Cimelidine

Structural formula
General
Non-proprietary name	Cimelidine
other names	Zimeldin; ( Z ) -3- (4′-Bromophenyl) -3- (3 ′ ′ - pyridyl) dimethylallylamine; ( Z ) -3- [1- ( p -bromophenyl) -3- (dimethylamino) propenyl] pyridine; ( Z ) -3- (4-bromophenyl) - N , N -dimethyl-3-pyridin-3-ylprop-2-en-1-amine ( IUPAC );
Molecular formula	C 16 H 17 BrN 2
External identifiers / databases
PubChem	5365247
DrugBank	DB04832
Wikidata	Q203483
Drug information
ATC code	N06 AB02
Drug class	antidepressant
Mechanism of action	Serotonin reuptake inhibitors
properties
Molar mass	317.22 g · mol -1
Physical state	firmly
Melting point	196-199 ° C (dihydrochloride)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	60 mg kg −1 ( LD 50 , mouse , iv ) ; 800 mg kg −1 ( LD 50 , mouse , oral ) ; 50 mg kg −1 ( LD 50 , rat , iv ) ; 900 mg kg −1 ( LD 50 , rat , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The drug zimelidine ( trade names : Normud ^® , Zelmid ^® ) was one of the first selective serotonin reuptake inhibitors (SSRIs) that came onto the market as an antidepressant . It was withdrawn in 1983 because it led to immunotoxic damage ("zimelidine syndrome") and cases of Guillain-Barré syndrome .

From a chemical point of view, it is a bromine-containing pyridyl allylamine .

Presentation and extraction

The compound can be prepared in a three-step synthesis. In the first step, 4-bromoacetophenone is reacted with formaldehyde and dimethylamine to give 3-dimethylamino-4'-bromopropiophenone. After introducing the pyridine function by means of 3-pyridyllithium and subsequent dehydration with sulfuric acid , the target compound is obtained.

Pharmacological properties

Zimelidine is a stronger serotonin reuptake inhibitor than clomipramine , the reuptake of norepinephrine is less pronounced with this active ingredient than with imipramine .

literature

O. Benkert et al .: Effect of zimelidine (H 102/09) in depressive patients. In: drug research. No. 27 (12), 1977, pp. 2421-2423.

Web links

TREATMENT FOR DEPRESSION: SELECTIVE SEROTONIN RECOVERY INHIBITORS (SSRI) OR TRICYCLICS? In: arznei-telegram . No. 9, 1997, p. 92 and 97-98.

Individual evidence

↑ Baeckvall, J.-E .; Nordberg, RE; Nystroem, J.-E .; Hoegberg, T .; Ulff, B .: Synthesis of 3-aryl-3-pyridylallylamines related to zimelidine via palladium-catalyzed amination in J. Org. Chem. 46 (1981) 3479-3483, doi : 10.1021 / jo00330a019 .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b ^c ^d ^e A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031 -9 .

[1] Baeckvall, J.-E .; Nordberg, RE; Nystroem, J.-E .; Hoegberg, T .; Ulff, B .: Synthesis of 3-aryl-3-pyridylallylamines related to zimelidine via palladium-catalyzed amination in J. Org. Chem. 46 (1981) 3479-3483, doi : 10.1021 / jo00330a019 .

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Kleemann-3] A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications , 4th edition (2001) Thieme-Verlag Stuttgart, ISBN 978-1-58890-031 -9 .