ContaminantDB: Modafinil

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:32 UTC

Update Date

2026-03-26 21:43:27 UTC

Accession Number

CHEM002263

Identification

Common Name

Modafinil

Class

Small Molecule

Description

Modafinil is a stimulant drug marketed as a 'wakefulness promoting agent' and is one of the stimulants used in the treatment of narcolepsy. Narcolepsy is caused by dysfunction of a family of wakefulness-promoting and sleep-suppressing peptides, the orexins, whose neurons are activated by modafinil. The prexin neuron activation is associated with psychoactivation and euphoria. The exact mechanism of action is unclear, although in vitro studies have shown it to inhibit the reuptake of dopamine by binding to the dopamine reuptake pump, and lead to an increase in extracellular dopamine. Modafinil activates glutamatergic circuits while inhibiting GABA.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anorexigenic Agent
Appetite Depressant
Central Nervous System Agent
Central Nervous System Stimulant
Drug
Metabolite
Neuroprotective Agent
Organic Compound
Stimulant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Provigil	Kegg
2-[(Diphenylmethyl)sulphinyl]acetamide	Generator
Moderateafinil	HMDB
2-((Diphenylmethyl)sulfinyl)acetamide	MeSH, HMDB
Alertec	MeSH, HMDB
Merckle brand OF modafinil	MeSH, HMDB
Cephalon brand OF modafinil	MeSH, HMDB
Cephalon brand OF modafinil, reformulated	MeSH, HMDB
Vigil	MeSH, HMDB
Benzhydrylsulfinylacetamide	MeSH, HMDB
CEPA brand OF modafinil	MeSH, HMDB
Lafon brand OF modafinil	MeSH, HMDB
Modiodal	MeSH, HMDB
Nourypharma brand OF modafinil	MeSH, HMDB
Sparlon	MeSH, HMDB
Draxis brand OF modafinil	MeSH, HMDB
Modafinil	MeSH
R-Modafinil	MeSH, HMDB
Nuvigil	MeSH, HMDB
2-((R)-(Diphenylmethyl)sulfinyl)acetamide	MeSH, HMDB
Armodafinil	MeSH, HMDB
R Modafinil	MeSH, HMDB

Chemical Formula

C₁₅H₁₅NO₂S

Average Molecular Mass

273.350 g/mol

Monoisotopic Mass

273.082 g/mol

CAS Registry Number

68693-11-8

IUPAC Name

2-diphenylmethanesulfinylacetamide

Traditional Name

modafinil

SMILES

NC(=O)CS(=O)C(C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)

InChI Key

YFGHCGITMMYXAQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as diphenylmethanes. Diphenylmethanes are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylmethanes

Direct Parent

Diphenylmethanes

Alternative Parents

Substituents

Diphenylmethane
Benzyl alkyl sulfoxide
Benzyl sulfoxide
Carboxamide group
Primary carboxylic acid amide
Sulfoxide
Sulfinyl compound
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:77585 )
sulfoxide (CHEBI:77585 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	164-166°C
Boiling Point	Not Available
Solubility	Slightly soluble

Predicted Properties

Property	Value	Source
Water Solubility	0.62 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.53	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	60.16 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.39 m³·mol⁻¹	ChemAxon
Polarizability	28.71 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-2900000000-528a0bbea5cbea3771e1	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
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014i-0900000000-e85eba164d5df6d6552e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0390000000-c3fbad26370e7ff03677	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0560-1190000000-55b81c4a8b771b4a2bf5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02bf-8920000000-9bdc4395d4fc1f10feaa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-2190000000-a8f51eb41df43ec99388	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-8390000000-595fb55087a29048faca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9500000000-66e73e7a840f3754f786	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-c692fb05e504a5da303a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0900000000-c692fb05e504a5da303a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0900000000-1fe50a8d9579a6198a36	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-024i-0190000000-06b6e8449d4102829ac2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-7900000000-4df9193e933f8acc3b4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-9310000000-7866ba7c4275aa6d34a0	Spectrum

Toxicity Profile

Route of Exposure

Rapid following oral administration.

Mechanism of Toxicity

The exact mechanism of action is unclear, although in vitro studies have shown it to inhibit the reuptake of dopamine by binding to the dopamine reuptake pump, and lead to an increase in extracellular dopamine. Modafinil activates glutamatergic circuits while inhibiting GABA. Modafinil is thought to have less potential for abuse than other stimulants due to the absence of any significant euphoric or pleasurable effects. It is possible that modafinil acts by a synergistic combination of mechanisms including direct inhibition of dopamine reuptake, indirect inhibition of noradrenalin reuptake in the VLPO and orexin activation. Modafinil has partial alpha 1B-adrenergic agonist effects by directly stimulating the receptors.

Metabolism

Hepatic Route of Elimination: The major route of elimination is metabolism (~90%), primarily by the liver, with subsequent renal elimination of the metabolites. Half Life: 23-215 hours

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

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

Uses/Sources

In the U.S, only for the treatment of narcolepsy, obstructive sleep apnea/hypopnea and shift work sleep disorder. In some countries, it is also approved for idiopathic hypersomnia. [Wikipedia]

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. 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

Side-effects can include sweating, dry mouth, blurred vision, insomnia, loss of appetite, and dizziness. In addition users can feel restless, anxious and moody, become excitable and have a false sense of power and security. Amphetamine overdose can also cause cardiac arrhythmias, headaches, convulsions, hypertension, rapid heart rate, coma and death. Amphetamines are psychologically and physically addictive.

Treatment

No specific antidote to the toxic effects of modafinil overdose has been identified to date. Such overdoses should be managed with primarily supportive care, including cardiovascular monitoring. If there are no contraindications, induced emesis or gastric lavage should be considered. (4)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

4088

ChEBI ID

77585

PubChem Compound ID

Not Available

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

DrugSyn.org

MSDS

Link

General References

Not Available

Modafinil (CHEM002263)

Structure for CHEM002263: Modafinil