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Rolziracetam: Difference between revisions

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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.<ref name="pmid3820221">{{cite journal | vauthors = Butler DE, Leonard JD, Caprathe BW, L'Italien YJ, Pavia MR, Hershenson FM, Poschel PH, Marriott JG | title = Amnesia-reversal activity of a series of cyclic imides | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 3 | pages = 498–503 | date = March 1987 | pmid = 3820221 | doi = 10.1021/jm00386a010 }}</ref> 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.<ref name="pmid3820221">{{cite journal | vauthors = Butler DE, Leonard JD, Caprathe BW, L'Italien YJ, Pavia MR, Hershenson FM, Poschel PH, Marriott JG | title = Amnesia-reversal activity of a series of cyclic imides | journal = Journal of Medicinal Chemistry | volume = 30 | issue = 3 | pages = 498–503 | date = March 1987 | pmid = 3820221 | doi = 10.1021/jm00386a010 }}</ref>
==Synthesis== ==Synthesis==
:]
]
The ] group of ] (1) is reduced by palladium-catalysed ] to an ], which cyclises to give a mixture of the ] ester (2) and its corresponding acid (3). The mixture is ] using ] to convert all of the ester to the acid, and this material is cyclised to give rolziracetam using ].<ref>{{cite patent |country=US |number=4663464 |inventor=Marvin S. Hoekstra |title=Process for the preparation of dihydro-1H-pyrrolizine-3,5-(2H,6H)-dione |status=patent |gdate=1987-05-05 |fdate=1986-03-21 |pridate=1986-03-21 |assign1=Warner Lambert Co LLC}}</ref>
*dimethyl 4-nitropimelate (1)

*methyl 3-(5-oxopyrrolidin-2-yl)propanoate (2)
*3-(5-oxopyrrolidin-2-yl)propanoic acid (3)
==See also== ==See also==
* ] * ]
*Rolziracetam is used as precursor to make a compound called (another racetam).


== References == == References ==

Revision as of 13:36, 4 July 2024

Chemical compound Pharmaceutical compound
Rolziracetam
Clinical data
Other names2,6,7,8-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
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC7H9N2O2
Molar mass153.161 g·mol
3D model (JSmol)
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.

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.

See also

References

  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. US patent 4663464, Marvin S. Hoekstra, "Process for the preparation of dihydro-1H-pyrrolizine-3,5-(2H,6H)-dione", issued 1987-05-05, assigned to Warner Lambert Co LLC 
Racetams
Racetams
Phenylpiracetams
Racetam-like


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