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Chemistry

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Also known as: Dexmethylphenidate hcl, Focalin, D-threo-methylphenidate hydrochloride, 19262-68-1, Focalin xr, 23655-65-4
Molecular Formula
C14H20ClNO2
Molecular Weight
269.77  g/mol
InChI Key
JUMYIBMBTDDLNG-OJERSXHUSA-N
FDA UNII
1678OK0E08

Dexmethylphenidate
A methylphenidate derivative, DOPAMINE UPTAKE INHIBITOR and CENTRAL NERVOUS SYSTEM STIMULANT that is used in the treatment of ATTENTION DEFICIT HYPERACTIVITY DISORDER.
1 2D Structure

Dexmethylphenidate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
methyl (2R)-2-phenyl-2-[(2R)-piperidin-2-yl]acetate;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/t12-,13-;/m1./s1
2.1.3 InChI Key
JUMYIBMBTDDLNG-OJERSXHUSA-N
2.1.4 Canonical SMILES
COC(=O)C(C1CCCCN1)C2=CC=CC=C2.Cl
2.1.5 Isomeric SMILES
COC(=O)[C@@H]([C@H]1CCCCN1)C2=CC=CC=C2.Cl
2.2 Other Identifiers
2.2.1 UNII
1678OK0E08
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dexmethylphenidate

2. Focalin

3. Focalin Xr

4. Hydrochloride, Dexmethylphenidate

5. Xr, Focalin

2.3.2 Depositor-Supplied Synonyms

1. Dexmethylphenidate Hcl

2. Focalin

3. D-threo-methylphenidate Hydrochloride

4. 19262-68-1

5. Focalin Xr

6. 23655-65-4

7. Metadate Cd

8. Metadate Er

9. Equasym Xl

10. Dexmethylphenidate Hydrochloride [usan]

11. Ritalin

12. 4b3sc438hi

13. Dex-methylphenidate Hydrochloride

14. Methyl (2r)-2-phenyl-2-[(2r)-piperidin-2-yl]acetate;hydrochloride

15. 1678ok0e08

16. Methylphenidate D-threo-form Hydrochloride

17. Methyl (2r)-phenyl((2r)-piperidin-2-yl)acetate Hydrochloride

18. 19262-68-1 (hcl)

19. Methyl (2r)-2-phenyl-2-[(2r)-piperidin-1-ium-2-yl]acetate;chloride

20. Quillichew

21. Quillivant

22. Aptensio

23. Foquest

24. Oros Mph

25. Aptensio Xr

26. Methylin Er

27. Ritalin La

28. Ritalin Sr

29. Chembl904

30. (r)-methyl 2-phenyl-2-((r)-piperidin-2-yl)acetate Hydrochloride

31. Daytrana

32. Dexmethylphenidate Hydrochloride (usan)

33. Spd544

34. Spd-544

35. Dl-threo-methylphenidate Hcl

36. Biphentin

37. Equasym

38. Methypatch

39. Metadate Mr

40. Unii-1678ok0e08

41. Equasym Ir

42. Ritalin Qd

43. Focalin (tn)

44. Dl-threo-methylphenidate Hydrochloride

45. Adhansia Xr

46. Jornay Pm

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

48. Unii-4b3sc438hi

49. Nwp-06

50. Dtxsid50940927

51. D-threo Methylphenidate Hydrochloride

52. Akos027321667

53. Rac-threo-methylphenidate Hydrochloride

54. 2-piperidineacetic Acid, Alpha-phenyl-, Methyl Ester, Hydrochloride, (alphar,2r)-

55. 2-piperidineacetic Acid, Alpha-phenyl-, Methyl Ester, Hydrochloride, (r*,r*)- (+-)-

56. 2-piperidineacetic Acid, Alpha-phenyl-, Methyl Ester, Hydrochloride, (r-(r*,r*))-

57. Methylphenidate Hydrochloride [mi]

58. (+/-)-threo-methylphenidate Hydrochloride

59. Methylphenidate Hydrochloride [jan]

60. Methylphenidate Hydrochloride [mart.]

61. Methylphenidate Hydrochloride [vandf]

62. Methylphenidate Hydrochloride [who-dd]

63. D03721

64. Dexmethylphenidate Hydrochloride [mart.]

65. Dexmethylphenidate Hydrochloride [vandf]

66. Dexmethylphenidate Hydrochloride [who-dd]

67. Methylphenidate Hydrochloride [orange Book]

68. Methylphenidate Hydrochloride Cii [usp-rs]

69. Methylphenidate Hydrochloride [ep Monograph]

70. Methylphenidate Hydrochloride [usp Monograph]

71. Dexmethylphenidate Hydrochloride [orange Book]

72. Methylphenidate D-threo-form Hydrochloride [mi]

73. Q47487562

74. Azstarys Component Dexmethylphenidate Hydrochloride

75. Dexmethylphenidate Hydrochloride Component Of Azstarys

76. Methyl Phenyl(piperidin-2-yl)acetate--hydrogen Chloride (1/1)

77. Methylphenidate Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

78. 2-piperidineacetic Acid, .alpha.-phenyl-, Methyl Ester, Hydrochloride, (r*,r*)-(+/-)-

79. 2-piperidineacetic Acid, .alpha.-phenyl-, Methyl Ester, Hydrochloride,(.alpha.r,2r)-

2.4 Create Date
2005-08-08
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 Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameDexmethylphenidate hydrochloride
Drug LabelFocalin (dexmethylphenidate hydrochloride) is the d-threo-enantiomer of racemic methylphenidate hydrochloride, which is a 50/50 mixture of the d-threo and l-threo-enantiomers. Focalin is a central nervous system (CNS) stimulant, available in 3 tabl...
Active IngredientDexmethylphenidate hydrochloride
Dosage FormTablet; Capsule, extended release
Routeoral; Oral
Strength2.5mg; 5mg; 25mg; 30mg; 10mg; 15mg; 40mg; 20mg
Market StatusTentative Approval; Prescription
CompanyWatson Labs; Mylan Pharms; Teva Pharms; Intellipharmaceutics; Teva Pharms Usa

2 of 6  
Drug NameFocalin
PubMed HealthDexmethylphenidate (By mouth)
Drug ClassesCNS Stimulant
Drug LabelFocalin (dexmethylphenidate hydrochloride) is the d-threo-enantiomer of racemic methylphenidate hydrochloride, which is a 50/50 mixture of the d-threo and l-threo-enantiomers. Focalin is a central nervous system (CNS) stimulant, available in 3 tabl...
Active IngredientDexmethylphenidate hydrochloride
Dosage FormTablet
RouteOral
Strength2.5mg; 5mg; 10mg
Market StatusPrescription
CompanyNovartis

3 of 6  
Drug NameFocalin xr
PubMed HealthDexmethylphenidate (By mouth)
Drug ClassesCNS Stimulant
Drug LabelFocalin XR is an extended-release formulation of dexmethylphenidate with a bi-modal release profile. Focalin XR uses the proprietary SODAS (Spheroidal Oral Drug Absorption System) technology. Each bead-filled Focalin XR capsule contains half the dose...
Active IngredientDexmethylphenidate hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strength25mg; 30mg; 15mg; 5mg; 10mg; 40mg; 20mg; 35mg
Market StatusPrescription
CompanyNovartis

4 of 6  
Drug NameDexmethylphenidate hydrochloride
Drug LabelFocalin (dexmethylphenidate hydrochloride) is the d-threo-enantiomer of racemic methylphenidate hydrochloride, which is a 50/50 mixture of the d-threo and l-threo-enantiomers. Focalin is a central nervous system (CNS) stimulant, available in 3 tabl...
Active IngredientDexmethylphenidate hydrochloride
Dosage FormTablet; Capsule, extended release
Routeoral; Oral
Strength2.5mg; 5mg; 25mg; 30mg; 10mg; 15mg; 40mg; 20mg
Market StatusTentative Approval; Prescription
CompanyWatson Labs; Mylan Pharms; Teva Pharms; Intellipharmaceutics; Teva Pharms Usa

5 of 6  
Drug NameFocalin
PubMed HealthDexmethylphenidate (By mouth)
Drug ClassesCNS Stimulant
Drug LabelFocalin (dexmethylphenidate hydrochloride) is the d-threo-enantiomer of racemic methylphenidate hydrochloride, which is a 50/50 mixture of the d-threo and l-threo-enantiomers. Focalin is a central nervous system (CNS) stimulant, available in 3 tabl...
Active IngredientDexmethylphenidate hydrochloride
Dosage FormTablet
RouteOral
Strength2.5mg; 5mg; 10mg
Market StatusPrescription
CompanyNovartis

6 of 6  
Drug NameFocalin xr
PubMed HealthDexmethylphenidate (By mouth)
Drug ClassesCNS Stimulant
Drug LabelFocalin XR is an extended-release formulation of dexmethylphenidate with a bi-modal release profile. Focalin XR uses the proprietary SODAS (Spheroidal Oral Drug Absorption System) technology. Each bead-filled Focalin XR capsule contains half the dose...
Active IngredientDexmethylphenidate hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strength25mg; 30mg; 15mg; 5mg; 10mg; 40mg; 20mg; 35mg
Market StatusPrescription
CompanyNovartis

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


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.)


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

DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 10MG

USFDA APPLICATION NUMBER - 21278

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DOSAGE - TABLET;ORAL - 2.5MG

USFDA APPLICATION NUMBER - 21278

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DOSAGE - TABLET;ORAL - 5MG

USFDA APPLICATION NUMBER - 21278

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 10M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 10MG

USFDA APPLICATION NUMBER - 21802

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 15M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 15MG

USFDA APPLICATION NUMBER - 21802

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 20M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 20MG

USFDA APPLICATION NUMBER - 21802

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 25M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 25MG

USFDA APPLICATION NUMBER - 21802

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 30M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 30MG

USFDA APPLICATION NUMBER - 21802

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 35M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 35MG

USFDA APPLICATION NUMBER - 21802

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 40M...DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 40MG

USFDA APPLICATION NUMBER - 21802

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DOSAGE - CAPSULE, EXTENDED RELEASE;ORAL - 5MG

USFDA APPLICATION NUMBER - 21802

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