Ritalinic acid

Ritalinic acid
Systematic (IUPAC) name

2-phenyl-2-piperidin-2-ylacetic acid
Clinical data
Legal status	US: Uncontrolled
Identifiers
CAS Registry Number	19395-41-6^Y
ATC code	None
PubChem	CID 86863
ChemSpider	78360^Y
Chemical data
Formula	C₁₃H₁₇N O₂
Molecular mass	219.28 g/mol
SMILES C1CCNC(C1)C(C2=CC=CC=C2)C(=O)O
InChI InChI=InChI=1S/C13H17NO2/c15-13(16)12(10-6-2-1-3-7-10)11-8-4-5-9-14-11/h1-3,6-7,11-12,14H,4-5,8-9H2,(H,15,16) ^Y Key:INGSNVSERUZOAK-UHFFFAOYSA-N ^Y
Y (what is this?) (verify)

Ritalinic acid is a substituted phenethylamine and an inactive major metabolite of the psychostimulant drug methylphenidate.^[1] When administered orally, methylphenidate is extensively metabolized in the liver by hydrolysis of the ester group yielding ritalinic acid.^[1] The hydrolysis was found to be catalyzed by carboxylesterase 1 (CES1).^[2]

References

↑ 1.0 1.1 Faraj, B. A.; Israili, Z. H.; Perel, J. M.; Jenkins, M. L.; Holtzman, S. G.; Cucinell, S. A.; Dayton, P. G. (1974). "Metabolism and disposition of methylphenidate-14C: Studies in man and animals". The Journal of Pharmacology and Experimental Therapeutics 191 (3): 535–47. PMID 4473537.
↑ Sun, Z.; Murry, D.; Sanghani, S.; Davis, W.; Kedishvili, N.; Zou, Q.; Hurley, T.; Bosron, W. (2004). "Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1". The Journal of Pharmacology and Experimental Therapeutics 310 (2): 469–476. doi:10.1124/jpet.104.067116. PMID 15082749.