TCA - TriCyclic Antidepressant (Wiki)

Please note: Dosage equivalents are provided for certain drugs below and are denoted as unit equivalents, i.e. one unit of drug x is roughly the equivalent as one unit of drug y, where the dosage equal to one unit varies.

The term "tricyclic antidepressant" specifically refers to the chemical structure of the compounds in question, which structurally possess three rings. Confusingly, drugs labelled as tricyclics do not always have three structural rings; they can have as few as one or as many as four. It is a classification that is often used in favour of mode descriptive categories such as SSRI and RIMA; this is in stark contrast with the status of bycyclic antidepressants and to a lesser extent tetracyclic antidepressants. They typically act on the monoamine neurotransmitters serotonin and noradrenaline but some can effect dopamine as well; in each case, the reuptake of these compounds is inhibited, thus increasing the amount of said monoamine neurotransmitters available to the neurons within the brain to soak in.

Developed in the mid 1950s, the first tricyclic antidepressant to appear was imipramine, introduced in 1960. Initially the drug had been developed in a search of a treatment for schizophrenia; the antidepressant effect was discovered by pure experimentation after it was shown to agitate psychotic patients. Tricyclics were the second family of antidepressants to be discovered, following the discovery of MAOI antidepressants. Whilst tricyclics weren't as effective as MAOI medications, they were still more than adequate as a treatment. In addition to this, the tricyclics were better tolerated by patients and fast established themselves as the gold standard treatments for depression, a position they still arguably hold today.

These medications should not typically be taken in conjunction with RIMA or MAOI antidepressants and a "cooling out" period is suggested in order to minimise the chance of a potentially serious condition known as serotonin syndrome; however, combinations are not totally out of the question.

"The tricyclic antidepressants act by inhibiting the inactivation of norepinephrine and serotonin within the brain. The tricyclics include imipramine, amitriptyline, desipramine, nortriptyline, and a number of other compounds. These drugs relieve symptoms in a high proportion (more than 70 percent) of depressed patients." - Encyclopædia Britannica

Amineptine (Wiki)

Brand names: Maneon®, Survector®
Formula: C22H28NO2
Half life: ~ 48 minutes
Single unit dose: Unknown
Recommended outpatient dose: 100mg per day [Not Verified]
Maximum outpatient dose: 200mg per day [Not Verified]

Amineptine is in usually viewed as an SNDRI antidepressant, but can also be classified as a tricyclic antidepressant as its chemical structure features three rings. It primarily inhibits the reuptake of dopamine and to a lesser extent noradrenaline as well; at higher doses it even promotes the release of dopamine. It exerts a particularly powerful and fast acting antidepressant effect on the patient concerned and acts as a stimulant, making it particularly suitable for melancholic depressive states. Due to its mode of action, amineptine was also useful in treating Parkinson's Disease.

It was introduced in 1978 and fast gained a bad reputation; although its beneficial properties are marked, it has a high capacity for abuse. Although the antidepressive effect took about a week to take hold when first started, the stimulant effect works pretty much out of the box. Although the risk of addiction is low, it is nevertheless present; women seem to be more susceptible than men.

As a result of this capacity for abuse, the drug was suspended in many countries in 1999 and largely ceased production worldwide in 2005, having gone out of patent; as a result, the medication is hard to obtain. Common side effects include sexual stimulation and an increased quality of sleep, which is odd seeing as the drug is stimulant.

Amitriptyline (Wiki)

Brand names: Adepril®, Amilit®, Amineurin®, Amiplin®, Amiprin®, Amitrip®, Amyline®, Anapsique®, Apo-Amitriptyline®, Domical®, Elatrol®, Elatrolet®, Elavil®, Enafon®, Endep®, Lantron®, Laroxyl®, Larozyl®, Miketorin®, Noriline®, Novoprotect®, Pinsaun®, Redomex®, Sarotard®, Saroten Retard®, Saroten®, Sarotena®, Sarotex®, Syneudon®, Teperin®, Trepiline®, Tridep®, Tripta®, Triptizol®, Trynol®, Tryptal®, Tryptanol®, Tryptizol®, Trytomer®, Uxen®, Vanatrip®
Formula: C20H23N
Half life: ~ 15 hours
Single unit dose: Unknown
Recommended outpatient dose: 75mg per day [Verified]
Maximum outpatient dose: 300mg per day [Verified]
No. 8 most prescribed antidepressant, 2005

This drug inhibits the reuptake of the monoamine neurotransmitters serotonin and noradrenaline fairly evenly and is useful in the treatment of depressive disorders, including those secondary to psychotic illnesses; it is also effective in the treatment of nocturnal enuresis. The drug is sedative and is therefore effective as a treatment for anxiety orientated disorders.

Amoxapine (Wiki)

Brand names: Amoxan®, Asendin®, Asendis®, Defanyl®, Demolox®, Moxadil®
Formula: C17H16ClN3O
Half life: ~ 8 hours
Single unit dose: Unknown
Recommended outpatient dose: 150mg per day [Not Verified]
Maximum outpatient dose: 600mg per day [Not Verified]

Amoxapine is classed frequently as a tricyclic antidepressant, yet it is structurally a tetracyclic drug; it is listed here for the sake of completeness. The mode of action is found in the inhibition of the monoamine neurotransmitter noradrenaline and, to a far lesser extent, the monoamine neurotransmitter serotonin.

Butriptyline (Wiki)

Brand names: Evadene®, Evadyne®
Formula: C21H27N
Half life: ~ 20 hours (not a trustworthy figure)
Single unit dose: Unknown
Recommended outpatient dose: 75mg per day
Maximum outpatient dose: 200mg per day

Butriptyline is a tricyclic antidepressant whose effects and mode of action is similar to those of the drug amitriptyline of the same family.

Clomipramine (Wiki)

Brand names: Anafranil®
Formula: C9H23CIN2
Half life: ~ 35 hours
Single unit dose: Unknown
Recommended outpatient dose: 150mg per day [Verified]
Maximum outpatient dose: 250mg per day [Verified]

A pretty standard TCA, clomipramine was developed in the 1960s and is indicated for the treatment of depressive disorders, anxiety related disorders, chronic pain and nocturnal enuresis. The drug is a stimulant and as such is useful in the treatment of narcolepsy.

Clomipramine is regarded as a gold standard drug in the treatment of compulsive disorders and is seen as an effective antidepressant in general; however, it suffers from higher seizure chances when compared to other medications of the same class - the incidence rate is 0.5% at standard doses and as high as 2% in high doses (300mg and up, higher than the maximum outpatient dose). It also causes problem during pregnancy and whilst nursing, so the benefit to cost ratio must be closely studied.

Desipramine (Wiki)

Brand names: Norpramin®, Pertofrane®
Formula: C18H22N2
Half life: ~ 21 hours
Single unit dose: Unknown
Recommended outpatient dose: 150mg per day [Not Verified]
Maximum outpatient dose: 300mg per day [Verified]

Desipramine is also known and classified as an NARI antidepressant, meaning that it selectively inhibits the reuptake of the monoamine neurotransmitter noradrenaline.

This drug inhibits the reuptake of the monoamine neurotransmitter noradrenaline. As with other similar antidepressants, desipramine has proven useful in the treatment of neuropathic pain; it may also be beneficial in the treatment of ADHD.

Dibenzepin (Wiki)

Brand names: Noveril®
Formula: C18H21N3O
Half life: ~ 63 to 68 hours
Single unit dose: Unknown
Recommended outpatient dose: 240mg per day [Highly Questionable]
Maximum outpatient dose: 560mg per day [Highly Questionable]

I have no information on this drug at this time.

Dosulepin (Dothiepin) (Wiki)

Brand names: Dothapax®, Prepadine®, Prothiaden®, Thaden®
Formula: C19H21NS
Half life: ~ 20 hours
Single unit dose: Unknown
Recommended outpatient dose: 150mg per day [Verified]
Maximum outpatient dose: 225mg per day [Verified]

Regarded as one of the few gold standard antidepressants, dosulepin is a sedative tricyclic antidepressant which is particularly effective as a treatment for anxiety related disorders and sleep disturbances secondary to depressive disorders or as a long term insomnia treatment. It can be mixed with MAOI antidepressants in dire cases, but is not advertised or recommended as such.

Doxepin (Wiki)

Brand names: Adapine®, Aponal®, Sinequan®, Sinquan®, Zonalon®
Formula: C19H21NO
Half life: ~ 17 hours
Single unit dose: Unknown
Recommended outpatient dose: 50mg per day [Not Verified]
Maximum outpatient dose: 300mg per day [Verified]

Doxepin inhibits the reuptake of the monoamine neurotransmitters serotonin and noradrenaline and to a far lesser extend dopamine as well. The drug is sedative and as such is effective against anxiety based or infected disorders; unfortunaltely, the drug also causes massive weight gain, something that should be emphasised in the decision whether to take this drug or not. Doxepin should be used with caution in cases where the patient suffers from a psychotic illness as it may potentiate the symptoms.

Imipramine (Wiki)

Brand names: Antideprin®, Antidep®, Apo-Imipramine®, Chrytemin®, Daypress®, Depsol®, Depsonil®, Ethipramine®, Fronil®, Imidol®, Imiprex®, Imiprin®, Janimine®, Melipramine®, Primonil®, Pryleugan®, Sermonil®, Talpramin®, Tofranil®, Venefon®
Formula: C17H18F3NOHCl
Half life: ~ 20 hours
Single unit dose: Unknown
Recommended outpatient dose: 75mg per day [Verified]
Maximum outpatient dose: 300mg per day [Verified]

The first tricyclic antidepressant to be developed and marketed, imipramine is regarded as a gold standard antidepressant; the drug is generally fairly neutral, but does tend towards being stimulant rather than sedative. It was initially engineered to be a treatment for psychotic disorders but proved to be impotent in that field; its antidepressant effects were discovered during those clinical trials. It is also used in the treatment of nocturnal enuresis.

Even though imipramine is one of the oldest antidepressants available, it is still used as a second or even first line treatment by more experienced psychiatrists, a testament to its effectiveness. It is thought to work by inhibiting the reuptake of the monoamine neurotransmitters serotonin and noradrenaline, which it effects in roughly equal amounts. Interestingly, when the drug enters the body, it is converted into desipramine, another antidepressant of the same family.

Common side effects include stimulation, tremor, a dry mouth, difficulties in focusing, constipation, insomnia, drowsiness, weight gain and flushes.

Iprindole (Wiki)

Brand names: Prondol®
Formula: C19H28N2
Half life: ~ 52.5 hours
Single unit dose: Unknown
Recommended outpatient dose: Unknown
Maximum outpatient dose: Unknown

All I know about this drug is that it is potentially fatal when combined with MDMA (marijuana).

Lofepramine (Wiki)

Brand names: Lomanate®
Formula: C26H27N2O
Half life: ~ 4 to 6 hours
Single unit dose: Unknown
Recommended outpatient dose: 140mg per day [Verified]
Maximum outpatient dose: 210mg per day [Verified]

Lofepramine is a sedative tricyclic antidepressant and is indicated for the treatment of depressive illnesses and sleep disorders.

Nortriptyline (Wiki)

Brand names: Allegron®, Ateben®, Aventyl®, Kareon®, Martimil®, Noritren®, Norline®, Norpress®, Nortrilen®, Nortrix®, Nortyline®, Norventyl®, Ortrip®, Pamelor®, Paxtibi®, Sensaval®, Sensival®, Vividyl®
Formula: C19H21N
Half life: ~ 25 hours
Single unit dose: Unknown
Recommended outpatient dose: 75mg per day [Verified]
Maximum outpatient dose: 200mg per day [Verified]

Seen as a second generation tricyclic antidepressant, nortriptyline is used to treat depressive illnesses, nocturnal enuresis and chronic pain. It primarily inhibits the reuptake of the monoamine neurotransmitter noradrenaline but also has an impact on serotonin as well; it has a stimulating effect and as such is effective against social withdrawal and melancholic depressive states.

Opipramol (Wiki)

Brand names: Opipramol-neuraxpharm®, Insidon®
Formula: C23H29N3O
Half life: ~ 11 hours (not a reliable figure)
Single unit dose: Unknown
Recommended outpatient dose: 150mg per day [Highly Questionable]
Maximum outpatient dose: 300mg per day [Highly Questionable]

Although not strictly an antidepressant, this drug is included for the sake of completeness. Interstingly it doesn't inhibit the reuptake of monoamine neurotransmitters yet has an anxiolytic effect on patients.

Protriptyline (Wiki)

Brand names: Vivactil®
Formula: C19H21N
Half life: ~ 74.3 hours
Single unit dose: Unknown
Recommended outpatient dose: 15mg per day [Not Verified]
Maximum outpatient dose: 60mg per day [Verified]

Indicated for the treatment of depressive disorders and ADHD, protriptyline is a tricyclic antidepressant that is very universal - it is effective against virtually every type of depressive illness typically experienced; it seems to have a minor stimulant effect.

Trimipramine (Wiki)

Brand names: Rhotrimine®, Stangyl®, Surmontil®
Formula: C20H26N2
Half life: ~ 4 to 6 days
Single unit dose: Unknown
Recommended outpatient dose: 75mg per day [Verified]
Maximum outpatient dose: 300mg per day [Verified]

A strongly sedative tricyclic antidepressant, trimipramine has a powerful anxiolytic effect on patients, making it a decent medication for depressive illnesses of the anxious type; its antidepressant effects are also very marked. Unlike most tricyclic medications, this drug exerts only weak inhibitions of monoamine neurotransmitter reuptakes; instead, it seems to exert its therapeutic effect by means of a strong postynaptic blockade.

Interestingly, this drug is one of the few treatments for insomnia that doesn't alter the stages of sleep, including REM-sleep. Happily, it also seems to brighten up the dreams experienced by patients which is no bad thing! It also exhibits antipsychotic effects, but is not as of yet established as a first or second line treatment for psychosis.

During trimipramine therapy, frequent blood pressure readings and EKG-profiles should be taken, especially at high doses. Blood tests every now and then are also a good idea and patients who are prone to seizures may also want to submit to the occasional EEG test.