Ritalinic acid

Ritalinic acid
Clinical data
ATC code	None;
Legal status
Legal status	US: Unscheduled;
Identifiers
	IUPAC name Phenyl(piperidin-2-yl)acetic acid;
CAS Number	19395-41-6 ;
PubChem CID	86863;
ChemSpider	78360 ;
CompTox Dashboard (EPA)	DTXSID20864888 ;
ECHA InfoCard	100.039.094
Chemical and physical data
Formula	C13H17NO2
Molar mass	219.28 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:INGSNVSERUZOAK-UHFFFAOYSA-N ;
	(verify)

Ritalinic acid is a substituted phenethylamine and an inactive major metabolite of the psychostimulant drugs methylphenidate and ethylphenidate.^[1]^[2] 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).^[3]

Uses

Ritalinic acid is used as an intermediate in the synthesis of methylphenidate and its analogues, such as ethylphenidate and isopropylphenidate.

^ ^a ^b 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.
^ Noelia Negreira; Claudio Erratico; Alexander L.N. van Nuijs; Adrian Covaci (January 2016). "Identification of in vitro metabolites of ethylphenidate by liquid chromatography coupled to quadrupole time-of-flight mass spectrometry". Journal of Pharmaceutical and Biomedical Analysis. 117 (5): 474–484. doi:10.1016/j.jpba.2015.09.029. PMID 26454340.
^ 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.