ContaminantDB: Desipramine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (25)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:27 UTC

Update Date

2026-03-31 19:07:16 UTC

Accession Number

CHEM002356

Identification

Common Name

Desipramine

Class

Small Molecule

Description

Desipramine hydrochloride is a dibenzazepine-derivative tricyclic antidepressant (TCA). TCAs are structurally similar to phenothiazines. They contain a tricyclic ring system with an alkyl amine substituent on the central ring. In non-depressed individuals, desipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, desipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Secondary amine TCAs, such as desipramine and nortriptyline, are more potent inhibitors of norepinephrine reuptake than tertiary amine TCAs, such as amitriptyline and doxepine. TCAs also down-regulate cerebral cortical β-adrenergic receptors and sensitize post-synaptic serotonergic receptors with chronic use. The antidepressant effects of TCAs are thought to be due to an overall increase in serotonergic neurotransmission. TCAs also block histamine-H₁ receptors, α₁-adrenergic receptors and muscarinic receptors, which accounts for their sedative, hypotensive and anticholinergic effects (e.g. blurred vision, dry mouth, constipation, urinary retention), respectively. See toxicity section below for a complete listing of side effects. Desipramine exerts less anticholinergic and sedative side effects compared to tertiary amine TCAs, such as amitriptyline and clomipramine. Desipramine may be used to treat depression, neuropathic pain (unlabeled use), agitation and insomnia (unlabeled use) and attention-deficit hyperactivity disorder (unlabeled use).

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins

Contaminant Type

Adrenergic Uptake Inhibitor
Amine
Antidepressant
Antidepressive Agent
Antidepressive Agent, Tricyclic
Drug
Enzyme Inhibitor
Metabolite
Norepinephrine Reuptake Inhibitor
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3-(10,11-DIHYDRO-5H-dibenzo[b,F]azepin-5-yl)-N-methylpropan-1-amine	ChEBI
5-(gamma-Methylaminopropyl)iminodibenzyl	ChEBI
Demethylimipramine	ChEBI
Desipramin	ChEBI
Desipramina	ChEBI
Desipraminum	ChEBI
Desmethylimipramine	ChEBI
DMI	ChEBI
Monodemethylimipramine	ChEBI
N-(3-Methylaminopropyl)iminobibenzyl	ChEBI
Norimipramine	ChEBI
5-(g-Methylaminopropyl)iminodibenzyl	Generator
5-(Γ-methylaminopropyl)iminodibenzyl	Generator
Desimipramine	HMDB
Desimpramine	HMDB
Dezipramine	HMDB
Dimethylimipramine	HMDB
Methylaminopropyliminodibenzyl	HMDB
Norpramine	HMDB
Hydrochloride, desipramine	HMDB
Norpramin	HMDB
Novartis brand OF desipramine hydrochloride	HMDB
Ratiopharm brand OF desipramine hydrochloride	HMDB
Apo-desipramine	HMDB
Apotex brand OF desipramine hydrochloride	HMDB
Novo-desipramine	HMDB
Novopharm brand OF desipramine hydrochloride	HMDB
Nu pharm brand OF desipramine hydrochloride	HMDB
Petylyl	HMDB
Rhône poulenc rorer brand OF desipramine hydrochloride	HMDB
Temmler brand OF desipramine hydrochloride	HMDB
Ratio-desipramine	HMDB
Aventis behring brand OF desipramine hydrochloride	HMDB
Desipramine hydrochloride	HMDB
Nu-desipramine	HMDB
Nu-pharm brand OF desipramine hydrochloride	HMDB
PMS-Desipramine	HMDB
Pertofran	HMDB
Pertofrane	HMDB
Rhône-poulenc rorer brand OF desipramine hydrochloride	HMDB
Aventis brand OF desipramine hydrochloride	HMDB
Pertrofran	HMDB
Pharmascience brand OF desipramine hydrochloride	HMDB
Apo desipramine	HMDB
Novo desipramine	HMDB
Nu desipramine	HMDB
PMS Desipramine	HMDB
Ratio desipramine	HMDB

Chemical Formula

C₁₈H₂₂N₂

Average Molecular Mass

266.381 g/mol

Monoisotopic Mass

266.178 g/mol

CAS Registry Number

50-47-5

IUPAC Name

(3-{2-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,11,13-hexaen-2-yl}propyl)(methyl)amine

Traditional Name

desipramine

SMILES

CNCCCN1C2=CC=CC=C2CCC2=CC=CC=C12

InChI Identifier

InChI=1S/C18H22N2/c1-19-13-6-14-20-17-9-4-2-7-15(17)11-12-16-8-3-5-10-18(16)20/h2-5,7-10,19H,6,11-14H2,1H3

InChI Key

HCYAFALTSJYZDH-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzazepines

Sub Class

Dibenzazepines

Direct Parent

Dibenzazepines

Alternative Parents

Substituents

Dibenzazepine
Alkyldiarylamine
Tertiary aliphatic/aromatic amine
Azepine
Benzenoid
Tertiary amine
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary amino compound (CHEBI:47781 )
dibenzoazepine (CHEBI:47781 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	214-218°C
Boiling Point	Not Available
Solubility	58.6 mg/L (at 24°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.04 g/L	ALOGPS
logP	4.02	ALOGPS
logP	3.9	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	10.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.31 m³·mol⁻¹	ChemAxon
Polarizability	31.74 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0544-7980000000-e155fe1ae5cd0aa22da3	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0544-7980000000-e155fe1ae5cd0aa22da3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-7290000000-31dae7fdcf8b3c932db1	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9000000000-9d894f4aaf8e1b079ae9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-00di-9010000000-d95c9900b55a02d37d08	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 55V, Positive	splash10-00di-9000000000-895ad2c1abb94cf08417	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00di-9000000000-a3bcb8056f136f98462c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 70V, Positive	splash10-00di-9100000000-c857242bee851cf6d962	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Positive	splash10-00di-9200000000-13988b88ebe6d4f912ec	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 65V, Positive	splash10-00di-9100000000-902945e304be65e028f6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-9000000000-bd1a9a5833730277c98c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 5V, Positive	splash10-00di-9050000000-e24b987ac494aaa66350	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00di-9000000000-634aaae69ddb8e7c1704	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-00di-9000000000-f2982105b086747f3572	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-9030000000-be667edd8614bddec865	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-9000000000-e07f3a28db908bb8eb70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 15V, Positive	splash10-00di-9030000000-829d9c4cefe3d8808afc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-00di-9510000000-0781df5d5659f26929cf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-9030000000-dc6d3d2086192efa8492	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9020000000-a1bc578d8526b9d58e44	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 25V, Positive	splash10-00di-9010000000-4b836a2ee6fb310a4bb1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 80V, Positive	splash10-00dl-7900000000-fbcc580b8e1b687dea9c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0090000000-80dacb090470e582c8f8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00rl-5190000000-a15a250e113df7cffdc6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9520000000-8eb58abd95c114e6b333	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0090000000-c941aca18da7b3ecea74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014l-1590000000-66b8b8550a46a769b52c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-2900000000-eac7951bde437dcb062d	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-4970000000-810535cb33c37107abc5	Spectrum

Toxicity Profile

Route of Exposure

Desipramine hydrochloride is rapidly and almost completely absorbed from the gastrointestinal tract. It undergoes extensive first-pass metabolism. Peak plasma concentrations are attained 4 - 6 hours following oral administration.

Mechanism of Toxicity

Desipramine is a tricyclic antidepressant (TCA) that selectively blocks reuptake of norepinephrine (noradrenaline) from the neuronal synapse. It also inhibits serotonin reuptake, but to a lesser extent compared to tertiary amine TCAs such as imipramine. Inhibition of neurotransmitter reuptake increases stimulation of the post-synaptic neuron. Chronic use of desipramine also leads to down-regulation of beta-adrenergic receptors in the cerebral cortex and sensitization of serotonergic receptors. An overall increase in serotonergic transmission likely confers desipramine its antidepressant effects. Desipramine also possesses minor anticholinergic activity, through its affinity for muscarinic receptors. TCAs are believed to act by restoring normal levels of neurotransmitters via synaptic reuptake inhibition and by increasing serotonergic neurotransmission via serotonergic receptor sensitization in the central nervous system.

Metabolism

Desipramine is extensively metabolized in the liver by CYP2D6 (major) and CYP1A2 (minor) to 2-hydroxydesipramine, an active metabolite. 2-hydroxydesipramine is thought to retain some amine reuptake inhibition and may possess cardiac depressant activity. The 2-hydroxylation metabolic pathway of desipramine is under genetic control. Route of Elimination: Desipramine is metabolized in the liver, and approximately 70% is excreted in the urine. Half Life: 7-60+ hours; 70% eliminated renally

Toxicity Values

LD50: 290 mg/kg (Mouse) (1) LD50: 320 mg/kg (Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For relief of symptoms in various depressive syndromes, especially endogenous depression. It has also been used to manage chronic peripheral neuropathic pain, as a second line agent for the management of anxiety disorders (e.g. panic disorder, generalized anxiety disorder), and as a second or third line agent in the ADHD management.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Obtain an ECG and immediately initiate cardiac monitoring. Protect the patient's airway, establish an intravenous line, and initiate gastric decontamination. A minimum of 6 hours of observation with cardiac monitoring and observation for signs of CNS or respiratory depression, hypotension, cardiac dysrhythmias and/or conduction blocks, and seizures is necessary. If signs of toxicity occur at any time during this period, extended monitoring is required. Follow ECG, renal function, CPK, and arterial blood gasses as clinically indicated. (3)

Concentrations

Not Available

External Links

DrugBank ID

DB01151

HMDB ID

HMDB0015282

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID