Dibenzocycloheptenes
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Dibenzocycloheptenes
Preferably called dibenzosuberane (other less common names are Dibenzocycloheptene 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. Numbering System See also * Dibenzazepine * Dibenzothiepin * Dibenzoxepin * Dibenzothiazepine Dibenzothiazepines are chemical compounds which are derivatives of thiazepine with two benzene rings. Examples include quetiapine, tianeptine Tianeptine, sold under the brand names Stablon and Coaxil among others, is an atypical antidepressa ... External links * References Tricyclic antide ...
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Dibenzosuberane Numbering System
Preferably called dibenzosuberane (other less common names are Dibenzocycloheptene 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. Numbering System See also * Dibenzazepine * Dibenzothiepin * Dibenzoxepin * Dibenzothiazepine Dibenzothiazepines are chemical compounds which are derivatives of thiazepine with two benzene rings. Examples include quetiapine, tianeptine Tianeptine, sold under the brand names Stablon and Coaxil among others, is an atypical antidepressa ... External links * References Tricyclic antide ...
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Demexiptiline
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. Synthesis The synthesis is similar to that reported for Noxiptiline but also differs in a couple of respects. The condensation between Dibenzosuberenone 222-33-5(1) and hydroxylamine Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–43 ... (2) gives the oxime, 021-91-6(3). Base catalyzed attachment of the sidechain by reaction with 2-Chloro-N-Methylethanamine 2315-92-7(4) completed the synthesis of demexiptiline (5). References Further reading * Dibenzocycloheptenes Ketoximes Tricyclic antidepressants {{nervous-system-drug-stub ...
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Cyclobenzaprine
Cyclobenzaprine (sold under the brand name Flexeril, among others) is a medication used for muscle spasms from musculoskeletal conditions of sudden onset. It is not useful in cerebral palsy. It is taken by mouth. Use is not recommended for more than a few weeks. Common side effects include headache, feeling tired, dizziness, and dry mouth. Serious side effects may include an irregular heartbeat. There is no evidence of harm in pregnancy, but it has not been well studied in this population. It should not be used with an MAO inhibitor. How it works is unclear. Cyclobenzaprine was approved for medical use in the United States in 1977. It is available as a generic medication. In 2020, it was the 39th most commonly prescribed medication in the United States, with more than 16million prescriptions. It was not available in the United Kingdom as of 2012. Medical use Cyclobenzaprine is used, in conjunction with physical therapy, to treat muscle spasms that occur because of acute m ...
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Amineptine
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. Amineptine was developed by the French Society of Medical research in the 1960s. Introduced in France in 1978 by the pharmaceutical company Servier, amineptine soon gained a reputation for abuse due to its short-lived, but pleasant, stimulant effect experienced by some patients. After its release into the European market, cases of hepatotoxicity emerged, some serious. This, along with the potential for abuse, led to the suspension of the French marketing authorization for Survector in 1999. Amineptine was never approved by the U.S. Food and Drug Administration (FDA) for marketing in the United States, meaning that it is not legal to market or sell amineptine for any medical uses in the U.S ...
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Amitriptyline
Amitriptyline, sold under the brand name Elavil among others, is a tricyclic antidepressant primarily used to treat cyclic vomiting syndrome (CVS), major depressive disorder and a variety of pain syndromes from neuropathic pain to fibromyalgia to migraine and tension headaches. Due to the frequency and prominence of side effects, amitriptyline is generally considered a second-line therapy for these indications. The most common side effects are dry mouth, drowsiness, dizziness, constipation, and weight gain. Of note is sexual dysfunction, observed primarily in males. Glaucoma, liver toxicity and abnormal heart rhythms are rare but serious side effects. Blood levels of amitriptyline vary significantly from one person to another, and amitriptyline interacts with many other medications potentially aggravating its side effects. Amitriptyline was discovered in the late 1950s by scientists at Merck and approved by the US Food and Drug Administration (FDA) in 1961. It is on th ...
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Amitriptylinoxide
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. Amitriptylinoxide is both an analogue and metabolite of amitriptyline, and has similar effects as well as equivalent efficacy as an antidepressant. However, it has a faster onset of action and fewer adverse effects, including reduced drowsiness, sedation, anticholinergic symptoms like dry mouth, sweating, and dizziness, orthostatic hypotension, and cardiotoxicity. In receptor binding assays, amitriptylinoxide was found to have generally equivalent pharmacology to amitriptyline, acting as a serotonin and norepinephrine reuptake inhibitor, serotonin receptor antagonist, and H1 receptor antagonist, among other properties, but with approximately 60-fold lower affinity for the α1-adrenergic receptor, and the weakest affinity of any of the TCAs analyzed for the muscarini ...
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Butriptyline
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. Medical uses Butriptyline was used in the treatment of depression. It was usually used at dosages of 150–300 mg/day. Side effects Butriptyline is closely related to amitriptyline, and produces similar effects as other TCAs, but its side effects like sedation are said to be reduced in severity and it has a lower risk of interactions with other medications. Butriptyline has potent antihistamine effects, resulting in sedation and somno ...
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Nortriptyline
Nortriptyline, sold under the brand name Pamelor, among others, is a medication used to treat depression. This medicine is used for: neuropathic pain, attention deficit hyperactivity disorder (ADHD), smoking cessation and anxiety. As with many antidepressants, 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 a less preferred treatment for ADHD and stopping smoking. It is taken by mouth. Common side effects include dry mouth, constipation, blurry vision, sleepiness, low blood pressure with standing, and weakness. Serious side effects may include seizures, an increased risk of suicide in those less than 25 years of age, urinary retention, glaucoma, mania, and a number of heart issues. Nortriptyline may cause problems if taken during pregnancy. Use during breastfeeding appears to be relatively safe. It is a tricyclic antidepressant (TCA) and is believed ...
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Noxiptiline
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. Synthesis Ths synthesis is similar to that for Demexiptiline. The condensation of dibenzosuberone (1) with hydroxylamine Hydroxylamine is an inorganic compound with the formula . The material is a white crystalline, hygroscopic compound.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–43 ... (2) gives the corresponding oxime 785-74-6(3). This is then reacted with 2-(dimethylamine)ethyl chloride 584-46-7(4). References Dibenzocycloheptenes Dimethylamino ...
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Protriptyline
Protriptyline, sold under the brand name Vivactil among others, is a tricyclic antidepressant (TCA), specifically a secondary amine, indicated for the treatment of depression and attention-deficit hyperactivity disorder (ADHD). 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. TCAs including protriptyline are also used to reduce the incidence of recurring headaches such as migraine, and for other types of chronic pain. Medical uses Protriptyline is used primarily to treat depression and to treat the combination of symptoms of anxiety and depression.DURAMED PHARMACEUTICALS, INC., . (Ed.). (2007). Protriptyline drug facts. Pomona, New York : Barr Pharmaceuticals, Inc. Like most antidepressants of this chemical and pharmacological class, protriptyline has also been used in limited numbers of patients to treat panic disorder, obsessive-compulsive disorder, atte ...
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Dibenzothiazepine
Dibenzothiazepines are chemical compounds which are derivatives of thiazepine with two benzene rings. Examples include quetiapine, tianeptine, and metiapine Metiapine is a typical antipsychotic medication of the dibenzothiazepine group. There is scarce research on the safety and efficacy of metiapine in humans, though limited human trials exist. Medical uses Metiapine has been investigated for the t .... References Dibenzothiazepines {{heterocyclic-stub ...
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Dibenzoxepin
Dibenzoxepin, or dibenz 'b'',''e''xepin, is a tricyclic compound. It is the parent structure of certain drugs such as the tricyclic antidepressant doxepin and the analgesic fluradoline. The former is the only tricyclic antidepressant that is a dibenzoxepin. See also * Dibenzazepine * Dibenzocycloheptene * Dibenzothiepin * Dibenzothiazepine Dibenzothiazepines are chemical compounds which are derivatives of thiazepine with two benzene rings. Examples include quetiapine, tianeptine Tianeptine, sold under the brand names Stablon and Coaxil among others, is an atypical antidepressa ... References Dibenzoxepins {{organic-compound-stub ...
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