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Chemistry

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Also known as: Melipramine, 50-49-7, Antideprin, Berkomine, Imidobenzyle, Dimipressin
Molecular Formula
C19H24N2
Molecular Weight
280.4  g/mol
InChI Key
BCGWQEUPMDMJNV-UHFFFAOYSA-N
FDA UNII
OGG85SX4E4

Imipramine
The prototypical tricyclic antidepressant. It has been used in major depression, dysthymia, bipolar depression, attention-deficit disorders, agoraphobia, and panic disorders. It has less sedative effect than some other members of this therapeutic group.
Imipramine is a Tricyclic Antidepressant.
1 2D Structure

Imipramine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N,N-dimethylpropan-1-amine
2.1.2 InChI
InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
2.1.3 InChI Key
BCGWQEUPMDMJNV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN(C)CCCN1C2=CC=CC=C2CCC3=CC=CC=C31
2.2 Other Identifiers
2.2.1 UNII
OGG85SX4E4
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 4,4'-methylenebis(3-hydroxy-2-naphthoic Acid)-3-(10,11-dihydro-5h-dibenzo(b,f)azepin-5-yl)-n,n-dimethyl-1-propanamine (1:2)

2. Imidobenzyle

3. Imipramine Hydrochloride

4. Imipramine Monohydrochloride

5. Imipramine Pamoate

6. Imizin

7. Janimine

8. Melipramine

9. Norchlorimipramine

10. Pryleugan

11. Tofranil

2.3.2 Depositor-Supplied Synonyms

1. Melipramine

2. 50-49-7

3. Antideprin

4. Berkomine

5. Imidobenzyle

6. Dimipressin

7. Melipramin

8. Tofranil

9. Intalpram

10. Nelipramin

11. Dynaprin

12. Timolet

13. Irmin

14. Dpid

15. Dyna-zina

16. Impramine

17. Promiben

18. Censtim

19. Censtin

20. Imiprin

21. Iramil

22. Janimine

23. Imipramina

24. 3-(10,11-dihydro-5h-dibenzo[b,f]azepin-5-yl)-n,n-dimethylpropan-1-amine

25. Declomipramine

26. Eupramin

27. Imipramin

28. Imipraminum

29. Psychoforin

30. Imavate

31. Surplix

32. Imizin

33. Tofranil, Base

34. Imizinum

35. N-(gamma-dimethylaminopropyl)iminodibenzyl

36. N-(3-dimethylaminopropyl)-o-iminodibenzyl

37. 2,2'-(3-dimethylaminopropylimino)bibenzyl

38. 2,2'-(3-dimethylaminopropylimino)dibenzyl

39. Tofranil (free Base)

40. Sk-pramine

41. Cristalia

42. Sermonil

43. Imipramine (inn)

44. Nsc 169866

45. 5-(3-(dimethylamino)propyl)-10,11-dihydro-5h-dibenz(b,f)azepine

46. 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-n,n-dimethylpropan-1-amine

47. Chembl11

48. 1-(3-dimethylaminopropyl)-4,5-dihydro-2,3,6,7-dibenzazepine

49. Nsc-169866

50. 10,11-dihydro-n,n-dimethyl-5h-dibenz[b,f]azepine-5-propanamine

51. 5,6-dihydro-n-(3-(dimethylamino)propyl)-11h-dibenz(b,e)azepine

52. 5-(3-dimethylaminopropyl)-10,11-dihydro-5h-dibenzo(b,f)azepine

53. 5h-dibenz(b,f)azepine-5-propanamine, 10,11-dihydro-n,n-dimethyl-

54. Ogg85sx4e4

55. N-(.gamma.-dimethylaminopropyl)iminodibenzyl

56. Chebi:47499

57. 5,e)azepine

58. 5,e]azepine

59. 5h-dibenz(b,f)azepine, 10,11-dihydro-5-(3-(dimethylamino)propyl)-

60. Org-2463

61. Imidol

62. Ncgc00015563-07

63. Imipramina [italian]

64. Imipramine [inn]

65. Tofranil (tn)

66. 10,11-dihydro-5-(3-(dimethylamino)propyl)-5h-dibenz[b,f]azepine

67. 3-(5h-dibenzo[b,f]azepin-5-yl)-n,n-dimethylpropan-1-amine

68. 5h-dibenz[b,f]azepine-5-propanamine, 10,11-dihydro-n,n-dimethyl-

69. 5h-dibenz(b,f)azepine, 5-(3-(dimethylamino)propyl)-10,11-dihydro-

70. Imipramine [inn:ban]

71. Dsstox_cid_23881

72. Dsstox_rid_80080

73. Dsstox_gsid_43881

74. Imipraminum [inn-latin]

75. Imipramina [inn-spanish]

76. 3-(10,11-dihydro-5h-dibenz[b,f]azepin-5-yl)propyldimethylamine

77. 5-[3-(dimethylamino)propyl]-10,11-dihydro-5h-dibenz[b,f]azepine

78. Cas-50-49-7

79. 3-(10,11-dihydro-5h-dibenzo[b,f]azepin-5-yl)-n,n-dimethylpropan-1-amine;3-(10,11-dihydro-5h-dibenzo[b,f]azepin-5-yl)-n,n-dimethylpropan-1-amine

80. N,n-dimethyl-10,11-dihydro-5h-dibenzo[b,f]azepine-5-propanamine-2,8-d2

81. Ccris 9173

82. 2241983-10-6

83. Hsdb 3100

84. 3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-n,n-dimethyl-propan-1-amine

85. Janimine (hydrochloride)

86. Tofranil (hydrochloride)

87. Cas-113-52-0

88. Einecs 200-042-1

89. Unii-ogg85sx4e4

90. Brn 0256892

91. 5h-dibenz(b, 5-(3-(dimethylamino)propyl)-10,11-dihydro-

92. 5h-dibenz[b, 5-[3-(dimethylamino)propyl]-10,11-dihydro-

93. Tofranil Base

94. 5h-dibenz[b,f]azepine, 5-[3-(dimethylamino)propyl]-10,11-dihydro-

95. Ixx

96. Imizin (salt/mix)

97. Imavate (salt/mix)

98. Imizine (salt/mix)

99. Surplix (salt/mix)

100. Eupramin (salt/mix)

101. Imizinum (salt/mix)

102. Tofranil (salt/mix)

103. Spectrum_000915

104. Imipramine [mi]

105. Psychoforin (salt/mix)

106. Prestwick0_000072

107. Prestwick1_000072

108. Prestwick2_000072

109. Prestwick3_000072

110. Sk-pramine (salt/mix)

111. Spectrum2_000990

112. Spectrum3_000466

113. Spectrum4_000016

114. Spectrum5_000864

115. Imipramine [hsdb]

116. Lopac-i-7379

117. Imipramine [vandf]

118. 3-(10,11-dihydro-5h-dibenzo[b,f]azepin-5-yl)-n,n-dimethyl-1-propanamine

119. Imipramine [mart.]

120. Imipramine [who-dd]

121. Lopac0_000702

122. Oprea1_200908

123. Schembl34282

124. Bspbio_000283

125. Bspbio_002172

126. Gtpl357

127. Kbiogr_000391

128. Kbioss_001395

129. Bidd:gt0116

130. Divk1c_000559

131. Spbio_001059

132. Spbio_002204

133. G-22355 (salt/mix)

134. Bpbio1_000313

135. Clomipramine Hcl Ep Impurity B

136. Dtxsid1043881

137. Hy-b1490a

138. Kbio1_000559

139. Kbio2_001395

140. Kbio2_003963

141. Kbio2_006531

142. Kbio3_001392

143. Zinc20245

144. Ninds_000559

145. Hms2089g08

146. Tox21_110174

147. Bdbm50010859

148. Ccg-36485

149. Mfcd31699979

150. Nsc169866

151. Stl416211

152. Akos016010320

153. Tox21_110174_1

154. Db00458

155. Sdccgsbi-0050680.p005

156. Idi1_000559

157. Mrf-0000592

158. Ncgc00015563-01

159. Ncgc00015563-02

160. Ncgc00015563-03

161. Ncgc00015563-04

162. Ncgc00015563-05

163. Ncgc00015563-06

164. Ncgc00015563-08

165. Ncgc00015563-09

166. Ncgc00015563-10

167. Ncgc00015563-11

168. Ncgc00015563-13

169. Ncgc00015563-25

170. Ncgc00024253-03

171. Ncgc00024253-04

172. 5-(3-dimethylaminopropyl)-10,f)azepine

173. Sy246340

174. Trimipramine Maleate Impurity, Imipramine-

175. Sbi-0050680.p004

176. Wln: T C676 Bn&t&j B3n1&1

177. 5-(3-(dimethylamino)propyl)-10,f)azepine

178. Ab00053486

179. Cs-0013621

180. Ft-0670319

181. Ft-0697093

182. 5h-dibenz[b, 10,11-dihydro-n,n-dimethyl-

183. C07049

184. D08070

185. Q58396

186. Ab00053486-15

187. Ab00053486_16

188. Ab00053486_17

189. 1-(3-dimethylaminopropyl)-4,3,6,7-dibenzazepine

190. L000739

191. W-109253

192. Brd-k38436528-003-05-5

193. Brd-k38436528-003-15-4

194. Trimipramine Maleate Impurity D [ep Impurity]

195. 5h-dibenz(b, 10,11-dihydro-5-(3-(dimethylamino)propyl)-

196. Clomipramine Hydrochloride Impurity B [ep Impurity]

197. Trimipramine Maleate Impurity, Imipramine- [usp Impurity]

198. 3-(10,11-dihydro-5h-dibenzo[b,f]azepin-5-yl)-n,n-dimethyl-1-propanamine #

199. 5h-dibenz(b,5-[3-(dimethylamino)propyl]-10,11-dihydro-mixed With Ethyl Alcohol

200. Clomipramine Ep Impurity B; 10,11-dihydro-n,n-dimethyl-5h-dibenz[b,f]azepine-5-propanamine

201. (3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine

202. 5-(3-(dimethylamino)propyl)-10,11-dihydro-5h-dibenz[b,f]azepine;10,11-dehydroimipramine;depramine

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 280.4 g/mol
Molecular Formula C19H24N2
XLogP34.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass280.193948774 g/mol
Monoisotopic Mass280.193948774 g/mol
Topological Polar Surface Area6.5 Ų
Heavy Atom Count21
Formal Charge0
Complexity291
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameTofranil
PubMed HealthImipramine (By mouth)
Drug ClassesAntidepressant, Urinary Enuresis Agent
Drug LabelTofranil is supplied in tablet form for oral administration.Tofranil, imipramine hydrochloride USP, the original tricyclic antidepressant, is a member of the dibenzazepine group of compounds. It is designated 5-3-(dimethylamino)propyl-10,11-dihydr...
Active IngredientImipramine hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; 50mg; 10mg
Market StatusPrescription
CompanyMallinckrodt

2 of 4  
Drug NameTofranil-pm
Active IngredientImipramine pamoate
Dosage FormCapsule
RouteOral
Strengtheq 75mg hcl; eq 125mg hcl; eq 100mg hcl; eq 150mg hcl
Market StatusPrescription
CompanyMallinckrodt

3 of 4  
Drug NameTofranil
PubMed HealthImipramine (By mouth)
Drug ClassesAntidepressant, Urinary Enuresis Agent
Drug LabelTofranil is supplied in tablet form for oral administration.Tofranil, imipramine hydrochloride USP, the original tricyclic antidepressant, is a member of the dibenzazepine group of compounds. It is designated 5-3-(dimethylamino)propyl-10,11-dihydr...
Active IngredientImipramine hydrochloride
Dosage FormTablet
RouteOral
Strength25mg; 50mg; 10mg
Market StatusPrescription
CompanyMallinckrodt

4 of 4  
Drug NameTofranil-pm
Active IngredientImipramine pamoate
Dosage FormCapsule
RouteOral
Strengtheq 75mg hcl; eq 125mg hcl; eq 100mg hcl; eq 150mg hcl
Market StatusPrescription
CompanyMallinckrodt

4.2 Therapeutic Uses

Adrenergic Uptake Inhibitors; Antidepressive Agents, Tricyclic

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


EFFECTIVE IN DEPRESSIVE SYNDROMES, PARTICULARLY THOSE ASSOC WITH MANIC-DEPRESSIVE & INVOLUTIONAL PSYCHOSES... /HYDROCHLORIDE/

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1040


2-HYDROXYIMIPRAMINE-HCL INHIBITED UPTAKE OF NOREPINEPHRINE & SEROTONIN BY RAT CEREBROCORTICAL SYNAPTOSOMES TO SAME EXTENT AS PARENT DRUGS.

POTTER WZ ET AL; BIOL PSYCHIATRY 14(4) 601 (1979)


METHODS OF TREATMENT OF ENURESIS IN CHILD ARE PRESENTED INCL IMIPRAMINE.

BINDELGLAS RM ET AL; J FAM PRACT 2 (OCT) 375 (1975)


For more Therapeutic Uses (Complete) data for IMIPRAMINE (8 total), please visit the HSDB record page.


4.3 Drug Warning

BECAUSE OF POSSIBLE CONGENITAL MALFORMATIONS ASSOC WITH USE OF THIS DRUG.../IT/ SHOULD NOT BE USED DURING FIRST TRIMESTER OF PREGNANCY. /IMIPRAMINE HYDROCHLORIDE/

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1040


TRICYCLIC COMPD ARE CONTRAINDICATED IN PT WITH CONGESTIVE HEART FAILURE, ANGINA PECTORIS, & PAROXYSMAL TACHYCARDIA; ALSO, THEY SHOULD BE USED WITH CAUTION IN PATIENTS WITH URINARY RETENTION, GLAUCOMA, DIABETES, IMPAIRED LIVER FUNCTION, ASTHMA, AND A HISTORY OF CONVULSIVE SEIZURES. /TRICYCLIC ANTIDEPRESSANTS/

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1038


OCCASIONAL PT WILL SHOW PHYSICAL DEPENDENCE ON TRICYCLIC ANTIDEPRESSANTS, WITH MALAISE, CHILLS, CORYZA, & MUSCLE ACHES FOLLOWING ABRUPT DISCONTINUATION OF HIGH DOSES OF IMIPRAMINE.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 441


ALTHOUGH MOST FATAL CASES...HAVE OCCURRED AFTER INGESTION OF MORE THAN 1.5 G ... DEATH HAS BEEN REPORTED AFTER AS LITTLE AS 500 TO 750 MG AND RECOVERY HAS BEEN REPORTED AFTER INGESTION OF 5.4 G. /IMIPRAMINE HYDROCHLORIDE/

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 5th ed. Chicago: American Medical Association, 1983., p. 256


For more Drug Warnings (Complete) data for IMIPRAMINE (33 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

4. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) 50-500 MG/KG; BETWEEN 1 TEASPOON AND 1 OZ FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-229


4.5 Drug Indication

For the relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older. May also be used off-label to manage panic disorders with or without agoraphobia, as a second line agent for ADHD in children and adolescents, to manage bulimia nervosa, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, for the treatment of acute stress disorder and posttraumatic stress disorder, and for symptomatic treatment of postherpetic neuralgia and painful diabetic neuropathy.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Imipramine is a tricyclic antidepressant with general pharmacological properties similar to those of structurally related tricyclic antidepressant drugs such as amitriptyline and doxepin. While it acts to block both, imipramine displays a much higher affinity for the serotonin reuptake transporter than for the norepinephrine reuptake transporter. Imipramine produces effects similar to other monoamine targeting antidepressants, increasing serotonin- and norepinephrine-based neurotransmission. This modulation of neurotransmission produces a complex range of changes in brain structure and function along with an improvement in depressive symptoms. The changes include increases in hippocampal neurogenesis and reduced downregulation of this neurogenesis in response to stress. These implicate brain derived neurotrophic factor signalling as a necessary contributor to antidepressant effect although the link to the direct increase in monoamine neurotransmission is unclear. Serotonin reuptake targeting agents may also produce a down-regulation in -adrenergic receptors in the brain.


5.2 MeSH Pharmacological Classification

Adrenergic Uptake Inhibitors

Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)


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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
IMIPRAMINE
5.3.2 FDA UNII
OGG85SX4E4
5.3.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Tricyclic Antidepressant
5.4 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AA - Non-selective monoamine reuptake inhibitors

N06AA02 - Imipramine


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and well absorbed (>95%) after oral administration. The primary site of absorption is the small intestine as the basic amine groups are ionized in the acidic environment of the stomach, preventing movement across tissues. Bioavailability ranges from 29-77% due to high inter-individual variability. Peak plasma concentration is usually attained 2-6 hours following oral administration. Absorption is unaffected by food.


Route of Elimination

Imipramine is primarily excreted in the urine with less than 5% present as the parent compound


Volume of Distribution

Imipramine has a high apparent volume of distribution of 10-20 L/kg. The drug is known to accumulate in the brain at concentrations 30-40 times that in systemic circulation.


Clearance

Imipramine has a mean clearance of 1 L/h/kg. Its active metabolite, desipramine has a mean clearance of 1.8 L/h/kg.


TRICYCLIC ANTIDEPRESSANTS ARE FAIRLY WELL ABSORBED AFTER ORAL ADMINISTRATION. ... ONCE ABSORBED /IT/ IS WIDELY DISTRIBUTED. ... ARE STRONGLY BOUND TO PLASMA PROTEIN AND TO THE CONSTITUENTS OF TISSUES./TRICYCLIC ANTIDEPRESSANTS

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 440


EXCRETION...IS RAPID... APPROX 40% OF DOSE OF RADIOACTIVE IMIPRAMINE APPEARS IN URINE IN 24 HR & TOTAL OF 70% DURING FIRST 72 HR. REMAINDER APPEARS IN FECES. SMALL PORTION...RECOVERED AS UNCHANGED DRUG OR AS ACTIVE DESMETHYL DERIV. LARGER PORTION...EXCRETED AS N-OXIDE OR AS NONCONJUGATED OR CONJUGATED 2-OH DERIV.

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 178


IN ANIMALS, PLACENTAL TRANSFER HAS BEEN OBSERVED WITH IMIPRAMINE & ITS DESMETHYL DERIVATIVE.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 433


DISTRIBUTION OF IV ADMIN.../(14)C, IMIPRAMINE/ IN MICE...STUDIED USING WHOLE-BODY AUTORADIOGRAPHY. 5 MIN AFTER DOSING, HIGH UPTAKE OF (14)C OCCURRED IN BRAIN, MYOCARDIUM, LUNGS, ADRENALS & KIDNEYS, BUT (14)C IN BLOOD WAS LOW. IN 1 HR...(14)C /LEVELS/...HIGH IN SALIVARY GLANDS, INTESTINES, LIVER, GALL BLADDER, & URINARY BLADDER & 3 HR LATER...LARGELY CONFINED TO ORGANS CONCERNED WITH EXCRETION OF IMIPRAMINE...INTESTINES, LIVER, & KIDNEYS.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 57


For more Absorption, Distribution and Excretion (Complete) data for IMIPRAMINE (8 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Imipramine is nearly exclusively metabolized by the liver. Imipramine is converted to desipramine by CYP1A2, CYP3A4, CYP2C19. Both imipramine and desipramine are hydroxylated by CYP2D6. Desipramine is an active metabolite. Minor metabolic pathways include dealkylation to form an imidodibenzyl product as well as demethylation of desipramine to didemethylimipramine and subsequent hydroxylation. Less than 5% of orally administered imipramine is excreted unchanged.


...STUDY OF METABOLISM OF IMIPRAMINE & ITS METABOLITES BY RAT LIVER MICROSOMES...REVEALED OPERATION OF 16 METABOLIC PATHWAYS, INCL N-DEMETHYLATION, AROMATIC HYDROXYLATIONS, SIDE-CHAIN DEALKYLATIONS, N-OXIDATION, N-OXIDE REDUCTION, & CONJUGATION REACTIONS.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 317


IMIPRAMINE N-OXIDE & IMINODIBENZYL...IDENTIFIED AS ADDITIONAL URINARY METABOLITES IN MAN.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 183


...METABOLIZED IN HUMANS BY N-DEMETHYLATION & BY HYDROXYLATION IN ONE OF THE AROMATIC RINGS OR IN ETHYLENE BRIDGE TO GIVE DESMONOMETHYLIMIPRAMINE (DMI) & DESDIMETHYLIMIPRAMINE (DDMI) & THE 2-HYDROXY & 10-HYDROXY DERIVATIVES OF IMIPRAMINE, DMI & DDMI, TOGETHER WITH THEIR GLUCURONIDE CONJUGATES.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 192


IMIPRAMINE (HALF-LIFE, 16 HOURS) IS BIOTRANSFORMED TO THE ACTIVE METABOLITE, DESIPRAMINE (HALF-LIFE, 18 HOURS).

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 5th ed. Chicago: American Medical Association, 1983., p. 779


Imipramine has known human metabolites that include 2-Hydroxyimipramine, Desipramine, and Imipramine N-glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

Imipramine has a mean half life of 12 h. Its active metabolite, desipramine has a mean half life of 22.5 h.


IMIPRAMINE (HALF-LIFE, 16 HOURS)...

American Medical Association, AMA Department of Drugs. AMA Drug Evaluations. 5th ed. Chicago: American Medical Association, 1983., p. 779


5.8 Mechanism of Action

Imipramine works by inhibiting the neuronal reuptake of the neurotransmitters norepinephrine and serotonin. It binds the sodium-dependent serotonin transporter and sodium-dependent norepinephrine transporter reducing the reuptake of norepinephrine and serotonin by neurons. Depression has been linked to a lack of stimulation of the post-synaptic neuron by norepinephrine and serotonin. Slowing the reuptake of these neurotransmitters increases their concentration in the synaptic cleft, producing knock-on effects in protein kinase signalling which is thought to contribute to changes in neurotransmission and brain physiology which relieves symptoms of depression.


MANNER IN WHICH IMIPRAMINE RELIEVES...DEPRESSION IS NOT CLEAR. ITS EFFECT HAS BEEN DESCRIBED AS DULLING OF DEPRESSIVE IDEATION... HOWEVER, REPORTS OF MANIC EXCITEMENT AS WELL AS EUPHORIA & INSOMNIA INDICATE THAT IMIPRAMINE DOES HAVE STIMULANT ACTION UNDER CERTAIN CIRCUMSTANCES.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 420


TRICYCLIC ANTIDEPRESSANTS HAVE THREE PRIMARY PHARMACOLOGIC ACTIONS, INCLUDING ANTICHOLINERGIC EFFECTS, REUPTAKE BLOCKADE OF CATECHOLAMINES AT THE ADRENERGIC NEURONAL SITE AND QUINIDINE-LIKE EFFECTS ON THE CARDIAC TISSUE. /TRICYCLIC ANTIDEPRESSANTS/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 983


API Reference Price

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KONG","quantity":"50.00","actualQuantity":"50","unit":"KGS","unitRateFc":"80","totalValueFC":"3891.6","currency":"USD","unitRateINR":6463.3680000000004,"date":"25-Jul-2024","totalValueINR":"323168.4","totalValueInUsd":"3891.6","indian_port":"Bangalore Air","hs_no":"29420024","bill_no":"2694233","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"HONG KONG","selfForZScoreResived":"Pharma Grade","supplierPort":"Bangalore Air","supplierAddress":"RAY HOUSE, HIG 2000,,MOTHER DIARY, BANGALORE,KARNATAKA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1721932200,"product":"PHARMACEUTICAL BULK DRUG, IMIPRAMINE HYDROCHLORIDE\/BP, BATCH NO: IMPN\/224008","address":"RAY HOUSE, HIG 2000,,MOTHER DIARY","city":"BANGALORE,KARNATAKA","supplier":"R L FINE CHEM","supplierCountry":"INDIA","foreign_port":"MEDELLIN","customer":"TO THE ORDER OF","customerCountry":"COLOMBIA","quantity":"150.00","actualQuantity":"150","unit":"KGS","unitRateFc":"81.3","totalValueFC":"10906.9","currency":"USD","unitRateINR":6038.2333333333336,"date":"26-Jul-2024","totalValueINR":"905735","totalValueInUsd":"10906.9","indian_port":"Bangalore Air","hs_no":"29420024","bill_no":"2718181","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"COLOMBIA","selfForZScoreResived":"Pharma Grade","supplierPort":"Bangalore Air","supplierAddress":"RAY HOUSE, HIG 2000,,MOTHER DIARY, BANGALORE,KARNATAKA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1722796200,"product":"TRIMIPRAMINE MALEATE","address":"H N.8-2-269\/W\/4,1ST FLOOR,PLOT NO.","city":"BANJARA HILLS HYDERABAD,TELANGANA","supplier":"HRV GLOBAL LIFE SCIENCES","supplierCountry":"INDIA","foreign_port":"DUBAI","customer":"TO THE ORDER OF","customerCountry":"UNITED ARAB EMIRATES","quantity":"1000.00","actualQuantity":"1000","unit":"KGS","unitRateFc":"874.8","totalValueFC":"232812.4","currency":"AED","unitRateINR":19333.367300000002,"date":"05-Aug-2024","totalValueINR":"19333367.3","totalValueInUsd":"232812.4","indian_port":"Bombay Air","hs_no":"29420090","bill_no":"2962317","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"UNITED ARAB EMIRATES","selfForZScoreResived":"Pharma Grade","supplierPort":"Bombay Air","supplierAddress":"H N.8-2-269\/W\/4,1ST FLOOR,PLOT NO., BANJARA HILLS HYDERABAD,TELANGANA","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724351400,"product":"IMIPRAMINE HYDROCHLORIDE - CONTROL BATCHNO 2001900223 MFG DT MARCH 2023 RETESTDT. FEBRUARY 2028","address":"M-34, SAKET,","city":"NEW DELHI,DELHI","supplier":"TEVA API","supplierCountry":"INDIA","foreign_port":"NEW YORK - JOHN F. K","customer":"TEVA API INC C\/O DHL SUPPLY CH.","customerCountry":"UNITED STATES","quantity":"125.00","actualQuantity":"125","unit":"KGS","unitRateFc":"299.5","totalValueFC":"34992.4","currency":"USD","unitRateINR":23246.878960000002,"date":"23-Aug-2024","totalValueINR":"2905859.87","totalValueInUsd":"34992.4","indian_port":"Delhi Air","hs_no":"29333990","bill_no":"3429063","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"Delhi Air","supplierAddress":"M-34, SAKET,, NEW DELHI,DELHI","customerAddress":""},{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1724351400,"product":"IMIPRAMINE HYDROCHLORIDE - CONTROL BATCHNO 2001901823 MFG DT. 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LUNDBECK AS","supplierCountry":"ITALY","foreign_port":"N\/A","customer":"GLENMARK PHARMACEUTICALS","customerCountry":"INDIA","quantity":"20.00","actualQuantity":"20","unit":"KGS","unitRateFc":"296.7","totalValueFC":"6004.3","currency":"USD","unitRateINR":"22374.2","date":"22-Jul-2021","totalValueINR":"447483","totalValueInUsd":"6004.3","indian_port":"Indore-EPZ\/SEZ","hs_no":"29339990","bill_no":"1005042","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"N\/A","supplierAddress":"N\/A","customerAddress":"B\/2 MAHALAXMI CHAMBERS"},{"dataSource":"API Import","activeIngredients":"","year":"2021","qtr":"Q4","strtotime":1639506600,"product":"IMIPRAMINE HYDROCHLORIDE (QTY: 1 X 200 MG, PRICE: USD 252)(FOC)","address":"P.NO. D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,","city":"TURKAPALLY-V SHAMIRPET HYDERABAD,TE","supplier":"USP","supplierCountry":"INDIA","foreign_port":"WASHINGTON DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.0002","unit":"KGS","unitRateFc":"1260000","totalValueFC":"259.2","currency":"USD","unitRateINR":"97748400","date":"15-Dec-2021","totalValueINR":"19549.68","totalValueInUsd":"259.2","indian_port":"HYDERABAD AIR","hs_no":"29339990","bill_no":"6685910","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON DULLES I","supplierAddress":"","customerAddress":"P.NO. 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D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,","city":"TURKAPALLY-V SHAMIRPET HYDERABAD,TE","supplier":"USP","supplierCountry":"INDIA","foreign_port":"WASHINGTON DULLES I","customer":"UNITED STATES PHARMACOPEIA - INDIA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.00","actualQuantity":"0.000025","unit":"KGS","unitRateFc":"37240000","totalValueFC":"957.6","currency":"USD","unitRateINR":"2889008000","date":"15-Dec-2021","totalValueINR":"72225.2","totalValueInUsd":"957.6","indian_port":"HYDERABAD AIR","hs_no":"29339990","bill_no":"6685910","productDescription":"Re-Import","marketType":"REGULATED MARKET","country":"INDIA","selfForZScoreResived":"Pharma Grade","supplierPort":"WASHINGTON DULLES I","supplierAddress":"","customerAddress":"P.NO. D6 & D8, SY.NO. 234\/2,234\/3, ,235\/2 & 542\/2, IKP KNOWLEDGE PARK,"},{"dataSource":"API Import","activeIngredients":"","year":"2023","qtr":"Q3","strtotime":1693852200,"product":"IMIPRAMINE HCI USP\/BP","address":"206, DEVAVRATA,","city":"NAVI MUMBAI, MAHARASHTRA.","supplier":"STRIDES PHARMA SCIENCE","supplierCountry":"UNITED STATES","foreign_port":"NEW YORK","customer":"STRIDES PHARMA SCIENCE","customerCountry":"INDIA","quantity":"33.00","actualQuantity":"33","unit":"KGS","unitRateFc":"200","totalValueFC":"8998.4","currency":"USD","unitRateINR":"22668.5","date":"05-Sep-2023","totalValueINR":"748059.87","totalValueInUsd":"8998.4","indian_port":"Bangalore Air","hs_no":"29420024","bill_no":"7693155","productDescription":"API","marketType":"REGULATED MARKET","country":"UNITED STATES","selfForZScoreResived":"Pharma Grade","supplierPort":"NEW YORK","supplierAddress":"1 RAM RIDGE ROAD CHESTNUT RIDGE, 10977SDNF US","customerAddress":"206, DEVAVRATA,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1715711400,"product":"TRIMIPRAMINE MALEATE PH EUR","address":"PLOT NO.2, MAITRIVIHAR,","city":"HYDERABAD\/ANDHRA PRADESH","supplier":"H. LUNDBECK AS","supplierCountry":"ITALY","foreign_port":"MILAN - MALPENSA","customer":"AUROBINDO PHARMA LIMITED","customerCountry":"INDIA","quantity":"40.00","actualQuantity":"40","unit":"KGS","unitRateFc":"305.5","totalValueFC":"13390.9","currency":"EUR","unitRateINR":"27800.5","date":"15-May-2024","totalValueINR":"1112020","totalValueInUsd":"13390.9","indian_port":"Hyderabad Air","hs_no":"29420090","bill_no":"3496339","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MILAN - MALPENSA","supplierAddress":"VIA QUARTA STRADA, 2 35129 PADOVA PD ITALYSDNF Italy","customerAddress":"PLOT NO.2, MAITRIVIHAR,"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1719772200,"product":"TRIMIPRAMINE MALEATE","address":"B\/2 MAHALAXMI CHAMBERS","city":"MUMBAI. MAHARASHTRA","supplier":"LUNDBACK PHARMACEUTICALS ITALY S.P.A.","supplierCountry":"ITALY","foreign_port":"MALPENSA APT\/MILANO","customer":"GLENMARK PHARMACEUTICALS","customerCountry":"INDIA","quantity":"25.00","actualQuantity":"25","unit":"KGS","unitRateFc":"317","totalValueFC":"8045.8","currency":"USD","unitRateINR":"26725.8","date":"01-Jul-2024","totalValueINR":"668145","totalValueInUsd":"8045.8","indian_port":"Indore-EPZ\/SEZ","hs_no":"29339990","bill_no":"1004829","productDescription":"API","marketType":"REGULATED MARKET","country":"ITALY","selfForZScoreResived":"Pharma Grade","supplierPort":"MALPENSA APT\/MILANO","supplierAddress":"N\/A","customerAddress":"B\/2 MAHALAXMI CHAMBERS"}]
18-Jan-2021
23-Aug-2024
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DOSAGE - CAPSULE;ORAL - EQ 100MG HYDROCHLORID...DOSAGE - CAPSULE;ORAL - EQ 100MG HYDROCHLORIDE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 17090

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DOSAGE - CAPSULE;ORAL - EQ 125MG HYDROCHLORID...DOSAGE - CAPSULE;ORAL - EQ 125MG HYDROCHLORIDE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 17090

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DOSAGE - CAPSULE;ORAL - EQ 150MG HYDROCHLORID...DOSAGE - CAPSULE;ORAL - EQ 150MG HYDROCHLORIDE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 17090

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DOSAGE - CAPSULE;ORAL - EQ 75MG HYDROCHLORIDE...DOSAGE - CAPSULE;ORAL - EQ 75MG HYDROCHLORIDE **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 17090

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MolPort-001-783-692 Manufacturers | Traders | Suppliers

MolPort-001-783-692 Manufacturers, Traders, Suppliers 1
73

We have 8 companies offering MolPort-001-783-692

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  1. Corden Pharma Bergamo S.p.A
  2. H. Lundbeck AS
  3. IIQUIAP
  4. Lupin Ltd
  5. Pisgah Labs
  6. R L Fine Chem
  7. Teva API
  8. Teva Pharmaceutical Industries
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