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2D Structure
Also known as: 298-59-9, Centedrin, Centedrine, Methylphenidate hcl, Concerta, Ritalin
Molecular Formula
C14H20ClNO2
Molecular Weight
269.77  g/mol
InChI Key
JUMYIBMBTDDLNG-UHFFFAOYSA-N

A central nervous system stimulant used most commonly in the treatment of ATTENTION DEFICIT DISORDER in children and for NARCOLEPSY. Its mechanisms appear to be similar to those of DEXTROAMPHETAMINE. The d-isomer of this drug is referred to as DEXMETHYLPHENIDATE HYDROCHLORIDE.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl 2-phenyl-2-piperidin-2-ylacetate;hydrochloride
2.1.2 InChI
InChI=1S/C14H19NO2.ClH/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;1H
2.1.3 InChI Key
JUMYIBMBTDDLNG-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC(=O)C(C1CCCCN1)C2=CC=CC=C2.Cl
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Centedrin

2. Concerta

3. Daytrana

4. Equasym

5. Hydrochloride, Methylphenidate

6. Metadate

7. Methylin

8. Methylphenidate

9. Phenidylate

10. Ritalin

11. Ritalin Sr

12. Ritalin-sr

13. Ritaline

14. Tsentedrin

2.2.2 Depositor-Supplied Synonyms

1. 298-59-9

2. Centedrin

3. Centedrine

4. Methylphenidate Hcl

5. Concerta

6. Ritalin

7. Methylphenidate.hcl

8. Metadate

9. Methylin

10. Metilfenidat Hydrochloride

11. Ritalin Sr

12. H-tic-otbu.hcl

13. Threo-methylphenidate Hydrochloride

14. Daytrana

15. Methylin Er

16. Methylphenidylacetate Hydrochloride

17. Ritalin La

18. Methylphenidate (hydrochloride)

19. Ritalin Hydrochloride

20. Ritalin-sr

21. Methyl 2-phenyl-2-piperidin-2-ylacetate;hydrochloride

22. Nsc-169868

23. Ncgc00091942-01

24. Rilaline

25. Dsstox_cid_886

26. Dsstox_rid_75843

27. Dsstox_gsid_20886

28. Methyl Phenyl(piperidin-2-yl)acetate Hydrochloride

29. Quillichew

30. Quillivant

31. Aptensio

32. Foquest

33. Meridil Hydrochloride

34. Oros Mph

35. Aptensio Xr

36. Rilatine

37. Quillivant Xr

38. Quillichew Er

39. Chebi:31836

40. Cas-298-59-9

41. Nsc 169868

42. Ccris 6258

43. Methyl 2-phenyl-2-(piperidin-2-yl)acetate Hydrochloride

44. Einecs 206-065-3

45. Spd544

46. Spd-544

47. Methylphenidate Hydrochloride Er

48. Concerta (tn)

49. Metadate (tn)

50. Methyl Phenidate Hcl

51. Ritalin (tn)

52. Methyl Alpha-phenyl-2-piperidineacetate Hydrochloride

53. Quillivant Xr (tn)

54. Methylphenidate Hydrochloride [usp:jan]

55. Methylphenidate(ritalin)

56. Methyl .alpha.-phenyl-2-piperidineacetate Hydrochloride

57. Chembl1722

58. Schembl41067

59. Mls003922100

60. Dtxsid8020886

61. Methylphenidate Hydrochloride Cii

62. Hy-b1091a

63. Pharmakon1600-01505907

64. Bcp34044

65. Tox21_111186

66. Tox21_200309

67. 2-piperidineacetic Acid, Alpha-phenyl-, Methyl Ester, Hydrochloride

68. Mfcd00058191

69. Nsc169868

70. Nsc759278

71. Akos016010356

72. Ccg-213572

73. Cs-4658

74. Nsc-759278

75. Sb13180

76. Wln: T6mtj Byr & Vo1 & Gh

77. 2-piperidineacetic Acid, Alpha-phenyl-, Methyl Ester, Hydrochloride, (r*,r*)-(+-)-

78. Methylphenidate Hydrochloride (jan/usp)

79. Ncgc00257863-01

80. Smr000058998

81. Ft-0672045

82. Ft-0672046

83. Ft-0672048

84. Ft-0672050

85. D01296

86. 298m599

87. 2-piperidineacetic Acid, Methyl Ester, Hydrochloride

88. Methylphenidate Hydrochloride(ritalin Hydrochloride)

89. Methylphenidate Hcl;threo-methylphenidate Hydrochloride

90. Q26840773

91. Methyl 2-phenyl-2-(piperidin-2-yl)acetate Hcl

92. Methylphenidate Hydrochloride, European Pharmacopoeia (ep) Reference Standard

93. Methylphenidate Hydrochloride Solution, (racemic Mixture), Ampule Of 1 Ml, 1.0 Mg/ml In Methanol (as Free Base), Certified Reference Material

2.3 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 269.77 g/mol
Molecular Formula C14H20ClNO2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count3
Rotatable Bond Count4
Exact Mass269.1182566 g/mol
Monoisotopic Mass269.1182566 g/mol
Topological Polar Surface Area38.3 Ų
Heavy Atom Count18
Formal Charge0
Complexity249
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 16  
Drug NameConcerta
PubMed HealthMethylphenidate
Drug ClassesCNS Stimulant, Central Nervous System Agent
Drug LabelCONCERTA is a central nervous system (CNS) stimulant. CONCERTA is available in four tablet strengths. Each extended-release tablet for once-a-day oral administration contains 18, 27, 36, or 54 mg of methylphenidate HCl USP and is designed to have...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength54mg; 18mg; 27mg; 36mg
Market StatusPrescription
CompanyJanssen Pharms

2 of 16  
Drug NameMetadate cd
PubMed HealthMethylphenidate
Drug ClassesCNS Stimulant, Central Nervous System Agent
Drug LabelMETADATE CD is a central nervous system (CNS) stimulant. The extended-release capsules comprise both immediate-release (IR) and extended-release (ER) beads such that 30% of the dose is provided by the IR component and 70% of the dose is provided by t...
Active IngredientMethylphenidate hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strength30mg; 50mg; 60mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyUcb

3 of 16  
Drug NameMetadate er
PubMed HealthMethylphenidate (By mouth)
Drug ClassesCNS Stimulant, Central Nervous System Agent
Drug LabelMETADATE ER Tablets (methylphenidate hydrochloride extended-release tablets, USP) are a mild central nervous system (CNS) stimulant. METADATE ER is available as 20 mg extended-release tablets for oral administration.Methylphenidate hydrochloride is m...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength20mg
Market StatusPrescription
CompanyUcb

4 of 16  
Drug NameMethylin er
PubMed HealthMethylphenidate
Drug ClassesCNS Stimulant, Central Nervous System Agent
Drug LabelMethylphenidate hydrochloride is a mild central nervous system (CNS) stimulant, available for oral administration as tablets of 5 mg, 10 mg, and 20 mg and as extended-release tablets of 10 mg and 20 mg. Methylphenidate hydrochloride is methyl -phen...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength10mg; 20mg
Market StatusPrescription
CompanyMallinckrodt

5 of 16  
Drug NameMethylphenidate hydrochloride
Drug LabelMethylphenidate hydrochloride is a mild central nervous system (CNS) stimulant, available for oral administration as tablets of 5 mg, 10 mg, and 20 mg and as extended-release tablets of 10 mg and 20 mg. Methylphenidate hydrochloride is methyl -phen...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet, extended release; Tablet; Capsule, extended release; Solution
Routeoral; Oral
Strength10mg/5ml; 18mg; 30mg; 27mg; 36mg; 5mg; 54mg; 50mg; 60mg; 10mg; 5mg/5ml; 40mg; 20mg
Market StatusTentative Approval; Prescription
CompanyCorepharma; Vintage Pharms; Actavis Labs Fl; Sun Pharm Inds; Barr Labs; Mallinckrodt; Watson Labs; Actavis S Atlantic; Teva Pharms; Caraco; Ucb; Kudco Ireland; Tris Pharma

6 of 16  
Drug NameQuillivant xr
Drug LabelQUILLIVANT XR is a powder that, after reconstitution with water, forms an extended-release oral suspension formulation of methylphenidate intended for once daily oral administration. QUILLIVANT XR contains approximately 20% immediate-release and 80%...
Active IngredientMethylphenidate hydrochloride
Dosage FormFor suspension, extended release
RouteOral
Strength5mg/ml
Market StatusPrescription
CompanyNextwave Pharms

7 of 16  
Drug NameRitalin
Drug LabelRitalin hydrochloride, methylphenidate hydrochloride USP, is a mild central nervous system (CNS) stimulant, available as tablets of 5, 10, and 20 mg for oral administration; Ritalin-SR is available as sustained-release tablets of 20 mg for oral admin...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet
RouteOral
Strength5mg; 10mg; 20mg
Market StatusPrescription
CompanyNovartis

8 of 16  
Drug NameRitalin la
Drug LabelMethylphenidate hydrochloride is a central nervous system (CNS) stimulant. Ritalin LA (methylphenidate hydrochloride) extended-release capsules is an extended-release formulation of methylphenidate with a bi-modal release profile. Ritalin LA uses t...
Active IngredientMethylphenidate hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strength30mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyNovartis

9 of 16  
Drug NameConcerta
PubMed HealthMethylphenidate
Drug ClassesCNS Stimulant, Central Nervous System Agent
Drug LabelCONCERTA is a central nervous system (CNS) stimulant. CONCERTA is available in four tablet strengths. Each extended-release tablet for once-a-day oral administration contains 18, 27, 36, or 54 mg of methylphenidate HCl USP and is designed to have...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength54mg; 18mg; 27mg; 36mg
Market StatusPrescription
CompanyJanssen Pharms

10 of 16  
Drug NameMetadate cd
PubMed HealthMethylphenidate
Drug ClassesCNS Stimulant, Central Nervous System Agent
Drug LabelMETADATE CD is a central nervous system (CNS) stimulant. The extended-release capsules comprise both immediate-release (IR) and extended-release (ER) beads such that 30% of the dose is provided by the IR component and 70% of the dose is provided by t...
Active IngredientMethylphenidate hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strength30mg; 50mg; 60mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyUcb

11 of 16  
Drug NameMetadate er
PubMed HealthMethylphenidate (By mouth)
Drug ClassesCNS Stimulant, Central Nervous System Agent
Drug LabelMETADATE ER Tablets (methylphenidate hydrochloride extended-release tablets, USP) are a mild central nervous system (CNS) stimulant. METADATE ER is available as 20 mg extended-release tablets for oral administration.Methylphenidate hydrochloride is m...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength20mg
Market StatusPrescription
CompanyUcb

12 of 16  
Drug NameMethylin er
PubMed HealthMethylphenidate
Drug ClassesCNS Stimulant, Central Nervous System Agent
Drug LabelMethylphenidate hydrochloride is a mild central nervous system (CNS) stimulant, available for oral administration as tablets of 5 mg, 10 mg, and 20 mg and as extended-release tablets of 10 mg and 20 mg. Methylphenidate hydrochloride is methyl -phen...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength10mg; 20mg
Market StatusPrescription
CompanyMallinckrodt

13 of 16  
Drug NameMethylphenidate hydrochloride
Drug LabelMethylphenidate hydrochloride is a mild central nervous system (CNS) stimulant, available for oral administration as tablets of 5 mg, 10 mg, and 20 mg and as extended-release tablets of 10 mg and 20 mg. Methylphenidate hydrochloride is methyl -phen...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet, extended release; Tablet; Capsule, extended release; Solution
Routeoral; Oral
Strength10mg/5ml; 18mg; 30mg; 27mg; 36mg; 5mg; 54mg; 50mg; 60mg; 10mg; 5mg/5ml; 40mg; 20mg
Market StatusTentative Approval; Prescription
CompanyCorepharma; Vintage Pharms; Actavis Labs Fl; Sun Pharm Inds; Barr Labs; Mallinckrodt; Watson Labs; Actavis S Atlantic; Teva Pharms; Caraco; Ucb; Kudco Ireland; Tris Pharma

14 of 16  
Drug NameQuillivant xr
Drug LabelQUILLIVANT XR is a powder that, after reconstitution with water, forms an extended-release oral suspension formulation of methylphenidate intended for once daily oral administration. QUILLIVANT XR contains approximately 20% immediate-release and 80%...
Active IngredientMethylphenidate hydrochloride
Dosage FormFor suspension, extended release
RouteOral
Strength5mg/ml
Market StatusPrescription
CompanyNextwave Pharms

15 of 16  
Drug NameRitalin
Drug LabelRitalin hydrochloride, methylphenidate hydrochloride USP, is a mild central nervous system (CNS) stimulant, available as tablets of 5, 10, and 20 mg for oral administration; Ritalin-SR is available as sustained-release tablets of 20 mg for oral admin...
Active IngredientMethylphenidate hydrochloride
Dosage FormTablet
RouteOral
Strength5mg; 10mg; 20mg
Market StatusPrescription
CompanyNovartis

16 of 16  
Drug NameRitalin la
Drug LabelMethylphenidate hydrochloride is a central nervous system (CNS) stimulant. Ritalin LA (methylphenidate hydrochloride) extended-release capsules is an extended-release formulation of methylphenidate with a bi-modal release profile. Ritalin LA uses t...
Active IngredientMethylphenidate hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strength30mg; 10mg; 40mg; 20mg
Market StatusPrescription
CompanyNovartis

4.2 Drug Indication

Treatment of Attention Deficit Hyperactivity Disorder (ADHD)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Central Nervous System Stimulants

A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here. (See all compounds classified as Central Nervous System Stimulants.)


Dopamine Uptake Inhibitors

Drugs that block the transport of DOPAMINE into axon terminals or into storage vesicles within terminals. Most of the ADRENERGIC UPTAKE INHIBITORS also inhibit dopamine uptake. (See all compounds classified as Dopamine Uptake Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Central Nervous System Stimulation [PE]; Central Nervous System Stimulant [EPC]