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Chemistry

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Also known as: 1229-29-4, Doxepin hcl, (e)-doxepin hydrochloride, 4698-39-9, Curatin, Novoxapin
Molecular Formula
C19H22ClNO
Molecular Weight
315.8  g/mol
InChI Key
MHNSPTUQQIYJOT-SJDTYFKWSA-N
FDA UNII
CU61C5RH24

Doxepin Hydrochloride
A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.
1 2D Structure

Doxepin Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine;hydrochloride
2.1.2 InChI
InChI=1S/C19H21NO.ClH/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19;/h3-6,8-12H,7,13-14H2,1-2H3;1H/b17-11+;
2.1.3 InChI Key
MHNSPTUQQIYJOT-SJDTYFKWSA-N
2.1.4 Canonical SMILES
CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31.Cl
2.1.5 Isomeric SMILES
CN(C)CC/C=C/1\C2=CC=CC=C2COC3=CC=CC=C31.Cl
2.2 Other Identifiers
2.2.1 UNII
CU61C5RH24
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Apo Doxepin

2. Apo-doxepin

3. Apodoxepin

4. Aponal

5. Deptran

6. Desidox

7. Doneurin

8. Doxepia

9. Doxepin

10. Doxepin Beta

11. Doxepin Hydrochloride, Cis-trans Isomer Mixture (approximately 1:5)

12. Doxepin Rph

13. Doxepin-rph

14. Espadox

15. Hydrochloride, Doxepin

16. Mareen

17. Novo Doxepin

18. Novo-doxepin

19. Prudoxin

20. Quitaxon

21. Sinequan

22. Sinquan

23. Xepin

24. Zonalon

2.3.2 Depositor-Supplied Synonyms

1. 1229-29-4

2. Doxepin Hcl

3. (e)-doxepin Hydrochloride

4. 4698-39-9

5. Curatin

6. Novoxapin

7. Silenor

8. Sinequan

9. Adapin

10. Aponal

11. Toruan

12. Doxepine Hydrochloride

13. Novoxapin Hydrochloride

14. Doxepin (hydrochloride)

15. Mls000069794

16. Cu61c5rh24

17. Mf 10 Hcl

18. Smr000058230

19. Sinequan (tn)

20. Nsc-108160

21. Dsstox_cid_25145

22. Dsstox_rid_80701

23. Dsstox_gsid_45145

24. Quitaxon

25. Sinequin

26. P-3693a

27. (3e)-3-(6h-benzo[c][1]benzoxepin-11-ylidene)-n,n-dimethylpropan-1-amine;hydrochloride

28. 3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n,n-dimethylpropan-1-amine Hydrochloride

29. Sr-01000075551

30. Ncgc00015344-03

31. Einecs 214-966-8

32. Cas-1229-29-4

33. Trans-doxepin Hydrochloride

34. Unii-3u9a0fe9n5

35. Unii-cu61c5rh24

36. Doxepin Hydrochloride (e)-isomer

37. (e)-3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n,n-dimethylpropan-1-amine Hydrochloride

38. Doxepin Hydrochloride [usan:usp]

39. Prestwick_187

40. Zonalon (tn)

41. (e)-doxepin Hcl

42. Mfcd00079135

43. Opera_id_675

44. 1-propanamine, 3-dibenz(b,e)oxepin-11(6h)ylidene-n,n-dimethyl-, Hydrochloride

45. 11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenz(b,e)oxepin Hydrochloride

46. N,n-dimethyldibenz(b,e)oxepin-delta(sup 11(6h),gamma)-propylamine Hydrochloride

47. Doxepin Hydrochloride (usp)

48. Schembl60287

49. Mls001148235

50. Mls002207250

51. Mls002222181

52. Mls002548858

53. Doxepin For System Suitability

54. E-doxepin Hydrochloride

55. 3u9a0fe9n5

56. Chebi:4711

57. Chembl1200462

58. Dtxsid8045145

59. Hms1568f08

60. Hy-b0725

61. Doxepin Hydrochloride, (e)-

62. Tox21_110130

63. Tox21_500339

64. S3120

65. Akos015895087

66. Dibenz(b,e)oxepin-delta11(6h),gamma-propylamine, N,n-dimethyl-, Hydrochloride

67. Tox21_110130_1

68. Ccg-220263

69. Ccg-221643

70. Ks-5094

71. Lp00339

72. Nc00447

73. Dibenz(b,e)oxepin-delta(sup 11(6h),gamma)-propylamine, N,n-dimethyl-, Hydrochloride

74. Ncgc00024623-04

75. Ncgc00093778-01

76. Ncgc00093778-02

77. Ncgc00261024-01

78. Bd166235

79. Eu-0100339

80. D 4526

81. D00814

82. 229d294

83. A804993

84. Q-201044

85. Sr-01000075551-1

86. Sr-01000075551-5

87. Q27275787

88. Doxepin Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

89. Doxepin Hydrochloride, European Pharmacopoeia (ep) Reference Standard

90. Doxepin Hydrochloride, United States Pharmacopeia (usp) Reference Standard

91. (3e)-3-(6h-benzo[c][1]benzoxepin-11-ylidene)-n,n-dimethyl-1-propanamine Hydrochloride

92. (3e)-3-(6h-benzo[c][1]benzoxepin-11-ylidene)-n,n-dimethyl-propan-1-amine Hydrochloride

93. Doxepin For System Suitability, European Pharmacopoeia (ep) Reference Standard

94. Doxepin Hydrochloride, ~85% E-isomer Basis, >=98% (gc), 15% Z-isomer Basis, Powder

95. 1-propanamine, 3-dibenz(b,e)oxepin-11(6h)-ylidene-n,n-dimethyl-, Hydrochloride (1:1), (3e)-

96. 1-propanamine, 3-dibenz(b,e)oxepin-11-(6h)-ylidene-n,n-dimethyl-dimethyl-, Hydrochloride, (e)-

2.4 Create Date
2006-04-14
3 Chemical and Physical Properties
Molecular Weight 315.8 g/mol
Molecular Formula C19H22ClNO
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass315.1389920 g/mol
Monoisotopic Mass315.1389920 g/mol
Topological Polar Surface Area12.5 Ų
Heavy Atom Count22
Formal Charge0
Complexity363
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameDoxepin hydrochloride
PubMed HealthDoxepin
Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
Drug LabelDoxepin hydrochloride is one of a class of psychotherapeutic agents known as dibenzoxepin tricyclic compounds. The molecular formula of the compound is C19H21NOHCl having a molecular weight of 316. It is a white crystalline solid readily soluble in w...
Active IngredientDoxepin hydrochloride
Dosage FormTablet; Concentrate; Capsule
Routeoral; Oral
Strengtheq 100mg base; eq 50mg base; 6mg; eq 6mg base; eq 150mg base; eq 10mg base; eq 10mg base/ml; eq 25mg base; 3mg; eq 3mg base; eq 75mg base
Market StatusTentative Approval; Prescription
CompanyWockhardt; Mylan Pharms; Silarx; Actavis Elizabeth; Teva Pharms; Zydus Pharms Usa; Par Pharm; Mylan

2 of 6  
Drug NameSilenor
PubMed HealthDoxepin
Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
Drug LabelSilenor (doxepin) is available in 3 mg and 6 mg strength tablets for oral administration. Each tablet contains 3.39 mg or 6.78 mg doxepin hydrochloride, equivalent to 3 mg and 6mg of doxepin, respectively.Chemically, doxepin hydrochloride is an (E) a...
Active IngredientDoxepin hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 6mg base; eq 3mg base
Market StatusPrescription
CompanyPernix Theraps

3 of 6  
Drug NameZonalon
Drug LabelZonalon (doxepin hydrochloride) Cream, 5% is a topical cream. Each gram contains: 50 mg of doxepin hydrochloride (equivalent to 44.3 mg of doxepin).Doxepin hydrochloride is one of a class of agents known as dibenzoxepin tricyclic antidepressant com...
Active IngredientDoxepin hydrochloride
Dosage FormCream
RouteTopical
Strength5%
Market StatusPrescription
CompanyFougera Pharms

4 of 6  
Drug NameDoxepin hydrochloride
PubMed HealthDoxepin
Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
Drug LabelDoxepin hydrochloride is one of a class of psychotherapeutic agents known as dibenzoxepin tricyclic compounds. The molecular formula of the compound is C19H21NOHCl having a molecular weight of 316. It is a white crystalline solid readily soluble in w...
Active IngredientDoxepin hydrochloride
Dosage FormTablet; Concentrate; Capsule
Routeoral; Oral
Strengtheq 100mg base; eq 50mg base; 6mg; eq 6mg base; eq 150mg base; eq 10mg base; eq 10mg base/ml; eq 25mg base; 3mg; eq 3mg base; eq 75mg base
Market StatusTentative Approval; Prescription
CompanyWockhardt; Mylan Pharms; Silarx; Actavis Elizabeth; Teva Pharms; Zydus Pharms Usa; Par Pharm; Mylan

5 of 6  
Drug NameSilenor
PubMed HealthDoxepin
Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
Drug LabelSilenor (doxepin) is available in 3 mg and 6 mg strength tablets for oral administration. Each tablet contains 3.39 mg or 6.78 mg doxepin hydrochloride, equivalent to 3 mg and 6mg of doxepin, respectively.Chemically, doxepin hydrochloride is an (E) a...
Active IngredientDoxepin hydrochloride
Dosage FormTablet
RouteOral
Strengtheq 6mg base; eq 3mg base
Market StatusPrescription
CompanyPernix Theraps

6 of 6  
Drug NameZonalon
Drug LabelZonalon (doxepin hydrochloride) Cream, 5% is a topical cream. Each gram contains: 50 mg of doxepin hydrochloride (equivalent to 44.3 mg of doxepin).Doxepin hydrochloride is one of a class of agents known as dibenzoxepin tricyclic antidepressant com...
Active IngredientDoxepin hydrochloride
Dosage FormCream
RouteTopical
Strength5%
Market StatusPrescription
CompanyFougera Pharms

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Histamine Antagonists

Drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Classical antihistaminics block the histamine H1 receptors only. (See all compounds classified as Histamine Antagonists.)


Antidepressive Agents, Tricyclic

Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system. (See all compounds classified as Antidepressive Agents, Tricyclic.)


Sleep Aids, Pharmaceutical

Drugs used to induce SLEEP, prevent SLEEPLESSNESS, or treat SLEEP INITIATION AND MAINTENANCE DISORDERS. (See all compounds classified as Sleep Aids, Pharmaceutical.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Tricyclic Antidepressant [EPC]

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12-Feb-2021
30-Sep-2024
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