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Encyclopedia > Tricyclic antidepressant
Chemical structure of the tricyclic antidepressant amitriptyline.
Chemical structure of the tricyclic antidepressant amitriptyline.

Tricyclic antidepressants (abbreviation TCA) are a class of antidepressant drugs first used in the 1950s. They are named after the drugs' molecular structure, which contains three rings of atoms (compare tetracyclic antidepressant). Image File history File links Download high-resolution version (1100x1195, 57 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Tricyclic antidepressant Amitriptyline ... Image File history File links Download high-resolution version (1100x1195, 57 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Tricyclic antidepressant Amitriptyline ... Amitriptyline (or Amitryptyline) hydrochloride (sold as Elavil, Tryptanol, Endep, Elatrol, Tryptizol, Trepiline, Laroxyl) is a tricyclic antidepressant drug. ... Prozac, a selective serotonin reuptake inhibitor (SSRI) Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant is a psychiatric medication or other substance (nutrient or herb) used for alleviating depression or dysthymia (milder depression). ... This article does not cite any references or sources. ... The 1950s decade refers to the years 1950 to 1959 inclusive. ... There are also several chemically unrelated tetracyclic antibiotics based on Tetracycline. ...

Contents

Example compounds

The first tricyclic antidepressant discovered was imipramine, which was discovered accidentally in a search for a new antipsychotic in the late 1950s. This article does not cite any references or sources. ... The term antipsychotic is applied to a group of drugs used to treat psychosis. ...


Antidepressant drugs in the tricyclic drug group (along with their actions as listed in MeSH) include: For other uses, see Mesh (disambiguation). ...

Name Brand Adrenergic uptake inhibitor Serotonin reuptake inhibitors Dopamine antagonist Histamine antagonist
amitriptyline (& butriptyline) Elavil, Endep, Tryptanol, Trepiline, Amyzol yes
amoxapine Asendin, Asendis, Defanyl, Demolox, Moxadil yes yes metabolite
clomipramine Anafranil yes
desipramine Norpramin, Pertofrane yes
dosulepin hydrochloride (dothiepin hydrochloride) Prothiaden, Thaden yes
doxepin Adapin, Sinequan yes yes
imipramine (& dibenzepin) Tofranil, Janimine yes
iprindole - yes
lofepramine Gamanil yes
nortriptyline Aventyl, Pamelor yes
opipramol Opipramol-neuraxpharm, Insidon yes
protriptyline Vivactil, Rhotrimine yes
trimipramine Surmontil yes

Note: Other sources suggest that most of the tricyclics combine adrenergic and serotonergic effects to some degree. This is often reported as selectivity ratios. Some of the above, in order from most selective for nor-epinephrine to most selective for serotonin: lofepramine, nortriptyline, amitriptyline, imipramine, clomipramine[1]. A adrenergic uptake inhibitor is a drug which blocks the reuptake of adrenergic neurotransmitters. ... Serotonin Selective serotonin reuptake inhibitors (SSRIs) are a class of antidepressants used in the treatment of depression, anxiety disorders and some personality disorders. ... A dopamine antagonist is a drug which blocks dopamine receptors (of which there are five types in the human body; they are found in the brain, peripheral nervous system, blood vessels, and the kidney). ... A histamine antagonist is an agent which serves to inhibit the release or action of histamine. ... Amitriptyline (or Amitryptyline) hydrochloride (sold as Elavil, Tryptanol, Endep, Elatrol, Tryptizol, Trepiline, Laroxyl) is a tricyclic antidepressant drug. ... Butriptyline (Dl-10,11-Dihydro-N,N,beta-trimethyl-5H-dibenzo[a,d]cycloheptene-5-propylamine) is a tricyclic antidepressant with sedative properties and uses similar to that of amitriptyline. ... Amoxapine (Asendin®; Asendis®; Defanyl®; Demolox®; Moxadil®) is a tricyclic antidepressant of the dibenzoxazepine class. ... Clomipramine (brand-name Anafranil®) is a tricyclic antidepressant. ... Desipramine is a tricyclic antidepressant (TCA) that inhibits the reuptake of norepinephrine. ... Dosulepin hydrochloride (sometimes known outside the USA as dothiepin hydrochloride) is an antidepressant of the tricyclic family. ... Categories: Antidepressants | Tricyclic antidepressants | Analgesics ... Doxepin is a tricyclic antidepressant, known under many brand-names such as Aponal®, the original preparation by Boehringer-Ingelheim, now part of the Roche group; Adapine®, Sinquan® and Sinequan® (Pfizer Inc. ... This article does not cite any references or sources. ... Dibenzepin (Noveril®) is a muscarinic antagonist. ... Iprindole (C19H28N2), a 5-HT2 antagonist, is a tricyclic antidepressant that can be fatal when combined with MDMA. Categories: | ... Lofepramine (trademarked Gamanil) is a tricyclic antidepressant prescribed primarily for sleeping and eating disorders. ... Nortriptyline is a tricyclic antidepressant marketed under the tradenames Aventyl® and Pamelor®. It is used to treat depression. ... Opipramol (Opipramol-neuraxpharm®, Insidon®), 4-[3-(5H-Dibenz[b,f]azepin-5-yl)propyl]-1-piperazinethanol, is a anxiolytic primarily used in Germany. ... Protriptyline (Vivactil®) is a tricyclic antidepressant indicated for depression and ADHD. Categories: | ... Trimipramine is an tricyclic antidepressant with sedative and anxiolytic properties. ...


Amine classification

Tricyclics are sometimes classified as tertiary amines and secondary amines. In general, the tertiary amines boost serotonin as well as nor-epinephrine (adrenergic) and produce more sedation, anticholinergic effects, and orthostatic hypotension.[2] The secondary amines act primarily on nor-epinephrine and tend to have a lower side-effect profile[3]. Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ...


Tertiary amines include: amitriptyline, imipramine, trimipramine, doxepin, clomipramine, and lofepramine.


Secondary amines include: nortriptyline, desipramine, protriptyline, and amoxapine.


Mechanism of action

The exact mechanism of action is not well understood, however it is generally thought that tricyclic antidepressants work by inhibiting the re-uptake of the neurotransmitters norepinephrine and serotonin by neurons. Tricyclics may also possess an affinity for muscarinic and histamine H1 receptors to varying degrees. Although the pharmacologic effect occurs immediately, often the patient's symptoms do not respond for 2 to 4 weeks.[4] Although norepinephrine and dopamine are generally considered stimulatory neurotransmitters, tricyclic antidepressants also increase the effects H1 histamine, and thus most have sedative effects.[5] Wikipedia does not yet have an article with this exact name. ... Chemical structure of D-aspartic acid, a common amino acid neurotransmitter. ... Norepinephrine (INN)(abbr. ... For the professional wrestling stable, see Ravens Nest#Serotonin. ... Pharmacology (in Greek: pharmakon (φάρμακον) meaning drug, and lego (λέγω) to tell (about)) is the study of how drugs interact with living organisms to produce a change in function. ... Norepinephrine (INN)(abbr. ... For other uses, see Dopamine (disambiguation). ... This article or section does not cite any references or sources. ... A sedative is a substance that depresses the central nervous system (CNS), resulting in calmness, relaxation, reduction of anxiety, sleepiness, and slowed breathing, as well as slurred speech, staggering gait, poor judgment, and slow, uncertain reflexes. ...


Chemistry of re-uptake inhibitors

The chemical action of re-uptake inhibitors in general was unknown for a long time. In August 2007, two research groups independently reported that the tricyclic molecule docks to the transporter protein in a cavity adjacent to where the neurotransmitter substrate binds, locking the substrate in place and thereby obstructing re-uptake transport.[6] For other uses, see Substrate. ...


Clinical use

Tricyclic antidepressants are used in numerous applications; mainly indicated for the treatment of clinical depression, neuropathic pain, nocturnal enuresis, and ADHD, but they have also been used successfully for headache (including migraine headache), anxiety, insomnia, smoking cessation, bulimia nervosa, irritable bowel syndrome, narcolepsy, pathological crying or laughing, persistent hiccups, interstitial cystitis, and ciguatera poisoning, and as an adjunct in schizophrenia.[4] On the Threshold of Eternity. ... Pain redirects here. ... Bedwetting (or enuresis) is involuntary urination while asleep in bed. ... DISCLAIMER Please remember that Wikipedia is offered for informational use only. ... A headache (cephalgia in medical terminology) is a condition of pain in the head; sometimes neck or upper back pain may also be interpreted as a headache. ... Anxiety is a physiological state characterized by cognitive, somatic, emotional, and behavioral components (Seligman, Walker & Rosenhan, 2001). ... This article is about the sleeping disorder. ... A No Smoking sign Smoking cessation (commonly known as quitting, or kicking the habit) is the effort to stop smoking tobacco products. ... Bulimia nervosa, commonly known as bulimia, is an eating disorder and psychological condition in which the subject engages in recurrent binge eating followed by feelings of guilt, depression, and self-condemnation and intentional purging to compensate for the excessive eating, usually to prevent weight gain (see anorexia nervosa). ... For other uses, see Narcolepsy (disambiguation). ... A hiccup is an involuntary spasm of the diaphragm. ... Interstitial cystitis (commonly abbreviated to IC) is a urinary bladder disease of unknown cause characterised by urinary frequency (as often as every 10 minutes), urgency, pressure and/or pain in the bladder and/or pelvis. ... Chemical structure of the ciguatoxin CTX1B Ciguatera is a foodborne illness poisoning in humans caused by eating marine species whose flesh is contaminated with a toxin known as ciguatoxin, which is present in many micro-organisms (particularly, the micro-algae Gambierdiscus toxicus) living in tropical waters. ...


Depression

For many years they were the first choice for pharmacological treatment of depression. Although still considered effective, they have been increasingly replaced by SSRIs and other newer drugs. Newer antidepressants are thought to have fewer side effects and are also thought to be less effective if used in a suicide attempt, as the treatment and lethal doses (see therapeutic index) are farther apart than with the tricyclic antidepressants. Tricyclic antidepressants are sometimes still used to treat refractory depression that has failed to respond to standard SSRI therapy.[7] They are not considered addictive and are preferable to the MAOIs. Side effects usually occur before depression is effectively suppressed; for this reason and via other mechanisms they can be dangerous, as volition may be increased, giving the patient greater ability to attempt suicide.[8] SSRI redirects here; for other uses, see SSRI (disambiguation). ... An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... For other uses, see Suicide (disambiguation). ... The therapeutic index of a medication is a comparison of the amount that causes the therapeutic effect to the amount that causes toxic effects. ... A term used in clinical psychiatry to describe cases of major depressive disorder that do not respond to typical modes of treatment, such as psychotherapy and common antidepressants such as SSRIs. ... MAOI redirects here. ... Volition is the study of will, choice, and decision. ...


ADHD

Tricyclic antidepressants have been shown to be effective in treating attention-deficit hyperactivity disorder.[9] ADHD is thought to be caused by dopamine and norepinephrine shortages in the brain's prefrontal cortex. Tricyclic antidepressants block the reuptake of these neurotransmitters.[10] They are commonly used in patients for whom psychostimulants (the primary medication for ADHD) are ineffective or contraindicted. TCAs are more effective in treating the behavioral aspects of ADHD than the cognitive deficits; they help limit hyperactivity and impulsivity but have little effect on attention.[11] Attention-Deficit Hyperactivity Disorder (ADHD), or Hyperkinetic Disorder as officially known in the UK though ADHD is more commonly used, is generally considered to be a developmental disorder, largely neurological in nature, affecting about 5% of the worlds population. ... For other uses, see Dopamine (disambiguation). ... Norepinephrine (INN)(abbr. ...


Analgesia

Tricyclics are also known as effective analgesics for different types of pain, especially neuropathic or neuralgic pain (like back pain in radiculitis).[12][13] A precise mechanism for their analgesic action is unknown, but it is thought that they modulate opioid systems in the CNS via an indirect serotonergic route.[14] Typically pain modification requires lower dosages than for treating depression (e.g. Amitriptyline at 10 to 30 mg rather than 75 to 150 mg). They are also effective in migraine prophylaxis, but not in relief of an acute migraine attack. This is also believed to be related to serotonergic effects. There is, however, little evidence for an analgesic effect in acute pain.[4] For other uses of painkiller, see painkiller (disambiguation) An analgesic (colloquially known as painkiller) is any member of the diverse group of drugs used to relieve pain. ... Neuropathy is usually short for peripheral neuropathy, meaning a disease of the peripheral nervous system. ... Radicular Pain, or Radiculitis, is transferred pain radiated along the dermatome (sensory distribution) of a nerve due to pressure on the radicle (nerve root; so named for its resemblance to plant roots) at its connection to the spinal column. ... An opioid is a chemical substance that has a morphine-like action in the body. ... A diagram showing the CNS: 1. ...


Nocturnal enuresis

Tricyclics with greater anti-muscarinic action (i.e., amitriptyline, imipramine and nortriptyline) may prove useful in helping to treat nocturnal enuresis (bedwetting) in children over the age of 7 years. The drug needs to be gradually withdrawn and the total treatment period is advised to be no greater than 3 months at a time. It is thought that the anticholinergic effects of tricyclics may inhibit urination, and/or the CNS stimulant effect may lead to easier arousal when the stimulus of a full bladder occurs.[15] However, one robust review of tricyclics for the treatment of enuresis found the benefits of tricyclics were relatively small and transient and due to potentially serious adverse effects suggested more research into other methods (bedwetting alarms, behavioural methods, desmopressin) which may be better suited for treatment of this condition.[16] An anticholinergic agent is a member of a class of pharmaceutical compounds which serve to reduce the effects mediated by acetylcholine in the central nervous system and peripheral nervous system. ... Amitriptyline (or Amitryptyline) hydrochloride (sold as Elavil, Tryptanol, Endep, Elatrol, Tryptizol, Trepiline, Laroxyl) is a tricyclic antidepressant drug. ... This article does not cite any references or sources. ... Nortriptyline is a tricyclic antidepressant marketed under the tradenames Aventyl® and Pamelor®. It is used to treat depression. ... Bedwetting (or enuresis) is involuntary urination while asleep in bed. ... Bedwetting Alarm Unit A bedwetting alarm is an electronic device which is used to alert children and adults that they are in the process of urinating while asleep (this is known as nocturnal enuresis). ... Desmopressin (DDAVP®, Stimate®, Minirin®) is a synthetic drug that mimics the action of antidiuretic hormone, also known as arginine vasopressin. ...


Side effects

Many side effects are related to tricyclics antimuscarinic actions. The antimuscarinic side effects are relatively common and include: An anticholinergic agent is a member of a class of pharmaceutical compounds which serve to reduce the effects mediated by acetylcholine in the central nervous system and peripheral nervous system. ...

  • Dry mouth (salivary secretion is affected)
  • Dry nose
  • Blurred vision (accommodation in the eye is affected)
  • Decreased gastro-intestinal motility and secretion. This may lead to constipation
  • Urinary retention or difficulty with urination
  • Hyperthermia

Tolerance to these adverse effects often develops if treatment is continued, side effects may also be less troublesome if treatment is initiated with low dose and then gradually increased, although this may delay the clinical effect. Constipation or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to egest; it may be extremely painful, and in severe cases (fecal impaction) lead to symptoms of bowel obstruction. ... Hyperthermia in its advanced state referred to as heat stroke or sunstroke, is an acute condition which occurs when the body produces or absorbs more heat than it can dissipate. ...


Other side effects may include drowsiness, anxiety, restlessness, cognitive and memory difficulties, confusion, dizziness, akathisia, hypersensitivity reactions, increased appetite with weight gain, sweating, decrease in sexual ability and desire, muscle twitches, weakness, nausea and vomiting, hypotension, tachycardia, and rarely, irregular heart rhythms.[4] Rhabdomyolysis or muscle breakdown has been rarely reported with this class of drugs. [1] Anxiety is a physiological state characterized by cognitive, somatic, emotional, and behavioral components (Seligman, Walker & Rosenhan, 2001). ... For other uses, see Memory (disambiguation). ... Look up Confusion in Wiktionary, the free dictionary Confusion can have the following meanings: Unclarity or puzzlement, e. ... Akathisia (or acathisia) is an often extremely unpleasant subjective sensation of inner restlessness that manifests itself with an inability to sit still or remain motionless, hence the origin of its name: Greek a (without) + kathesis (sitting). ... Hypersensitivity refers to undesirable (damaging, discomfort-producing and sometimes fatal) reactions produced by the normal immune system. ... For other uses of Muscles, see Muscles (disambiguation). ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... This article or section does not cite any references or sources. ... Cardiac arrhythmia is a group of conditions in which the muscle contraction of the heart is irregular or is faster or slower than normal. ...


Interactions

TCAs are highly metabolized by the cytochrome P450 hepatic enzymes. Drugs that inhibit cytochrome P450 (for example cimetidine, methylphenidate, antipsychotics, and calcium channel blockers) may produce decreases in the tricyclic's metabolism leading to increases in tricyclic blood concentrations and accompanying toxicity. Drugs which prolong the QT interval including antiarrythmics such as quinidine, the antihistamines astemizole and terfenadine, and some antipsychotics may increase the chance of ventricular dysrhythmias. TCAs may enhance the response to alcohol and the effects of barbiturates and other CNS depressants. Side effects may also be enhanced by other drugs which have antimuscarinic properties. [4] Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ... Cytochrome P450 Oxidase (CYP2E1) Cytochrome P450 oxidase (commonly abbreviated CYP) is a generic term for a large number of related, but distinct, oxidative enzymes (EC 1. ... Cimetidine (INN) (IPA: ) is a histamine H2-receptor antagonist that inhibits the production of acid in the stomach. ... Vitamin R redirects here. ... Calcium channel blockers are a class of drugs and natural substances with effects on many excitable cells of the body, like the muscle of the heart, smooth muscles of the vessels or neuron cells. ... Schematic representation of normal ECG trace (sinus rhythm), with waves, segments, and intervals labeled. ... Quinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent in the heart. ... Astemizole is a second generation antihistamine that has a long duration of action. ... Terfenadine is an antihistamine formerly used for the treatment of allergic conditions. ... The term antipsychotic is applied to a group of drugs used to treat psychosis. ... This article does not cite any references or sources. ... Barbituric acid, the basic structure of all barbiturates Barbiturates are drugs that act as central nervous system depressants, and by virtue of this they produce a wide spectrum of effects, from mild sedation to anesthesia. ...


Overdose

Tricyclic antidepressant overdose is a significant cause of fatal drug poisoning. The severe morbidity and mortality associated with these drugs is well documented due to their cardiovascular and neurological toxicity. Additionally, they are a serious problem in the pediatric population due to their inherent toxicity[17] and the availability of these in the home when prescribed for bed wetting and depression. For other uses, see Poison (disambiguation). ... In medicine, epidemiology and actuarial science, the term morbidity can refer to the state of being diseased (from Latin morbidus: sick, unhealthy), the degree or severity of a disease, the prevalence of a disease: the total number of cases in a particular population at a particular point in time, the... For transport in plants, see Vascular tissue. ... Neurology is a branch of medicine dealing with disorders of the nervous system. ...


Symptoms

The central nervous system and heart are the two main systems that are affected. Initial or mild symptoms include drowsiness, a dry mouth, nausea, and vomiting. More severe complications, include hypotension, cardiac rhythm disturbances, hallucinations, and seizures. Electrocardiogram (ECG) abnormalities are frequent and a wide variety of cardiac dysrhythmias can occur, the most common being sinus tachycardia and intraventricular conduction delay (QRS prolongation).[18] Seizures and cardiac dysrhythmias are the most important life threatening complications. A diagram showing the CNS: 1. ... The heart and lungs, from an older edition of Grays Anatomy. ... Somnolence (or drowsiness, or hypersomnia) is a state of near-sleep, a strong desire for sleep, or sleeping unusually long periods. ... For other uses, see Nausea (disambiguation). ... Emesis redirects here. ... In physiology and medicine, hypotension refers to an abnormally low blood pressure. ... A hallucination is a false sensory perception in the absence of an external stimulus, as distinct from an illusion, which is a misperception of an external stimulus. ... This article is about the medical condition. ... “QRS” redirects here. ... Cardiac arrhythmia is any of a group of conditions in which the electrical activity of the heart is irregular or is faster or slower than normal. ...


Toxicity

Tricyclics have a narrow therapeutic index, i.e. the therapeutic dose is close to the toxic dose. In the medical literature the lowest reported toxic dose is 6.7 mg per kg body weight, ingestions of 10 to 20 mg per kilogram of body weight are a risk for moderate to severe poisoning, although doses ranging from 1.5 to 5 mg/kg may even present a risk. Most poison control centers refer any case of TCA poisoning (especially in children) to a hospital for monitoring.[19] Factors that increase the risk of toxicity include advancing age, cardiac status, and concomitant use of other drugs.[20] However, serum drug levels are not useful for evaluating risk of arrhythmia or seizure in tricyclic overdose.[21] The therapeutic index of a medication is a comparison of the amount that causes the therapeutic effect to the amount that causes toxic effects. ... Dose can refer to: Dose (album), an album by the jam band Govt Mule Dose (song), a song by the band Filter Dose (magazine), a free daily Canadian magazine In medicine: Effective dose, the smallest amount of a substance required to produce a measurable effect on a living organism... Poison Control Centers (PCC) provide immediate, free and expert treatment advice and assistance over the telephone in case of exposure to poisonous, hazardous or toxic substances. ...


Toxic mechanism

Most of the toxic effects of TCAs are caused by four major pharmacological effects. TCAs have anticholinergic effects, cause excessive blockade of norepinephrine reuptake at the postganglionic synapse, direct alpha adrenergic blockade, and importantly they block sodium membrane channels with slowing of membrane depolarization, thus having quinidine like effects on the myocardium.[22] An anticholinergic agent is a member of a class of pharmaceutical compounds which serve to reduce the effects mediated by acetylcholine in the central nervous system and peripheral nervous system. ... Norepinephrine (INN)(abbr. ... Illustration of the major elements in a prototypical synapse. ... Quinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent in the heart. ... Myocardium is the muscular tissue of the heart. ...


Treatment

Initial treatment of an acute overdose includes gastric decontamination of the patient. This is achieved by administering activated charcoal which adsorbs the drug in the gastrointestinal tract either orally or via a nasogastric tube. Other decontamination methods such as stomach pumps, ipecac induced emesis, or whole bowel irrigation are not recommended in TCA poisoning.[23][24] Activated carbon (also called activated charcoal) is the more general term which includes material mostly derived from charcoal. ... Adsorption is a process that occurs when a liquid or gas (called adsorbate) accumulates on the surface of a solid or liquid (adsorbent), forming a molecular or atomic film (adsorbate). ... Gut redirects here. ... A nasogastric tube (NG tube) is a plastic tube, inserted into a nostril through the nose, into the throat, down the oesophagus and into the stomach. ... Gastric lavage, also commonly called a stomach pump, is the process of cleaning out the contents of the stomach. ... Syrup of Ipecac (derived from the dried rhizome and roots of the Ipecacuanha plant), is an emetic—a substance used to induce vomiting. ... Whole bowel irrigation (WBI) is a medical process involving the rapid administration of large volumes of an osmotically balanced polyethylene glycol solution (GoLYTELY®, CoLyte®), either orally or via a nasogastric tube, to flush out the entire gastrointestinal tract. ...


Symptomatic patients are usually monitored in an intensive care unit for a minimum of 12 hours, with close attention paid to maintenance of the airways, along with monitoring of blood pressure, arterial pH, and continuous ECG monitoring.[22] Supportive therapy is given if necessary, including respiratory assistance, maintenance of body temperature, and administration of sodium bicarbonate as an antidote. Sodium bicarbonate is given intravenously and it has been shown to be an effective treatment for resolving the metabolic acidosis and cardiovascular complications of TCA poisoning. If sodium bicarbonate therapy fails to improve cardiac symptoms, conventional antidysrhythmic drugs such as phenytoin and magnesium can be used to reverse any cardiac abnormalities. However, no benefit has been shown from lidocaine or other class 1a and 1c antiarrhythmic drugs; it appears they worsen the sodium channel blockade, slow conduction velocity, and depress contractility and should be avoided in TCA poisoning.[25] Hypotension is initially treated with fluids along with bicarbonate to reverse metabolic acidosis (if present), if the patient remains hypotensive despite fluids then further measures such as the administration of epinephrine, norepinephrine, or dopamine can be used to increase blood pressure.[25] Another potentially severe symptom is seizures; often seizures resolve without treatment but administration of a benzodiazepine or other anticonvulsive may be required for persistent muscular overactivity. There is no role for physostigmine in the treatment of tricyclic toxicity as it may increase cardiac toxicity and cause seizures.[22] Flash point Non-flammable. ... An antidote is a substance which can counteract a form of poisoning. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... In medicine, metabolic acidosis is a state in which the blood pH is low (under 7. ... Phenytoin sodium (marketed as Dilantin® in the USA and as Epanutin® in the UK, by Parke-Davis, now part of Pfizer) is a commonly used antiepileptic. ... General Name, symbol, number magnesium, Mg, 12 Chemical series alkaline earth metals Group, period, block 2, 3, s Appearance silvery white solid at room temp Standard atomic weight 24. ... Lidocaine (INN) (IPA: ) or lignocaine (former BAN) (IPA: ) is a common local anesthetic and antiarrhythmic drug. ... In medicine, metabolic acidosis is a state in which the blood pH is low (under 7. ... Adrenaline redirects here. ... Norepinephrine (INN)(abbr. ... For other uses, see Dopamine (disambiguation). ... Alprazolam 2 mg tablets The benzodiazepines (pronounced , or benzos for short) are a class of psychoactive drugs considered minor tranquilizers with varying hypnotic, sedative, anxiolytic, anticonvulsant, muscle relaxant and amnesic properties, which are mediated by slowing down the central nervous system. ... Physostigmine is a parasympathomimetic, specifically, an irreversible cholinesterase inhibitor obtained from the Calabar bean. ...


Tricyclic antidepressants are highly protein bound and have a large volume of distribution; therefore removal of these compounds from the blood with hemodialysis, hemoperfusion or other techniques are unlikely to be of any significant benefit.[24] The volume of distribution (VD) is a pharmacological term used to quantify the distribution of a drug throughout the body after oral or intravenous dosing. ... It has been suggested that Artificial kidney be merged into this article or section. ... Hemoperfusion (British English: haemoperfusion) is a medical process used to remove toxic substances from a patients blood. ...


Epidemiology

Studies in the 1990s in Australia and the United Kingdom showed that between 8 and 12% of drug overdoses were following TCA ingestion. TCAs may be involved in up to 33% of all fatal poisonings, second only to analgesics.[26][27]


Development history

Tricyclic antidepressants were developed amid the "explosive birth" of psychopharmacology in the early 1950s. The story begins with the synthesis of Chlorpromazine in December 1950 by Rhône-Poulenc's chief chemist, Paul Charpentier, from synthetic antihistamines developed by Rhône-Poulenc in the 1940s.[28] Its psychiatric effects were first noticed at a hospital in Paris in 1952. The first widely-used psychiatric drug, by 1955 it was already generating significant revenue as an antipsychotic.[29] Research chemists quickly began to explore other derivatives of chlorpromazine. Chlorpromazine was the first antipsychotic drug, used during the 1950s and 1960s. ... Rhône-Poulenc was a French chemical and pharmaceutical company founded in 1928 with the merger of Société Chemique des Usines du Rhône and Établissements Poulenc Frères. ... An antihistamine is a drug which serves to reduce or eliminate effects mediated by histamine, an endogenous chemical mediator released during allergic reactions, through action at the histamine receptor. ... The term antipsychotic is applied to a group of drugs used to treat psychosis. ...


The first TCA reported for the treatment of depression was imipramine, an imino-dibenzyl analogue of chlorpromazine code-named G22355. It was not originally targeted for the treatment of depression. The drug's tendency to induce manic effects was "later described as 'in some patients, quite disastrous'". The paradoxical observation of a sedative inducing mania lead to testing with depressed patients. The first trial of imipramine took place in 1955 and the first report of antidepressant effects was published by Swiss psychiatrist Ronald Kuhn in 1957.[30] Some testing of Geigy’s imipramine, then known as Tofranil, took place at the Münsterlingen Hospital near Konstanz.[31] Geigy later became Ceiba-Geigy and eventually Novartis. This article does not cite any references or sources. ... Novartis headquarters in Basel Suffern, New York: the sole Novartis pharmaceutical production facility in the United States. ...


Many patents were filed in the 1950s and 1960s concerning variations on these three-ring structures with applications to psychiatric conditions.

  • Phenothiazine derivatives are described in U.S. patent 2,591,679 issued 1952-04-08 to John W. Cusic. The compounds described contain a sulphur group on the central carbon ring, and a nitrogen atom in the cental ring to which the side chain attaches, in the manner of chlorpromazine. Most of the illustrated side chains contain an amine group.

Merck introduced the second member of the TCA family, amitriptyline (Elavil), in 1961.[32] Phenothiazines are the largest of the 5 main classes of antipsychotic drugs. ... Year 1952 (MCMLII) was a leap year starting on Tuesday (link will display full calendar) of the Gregorian calendar. ... April 8 is the 98th day of the year (99th in leap years) in the Gregorian calendar. ... Fenoldopam Galantamine Benzazepines are heterocyclic compounds consisting of a benzene ring fused to an azepine ring. ... For other uses, see 1963 (disambiguation). ... is the 22nd day of the year in the Gregorian calendar. ... GlaxoSmithKline plc (LSE: GSK NYSE: GSK) is a British based pharmaceutical, biological, and healthcare company. ... Amitriptyline (or Amitryptyline) hydrochloride (sold as Elavil, Tryptanol, Endep, Elatrol, Tryptizol, Trepiline, Laroxyl) is a tricyclic antidepressant drug. ... Merck & Co. ...


These patents cover the structures of the compounds and their mode of chemical synthesis. Understanding of their mode of action as re-uptake inhibitors and development of the serotonin theory of depression came in the years to follow.


References

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  26. ^ Thomas S, Bevan L, Bhattacharyya S, Bramble M, Chew K, Connolly J, Dorani B, Han K, Horner J, Rodgers A, Sen B, Tesfayohannes B, Wynne H, Bateman D (1996). "Presentation of poisoned patients to accident and emergency departments in the north of England". Hum Exp Toxicol 15 (6): 466-70. PMID 8793528.
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  32. ^ Becoming Neurochemical Selves, Nikolas Rose, p.3

See also

Prozac, a selective serotonin reuptake inhibitor (SSRI) Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant is a psychiatric medication or other substance (nutrient or herb) used for alleviating depression or dysthymia (milder depression). ... On the Threshold of Eternity. ... There are also several chemically unrelated tetracyclic antibiotics based on Tetracycline. ...

External links

v • d • e
Psychoanaleptics: antidepressants (N06A)
MAOIs Iproclozide • Iproniazid • Isocarboxazid • Nialamide • Pargyline • Phenelzine • Rasagiline • Selegiline • Toloxatone • Tranylcypromine
RIMAs: Brofaromine • Beta-carbolines (Harmaline) • Moclobemide
RIs
S RI SS RI (Alaproclate, Citalopram, Dapoxetine, Escitalopram, Etoperidone, Fluoxetine, Fluvoxamine, Paroxetine, Sertraline, Zimelidine)
• TCAs/Tetras (Clomipramine, Nefazodone, Trazodone)
N RI / A RI Atomoxetine • Maprotiline • Reboxetine • Viloxazine • TCAs/Tetras (Amitriptyline, Amoxapine, Butriptyline, Desipramine/Lofepramine, Dibenzepin, Dothiepin, Doxepin, Imipramine, Iprindole, Melitracen, Nortriptyline, Opipramol, Protriptyline, Trimipramine, Maprotiline)
D RI Vanoxerine • Phenmetrazine • TCAs (Amineptine)
SN RI Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Nefazodone • Venlafaxine
ND RI Bupropion
SND RI Brasofensine • Tesofensine • Nomifensine
SSREs Tianeptine
AAs Tetras (Mianserin, Mirtazapine)
Medical Subject Headings (MeSH) is a huge controlled vocabulary (or metadata system) for the purpose of indexing journal articles and books in the life sciences. ... In pharmacology, a psychoanaleptic is a medication which produces an arousing effect upon the patient. ... Prozac, a selective serotonin reuptake inhibitor (SSRI) Serotonin-norepinephrine reuptake inhibitor, Venlafaxine An antidepressant is a psychiatric medication or other substance (nutrient or herb) used for alleviating depression or dysthymia (milder depression). ... A section of the Anatomical Therapeutic Chemical Classification System containing Psychoanaleptics. ... MAOI redirects here. ... Iproclozide is a monoamine oxidase inhibitor antidepressant. ... Iproniazid is a monamine oxidase inhibitor (MAOI) that was developed as the first anti-depressant (Also first psychiatric drug). ... Isocarboxazid is a nonselective hydrazine-derived monoamine oxidase inhibitor used in treatment resistant depression. ... Nialamide (Espril®, Niamid®, Niaquitil®, Nuredal®, Nyazin®, and Psicodisten®) was one of the first MAOI (monoamine oxidase inhibitor) antidepressants. ... Pargyline is a monoamine oxidase B (MAO-B) inhibitor indicated for the treatment of moderate to severe hypertension. ... Phenelzine (brand name Nardil) is an antidepressant drug that belongs to the monoamine oxidase inhibitor (MAOI) class of drugs. ... Rasagiline (trade name Azilect®) is a irreversible inhibitor of monoamine oxidase used as a monotherapy in early Parkinsons disease or as an adjunct therapy in more advanced cases. ... Selegiline (l-deprenyl, Eldepryl® or Anipryl® [veterinary]) is a drug used for the treatment of early-stage Parkinsons disease and senile dementia. ... Toloxatone is a monoamine oxidase inhibitor antidepressant. ... Tranylcypromine (sold under the brand name Parnate®) is a monoamine oxidase inhibitor (MAOI) used as an antidepressant drug. ... These drugs, a subset of monoamine oxidase inhibitors (MAOIs), inhibit only isoenzyme A and are reversible. ... Brofarmine is a psychiatric drug primarily used to treat depression and anxiety. ... β-Carboline (9H-pyrid-[3,4-b]-indole) is an organic amine that is the prototype of a class of compounds known as β-Carbolines. ... Harmala, also known at various times as Telepathine and Banisterine, is a blanket term for a group of naturally occurring beta-carbolines including harmine, harmaline, and others. ... Moclobemide (sold as Aurorix®, Manerix®) is a psychiatric drug primarily used to treat depression and social anxiety. ... A neurotransmitter uptake inhibitor is a drug which inhibits the reuptake of the neurotransmitter, thus extending the duration of its effect. ... A serotonin uptake inhibitor is a drug which acts as a neurotransmitter uptake inhibitor on serotonin receptors. ... SSRI redirects here; for other uses, see SSRI (disambiguation). ... Alaproclate is an antidepressant that increases serotonin levels by inhibiting the uptake of 5-HT. Today, its primarily used to stagment the cravings for cocaine. ... Citalopram is an antidepressant drug used to treat depression associated with mood disorders. ... Dapoxetine is the International Nonproprietary Name of a drug currently being considered for approval by the FDA for the treatment of premature ejaculation in men, which would make it the first drug approved for such treatment. ... Lexapro pills Escitalopram (Lexapro, Lexaprin, Cipralex, Sipralexa, Entact and Seroplex)[1] is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... Etoperidone is a 5-HT agonist used primarily in the 1970s to impede the effects of LSD. ... Prozac redirects here. ... Fluvoxamine (brand name as Luvox®, Faverin®, Fevarin® and Dumyrox®) is an antidepressant which functions pharmacologically as a selective serotonin reuptake inhibitor. ... Paroxetine (Paxil, Seroxat, Pexeva) is a selective serotonin reuptake inhibitor (SSRI) antidepressant. ... Zoloft bottles, with blue and green tablets Sertraline hydrochloride (also sold under brand names Zoloft, Lustral, Apo-Sertral, Asentra, Gladem, Serlift, Stimuloton, Xydep, Serlain, Concorz) is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. ... // General Remars and History Zimelidine is a pyridylallylamine and has a structure different from other antidepressants. ... There are also several chemically unrelated tetracyclic antibiotics based on Tetracycline. ... Clomipramine (brand-name Anafranil®) is a tricyclic antidepressant. ... Nefazodone hydrochloride (trade name Serzone) is an antidepressant drug marketed by Bristol-Myers Squibb. ... Trazodone (trade names Desyrel, Molipaxin, Trittico, Thombran, Trialodine) is a psychoactive compound with sedative, anxiolytic, and antidepressant properties. ... Norepinephrine reuptake inhibitors (NRIs) are compounds that increase amounts of the neurotransmitter norepinephrine in the brain by inhibiting its reuptake at synapses. ... A adrenergic uptake inhibitor is a drug which blocks the reuptake of adrenergic neurotransmitters. ... Atomoxetine is the first non-stimulant drug approved for the treatment of attention-deficit hyperactivity disorder (ADHD). ... To meet Wikipedias quality standards, this article may require cleanup. ... Reboxetine is an antidepressant drug used in the treatment of clinical depression, panic disorder and ADD/ADHD. Its mesilate ( methanesulfonate) salt is sold under tradenames including Edronax®, Norebox®, Prolift®, Solvex® or Vestra®. Reboxetine has two chiral centers, but it only exists as two enantiomers, (R,R)-(-)- and (S,S)-(+)-reboxetine. ... Viloxazine is a bicyclic antidepressants[2] that inhibits the reuptake of serotonin, and to a lesser extent, dopamine and norepinephrine. ... There are also several chemically unrelated tetracyclic antibiotics based on Tetracycline. ... Amitriptyline (or Amitryptyline) hydrochloride (sold as Elavil, Tryptanol, Endep, Elatrol, Tryptizol, Trepiline, Laroxyl) is a tricyclic antidepressant drug. ... Amoxapine (Asendin®; Asendis®; Defanyl®; Demolox®; Moxadil®) is a tricyclic antidepressant of the dibenzoxazepine class. ... Butriptyline (Dl-10,11-Dihydro-N,N,beta-trimethyl-5H-dibenzo[a,d]cycloheptene-5-propylamine) is a tricyclic antidepressant with sedative properties and uses similar to that of amitriptyline. ... Desipramine is a tricyclic antidepressant (TCA) that inhibits the reuptake of norepinephrine. ... Lofepramine (trademarked Gamanil) is a tricyclic antidepressant prescribed primarily for sleeping and eating disorders. ... Dibenzepin (Noveril®) is a muscarinic antagonist. ... Dosulepin hydrochloride (sometimes known outside the USA as dothiepin hydrochloride) is an antidepressant of the tricyclic family. ... Doxepin is a tricyclic antidepressant, known under many brand-names such as Aponal®, the original preparation by Boehringer-Ingelheim, now part of the Roche group; Adapine®, Sinquan® and Sinequan® (Pfizer Inc. ... This article does not cite any references or sources. ... Iprindole (C19H28N2), a 5-HT2 antagonist, is a tricyclic antidepressant that can be fatal when combined with MDMA. Categories: | ... Melitracen (or melitracene) is a tricyclic antidepressant. ... Nortriptyline is a tricyclic antidepressant marketed under the tradenames Aventyl® and Pamelor®. It is used to treat depression. ... Opipramol (Opipramol-neuraxpharm®, Insidon®), 4-[3-(5H-Dibenz[b,f]azepin-5-yl)propyl]-1-piperazinethanol, is a anxiolytic primarily used in Germany. ... Protriptyline (Vivactil®) is a tricyclic antidepressant indicated for depression and ADHD. Categories: | ... Trimipramine is an tricyclic antidepressant with sedative and anxiolytic properties. ... To meet Wikipedias quality standards, this article may require cleanup. ... This does not cite any references or sources. ... Vanoxerine, also known as GBR-12909, is a piperazine derivative which is a potent and selective dopamine reuptake inhibitor. ... Phenmetrazine is an amphetamine-like drug. ... Amineptine is an atypical tricyclic antidepressant that selectively inhibits the reuptake of dopamine and to a lesser extent norepinephrine, thus exerting a powerful and fast-acting antidepressant effect. ... Serotonin Norepinephrine Serotonin-norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant used in the treatment of clinical depression and other affective disorders. ... Desvenlafaxine succinate, marketed under the name Pristiq, is an antidepressant of the serotonin-norepinephrine reuptake inhibitor class from Wyeth. ... Duloxetine (brand names Cymbalta, Yentreve, and in parts of Europe, Xeristar or Ariclaim) is a drug which primarily targets major depressive disorder (MDD), generalized anxiety disorder (GAD), pain related to diabetic peripheral neuropathy and in some countries stress urinary incontinence (SUI). ... Milnacipran is an antidepressant of the serotonin-norepinephrine reuptake inhibitor class. ... Nefazodone hydrochloride (trade name Serzone) is an antidepressant drug marketed by Bristol-Myers Squibb. ... Venlafaxine (Effexor) is an antidepressant of the serotonin-norepinephrine reuptake inhibitor (SNRI) class first introduced by Wyeth in 1993. ... A Norepinephrine-dopamine reuptake inhibitor is a class of drugs that is both: Dopamine reuptake inhibitor Norepinephrine reuptake inhibitor An example is Bupropion. ... Bupropion (INN; also amfebutamone,[1] brand names Wellbutrin, Zyban, Budeprion and Buproban) is an atypical antidepressant, which acts as a norepinephrine reuptake inhibitor and dopamine reuptake inhibitor,[2] and a nicotinic antagonist. ... Serotonin-norepinephrine-dopamine-reuptake-inhibitors (SNDRI) are a class of psychoactive antidepressants. ... Brasofensine is a serotonin-noradrenaline-dopamine reuptake inhibitor. ... Tesofensine is a serotonin-noradrenaline-dopamine reuptake inhibitor, which also seems to increase the action of acetylcholine in the brain, probably due to downstream effects. ... Nomifensine is a dopamine reuptake inhibitor that increases the amount of synaptic dopamine available to receptors by blocking dopamines re-uptake transporter. ... Tianeptine (INN) (Stablon®, Coaxil®, Tatinol®), is structurally similar to the tricyclic antidepressants. ... Tianeptine (INN) (Stablon®, Coaxil®, Tatinol®), is an SSRE, or Selective Serotonin Reuptake Enhancer, structurally similar to the tricyclic antidepressants. ... An Adrenergic antagonist is a pharmaceutical substance that acts to inhibit the action of the adrenergic receptors. ... There are also several chemically unrelated tetracyclic antibiotics based on Tetracycline. ... Mianserin is a tetracyclic antidepressant that has antihistaminic and hypnosedative, but almost no anticholinergic, effect. ... Mirtazapine is an antidepressant introduced by Organon International in 1996 used for the treatment of mild to severe depression. ...

  Results from FactBites:
 
Tricyclic antidepressant - Wikipedia, the free encyclopedia (747 words)
Tricyclic antidepressants are a class of antidepressant drugs first used in the 1950s.
These newer antidepressants are thought to have fewer side effects and are also thought to be less effective if used in a suicide attempt, as the treatment and lethal doses (see therapeutic index) are farther apart than with the tricyclic antidepressants.
Tricyclic antidepressants: {Amitriptyline} {Clomipramine} {Desipramine} {Dothiepin} {Doxepin} {Imipramine} {Lofepramine} {Nortriptyline} {Protriptyline} {Trimipramine} {Iprindole} {Opipramol}
  More results at FactBites »


 

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