Chemistry:Ritalinic acid

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 ;
PubChem CID	86863;
ChemSpider	78360 ;
UNII	GT4165RS9H;
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 ;
	(verify)

Short description: Major metabolite of the psychostimulant drug methylphenidate

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]

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.

↑ ^1.0 ^1.1 "Metabolism and disposition of methylphenidate-14C: studies in man and animals". The Journal of Pharmacology and Experimental Therapeutics 191 (3): 535–47. December 1974. PMID 4473537.
↑ "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. January 2016. doi:10.1016/j.jpba.2015.09.029. PMID 26454340.
↑ "Methylphenidate is stereoselectively hydrolyzed by human carboxylesterase CES1A1". The Journal of Pharmacology and Experimental Therapeutics 310 (2): 469–76. August 2004. doi:10.1124/jpet.104.067116. PMID 15082749.

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Original source: https://en.wikipedia.org/wiki/Ritalinic acid. Read more

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
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
(verify)