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Substance Name: Methylphenidate [USAN:INN:BAN]
RN: 113-45-1
InChIKey: DUGOZIWVEXMGBE-UHFFFAOYSA-N

Note

  • A central nervous system stimulant used most commonly in the treatment of attention-deficit disorders in children and for narcolepsy. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE.

Molecular Formula

  • C14-H19-N-O2

Molecular Weight

  • 233.3091
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Central Nervous System Stimulants
  • Dopamine Agents
  • Dopamine Uptake Inhibitors
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Reproductive Effect
  • Stimulant (CNS)

Superlist Classification Code

  • DEA Schedule II

Names and Synonyms

Name of Substance

  • Methylphenidate
  • Methylphenidate [USAN:INN:BAN]

MeSH Heading

  • Methylphenidate

Synonyms

  • 2-Piperidineacetic acid, alpha-phenyl-, methyl ester
  • 4311/B Ciba
  • alpha-Phenyl-2-piperidineacetic acid methyl ester
  • alpha-Phenyl-alpha-(2-piperidyl)acetic acid methyl ester
  • C 4311
  • Calocain
  • Cotempla XR-ODT
  • Daytrana
  • EINECS 204-028-6
  • HSDB 3126
  • Meridil
  • Methyl (2-phenyl-2-(2-piperidyl)acetate)
  • Methyl alpha-phenyl-alpha-(2-piperidyl)acetate
  • Methyl phenidate
  • Methyl phenidylacetate
  • Methylfenidan
  • Methylphenidan
  • Methylphenidate
  • Methylphenidatum
  • Methylphenidatum [INN-Latin]
  • Metilfenidato
  • Metilfenidato [INN-Spanish]
  • Metilfenidato [Italian]
  • NCI-C56280
  • Phenidylate
  • Plimasine

Systematic Names

  • 2-Piperidineacetic acid, alpha-phenyl-, methyl ester
  • Methylphenidate

Superlist Names

  • DEA No. 1724
  • Methylphenidate

Registry Numbers

CAS Registry Number

  • 113-45-1

Related Registry Number

  • 298-59-9 (hydrochloride)

System Generated Number

  • 0000113451

Structure Descriptors

InChI

1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3

InChIKey

DUGOZIWVEXMGBE-UHFFFAOYSA-N

Smiles

COC(=O)C(C1CCCCN1)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 2500ug/kg/5D- (2.5mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" Annals of Pharmacotherpy. Vol. 26, Pg. 1378, 1992.
child TDLo oral 180mg/kg/26W- (180mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) American Journal of Psychiatry. Vol. 143, Pg. 1176, 1985.
man LDLo intravenous 445mg/kg/34W- (445mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA Human Pathology. Vol. 3, Pg. 67, 1972.
mouse LD50 intraperitoneal 32mg/kg (32mg/kg)   Journal de Pharmacologie. Vol. 17, Pg. 37, 1986.
mouse LD50 intravenous 41mg/kg (41mg/kg) BEHAVIORAL: WAKEFULNESS Biochemical Pharmacology. Vol. 8, Pg. 263, 1961.
mouse LD50 oral 150mg/kg (150mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 139, Pg. 100, 1972.
mouse LD50 subcutaneous 218mg/kg (218mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 184, Pg. 34, 1970.
rabbit LDLo intravenous 60mg/kg (60mg/kg)   Agents and Actions, A Swiss Journal of Pharmacology. Vol. 3, Pg. 28, 1973.
rat LD50 intraperitoneal 430mg/kg (430mg/kg)   Acta Pharmacologica et Toxicologica. Vol. 17, Pg. 121, 1960.
rat LD50 intravenous 48mg/kg (48mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
rat LD50 oral 367mg/kg (367mg/kg)   Psychopharmacology Service Center, Bulletin. Vol. 2, Pg. 17, 1963.
women LDLo intravenous 800ug/kg (0.8mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Analytical Toxicology. Vol. 10, Pg. 209, 1986.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.77 (none)   EXP
log P (octanol-water) 0.2 (none)   EXP
Water Solubility 2.01E+05 mg/L 25 EST
Vapor Pressure 5.89E-05 mm Hg 25 EST
Henry's Law Constant 4.38E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.11E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.