Aniracetam

Structural formula
General
Non-proprietary name	Aniracetam
other names	1- (4-methoxybenzoyl) pyrrolidin-2-one ( IUPAC )
Molecular formula	C 12 H 13 NO 3
External identifiers / databases
EC number	615-758-3
ECHA InfoCard	100.108.230
PubChem	2196
ChemSpider	2111
DrugBank	DB04599
Wikidata	Q417630
Drug information
ATC code	N06 BX11
Drug class	Nootropics
properties
Molar mass	219.24 g · mol -1
Physical state	firmly
Melting point	121-122 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	4500 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 .

Aniracetam (trade name: Ampamet ^® (I), manufacturer: Menarini ) is a drug similar to Piracetam from the group of nootropics that is used to change cognitive functions.

Presentation and extraction

The active ingredient was developed by Hoffmann-La Roche in the 1970s . One synthesis is based on anisoyl chloride , which is reacted with 2-pyrrolidone in the presence of triethylamine .

In an alternative synthesis, anisoyl chloride is first reacted with 4-aminobutyric acid. The ring closure then takes place by reaction with thionyl chloride .

Chemical properties

Aniracetam is white; it is mostly in the form of a crystalline powder, is odorless and has a bitter taste. The solubility in water is 1.065 g / L, in methanol 25 g / L, in acetonitrile 217 g / L, in chloroform 400 g / L.

dose

The therapeutic dose is usually 750 mg twice a day.

possible side effects

Individual evidence

^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition. 2006, ISBN 0-911910-00-X , p. 108.
↑ ^a ^b ^c data sheet aniracetam from Sigma-Aldrich , accessed on June 16, 2011 ( PDF ).
↑ Patent EP 5 143 Hoffmann-La Roche 1978.
↑ Patent EP 44 088 Hoffmann-La Roche 1978.
^ ^A ^b A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications. 4th edition. Thieme 2001, ISBN 3-13-115134-X .

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition. 2006, ISBN 0-911910-00-X , p. 108.

[sigma-2] ta sheet aniracetam from Sigma-Aldrich , accessed on June 16, 2011 ( PDF ).

[3] Patent EP 5 143 Hoffmann-La Roche 1978.

[4] Patent EP 44 088 Hoffmann-La Roche 1978.

[Kleemann-5] A ^b A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances - Synthesis, Patents, Applications. 4th edition. Thieme 2001, ISBN 3-13-115134-X .