Methylphenidate
Title: Methylphenidate
CAS Registry Number: 113-45-1
CAS Name: a-Phenyl-2-piperidineacetic acid methyl ester
Additional Names: methyl phenidylacetate; methyl a-phenyl-a-(2-piperidyl)acetate; methylphenidan
Molecular Formula: C14H19NO2
Molecular Weight: 233.31
Percent Composition: C 72.07%, H 8.21%, N 6.00%, O 13.72%
Literature References: Prepn: L. Panizzon, Helv. Chim. Acta 27, 1748 (1944); M. Hartmann, L. Panizzon, US 2507631 (1950 to Ciba). Sepn of isomers: R. Rometsch, US 2957880 (1960 to Ciba). Toxicity data: E. N. Greenblatt, A. C. Osterberg, J. Pharmacol. Exp. Ther. 131, 115 (1961). Comprehensive description: G. R. Padmanabhan, Anal. Profiles Drug Subs. 10, 473-497 (1981). Pharmacokinetics: N. R. Srinivas et al., Pharm. Res. 10, 14 (1993). Clinical efficacy in attention deficit-hyperactivity disorder (ADHD): W. E. Pelham, Jr. et al., J. Consult. Clin. Psychol. 61, 506 (1993); R. G. Klein, Encephale 19, 89 (1993).
Properties: bp0.6mm 135-137°. Sol in alcohol, ethyl acetate, ether. Practically insol in water, petr ether.
Boiling point: bp0.6mm 135-137°
 
Derivative Type: Hydrochloride
CAS Registry Number: 298-59-9
Manufacturers' Codes: Ciba 4311b
Trademarks: Centedrin (Gedeon Richter); Concerta (Alza); Equasym (UCB); Metadate (Medeva); Ritalin (Novartis)
Molecular Formula: C14H19NO2.HCl
Molecular Weight: 269.77
Percent Composition: C 62.33%, H 7.47%, N 5.19%, O 11.86%, Cl 13.14%
Properties: Crystals, mp 224-226°. pKa 8.9. Sol in water, alc, chloroform. A 5% aq soln is neutral to litmus. LD50 orally in mice: 190 mg/kg (Greenblatt, Osterberg).
Melting point: mp 224-226°
pKa: pKa 8.9
Toxicity data: LD50 orally in mice: 190 mg/kg (Greenblatt, Osterberg)
 
Derivative Type: d-threo-Form
CAS Registry Number: 40431-64-9
CAS Name: (aR,2R)-a-Phenyl-2-piperidineacetic acid methyl ester
Additional Names: dexmethylphenidate
Literature References: Enantioselective synthesis: J. M. Axten et al., J. Am. Chem. Soc. 121, 6511 (1999).
 
Derivative Type: d-threo-Form hydrochloride
CAS Registry Number: 19262-68-1
Additional Names: Dexmethylphenidate hydrochloride
Trademarks: Focalin (Novartis)
Literature References: Clinical trials in ADHD: L. E. Arnold et al., J. Child Adolesc. Psychopharmacol. 14, 542 (2004); R. Silva et al., ibid. 555.
Properties: White to off-white powder. Freely sol in water, methanol; sol in alcohol; slightly sol in chloroform, acetone.
 
NOTE: This is a controlled substance (stimulant): 21 CFR, 1308.12.
Therap-Cat: CNS stimulant.
Keywords: CNS Stimulant.

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