ContaminantDB: Methylphenidate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:26:52 UTC

Update Date

2026-03-31 19:07:34 UTC

Accession Number

CHEM002191

Identification

Common Name

Methylphenidate

Class

Small Molecule

Description

Methylphenidate is only found in individuals that have used or taken this drug. It is 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. Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Alteration of serotonergic pathways via changes in dopamine transport may result.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Adrenergic Agent
Adrenergic Uptake Inhibitor
Amine
Central Nervous System Stimulant
Dopamine Uptake Inhibitor
Drug
Ester
Ether
Metabolite
Organic Compound
Sympathomimetic
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
alpha-Phenyl-2-piperidineacetic acid methyl ester	ChEBI
Methyl alpha-phenyl-alpha-(2-piperidyl)acetate	ChEBI
Methyl alpha-phenyl-alpha-2-piperidinylacetate	ChEBI
Methyl phenidylacetate	ChEBI
Methylphenidan	ChEBI
Daytrana	Kegg
a-Phenyl-2-piperidineacetate methyl ester	Generator
a-Phenyl-2-piperidineacetic acid methyl ester	Generator
alpha-Phenyl-2-piperidineacetate methyl ester	Generator
Α-phenyl-2-piperidineacetate methyl ester	Generator
Α-phenyl-2-piperidineacetic acid methyl ester	Generator
Methyl a-phenyl-a-(2-piperidyl)acetate	Generator
Methyl a-phenyl-a-(2-piperidyl)acetic acid	Generator
Methyl alpha-phenyl-alpha-(2-piperidyl)acetic acid	Generator
Methyl α-phenyl-α-(2-piperidyl)acetate	Generator
Methyl α-phenyl-α-(2-piperidyl)acetic acid	Generator
Methyl a-phenyl-a-2-piperidinylacetate	Generator
Methyl a-phenyl-a-2-piperidinylacetic acid	Generator
Methyl alpha-phenyl-alpha-2-piperidinylacetic acid	Generator
Methyl α-phenyl-α-2-piperidinylacetate	Generator
Methyl α-phenyl-α-2-piperidinylacetic acid	Generator
Methyl phenidylacetic acid	Generator
Methylphenidic acid	Generator
D-Methylphenidate HCL	HMDB
Methyl phenidyl acetate	HMDB
Methylphenidate HCL	HMDB
Methylphenidate hydrochloride	HMDB
Methylphenidylacetate hydrochloride	HMDB
Metilfenidat hydrochloride	HMDB
Phenidylate	HMDB
Methylin	HMDB
Novartis brand 1 OF methylphenidate hydrochloride	HMDB
Ritaline	HMDB
Centedrin	HMDB
Concerta	HMDB
Equasym	HMDB
Hydrochloride, methylphenidate	HMDB
Metadate	HMDB
Cephalon brand OF methylphenidate hydrochloride	HMDB
Ritalin	HMDB
Ritalin SR	HMDB
Tsentedrin	HMDB
Celltech brand OF methylphenidate hydrochloride	HMDB
Mallinckrodt brand OF methylphenidate hydrochloride	HMDB
Novartis brand 2 OF methylphenidate hydrochloride	HMDB
Ritalin-SR	HMDB
Methyl phenyl(piperidin-2-yl)acetic acid	HMDB
Methylphenidate	MeSH

Chemical Formula

C₁₄H₁₉NO₂

Average Molecular Mass

233.306 g/mol

Monoisotopic Mass

233.142 g/mol

CAS Registry Number

113-45-1

IUPAC Name

methyl 2-phenyl-2-(piperidin-2-yl)acetate

Traditional Name

methylphenidate

SMILES

COC(=O)C(C1CCCCN1)C1=CC=CC=C1

InChI Identifier

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

InChI Key

DUGOZIWVEXMGBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Aralkylamines

Alternative Parents

Substituents

Aralkylamine
Monocyclic benzene moiety
Piperidine
Benzenoid
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:84276 )
methyl ester (CHEBI:84276 )
beta-amino acid ester (CHEBI:84276 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	224-226°C
Boiling Point	Not Available
Solubility	1255mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	1.47	ALOGPS
logP	2.25	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	66.73 m³·mol⁻¹	ChemAxon
Polarizability	26.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-001i-0090000000-b461cd02e59ebf84d3f9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9100000000-c75de12fbdae54dce658	Spectrum
GC-MS	GC-MS Spectrum - CI-B (Non-derivatized)	splash10-001i-0090000000-b461cd02e59ebf84d3f9	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9100000000-c75de12fbdae54dce658	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0089-9610000000-8e4c1241e36274356032	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-1190000000-8803b6fb1d54baf20a6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-6390000000-63f6ddbd32540d6c0e4e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9500000000-dab6b5667313005cbcd2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-dbf1d73eb0c9410efbf6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2290000000-4a7ee5089439605a9759	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00w9-9520000000-aa484f1df63a11905d5a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-2190000000-aa6695fd8b35db2e4b41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9440000000-3e2430ca32eb71f561e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9300000000-2d49d7918e562aad8156	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-96a8c87419b47af6da2a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-4790000000-8bbed2d476f383bd9813	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9400000000-dabf09c5d3b6f3c788fe	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9100000000-1a9c5badbee827946da1	Spectrum

Toxicity Profile

Route of Exposure

Oral. Readily absorbed in a biphasic manner when orally administered (tablets) to children diagnosed with ADHD and to healthy adults. In children and adults males, after administration of a single oral dose of Ritalin LA and Ritalin given in two doses 4 hours apart, peak plasma concentration is reached approximately 2 hours for the first phase and 5-6 hours for the second phase. The absolute oral bioavailability of methylphenidate in children was 22±8% for d-methylphenidate and 5±3% for l-methylphenidate. These low values suggest that methylphenidate is highly metabolized presystemically.

Mechanism of Toxicity

Methylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Alteration of serotonergic pathways via changes in dopamine transport may result.

Metabolism

Methylphenidate is hepatically metabolized. More specifically, it is rapidly and extensively metabolized by carboxylesterase CES1A1. Via this enzyme, methylphenidate undergoes de-esterification to ritalinic acid (a-phenyl-2-piperidine acetic acid, PPAA), which has little to no pharmacologic activity. Route of Elimination: After oral administration of an immediate release formulation of methylphenidate, 78%-97% of the dose is excreted in the urine and 1%-3% in the feces in the form of metabolites within 48-96 hours. Only small quantities (<1%) of unchanged methylphenidate appear in the urine. Most of the dose is excreted in the urine as ritalinic acid (60%-86%), the remainder being accounted for by minor metabolites. Half Life: d-methylphenidate = 3-4 hours; l-methylphenidate = 1-3 hours; Ritalinic acid = 3-4 hours;

Toxicity Values

LD50: 190 mg/kg (oral, mice)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For use as an integral part of a total treatment program which typically includes other remedial measures (psychological, educational, social) for a stabilizing effect in children with a behavioral syndrome characterized by the following group of developmentally inappropriate symptoms: moderate-to-severe distractibility, short attention span, hyperactivity, emotional lability, and impulsivity.

Minimum Risk Level

Not Available

Health Effects

Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.

Symptoms

Symptoms of overdose include vomiting, agitation, tremors, hyperreflexia, muscle twitching, convulsions (may be followed by coma), euphoria, confusion, hallucinations, delirium, sweating, flushing, headache, hyperpyrexia, tachycardia, palpitations, cardiac arrhythmias, hypertension, mydriasis, and dryness of mucous membranes.

Treatment

Treatment consists of appropriate supportive measures. The patient must be protected against self-injury and against external stimuli that would aggravate overstimulation already present. Gastric contents may be evacuated by gastric lavage. In the presence of severe intoxication, use a carefully titrated dosage of a short-acting barbiturate before performing gastric lavage. Other measures to detoxify the gut include administration of activated charcoal and a cathartic. Intensive care must be provided to maintain adequate circulation and respiratory exchange; external cooling procedures may be required for hyperpyrexia. (7)

Concentrations

Not Available

External Links

DrugBank ID

DB00422

HMDB ID

HMDB0014566

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID