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ing pain and the symptoms associated with mast cell activation such as ibs pain people with ibs exhibit increased mucosal mast cells elevated tryptase histamine and enhanced proximity of degranulating mast cells to enteric nerves each correlating with subjective pain scores 23 24 the ability of tricyclic antidepressants that have mast cell stabilizing effects such as amitriptyline to reduce subjective pain score are believed to help not simply by altering mood but by reducing visceral afferent firing possibly through attenuation of nerve mast cell crosstalk 23 24 25 side effects edit many side effects may be related to the antimuscarinic properties of the tcas such side effects are relatively common and may include dry mouth dry nose blurry vision lowered gastrointestinal motility or constipation urinary retention cognitive and or memory impairment and increased body temperature other side effects may include drowsiness anxiety emotional blunting apathy anhedonia confusion restlessness dizziness akathisia hypersensitivity changes in appetite and weight sweating muscle twitches weakness nausea and vomiting hypotension tachycardia and rarely irregular heart rhythms twitching hallucinations delirium and coma are also some of the toxic effects caused by overdose 26 rhabdomyolysis or muscle breakdown has been rarely reported with this class of drugs as well 27 delayed ejaculation may be experienced by some tricyclic antidepressants such as clomipramine tolerance to these adverse effects of these drugs often develops if treatment is continued side effects may also be less troublesome if treatment is initiated with low doses and then gradually increased although this may also delay the beneficial effects tcas can behave like class 1a antiarrhythmics as such they can theoretically terminate ventricular fibrillation decrease cardiac contractility and increase collateral blood circulation to ischemic heart muscle naturally in overdose they can be cardiotoxic prolonging heart rhythms and increasing myocardial irritability new research has also revealed compelling evidence of a link between long term use of anticholinergic medications like tcas and dementia 28 although many studies have investigated this link this was the first study to use a long term approach over seven years to find that dementias associated with anticholinergics may not be reversible even years after drug use stops 29 anticholinergic drugs block the action of acetylcholine which transmits messages in the nervous system in the brain acetylcholine is involved in learning and memory discontinuation edit main article antidepressant discontinuation syndrome see also tapering medicine antidepressants in general may produce withdrawal however since the term withdrawal has been linked to addiction to recreational drugs like opioids the medical profession and pharmaceutical public relations prefer that a different term be used hence discontinuation syndrome 30 discontinuation symptoms can be managed by a gradual reduction in dosage over a period of weeks or months to minimise symptoms 31 in tricyclics discontinuation syndrome symptoms include anxiety insomnia cholinergic rebound headache nausea malaise or motor disturbance 32 overdose edit main article tricyclic antidepressant overdose tca 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 it is a serious problem in the pediatric population due to their inherent toxicity 33 and the availability of these in the home when prescribed for bed wetting and depression in the event of a known or suspected overdose medical assistance should be sought immediately a number of treatments are effective in a tca overdose an overdose on tca is especially fatal as it is rapidly absorbed from the gi tract in the alkaline conditions of the small intestines as a result toxicity often becomes apparent in the first hour after an overdose however symptoms may take several hours to appear if a mixed overdose has caused delayed gastric emptying many of the initial signs are those associated to the anticholinergic effects of tcas such as dry mouth blurred vision urinary retention constipation dizziness and emesis or vomiting due to the location of norepinephrine receptors all over the body many physical signs are also associated with a tca overdose 34 anticholinergic effects altered mental status e g agitation confusion lethargy etc resting sinus tachycardia dry mouth mydriasis blurred vision fever cardiac effects hypertension early and transient should not be treated tachycardia orthostasis and hypotension arrhythmias including ventricular tachycardia and ventricular fibrillation most serious consequence ecg changes prolonged qrs qt and pr intervals cns effects syncope seizure coma myoclonus hyperreflexia convulsions drowsiness pulmonary effects hypoventilation resulting from cns depression 35 gastrointestinal effects decreased or absent bowel sounds constipation treatment of tca overdose depends on severity of symptoms initially gastric decontamination of the patient is achieved by administering either orally or via a nasogastric tube activated charcoal pre mixed with water which adsorbs the drug in the gastrointestinal tract most useful if given within 2 hours of drug ingestion other decontamination methods such as stomach pumps gastric lavage whole bowel irrigation or ipecac induced emesis are not recommended in tca poisoning if there is metabolic acidosis intravenous infusion of sodium bicarbonate is recommended by toxbase org the uk and ireland poisons advice database tcas are protein bound and become less bound in more acidic conditions so by reversing the acidosis protein binding increases and bioavailability thus decreases the sodium load may also help to reverse the na channel blocking effects of the tca interactions edit the tcas are highly metabolised by the cytochrome p450 cyp hepatic enzymes drugs that inhibit cytochrome p450 for example cimetidine methylphenidate fluoxetine antipsychotics and calcium channel blockers may produce decreases in the tcas metabolism leading to increases in their blood concentrations and accompanying toxicity 36 drugs that prolong the qt interval including antiarrhythmics 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 that have antimuscarinic properties pharmacology edit the majority of the tcas act primarily as snris by blocking the serotonin transporter sert and the norepinephrine transporter net which results in an elevation of the synaptic concentrations of these neurotransmitters and therefore an enhancement of neurotransmission 37 7 notably with the sole exception of amineptine the tcas have weak affinity for the dopamine transporter dat and therefore have low efficacy as dopamine reuptake inhibitors dris 37 both serotonin and norepinephrine have been highly implicated in depression and anxiety and it has been shown that facilitation of their activity has beneficial effects on these mental disorders 38 in addition to their reuptake inhibition many tcas also have high affinity as antagonists at the 5 ht 1 5 ht 2 39 5 ht 2a 40 and 5 ht 2c 40 5 ht 6 41 5 ht 7 42 α 1 adrenergic 39 and nmda receptors 43 and as agonists at the sigma receptors 44 σ 1 44 and σ 2 45 some of which may contribute to their therapeutic efficacy as well as their side effects 46 the tcas also have varying but typically high affinity for antagonising the h 1 39 and h 2 47 48 histamine receptors as well as the muscarinic acetylcholine receptors 39 as a result they also act as potent antihistamines and anticholinergics these properties are often beneficial in antidepressants especially with comorbid anxiety as it provides a sedative effect 49 most if not all of the tcas also potently inhibit sodium channels and l type calcium channels and therefore act as sodium channel blockers and calcium channel blockers respectively 50 51 the former property is responsible for the high mortality rate upon overdose seen with the tcas via cardiotoxicity 52 it may also be involved in their efficacy as analgesics however 53 in summary tricyclic antidepressants can act through nmda antagonism opioidergic effects sodium potassium and calcium channel blocking through interfering with the reuptake of serotonin and acting as antagonists to sham serotonin histamine alpha muscarinic receptors binding profiles edit see also tetracyclic antidepressant binding profiles the binding profiles of various tcas and some metabolites in terms of their affinities k i nm for various receptors and transporters are as follows 54 compound sert tooltip serotonin transporter net tooltip norepinephrine transporter dat tooltip dopamine transporter 5 ht 1a 5 ht 2a 5 ht 2c 5 ht 6 5 ht 7 α 1 α 2 d 2 h 1 h 2 mach tooltip muscarinic acetylcholine receptor σ 1 σ 2 amineptine 100 000 10 000 1 000 1 400 100 000 74 000 nd nd nd 100 000 100 000 100 000 13 000 nd 100 000 nd nd amitriptyline 2 8 4 3 19 35 3 250 450 18 23 4 0 65 141 93 123 4 4 24 114 690 196 1 460 0 5 1 1 66 9 6 300 nd amoxapine 58 16 4 310 nd 0 5 2 0 6 0 50 41 50 2 600 3 6 160 7 9 25 nd 1 000 nd nd butriptyline 1 360 5 100 3 940 7 000 380 nd nd nd 570 4 800 nd 1 1 nd 35 nd nd clomipramine 0 14 0 28 38 54 2 190 7 000 27 36 65 54 127 3 2 38 535 78 190 13 31 209 37 546 nd desipramine 18 163 0 63 3 5 3 190 6 400 115 350 244 748 nd 1 000 23 130 1 379 3 400 60 110 1 550 66 198 1 990 1 610 dibenzepin nd nd 10 000 10 000 1 500 nd nd nd 10 000 10 000 10 000 23 1 950 1 750 nd nd dosulepin 8 6 78 46 70 5 310 4 000 152 nd nd nd 419 2 400 nd 3 6 4 0 nd 25 26 nd nd doxepin 68 210 13 58 4 600 276 11 27 8 8 200 136 nd 24 28 1 270 360 0 09 1 23 174 23 80 nd nd imipramine 1 3 1 4 20 37 8 500 5 800 80 150 120 190 209 1 000 32 3 100 620 726 7 6 37 550 46 332 520 327 2 100 iprindole 1 620 1 260 6 530 2 800 217 280 206 nd nd 2 300 8 600 6 300 100 130 200 8 300 2 100 10 000 nd lofepramine 70 5 4 10 000 4 600 200 nd nd nd 100 2 700 2 000 245 360 4 270 67 2 520 nd maprotiline 5 800 11 12 1 000 nd 51 122 nd 50 90 9 400 350 665 0 79 2 0 776 570 nd nd norclomipramine 40 0 45 2 100 19 000 130 nd nd nd 190 1 800 1 200 450 nd 92 nd nd northiaden 192 25 2 539 2 623 141 nd nd nd 950 nd nd 25 nd 110 nd nd nortriptyline 15 18 1 8 4 4 1 140 294 5 0 41 8 5 148 nd 55 2 030 2 570 3 0 15 646 37 2 000 nd opipramol 2 200 700 3 000 10 000 120 nd nd nd 200 6 100 120 300 6 0 4 470 3 300 0 2 50 110 protriptyline 19 6 1 41 2 100 3 800 70 nd nd nd 130 6 600 2 300 7 2 25 398 25 nd nd tianeptine 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 10 000 trimipramine 149 2 110 2 450 3 780 8 000 32 537 nd nd 24 680 143 210 0 27 1 5 41 58 nd nd values are k i nm the smaller the value the more strongly the drug binds to the site for assay species and references see the individual drug articles most but not all values are for human proteins with the exception of the sigma receptors the tcas act as antagonists or inverse agonists of the receptors and as inhibitors of the transporters tianeptine is included in this list due to it technically being a tca but with a vastly different pharmacology therapeutic levels of tcas are generally in the range of about 100 to 300 ng ml or 350 to 1 100 nm 55 plasma protein binding is generally 90 or greater 55 chemistry edit there are two major groups of tcas in terms of chemical structure which most but not all tcas fall into 56 57 58 the groupings are based on the tricyclic ring system 56 57 58 they are the dibenzazepines imipramine desipramine clomipramine trimipramine lofepramine and the dibenzocycloheptadienes amitriptyline nortriptyline protriptyline butriptyline 56 57 minor tca groups based on ring system include the dibenzoxepins doxepin the dibenzothiepines dosulepin and the dibenzoxazepines amoxapine 56 57 in addition to classification based on the ring system tcas can also be usefully grouped based on the number of substitutions of the side chain amine 58 59 these groups include the tertiary amines imipramine clomipramine trimipramine amitriptyline butriptyline doxepin dosulepin and the secondary amines desipramine nortriptyline protriptyline 58 59 lofepramine is technically a tertiary amine but acts largely as a prodrug of desipramine a secondary amine and hence is more similar in profile to the secondary amines than to the tertiary amines 59 amoxapine does not have the tca side chain and hence is neither a tertiary nor secondary amine although it is often grouped with the secondary amines due to sharing more in common with them 60 in 2021 a new method was developed at the institute for bioengineering of catalonia for designing photochromic analogs of tricyclic drugs like pirenzepine via 1 isosteric replacement of the two atom bridge between the aromatic systems with an azo group and 2 opening of the central ring the authors named the strategy crypto azologization 61 new photoswitchable analogs of the tricyclic drug carbamazepine have beed developed including crypto azologues and a tricyclic direct analog 62 carbadiazocine is the first diazocine bridged azobenzene to be tested in vivo in photopharmacology and has demonstrated noninvasive analgesia with amber light in an rat model of neuropathic pain 62 history edit the tcas 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 63 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 64 research chemists quickly began to explore other derivatives of chlorpromazine the first tca reported for the treatment of depression was imipramine a dibenzazepine 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 led 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 roland kuhn in 1957 65 some testing of geigy s imipramine then known as tofranil took place at the münsterlingen hospital near konstanz 64 geigy later became ciba geigy and eventually novartis dibenzazepine derivatives are described in u s patent 3 074 931 issued 1963 01 22 by assignment to smith kline french labo...