidopaminergic, and antiserotonergic properties.
Setastine (Loderix) is an antihistamine used to treat allergies and rhinitis.
Bisulepin is strong and relatively selective antihistamine (H1 antagonist) with hypnotic, antiadrenergic and very weak anticholinergic and antiserotonergic effects. Bisulepin is marketed in the Czech Republic and Slovakia under the trademark Dithiaden as tablets and injections.
Amixetrine (INN) is a drug that was formerly marketed in France but is now no longer sold. According to various sources it has been said to be an anti-inflammatory, antidepressant, antispasmodic, anticholinergic, antihistamine, and antiserotonergic, but its definitive indications and pharmacology are unclear. The drug was first synthesized in 1969 and was introduced in France in 1972.
Daledalin (UK-3557-15) is an antidepressant which was synthesized and trialed for depression in the early 1970s, but was never marketed. It is a selective norepinephrine reuptake inhibitor, with no significant effects on the reuptake of serotonin and dopamine, and no antihistamine or anticholinergic properties.
