Транилципромин

Description

(-)-Tranylcypromine is a levorotatory enantiomer of tranylcypromine with the (1R,2S) configuration. Structurally, it is trans-2-phenylcyclopropan-1-amine: the primary amino group and the phenyl substituent are located at neighboring atoms of the three-membered ring in the trans position. The substance belongs to cyclopropylamines and to the pharmacological group of irreversible non-selective monoamine oxidase inhibitors. The racemic mixture (CAS 155-09-9) is used as an antidepressant; a separate (-)-enantiomer is available for research purposes.

Basic Attributes

• CAS No.: 3721-26-4
• Chemical formula: C9H11N
• Molecular weight: 133.19
• Configuration: (1R,2S), trans series, levorotatory isomer
• Racemate: tranylcypromine, CAS 155-09-9

Pharmacological group and mechanism

Tranylcypromine irreversibly inhibits both forms of monoamine oxidase - MAO-A and MAO-B. The enzyme stops destroying norepinephrine, serotonin and dopamine, their concentration in brain tissue increases. The activity of the enzyme is restored only after its synthesis again. Unlike other non-selective MAO inhibitors, tranylcypromine is not a hydrazine derivative, which is associated with a lower risk of liver damage compared to phenelzine.

Stereoselectivity

Enantiomers vary in potency. According to published data, (+)-tranylcypromine with the (1S,2R) configuration inhibits MAO in vitro approximately 60 times more strongly than the (-)-isomer. In ex vivo experiments on the rat brain, with a single injection, the gap is reduced to approximately 10 times due to differences in pharmacokinetics. In a clinical observation of 10 patients receiving 5 mg per day for three days, platelet MAO-B suppression averaged 90% for the (+) form and 70% for the (-) form.

Scope of application

• standard sample for monitoring the enantiomeric purity of the substance tranylcypromine
• development of chiral separation techniques: HPLC on chiral phases, capillary electrophoresis
• studies of monoamine oxidase stereoselectivity and irreversible inhibition kinetics
• pharmacological work on the contribution of individual enantiomers to the effect of the racemate

Storage and handling

The free base is a volatile low molecular weight primary amine that oxidizes in air and absorbs carbon dioxide. Stable commercial forms are sulfate and hydrochloride. Keep the container tightly closed, in the cold, away from light. There are no product data sheets for this item; the GHS classification is based on the racemate. Work only in a fume hood, wearing gloves and safety glasses.