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^N
PubChem CID	71893
ChemSpider	64906^Y
UNII	RES9I0LGG5
ChEMBL	ChEMBL51396^Y
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^Y Key:IEZDOKQWPWZVQF-UHFFFAOYSA-N^Y
^NY (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

The nitro group of dimethyl 4-nitropimelate (1) is reduced by palladium-catalysed hydrogenation to an amino group, which cyclises to give a mixture of the lactam ester (2) and its corresponding acid (3). The mixture is hydrolysed using sodium hydroxide to convert all of the ester to the acid, and this material is cyclised to give rolziracetam using acetic anhydride.^[2][3]

See also

• Piracetam

References

1. Butler DE, Leonard JD, Caprathe BW, L'Italien YJ, Pavia MR, Hershenson FM, et al. (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. Leonard NJ, Hruda LR, Long FW (March 1947). "The synthesis of pyrrolizidines". Journal of the American Chemical Society. 69 (3): 690–692. doi:10.1021/ja01195a067. PMID 20289459.
3. US patent 4663464, Hoekstra MS, "Process for the preparation of dihydro-1H-pyrrolizine-3,5-(2H,6H)-dione", issued 1987-05-05, assigned to Warner Lambert Co LLC