Tranylcypromine

• (±)- trans-2- phenylcyclopropylamine
• ( 1SR, 2RS )-2- phenylcyclopropylamine

N06AF04

Antidepressants

Irreversible MAOIs

44-45 ° C

79-80 ° C (about 200 Pa)

8.2

Hemisulfate

Risk

64 mg · kg -1 ( LD50, mouse, oral)

Template: Infobox chemical / molecular formula search available

Tranylcypromine ( Jatrosom N ® ) is an irreversible MAO inhibitor and an inhibitor of cytochrome P450 2A6. It is chemically related to iproniazid, which was developed to treat tuberculosis, and is used as a racemate. In 1952 this fell to its antidepressant effects, which can be explained by the inhibition of monoamine oxidase. Thus a number of endogenous amines are degraded slows ( tryptamines, serotonin, norepinephrine, epinephrine, dopamine, melatonin, phenethylamine and histamine), which then are increasingly available in the metabolic processes. The same is also true of exogenous amines such as tyramine, as occurs for example in red wine and some cheese. When consumption of such foods may under therapy with tranylcypromine to hypertensive crisis with life-threatening consequences ( cerebral hemorrhage ).

Since this requires an additional strictly tyraminarme diet must be adhered to when taking, tranylcypromine is not the drug of choice for depression. For use occurs only in treatment- resistant depression, when other antidepressants have proven ineffective. Therapeutically useful doses employed range usually between 20 and 60 mg, but some patients respond only to higher doses. Tranylcypromine can only be combined with a few other antidepressants or sympathomimetic agents, as this most serious side-effects has (blood pressure crisis, serotonin syndrome, seizures, death). However, concomitant treatment with lithium salts and some specific neuroleptics is possible. Current treatment strategies are then used when monotherapy with tranylcypromine showing yet no satisfactory treatment outcome.

Stereochemistry

Tranylcypromine has two stereogenic centers on the cyclopropane ring. Consequently may be theoretically are four stereoisomers of this substance:

• (1S, 2R )-form
• (1R, 2S )-form
• (1S, 2S )-form
• (1R, 2R )-form

The 1:1 mixture (racemate ) of the (1S, 2R) - and (1R, 2S )-form is used as a drug tranylcypromine. These two stereoisomers (more precisely, enantiomers) have the trans configuration, ie, the amino and the phenyl group are on opposite sides of the planar Cylopropanringes. The two cis- stereoisomers, that is, the (1S, 2S) - and (1R, 2R )-form have no practical significance in that the enantiomers are amino and the phenyl radical on the same side of the plane Cylopropanringes.