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Record Information
Version4.0
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-09-22 02:29:04 UTC
HMDB IDHMDB0014864
Secondary Accession Numbers
  • HMDB14864
Metabolite Identification
Common NameTrimipramine
DescriptionTrimipramine is only found in individuals that have used or taken this drug. It is a tricyclic antidepressant similar to imipramine, but with more antihistaminic and sedative properties. [PubChem]Trimipramine's mechanism of action differs from other tricyclic antidepressants. Trimipramine acts by decreasing the reuptake of norepinephrine and serotonin (5-HT).
Structure
Thumb
Synonyms
ValueSource
10,11-dihydro-N,N,beta-Trimethyl-5H-dibenz[b,F]azepine-5-propanamineChEBI
5-(gamma-dimethylamino-beta-Methylpropyl)-10,11-dihydro-5H-dibenzo[b,F]azepineChEBI
5-[3-(dimethylamino)-2-Methylpropyl]-10,11-dihydro-5H-dibenz[b,F]azepineChEBI
beta-MethylimipramineChEBI
RP-7162ChEBI
SapilentChEBI
TrimeprimineChEBI
TrimeproprimineChEBI
10,11-dihydro-N,N,b-Trimethyl-5H-dibenz[b,F]azepine-5-propanamineGenerator
10,11-dihydro-N,N,β-trimethyl-5H-dibenz[b,F]azepine-5-propanamineGenerator
5-(g-dimethylamino-b-Methylpropyl)-10,11-dihydro-5H-dibenzo[b,F]azepineGenerator
5-(γ-dimethylamino-β-methylpropyl)-10,11-dihydro-5H-dibenzo[b,F]azepineGenerator
b-MethylimipramineGenerator
β-methylimipramineGenerator
ApoTrimipMeSH
Aventis brand OF trimipramineMeSH
EldoralMeSH
Nu pharm brand OF trimipramine maleateMeSH
Rhone-poulenc rorer brand OF trimipramine maleateMeSH
TrimiduraMeSH
Trimipramine aventis brandMeSH
Neurazpharm brand OF trimipramine maleateMeSH
Aventis brand OF trimipramine maleateMeSH
Azupharma brand OF trimipramine maleateMeSH
Nu-pharm brand OF trimipramine maleateMeSH
NuTrimipramineMeSH
Odyssey brand OF trimipramine maleateMeSH
Trimineurin maleateMeSH
Trimipramin stadaMeSH
Trimipramine hexal brandMeSH
Trimipramine maleateMeSH
Trimipramine maleate (1:1)MeSH
10,11 dihydro-N,N,beta-Trimethyl-5H-dibenz(b,F)azepine-5-propanamineMeSH
AWD.pharma brand OF trimipramine maleateMeSH
apo TrimipMeSH
Merck dura brand OF trimipramine maleateMeSH
novo TripramineMeSH
novo-TripramineMeSH
Novopharm brand OF trimipramine maleateMeSH
Nu-trimipramineMeSH
Rhodiapharm brand OF trimipramine maleateMeSH
RhotrimineMeSH
Surmontil maleateMeSH
TrimineurinMeSH
Trimipramine maleate (1:1), (+)-isomerMeSH
Trimipramine maleate (1:1), (+-)-isomerMeSH
Trimipramine mesylateMeSH
TrimipraminneurazpharmMeSH
Betapharm brand OF trimipramine maleateMeSH
apo-TrimipMeSH
Apotex brand OF trimipramine maleateMeSH
HerphonalMeSH
Hexal brand OF trimipramineMeSH
neuro Hexal brand OF trimipramine maleateMeSH
NovoTripramineMeSH
Nu trimipramineMeSH
Rhone poulenc rorer brand OF trimipramine maleateMeSH
Stadapharm brand OF trimipramine maleateMeSH
StangylMeSH
SurmontilMeSH
Temmler brand OF trimipramine maleateMeSH
Trimipramin azuMeSH
Trimipramin betaMeSH
Trimipramin neurazpharmMeSH
Trimipramin-neurazpharmMeSH
Trimipramine maleate (1:1), (-)-isomerMeSH
Trimipramine monohydrochlorideMeSH
Trimipramine, (+-)-isomerMeSH
Trimipramine, (-)-isomerMeSH
Chemical FormulaC20H26N2
Average Molecular Weight294.4338
Monoisotopic Molecular Weight294.209598842
IUPAC Name(3-{2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}-2-methylpropyl)dimethylamine
Traditional Nametrimipramine
CAS Registry Number739-71-9
SMILES
CC(CN(C)C)CN1C2=CC=CC=C2CCC2=CC=CC=C12
InChI Identifier
InChI=1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3
InChI KeyZSCDBOWYZJWBIY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dibenzazepines. These are compounds with two benzene rings connected by an azepine ring. Azepine is an unsaturated seven-member heterocycle with one nitrogen atom replacing a carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassBenzazepines
Direct ParentDibenzazepines
Alternative Parents
Substituents
  • Dibenzazepine
  • Alkyldiarylamine
  • Tertiary aliphatic/aromatic amine
  • Azepine
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Adrenergic Uptake Inhibitors
  • Antidepressants
  • Antidepressive Agents, Tricyclic
  • Norepinephrine-Reuptake Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point45 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.60e-02 g/LNot Available
LogP4.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.026 mg/mLALOGPS
logP4.67ALOGPS
logP4.76ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity95.02 m3·mol-1ChemAxon
Polarizability35.67 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-68bace4e48742b76d7b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0090000000-683044c8af33df070967View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udj-1960000000-2c69c2591b0ff915ccc2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zfr-3920000000-7c68e89e7f53026fdb80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zfr-4930000000-f1fe2a4f61bfbec6d778View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pb9-7920000000-b085a14dd7e5d88d4922View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-9810000000-b67a0e6866c4bcb27488View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0090000000-90da643ba602b4854ad4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udj-1960000000-953dd8f5d50ce412ae55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zfr-2920000000-493d39be6384cb3b09d4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0zfr-4920000000-02c877be6bc360fbe70eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0pb9-6920000000-eb3878e47d12e4792744View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4l-8910000000-5341bd1feea3e6a75bc8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0900000000-875e7a40df38e129227cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0a4m-5790000000-53c724efbeeb45818f39View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00726 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00726 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00726
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5382
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrimipramine
NuGOwiki LinkHMDB0014864
METLIN IDNot Available
PubChem Compound5584
PDB IDNot Available
ChEBI ID9738
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Baumann P: Pharmacokinetic-pharmacodynamic relationship of the selective serotonin reuptake inhibitors. Clin Pharmacokinet. 1996 Dec;31(6):444-69. [PubMed:8968657 ]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:
ADRA2B
Uniprot ID:
P18089
Molecular weight:
49953.1
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [PubMed:8863001 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
DRD2
Uniprot ID:
P14416
Molecular weight:
50618.9
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [PubMed:8863001 ]
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular weight:
68494.255
References
  1. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1A
Uniprot ID:
P08908
Molecular weight:
46106.3
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [PubMed:8863001 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [PubMed:8863001 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [PubMed:8863001 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [PubMed:8863001 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Gene Name:
ADRA1B
Uniprot ID:
P35368
Molecular weight:
56835.4
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [PubMed:8863001 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the five types (D1 to D5) of receptors for dopamine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase
Gene Name:
DRD1
Uniprot ID:
P21728
Molecular weight:
49292.8
References
  1. Berger M, Gastpar M: Trimipramine: a challenge to current concepts on antidepressives. Eur Arch Psychiatry Clin Neurosci. 1996;246(5):235-9. [PubMed:8863001 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular weight:
69331.42
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in neurotransmitter:sodium symporter activity
Specific function:
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into the pre-synaptic terminal for re-utilization. Plays a key role in mediating regulation of the availability of serotonin to other receptors of serotonergic systems. Terminates the action of serotonin and recycles it in a sodium-dependent manner.
Gene Name:
SLC6A4
Uniprot ID:
P31645
Molecular weight:
70324.165
References
  1. Diamond M, Kelly JP, Connor TJ: Antidepressants suppress production of the Th1 cytokine interferon-gamma, independent of monoamine transporter blockade. Eur Neuropsychopharmacol. 2006 Oct;16(7):481-90. Epub 2006 Jan 4. [PubMed:16388933 ]
  2. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. [PubMed:9537821 ]