Levoprotiline

Levoprotiline is a tricyclic antidepressant (TCA) that was developed in the 1970s but was never marketed. It is similar in structure to other TCAs and shares some of their effects. However, it is not currently used in clinical practice.

Chemistry

Levoprotiline is a tricyclic compound, specifically a dibenzocycloheptadiene, and possesses three rings fused together with a side chain attached at one of the ring junctions. It is a tertiary amine TCA, with its side chain-demethylated metabolite nortriptyline being a secondary amine. Other tertiary amine TCAs include amitriptyline, imipramine, dosulepin (dothiepin), doxepin, and trimipramine. The chemical name for levoprotiline is (3R)-3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-N,N,2-trimethylpropan-1-amine.

Pharmacology

Like other TCAs, levoprotiline acts as a norepinephrine reuptake inhibitor and to a lesser extent as a serotonin reuptake inhibitor, meaning it increases the levels of these neurotransmitters in the brain. It also has anticholinergic effects, which can lead to side effects such as dry mouth, constipation, and confusion.

Side Effects

The side effects of levoprotiline are similar to those of other TCAs. The most common side effects include dry mouth, blurred vision, constipation, urinary retention, and dizziness. More serious side effects may include cardiac arrhythmias, seizures, and an increased risk of suicide.

History

Levoprotiline was developed in the 1970s as a potential antidepressant. However, it was never marketed and is not currently used in clinical practice.

See Also

• Tricyclic antidepressant
• Norepinephrine reuptake inhibitor
• Serotonin reuptake inhibitor
• Anticholinergic