METHYLPHENIDATE

Search structure
Trade Names:
Synonyms:
Status: Approved (1955)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N06BA04
UNII: 207ZZ9QZ49

Structure
InChI Key DUGOZIWVEXMGBE-UHFFFAOYSA-N
Smile COC(=O)C(c1ccccc1)C1CCCCN1
InChI
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H19NO2
Molecular Weight 233.31
AlogP 2.09
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 38.33
Molecular species BASE
Aromatic Rings 1.0
Heavy Atoms 17.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Dopamine transporter inhibitor PubMed DailyMed
Primary Target
DAT
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 17-79 - 340-660 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Brain Neoplasms 3 D001932 ClinicalTrials
Asthenia 3 D001247 ClinicalTrials
Bipolar Disorder 3 D001714 ClinicalTrials
Multiple Sclerosis 3 D009103 ClinicalTrials
Anemia, Sickle Cell 3 D000755 ClinicalTrials
Alzheimer Disease 3 D000544 ClinicalTrials
Tobacco Use Disorder 3 D014029 ClinicalTrials
Hematologic Neoplasms 3 D019337 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
Delirium 3 D003693 ClinicalTrials
Depressive Disorder, Major 3 D003865 ClinicalTrials
Depressive Disorder 3 D003866 ClinicalTrials
Amphetamine-Related Disorders 2 D019969 ClinicalTrials
Substance-Related Disorders 2 D019966 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Feeding and Eating Disorders 2 D001068 ClinicalTrials
Brain Injuries 2 D001930 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Parkinson Disease 2 D010300 ClinicalTrials
Cocaine-Related Disorders 2 D019970 ClinicalTrials
Postoperative Complications 1 D011183 ClinicalTrials
Alcoholism 1 D000437 ClinicalTrials
Hypotension, Orthostatic 1 D007024 ClinicalTrials
Opioid-Related Disorders 1 D009293 ClinicalTrials
Fatigue 1 D005221 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Stress Disorders, Post-Traumatic 0 D013313 ClinicalTrials

Related Entries

Scaffolds

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Nervous system disorders Nervous system disorder 50.0
Psychiatric disorders Mental disorder 46.0
Gastrointestinal disorders Gastrointestinal disorder 44.0
Psychiatric disorders Mental disorder 43.0
Psychiatric disorders Mental disorder 40.0
Nervous system disorders Headache 39.0
Nervous system disorders Nervous system disorder 39.0
Gastrointestinal disorders Gastrointestinal disorder 38.0
Psychiatric disorders Mental disorder 38.0
Nervous system disorders Nervous system disorder 37.0
Metabolism and nutrition disorders Malnutrition 34.0
Gastrointestinal disorders Gastrointestinal disorder 32.0
General disorders and administration site conditions Decreased appetite 30.0
Nervous system disorders Headache 30.0
Psychiatric disorders Mental disorder
Psychiatric disorders Mental disorder 30.0
Nervous system disorders Nervous system disorder 30.0
Gastrointestinal disorders Gastrointestinal disorder 29.0
Gastrointestinal disorders Gastrointestinal disorder 28.0
Nervous system disorders Nervous system disorder
Nervous system disorders Nervous system disorder 28.0
Nervous system disorders Headache 26.0
Psychiatric disorders Mental disorder 26.0
General disorders and administration site conditions Decreased appetite 25.5
General disorders and administration site conditions Decreased appetite 25.3
Metabolism and nutrition disorders Malnutrition 25.3
Nervous system disorders Headache 25.0
General disorders and administration site conditions Decreased appetite 24.8
Nervous system disorders Headache 24.2
Gastrointestinal disorders Gastrointestinal disorder
Gastrointestinal disorders Gastrointestinal disorder 23.0
Nervous system disorders Headache 22.2
Gastrointestinal disorders Gastrointestinal disorder 22.0
Metabolism and nutrition disorders Malnutrition 22.0
Gastrointestinal disorders Dry mouth 20.0
Psychiatric disorders Mental disorder 20.0
Gastrointestinal disorders Gastrointestinal disorder
Nervous system disorders Headache
Nervous system disorders Headache 19.0
Psychiatric disorders Mental disorder 19.0
Nervous system disorders Headache
Nervous system disorders Insomnia 17.0
Metabolism and nutrition disorders Malnutrition 17.0
Nervous system disorders Headache 16.1
Metabolism and nutrition disorders Malnutrition 16.0
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 16.0
Nervous system disorders Headache
Nervous system disorders Headache 15.3
Gastrointestinal disorders Dry mouth 15.1
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 15.0
Psychiatric disorders Mental disorder
Gastrointestinal disorders Nausea 14.3
Gastrointestinal disorders Dry mouth 14.0
Nervous system disorders Insomnia 13.3
Nervous system disorders Nervous system disorder
Gastrointestinal disorders Nausea 12.8
Nervous system disorders Headache
Nervous system disorders Headache 12.4
Nervous system disorders Insomnia 12.3
Gastrointestinal disorders Nausea 12.2
Nervous system disorders Headache
Nervous system disorders Headache
Psychiatric disorders Anxiety 11.0
Nervous system disorders Headache
General disorders and administration site conditions Irritability 11.0
Metabolism and nutrition disorders Malnutrition
Nervous system disorders Headache 10.6
Nervous system disorders Insomnia 10.6
Gastrointestinal disorders Vomiting 10.2
Gastrointestinal disorders Nausea 9.66
Investigations Weight decreased 9.18
Psychiatric disorders Affect lability 9.0
General disorders and administration site conditions Decreased appetite
Gastrointestinal disorders Dyspepsia 9.0
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 9.0
Gastrointestinal disorders Vomiting 9.0
Investigations Weight decreased 8.7
Psychiatric disorders Anxiety 8.4
Psychiatric disorders Anxiety 8.2
Gastrointestinal disorders Dyspepsia 8.0
Nervous system disorders Insomnia 8.0
Respiratory, thoracic and mediastinal disorders Mediastinal disorder
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 8.0
Psychiatric disorders Mental disorder
Gastrointestinal disorders Vomiting 8.0
Nervous system disorders Insomnia
Gastrointestinal disorders Abdominal pain upper 7.45
Cardiac disorders Dizziness 7.4
Gastrointestinal disorders Abdominal pain 7.14
Gastrointestinal disorders Gastrointestinal pain 7.14
General disorders and administration site conditions Irritability 7.14
General disorders and administration site conditions Decreased appetite 7.0
Gastrointestinal disorders Dry mouth 7.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 7.0
General disorders and administration site conditions Irritability
General disorders and administration site conditions Decreased appetite 6.83
Infections and infestations Nasopharyngitis 6.83
Cardiac disorders Dizziness 6.7
General disorders and administration site conditions Decreased appetite
Metabolism and nutrition disorders Malnutrition
Investigations Weight decreased 6.5
Nervous system disorders Insomnia 6.21
Gastrointestinal disorders Abdominal pain upper 6.2
Psychiatric disorders Affect lability 6.12
General disorders and administration site conditions Decreased appetite
Nervous system disorders Insomnia
Psychiatric disorders Anxiety 6.0
Cardiac disorders Tachycardia 6.0
Gastrointestinal disorders Abdominal pain upper 5.9
Gastrointestinal disorders Gastrointestinal disorder 5.9
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Gastrointestinal pain
Infections and infestations Infection 5.8
Infections and infestations Infestation 5.8
General disorders and administration site conditions Irritability 5.8
General disorders and administration site conditions Hyperhidrosis 5.7
Nervous system disorders Initial insomnia 5.7
Cardiac disorders Dizziness 5.52
Investigations Weight decreased 5.52
Cardiac disorders Dizziness
Cardiac disorders Dizziness
General disorders and administration site conditions Irritability 5.2
General disorders and administration site conditions Decreased appetite 5.1
General disorders and administration site conditions Hyperhidrosis 5.1
Psychiatric disorders Anxiety 5.0
General disorders and administration site conditions Decreased appetite 5.0
Gastrointestinal disorders Dyspepsia 5.0
Nervous system disorders Insomnia 5.0
General disorders and administration site conditions Irritability 5.0
Metabolism and nutrition disorders Malnutrition
Respiratory, thoracic and mediastinal disorders Nasal congestion 5.0
General disorders and administration site conditions Irritability 4.97
General disorders and administration site conditions Lethargy 4.97
Gastrointestinal disorders Nausea
Gastrointestinal disorders Abdominal pain 4.83
General disorders and administration site conditions Decreased appetite 4.83
Gastrointestinal disorders Gastrointestinal pain 4.83
Cardiac disorders Cardiac disorder 4.8
Cardiac disorders Tachycardia 4.8
General disorders and administration site conditions Decreased appetite
Nervous system disorders Insomnia
General disorders and administration site conditions Irritability
Gastrointestinal disorders Vomiting
General disorders and administration site conditions Asthenia 4.7
General disorders and administration site conditions Fatigue 4.7
Cardiac disorders Palpitations 4.5
Psychiatric disorders Depressed mood 4.4
Nervous system disorders Initial insomnia 4.3
General disorders and administration site conditions Decreased appetite
General disorders and administration site conditions Asthenia
General disorders and administration site conditions Decreased appetite 4.2
General disorders and administration site conditions Fatigue
Nervous system disorders Agitation 4.0
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Dry mouth 4.0
Gastrointestinal disorders Dyspepsia
Excoriation 4.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 4.0
Psychiatric disorders Depressed mood 3.9
Gastrointestinal disorders Abdominal pain upper
Gastrointestinal disorders Dry mouth
Gastrointestinal disorders Gastrointestinal disorder
Nervous system disorders Headache 3.73
Gastrointestinal disorders Dry mouth
Investigations Weight decreased
Gastrointestinal disorders Vomiting 3.45
Nervous system disorders Tremor 3.4
Gastrointestinal disorders Nausea
Investigations Weight decreased
Nervous system disorders Agitation 3.2
Gastrointestinal disorders Abdominal pain upper 3.11
General disorders and administration site conditions Decreased appetite 3.11
Nervous system disorders Insomnia 3.11
Nervous system disorders Agitation 3.1
Psychiatric disorders Nervousness 3.1
Cardiac disorders Palpitations 3.1
Psychiatric disorders Tension 3.1
General disorders and administration site conditions Decreased appetite 3.08
Nervous system disorders Insomnia 3.08
Psychiatric disorders Affect lability 3.0
Psychiatric disorders Depression 3.0
Nervous system disorders Insomnia
Psychiatric disorders Mood swings 3.0
Skin and subcutaneous tissue disorders Pruritus 3.0
Cardiac disorders Tachycardia 3.0
Psychiatric disorders Anxiety
General disorders and administration site conditions Irritability
Nervous system disorders Insomnia
Nervous system disorders Initial insomnia
Nervous system disorders Insomnia 2.8
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 2.8
Infections and infestations Nasopharyngitis 2.8
Nervous system disorders Nervous system disorder 2.8
Gastrointestinal disorders Vomiting 2.8
Nervous system disorders Insomnia
Gastrointestinal disorders Nausea
Nervous system disorders Tremor 2.7
Psychiatric disorders Depressed mood
Nervous system disorders Initial insomnia
Investigations Blood pressure increased 2.5
General disorders and administration site conditions Irritability 2.48
Infections and infestations Nasopharyngitis 2.48
Psychiatric disorders Anxiety
Gastrointestinal disorders Diarrhoea 2.4
Gastrointestinal disorders Nausea
Psychiatric disorders Nervousness 2.3
Psychiatric disorders Tension 2.3
Nervous system disorders Agitation 2.2
Investigations Body temperature increased 2.2
Gastrointestinal disorders Dyspepsia 2.2
Vascular disorders Hypertension 2.2
Infections and infestations Infection 2.2
Infections and infestations Infestation 2.2
Infections and infestations Nasopharyngitis
Nervous system disorders Nervous system disorder
Infections and infestations Upper respiratory tract infection 2.2
Psychiatric disorders Affect lability
Psychiatric disorders Anxiety
Psychiatric disorders Anxiety 2.0
General disorders and administration site conditions Application site reaction 2.0
General disorders and administration site conditions Decreased appetite 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 2.0
Eye disorders Eye pain 2.0
Nervous system disorders Initial insomnia 2.0
General disorders and administration site conditions Irritability 2.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Respiratory, thoracic and mediastinal disorders Laryngeal pain 2.0
Psychiatric disorders Mood swings
Ear and labyrinth disorders Motion sickness 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Ear and labyrinth disorders Vertigo 2.0
Gastrointestinal disorders Vomiting 2.0
Investigations Blood pressure increased
Respiratory, thoracic and mediastinal disorders Cough 1.9
Cardiac disorders Dizziness 1.9
Gastrointestinal disorders Dyspepsia
Psychiatric disorders Mental disorder 1.9
Musculoskeletal and connective tissue disorders Muscle tightness 1.9
Nervous system disorders Nervous system disorder 1.9
Cardiac disorders Tachycardia
General disorders and administration site conditions Thirst 1.8
Gastrointestinal disorders Vomiting 1.8
Psychiatric disorders Aggression 1.7
Psychiatric disorders Anxiety 1.7
Gastrointestinal disorders Bruxism 1.7
Musculoskeletal and connective tissue disorders Connective tissue disorder 1.7
General disorders and administration site conditions Decreased appetite 1.7
Psychiatric disorders Depression 1.7
Psychiatric disorders Disturbance in sexual arousal 1.7
Eye disorders Eye disorder 1.7
Gastrointestinal disorders Gastrointestinal disorder 1.7
Respiratory, thoracic and mediastinal disorders Laryngeal pain 1.7
Psychiatric disorders Libido decreased 1.7
Gastrointestinal disorders Oropharyngeal pain 1.7
General disorders and administration site conditions Pain 1.7
Skin and subcutaneous tissue disorders Skin disorder 1.7
Infections and infestations Upper respiratory tract infection 1.7
Ear and labyrinth disorders Vertigo 1.7
Eye disorders Vision blurred 1.7
Gastrointestinal disorders Vomiting 1.7
Vascular disorders Hypertension
Gastrointestinal disorders Vomiting
Gastrointestinal disorders Bruxism 1.5
Gastrointestinal disorders Constipation 1.5
Psychiatric disorders Depression 1.5
Nervous system disorders Insomnia 1.5
Gastrointestinal disorders Oropharyngeal pain 1.5
Psychiatric disorders Affect lability 1.4
Gastrointestinal disorders Constipation 1.4
General disorders and administration site conditions Decreased appetite 1.4
Psychiatric disorders Depressed mood
General disorders and administration site conditions Feeling jittery 1.4
Infections and infestations Infection
Infections and infestations Infestation
General disorders and administration site conditions Irritability
General disorders and administration site conditions Irritability 1.4
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Psychiatric disorders Nervousness 1.4
Gastrointestinal disorders Oropharyngeal pain
General disorders and administration site conditions Pain
Skin and subcutaneous tissue disorders Skin disorder
Psychiatric disorders Affect lability
General disorders and administration site conditions Decreased appetite
Cardiac disorders Dizziness
Gastrointestinal disorders Vomiting
Investigations Weight decreased
Gastrointestinal disorders Abdominal discomfort 1.3
Psychiatric disorders Affect lability 1.3
General disorders and administration site conditions Decreased appetite
Skin and subcutaneous tissue disorders Dermatitis 1.3
Psychiatric disorders Disturbance in sexual arousal 1.3
General disorders and administration site conditions Hot flush 1.3
General disorders and administration site conditions Hyperhidrosis
Nervous system disorders Insomnia 1.3
Psychiatric disorders Libido decreased 1.3
Reproductive system and breast disorders Menopausal symptoms 1.3
Musculoskeletal and connective tissue disorders Muscle tightness 1.3
Gastrointestinal disorders Oropharyngeal pain
Psychiatric disorders Panic attack 1.3
Skin and subcutaneous tissue disorders Rash 1.3
Infections and infestations Sinusitis 1.3
Psychiatric disorders Tension 1.3
Eye disorders Vision blurred 1.3
Gastrointestinal disorders Abdominal pain 1.2
Psychiatric disorders Aggression 1.2
General disorders and administration site conditions Asthenia 1.2
Nervous system disorders Confusional state 1.2
Respiratory, thoracic and mediastinal disorders Cough 1.2
Cardiac disorders Dyspnoea 1.2
General disorders and administration site conditions Feeling abnormal 1.2
Gastrointestinal disorders Gastrointestinal pain 1.2
Nervous system disorders Insomnia 1.2
Respiratory, thoracic and mediastinal disorders Laryngeal pain 1.2
Respiratory, thoracic and mediastinal disorders Mediastinal disorder 1.2
Psychiatric disorders Mental disorder 1.2
Gastrointestinal disorders Oropharyngeal pain 1.2
General disorders and administration site conditions Pain 1.2
Nervous system disorders Paraesthesia 1.2
Psychiatric disorders Tension 1.2
Nervous system disorders Tension headache 1.2
General disorders and administration site conditions Decreased appetite
Cardiac disorders Dizziness
Psychiatric disorders Affect lability 1.1
Psychiatric disorders Mood swings 1.1
Cardiac disorders Tachycardia 1.02
Investigations Alanine aminotransferase increased 1.0
Investigations Blood pressure increased 1.0
Nervous system disorders Confusional state 1.0
Respiratory, thoracic and mediastinal disorders Cough
Psychiatric disorders Erectile dysfunction 1.0
General disorders and administration site conditions Feeling abnormal 1.0
Nervous system disorders Headache 1.0
General disorders and administration site conditions Irritability 1.0
Musculoskeletal and connective tissue disorders Muscle spasms 1.0
Infections and infestations Sinusitis
Nervous system disorders Somnolence 1.0
Nervous system disorders Tension headache 1.0
Infections and infestations Upper respiratory tract infection
Eye disorders Vision blurred
Psychiatric disorders Affect lability
Investigations Body temperature increased
Gastrointestinal disorders Constipation
Respiratory, thoracic and mediastinal disorders Cough
Psychiatric disorders Depression
Gastrointestinal disorders Dyspepsia
General disorders and administration site conditions Hyperhidrosis
Infections and infestations Infection
Infections and infestations Infestation
Respiratory, thoracic and mediastinal disorders Laryngeal pain
Gastrointestinal disorders Oropharyngeal pain
General disorders and administration site conditions Pain
Cardiac disorders Palpitations
Infections and infestations Upper respiratory tract infection
Psychiatric disorders Anxiety 0.8
General disorders and administration site conditions Irritability 0.8
Gastrointestinal disorders Abdominal pain 0.7
Psychiatric disorders Affect lability 0.7
Psychiatric disorders Anxiety 0.7
General disorders and administration site conditions Decreased appetite 0.7
Gastrointestinal disorders Gastrointestinal pain 0.7
Psychiatric disorders Mood swings 0.7
Psychiatric disorders Nervousness 0.7
Psychiatric disorders Tension 0.7
Cardiac disorders Tachycardia 0.69
Psychiatric disorders Affect lability
Psychiatric disorders Aggression
Nervous system disorders Agitation
Gastrointestinal disorders Bruxism
Gastrointestinal disorders Constipation
Psychiatric disorders Depression
Psychiatric disorders Disturbance in sexual arousal
Cardiac disorders Dyspnoea
Nervous system disorders Headache 0.6
General disorders and administration site conditions Hot flush
Psychiatric disorders Libido decreased
Reproductive system and breast disorders Menopausal symptoms
Psychiatric disorders Nervousness
Cardiac disorders Palpitations
Psychiatric disorders Tension
General disorders and administration site conditions Thirst
Nervous system disorders Tremor
Gastrointestinal disorders Vomiting
Psychiatric disorders Aggression
Nervous system disorders Agitation
Gastrointestinal disorders Bruxism
Nervous system disorders Confusional state
Psychiatric disorders Disturbance in sexual arousal
General disorders and administration site conditions Feeling abnormal
Gastrointestinal disorders Gastrointestinal disorder
Psychiatric disorders Libido decreased
Respiratory, thoracic and mediastinal disorders Mediastinal disorder
Psychiatric disorders Mental disorder
Psychiatric disorders Nervousness
Psychiatric disorders Tension
Nervous system disorders Tension headache
Nervous system disorders Tremor
Eye disorders Vision blurred
Gastrointestinal disorders Vomiting
Nervous system disorders Confusional state
Respiratory, thoracic and mediastinal disorders Cough
Psychiatric disorders Erectile dysfunction
General disorders and administration site conditions Feeling abnormal
Nervous system disorders Insomnia
Respiratory, thoracic and mediastinal disorders Mediastinal disorder
Musculoskeletal and connective tissue disorders Muscle spasms
Psychiatric disorders Panic attack
Psychiatric disorders Tension
Nervous system disorders Tension headache
Ear and labyrinth disorders Vertigo

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
29.94
Injury, poisoning and procedural complications
28.75
Psychiatric disorders
11.35
Product issues
10.09
Skin and subcutaneous tissue disorders
7.15
Nervous system disorders
6.46

Cross References

Resources Reference
CAS NUMBER 113-45-1
ChEBI 84276
ChEMBL CHEMBL796
DrugBank DB00422
DrugCentral 1767
EPA CompTox DTXSID5023299
FDA SRS 207ZZ9QZ49
Human Metabolome Database HMDB0014566
Guide to Pharmacology 7236
KEGG C07196
PharmGKB PA10054
PubChem 10657292
SureChEMBL SCHEMBL37178
ZINC ZINC02522648
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