Ritalinic acid

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]

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	219.284 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) Key:INGSNVSERUZOAK-UHFFFAOYSA-N
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Uses

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

References

1. Faraj BA, Israili ZH, Perel JM, Jenkins ML, Holtzman SG, Cucinell SA, Dayton PG (December 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.
2. Negreira N, Erratico C, van Nuijs AL, Covaci A (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): 474–84. doi:10.1016/j.jpba.2015.09.029. hdl:10067/1301870151162165141. PMID 26454340.
3. Sun Z, Murry DJ, Sanghani SP, Davis WI, Kedishvili NY, Zou Q, et al. (August 2004). "Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1". The Journal of Pharmacology and Experimental Therapeutics. 310 (2): 469–76. doi:10.1124/jpet.104.067116. PMID 15082749. S2CID 24233422.