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Also known as: 143388-64-1, Naratriptan hcl, Amerge, Naramig, Gr-85548a, Gr 85548a
Molecular Formula
C17H26ClN3O2S
Molecular Weight
371.9  g/mol
InChI Key
AWEZYKMQFAUBTD-UHFFFAOYSA-N
FDA UNII
10X8X4P12Z

Naratriptan Hydrochloride
Naratriptan Hydrochloride is the hydrochloride salt form of naratriptan, a sulfonamide with selective serotonin (5-HT) 1 receptor agonistic activity and anti-migraine property. Naratriptan hydrochloride binds selectively and with high affinity to the 5-HT1D and 5-HT1B receptor subtypes. Activation of these 5-HT1D/B receptors located on intracranial blood vessels leads to vasoconstriction and provides relief of migraine headaches. Naratriptan hydrochloride may also exerts its effect by stimulation of 5-HT1D/1B receptors on sensory nerve endings in the trigeminal system thereby decreasing the release of pro-inflammatory neuropeptides.
1 2D Structure

Naratriptan Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide;hydrochloride
2.1.2 InChI
InChI=1S/C17H25N3O2S.ClH/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14;/h3-4,11-12,14,18-19H,5-10H2,1-2H3;1H
2.1.3 InChI Key
AWEZYKMQFAUBTD-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CNS(=O)(=O)CCC1=CC2=C(C=C1)NC=C2C3CCN(CC3)C.Cl
2.2 Other Identifiers
2.2.1 UNII
10X8X4P12Z
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1h-indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, Monohydrochloride

2. Amerge

3. Colatan

4. Gr 85548a

5. N-methyl-3-(1-methyl-4-piperidinyl)-1h-indole-5-ethanesulfonamide

6. N-methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide Monohydrochloride

7. Naramig

8. Naratriptan

2.3.2 Depositor-Supplied Synonyms

1. 143388-64-1

2. Naratriptan Hcl

3. Amerge

4. Naramig

5. Gr-85548a

6. Gr 85548a

7. Naratriptan (hydrochloride)

8. Gr-85548a Hydrochloride

9. N-methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide Monohydrochloride

10. 10x8x4p12z

11. 1h-indole-5-ethanesulfonamide, N-methyl-3-(1-methyl-4-piperidinyl)-, Monohydrochloride

12. Dsstox_cid_28990

13. Dsstox_rid_83255

14. N-methyl-2-(3-(1-methylpiperidin-4-yl)-1h-indol-5-yl)ethanesulfonamide Hydrochloride

15. N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethanesulfonamide;hydrochloride

16. Dsstox_gsid_49064

17. Chebi:7479

18. N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethanesulfonamide Hydrochloride

19. Cas-143388-64-1

20. Naratriptan Hydrochloride [usan]

21. Ncgc00181786-01

22. Unii-10x8x4p12z

23. Amerge Hydrochloride

24. Amerge (tn)

25. Mfcd08141821

26. Naratriptan Hydrochloride [usan:usp]

27. N-methyl-2-[3-(1-methyl-4-piperidyl)-1h-indol-5-yl]ethanesulfonamide Hydrochloride

28. Schembl41527

29. Mls006010726

30. Chembl1200601

31. Dtxsid6049064

32. Hy-b0197a

33. Amy41021

34. Bcp04270

35. Tox21_113617

36. Tox21_500466

37. Gg-548

38. Naratriptan Hydrochloride (jan/usp)

39. Rb3224

40. S1488

41. Naratriptan Hydrochloride [mi]

42. Akos005145806

43. Tox21_113617_1

44. Ac-5014

45. Ccg-221770

46. Naratriptan Hydrochloride [jan]

47. Naratriptan Hydrochloride [mart.]

48. Naratriptan Hydrochloride [vandf]

49. Ncgc00181786-02

50. Ncgc00261151-01

51. As-58417

52. Naratriptan Hydrochloride [usp-rs]

53. Naratriptan Hydrochloride [who-dd]

54. Smr002529694

55. Naratriptan Hydrochloride, >=98% (hplc)

56. Ft-0672649

57. Sw219416-1

58. D00674

59. Naratriptan Hydrochloride [orange Book]

60. Naratriptan Hydrochloride [usp Monograph]

61. 388n641

62. A808063

63. J-007804

64. Q-201448

65. Q27107505

66. N-methyl-2-[3-(1-methyl-4-piperidinyl)-1h-indol-5-yl]ethanesulfonamide Hydrochloride

67. N-methyl-2-[3-(1-methylpiperidin-4-yl)-1h-indol-5-yl]ethane-1-sulfonamide Hydrochloride

68. N-methyl-3-(1-methyl-4-piperidinyl)-1h-indole-5-ethanesulphonamide Hydrochloride

69. N-methyl-3-(1-methyl-4-piperidinyl)-1h-indole-5-ethanesulphonamide, Hydrochloride

70. Naratriptan Hydrochloride, United States Pharmacopeia (usp) Reference Standard

71. 2-[3-(1-methyl-piperidin-4-yl)-1h-indol-5-yl]-ethanesulfonic Acid Methylamide Hydrochloride

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 371.9 g/mol
Molecular Formula C17H26ClN3O2S
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count5
Exact Mass371.1434259 g/mol
Monoisotopic Mass371.1434259 g/mol
Topological Polar Surface Area73.6 Ų
Heavy Atom Count24
Formal Charge0
Complexity483
Isotope Atom Count0
Defined Atom Stereocenter Count0
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 2  
Drug NameAmerge
PubMed HealthNaratriptan (By mouth)
Drug ClassesAntimigraine
Drug LabelAMERGE contains naratriptan hydrochloride, a selective 5-HT1B/1D receptor agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide monohydrochloride, and it has the following str...
Active IngredientNaratriptan hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 2.5mg base; eq 1mg base
Market StatusPrescription
CompanyGlaxosmithkline

2 of 2  
Drug NameAmerge
PubMed HealthNaratriptan (By mouth)
Drug ClassesAntimigraine
Drug LabelAMERGE contains naratriptan hydrochloride, a selective 5-HT1B/1D receptor agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-(1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide monohydrochloride, and it has the following str...
Active IngredientNaratriptan hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 2.5mg base; eq 1mg base
Market StatusPrescription
CompanyGlaxosmithkline

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Serotonin 5-HT1 Receptor Agonists

Endogenous compounds and drugs that specifically stimulate SEROTONIN 5-HT1 RECEPTORS. Included under this heading are agonists for one or more of the specific 5-HT1 receptor subtypes. (See all compounds classified as Serotonin 5-HT1 Receptor Agonists.)


Vasoconstrictor Agents

Drugs used to cause constriction of the blood vessels. (See all compounds classified as Vasoconstrictor Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Serotonin 1d Receptor Agonists [MoA]; Serotonin-1b and Serotonin-1d Receptor Agonist [EPC]; Serotonin 1b Receptor Agonists [MoA]

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11-Jan-2021
09-Aug-2024
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DOSAGE - TABLET;ORAL - EQ 1MG BASE **Federal ...DOSAGE - TABLET;ORAL - EQ 1MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20763

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DOSAGE - TABLET;ORAL - EQ 2.5MG BASE **Federa...DOSAGE - TABLET;ORAL - EQ 2.5MG BASE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20763

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