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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-02-16 08:59:19 UTC
Update Date2020-02-26 21:23:32 UTC
HMDB IDHMDB0001848
Secondary Accession Numbers
  • HMDB01848
Metabolite Identification
Common NameImipramine
DescriptionImipramine, also known as tofranil or imizine, belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines 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. The antipsychotic effects of chlorpromazine were discovered in 1952, and imipramine was then developed and studied as an antipsychotic for use in patients with schizophrenia. Imipramine is a drug. Imipramine is a very strong basic compound (based on its pKa). Within humans, imipramine participates in a number of enzymatic reactions. In particular, imipramine can be converted into 2-hydroxyimipramine through the action of the enzyme cytochrome P450 2D6. In addition, imipramine can be converted into desipramine and formaldehyde; which is catalyzed by the enzymes cytochrome P450 2C19, cytochrome P450 1A2, and cytochrome P450 3A4. In humans, imipramine is involved in imipramine metabolism pathway. Imipramine is a potentially toxic compound. The drug is used commercially mostly as the hydrochloride salt; the embonate (pamoate) salt is used for intramuscular administration and the free base form is not used.
Structure
Data?1582752212
Synonyms
ValueSource
10,11-Dihydro-N,N-dimethyl-5H-dibenz[b,F]azepine-5-propanamineChEBI
3-(5H-DIBENZO[b,F]azepin-5-yl)-N,N-dimethylpropan-1-amineChEBI
5-[3-(Dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,F]azepineChEBI
AntideprinChEBI
ImipraminChEBI
ImipraminumChEBI
ImizineChEBI
IrminChEBI
MelipramineChEBI
N-(gamma-Dimethylaminopropyl)iminodibenzylChEBI
TofranilKegg
N-(g-Dimethylaminopropyl)iminodibenzylGenerator
N-(Γ-dimethylaminopropyl)iminodibenzylGenerator
BerkomineHMDB
ChimoreptinHMDB
DeclomipramineHMDB
DimipressinHMDB
DPIDHMDB
Dyna-zinaHMDB
DynaprinHMDB
EupraminHMDB
FeinalminHMDB
ImavateHMDB
ImidobenzyleHMDB
ImilanyleHMDB
JanimineHMDB
LofepramineHMDB
MelipraminHMDB
PsychoforinHMDB
SurmontilHMDB
SurplixHMDB
TeperineHMDB
TimoletHMDB
Tofranil baseHMDB
Tofranil-PMHMDB
Trimipramine maleateHMDB
Imipramine hydrochlorideHMDB
NorchlorimipramineHMDB
Imipramine monohydrochlorideHMDB
ImizinHMDB
PryleuganHMDB
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)HMDB
Imipramine pamoateHMDB
Chemical FormulaC19H24N2
Average Molecular Weight280.4073
Monoisotopic Molecular Weight280.193948778
IUPAC Name(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine
Traditional Name(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)dimethylamine
CAS Registry Number50-49-7
SMILES
CN(C)CCCN1C2=CC=CC=C2CCC2=CC=CC=C12
InChI Identifier
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
InChI KeyBCGWQEUPMDMJNV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as dibenzazepines. Dibenzazepines 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzazepines
Sub ClassDibenzazepines
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point174.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility18.2 mg/L at 24 °CNot Available
LogP4.80HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP4.53ALOGPS
logP4.28ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)9.2ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity90.61 m³·mol⁻¹ChemAxon
Polarizability33.39 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0019-7490000000-3fb4d40b6a219f088ec8Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0019-7490000000-3fb4d40b6a219f088ec8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-7490000000-746fcd08b0a7d6e7bc83Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-9000000000-55d924fd00e5b357ce9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9000000000-eb3c0ecdffc5d9d95e33Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ab9-9432000000-033c51459b692622ee7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0019-7490000000-bb99ef31a755d9f6ba14Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-052r-9010000000-961429188e57c1480db8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1090000000-d8b2753be1e55651ebe7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0019-5190000000-884d5f80618ae379a408Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9420000000-655018838b0eb1b10c77Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-115aa4768e53e232aa16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004l-1590000000-bf5870eaefcecc8340c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-2910000000-568ea79e9375b6365408Spectrum
MSMass Spectrum (Electron Ionization)splash10-0543-8890000000-6cf8e84f007ce7c750f2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00458
Phenol Explorer Compound IDNot Available
FooDB IDFDB022706
KNApSAcK IDNot Available
Chemspider ID3568
KEGG Compound IDC07049
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkImipramine
METLIN ID500
PubChem Compound3696
PDB IDNot Available
ChEBI ID47499
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Only showing the first 10 proteins. There are 11 proteins in total.

Enzymes

General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Catalyzes the N-oxidation of certain primary alkylamines to their oximes via an N-hydroxylamine intermediate. Inactive toward certain tertiary amines, such as imipramine or chloropromazine. Can catalyze the S-oxidation of methimazole. The truncated form is catalytically inactive.
Gene Name:
FMO2
Uniprot ID:
Q99518
Molecular weight:
53643.29
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
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
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
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
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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase
Gene Name:
ADORA1
Uniprot ID:
P30542
Molecular weight:
36511.3

Transporters

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
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

Only showing the first 10 proteins. There are 11 proteins in total.