Rolziracetam

Chemical compound

none

Legal statusLegal 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 dataFormulaC₇H₉N₂O₂Molar mass153.161 g·mol⁻¹3D 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]

References

^ 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.
^ 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.
^ 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