Tranylcypromine

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Structural formula
Structural formulas of the tranylcypromine enantiomers
1: 1 mixture of (1 R , 2 S ) -enantiomer (top) and (1 S , 2 R ) -enantiomer (bottom)
General
Non-proprietary name Tranylcypromine
other names
  • (±) - trans -2-phenylcyclopropylamine
  • (1 SR , 2 RS ) -2-phenylcyclopropylamine
Molecular formula C 9 H 11 N
External identifiers / databases
CAS number
PubChem 5530
DrugBank DB00752
Wikidata Q420885
Drug information
ATC code

N06 AF04

Drug class

Antidepressants

Mechanism of action

irreversible MAO inhibitor

properties
Molar mass 133.19 g · mol -1
Physical state

firmly

Melting point

44-45 ° C

boiling point

79–80 ° C (approx. 200 Pa )

pK s value

8.2

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances

Hemisulfate

06 - Toxic or very toxic

danger

H and P phrases H: 300-311-331
P: 261-264-280-301 + 310-311
Toxicological data

64 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tranylcypromine (trade name Jatrosom et al.) Is an irreversible MAO-inhibitor and inhibitor of cytochrome P450 -2A6. It is used as a racemate . By inhibiting monoamine oxidase , a number of endogenous amines are slowly broken down ( tryptamine , serotonin , noradrenaline , adrenaline , dopamine , melatonin , phenethylamine and histamine ), which are then increasingly available during metabolic processes. However, the same also applies to exogenous amines such as tyramine , as found in red wine and some types of cheese. The consumption of such foods can lead to hypertensive crises with life-threatening consequences (cerebral haemorrhage) under therapy with tranylcypromine. The risk of developing a tyramine-induced hypertensive crisis not only depends on the dose, but also varies from patient to patient.

Since a strict low-tyramine diet must be adhered to when taking, tranylcypromine is not the drug of choice for depression. It is mainly used for therapy-resistant depression or other serious psychological disorders (such as anxiety disorders), in the treatment of which other antidepressants have proven to be ineffective. Therapeutically sensible doses are usually between 20 and 60 mg; however, some patients only respond to higher doses. Also, the drug is rarely prescribed today due to the unfavorable side effect profile: Typical side effects include dry mouth, sleep disorders and weight change and the like. a. also disorders of the blood circulation and associated general symptoms of weakness and increased sensation of cold. Rather untypical for an antidepressant, the active ingredient (similar to bupropion) can also significantly increase libido, which is due to the amphetamine component of the active ingredient.

Tranylcypromine can only be combined with a few other antidepressants or sympathomimetics , as this usually has serious side effects ( blood pressure crisis , serotonin syndrome , seizures , death). Simultaneous treatment with lithium salts and some certain neuroleptics and benzodiazepines is possible, however. These treatment strategies are used when monotherapy with tranylcypromine does not yet produce a satisfactory treatment result.

Stereochemistry

Tranylcypromine has two stereogenic centers on the cyclopropane ring . Consequently, the following four stereoisomers of this substance can theoretically exist:

  • (1 S , 2 R ) shape
  • (1 R , 2 S ) shape
  • (1 S , 2 S ) shape
  • (1 R , 2 R ) shape

The 1: 1 mixture ( racemate ) of the (1 S , 2 R ) - and the (1 R , 2 S ) form is used as the medicinal substance tranylcypromine. These two stereoisomers (more precisely: enantiomers ) have the trans configuration, i.e. That is, the amino and phenyl radicals are on opposite sides of the planar cyclopropane ring. The two cis stereoisomers, i.e. the (1 S , 2 S ) and the (1 R , 2 R ) form, have no practical significance; in this pair of enantiomers, the amino and phenyl radicals are on the same side of the planar cyclopropane ring.

Individual evidence

  1. ↑ a b c d Entry on tranylcypromine. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
  2. ↑ a b Data sheet trans-2-Phenylcyclopropylamine hemisulfate salt from Sigma-Aldrich , accessed on April 24, 2011 ( PDF ).
  3. ↑ Jatrosom Technical Information, 02/2020 . accessed on August 24, 2020

Web links

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