Ritalinic acid

Ritalinic acid is a substituted phenethylamine and an inactive major metabolite of the psychostimulant drugs methylphenidate, dexmethylphenidate 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]

Ritalinic acid

Clinical data
ATC code	None
Legal status
Legal status	US: Unscheduled and Uncontrolled
Identifiers
IUPAC name Phenyl(piperidin-2-yl)acetic acid
CAS Number	19395-41-6 Y
PubChem CID	86863
ChemSpider	78360 Y
UNII	GT4165RS9H
CompTox Dashboard (EPA)	DTXSID20864888
ECHA InfoCard	100.039.094
Chemical and physical data
Formula	C13H17NO2
Molar mass	219.284 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) Y Key:INGSNVSERUZOAK-UHFFFAOYSA-N Y
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Etymologically, ritalinic acid shares its roots with Ritalin, a common brand name for methylphenidate.

Uses

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