Nomifensin

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Structural formula
Nomifensin
( R ) -isomer (left) and ( S ) -isomer (right)
General
Non-proprietary name Nomifensin
other names
  • ( RS ) -8-Amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline
  • (±) -8-Amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline
Molecular formula C 16 H 18 N 2
External identifiers / databases
CAS number
PubChem 4528
ChemSpider 4371
DrugBank DB04821
Wikidata Q409948
Drug information
ATC code

N06 AX04

Drug class

antidepressant

properties
Molar mass 238.33 g mol −1
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances

Maleate salt

07 - Warning

Caution

H and P phrases H: 302-315-319-335
P: 261-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nomifensin is an antidepressant in the group of dopamine reuptake inhibitors (DRI, DARI) that has been used to treat depression and attention deficit disorder .

Isomerism

Nomifensin contains a stereocenter and is therefore chiral . Thus there are two enantiomers, the ( R ) form and the mirror image ( S ) form. Nomifensin was obtained as a racemate [1: 1 mixture of ( R ) -8-amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline and ( S ) -8-amino-2-methyl-4 -phenyl-1,2,3,4-tetrahydroisoquinoline] is used.

history

Nomifensin was launched in 1976 by Hoechst (now Sanofi ) as Alival with the advertising slogan "Alival leads from psychological depression to active life". It was a very popular antidepressant in the 1980s, but was withdrawn from the market in 1986 because of massive side effects and deaths, such as immunological overreactions, high fever, liver dysfunction, lung infiltrates, etc. The behavior of the manufacturer led to heated discussions in public. The manufacturer informed doctors and pharmacists about deaths six months before the worldwide take-back, but emphasized that the benefits of the drug outweigh the risks.

In 2018 the BR reported that Alival was being tested on children in care under the name Nomifensin

Mechanism of action

The special mechanism of action of nomifensin is probably the inhibition of the reuptake of dopamine in the synaptic cleft in the CNS (similar to methylphenidate ). This could be the reason for its particularly good effectiveness in inhibited, low-drive depression. Nomifensin has a partial phenylethylamine structure .

Individual evidence

  1. a b Datasheet Nomifensine maleate salt from Sigma-Aldrich , accessed on April 16, 2011 ( PDF ).
  2. ^ A b c d Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , 4th edition (2000), Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .
  3. DRUGS Extremely dangerous . In: Der Spiegel . tape 6 , February 3, 1986 ( spiegel.de [accessed March 26, 2016]).
  4. Cornelia Stolze : horror of the pill-turner . The Bremen pharmacologist Peter Schönhöfer is fighting for a better supply of medicines. In: DZ from June 12, 2003.
  5. The story: How home children became test objects, https://www.youtube.com/watch?v=Q_htn25ZfnE , accessed on May 11, 2018.
  6. The story: How home children became test objects, https://www.youtube.com/watch?v=Q_htn25ZfnE , accessed on May 11, 2018.