Rolziracetam

Rolziracetam
Clinical data
Other names	2,6,7,8-tetrahydro-1H-pyrrolizine-3,5-dione, CI 911 & Lukes-Šorm dilactam.
Routes of; administration	Oral
ATC code	none;
Legal status
Legal status	AU: S4 (Prescription only); US: Unscheduled;
Identifiers
	IUPAC name dihydro-1H-pyrrolizine-3,5(2H,6H)-dione;
CAS Number	18356-28-0 ;
PubChem CID	71893;
ChemSpider	64906 ;
UNII	RES9I0LGG5;
ChEMBL	ChEMBL51396 ;
CompTox Dashboard (EPA)	DTXSID80171444 ;
Chemical and physical data
Formula	C7H9N2O2
Molar mass	153.161 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N1C(=O)CCC1CC2;
	InChI InChI=1S/C7H9NO2/c9-6-3-1-5-2-4-7(10)8(5)6/h5H,1-4H2 ; Key:IEZDOKQWPWZVQF-UHFFFAOYSA-N ;
	(what is this?) (verify)

Rolziracetam is a nootropic drug of the racetam family.

Rolziracetam was found to improve performance on a delayed-response task in aged rhesus monkeys. It has a wide margin of safety in animals and has been evaluated for use in cognitively impaired human subjects.^[1]

Synthesis[edit]

dimethyl 4-nitropimelate [7766-83-8] (1)
methyl 3-(5-oxopyrrolidin-2-yl)propanoate [81980-11-2] (2)
3-(5-oxopyrrolidin-2-yl)propanoic acid [7766-86-1] (3)

References[edit]

^ ^a ^b Butler DE, Leonard JD, Caprathe BW, L'Italien YJ, Pavia MR, Hershenson FM, Poschel PH, Marriott JG (March 1987). "Amnesia-reversal activity of a series of cyclic imides". Journal of Medicinal Chemistry. 30 (3): 498–503. doi:10.1021/jm00386a010. PMID 3820221.
^ Lukeš, R.; Šorm, F. (1947). "Sur les acides aminodicarboxyliques symétriques et leur cyclisation". Collection of Czechoslovak Chemical Communications. 12: 278–291. doi:10.1135/cccc19470278.
^ Micheel, Fritz; Flitsch, Wilhelm (1955). "Eine einfache Synthese des 3.4-Dioxo-pyrrolizidins (Pyrrolizidinderivate III.)". Chemische Berichte. 88 (4): 509–510. doi:10.1002/cber.19550880410.
^ Micheel, Fritz; Flitsch, Wilhelm (1956). "Synthesen mit 3.4-Dioxopyrrolizidin (IV. Mitteil.)". Chemische Berichte. 89 (1): 129–132. doi:10.1002/cber.19560890121.
^ Alonso, Ricardo; Gessner, Wieslaw; Takahashi, Kimio; Brossi, Arnold (1988). "Improved Synthesis of the Lukes-ŜOrm Dilactam. Nucleophilic Opening to 5-Substituted 2-Pyrrolidine-2-Ones". Synthetic Communications. 18 (1): 37–43. doi:10.1080/00397918808057817.
^ Donald E. Butler, U.S. patent 4,372,966 (1983 to Warner Lambert Co LLC).
^ Herman A Bruson, U.S. patent 2,390,918 (1945 to Resinous Prod & Chemical Co).
^ Marvin S. Hoekstra, U.S. patent 4,663,464 (1987 to Warner Lambert Co LLC).

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[pmid3820221-1] Butler DE, Leonard JD, Caprathe BW, L'Italien YJ, Pavia MR, Hershenson FM, Poschel PH, Marriott JG (March 1987). "Amnesia-reversal activity of a series of cyclic imides". Journal of Medicinal Chemistry. 30 (3): 498–503. doi:10.1021/jm00386a010. PMID 3820221.

[2] Lukeš, R.; Šorm, F. (1947). "Sur les acides aminodicarboxyliques symétriques et leur cyclisation". Collection of Czechoslovak Chemical Communications. 12: 278–291. doi:10.1135/cccc19470278.

[3] Micheel, Fritz; Flitsch, Wilhelm (1955). "Eine einfache Synthese des 3.4-Dioxo-pyrrolizidins (Pyrrolizidinderivate III.)". Chemische Berichte. 88 (4): 509–510. doi:10.1002/cber.19550880410.

[4] Micheel, Fritz; Flitsch, Wilhelm (1956). "Synthesen mit 3.4-Dioxopyrrolizidin (IV. Mitteil.)". Chemische Berichte. 89 (1): 129–132. doi:10.1002/cber.19560890121.

[5] Alonso, Ricardo; Gessner, Wieslaw; Takahashi, Kimio; Brossi, Arnold (1988). "Improved Synthesis of the Lukes-ŜOrm Dilactam. Nucleophilic Opening to 5-Substituted 2-Pyrrolidine-2-Ones". Synthetic Communications. 18 (1): 37–43. doi:10.1080/00397918808057817.

[6] Donald E. Butler, U.S. patent 4,372,966 (1983 to Warner Lambert Co LLC).

[7] Herman A Bruson, U.S. patent 2,390,918 (1945 to Resinous Prod & Chemical Co).

[8] Marvin S. Hoekstra, U.S. patent 4,663,464 (1987 to Warner Lambert Co LLC).

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Synthesis[edit]

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References[edit]