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Details

Stereochemistry ACHIRAL
Molecular Formula C18H22N2
Molecular Weight 266.3813
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESIPRAMINE

SMILES

CNCCCN1c2ccccc2CCc3ccccc31

InChI

InChIKey=HCYAFALTSJYZDH-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H22N2
Molecular Weight 266.3813
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Desipramine is a tricyclic antidepressant that was approved by the FDA in 1964. It was derived from imipramine, which was the first tricyclic antidepressant to be manufactured. Desipramine is one of many tricyclic antidepressants, and this type of antidepressant gets its name due to its three-ring chemical structure. Desipramine, a secondary amine tricyclic antidepressant, is structurally related to both the skeletal muscle relaxant cyclobenzaprine and the thioxanthene antipsychotics such as thiothixene. It is the active metabolite of imipramine, a tertiary amine TCA. The acute effects of desipramine include inhibition of noradrenaline re-uptake at noradrenergic nerve endings and inhibition of serotonin (5-hydroxy tryptamine, 5HT) re-uptake at the serotoninergic nerve endings in the central nervous system. Desipramine exhibits greater noradrenergic re-uptake inhibition compared to the tertiary amine TCA imipramine. In addition to inhibiting neurotransmitter re-uptake, desipramine down-regulates beta-adrenergic receptors in the cerebral cortex and sensitizes serotonergic receptors with chronic use. The overall effect is increased serotonergic transmission. Antidepressant effects are typically observed 2 - 4 weeks following the onset of therapy though some patients may require up to 8 weeks of therapy prior to symptom improvement. Patients experiencing more severe depressive episodes may respond quicker than those with mild depressive symptoms. Desipramine is marketed under the trade name Norpramin, indicated for the treatment of depression.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
21.8 ng/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
656 ng × h/mL
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
21 h
50 mg single, oral
dose: 50 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DESIPRAMINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
9.78%
DESIPRAMINE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy, 2 years
Health Status: healthy
Age Group: 2 years
Sex: F
Sources:
Other AEs: Coma, Seizures...
Other AEs:
Coma (grade 5, 1 patient)
Seizures (grade 5, 1 patient)
Hypotension (grade 5, 1 patient)
Sources:
300 mg 1 times / day multiple, oral
Highest studied dose
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
25 mg 1 times / day multiple, oral
Recommended
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, children | adolescents | and young adults
Health Status: unhealthy
Age Group: children | adolescents | and young adults
Sources:
Other AEs: Suicidal ideation...
AEs

AEs

AESignificanceDosePopulation
Coma grade 5, 1 patient
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy, 2 years
Health Status: healthy
Age Group: 2 years
Sex: F
Sources:
Hypotension grade 5, 1 patient
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy, 2 years
Health Status: healthy
Age Group: 2 years
Sex: F
Sources:
Seizures grade 5, 1 patient
2500 mg single, oral
Overdose
Dose: 2500 mg
Route: oral
Route: single
Dose: 2500 mg
Sources:
healthy, 2 years
Health Status: healthy
Age Group: 2 years
Sex: F
Sources:
Suicidal ideation
25 mg 1 times / day multiple, oral
Recommended
Dose: 25 mg, 1 times / day
Route: oral
Route: multiple
Dose: 25 mg, 1 times / day
Sources:
unhealthy, children | adolescents | and young adults
Health Status: unhealthy
Age Group: children | adolescents | and young adults
Sources:
Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
no (co-administration study)
Comment: Ketoconazole did not alter the pharmacokinetics of orally administered desipramine in healthy volunteers; Genetic deficiency in CYP2D6 activity results in a 85% lower oral clearance of desipramine, as shown by a single dose pharmacokinetic study in healthy volunteers
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Repeated administration of desmethylimipramine blocks the reserpine-induced increase in tyrosine hydroxylase mRNA in locus coeruleus neurons of the rat.
1991 Jul
Desipramine-induced oral-pharyngeal disturbances: stuttering and jaw myoclonus.
1992 Dec
Reversal of desipramine toxicity in rats using drug-specific antibody Fab' fragment: effects on hypotension and interaction with sodium bicarbonate.
1992 Mar
Desipramine in opioid-dependent cocaine abusers maintained on buprenorphine vs methadone.
1999 Sep
Antidepressant drugs appear to enhance cocaine-induced toxicity.
2000 Feb
Tricyclic antidepressants and the Brugada syndrome: an example of Brugada waves appearing after the administration of desipramine.
2002 Aug
Effects of catecholamine uptake blockers in the caudate-putamen and subregions of the medial prefrontal cortex of the rat.
2002 May 17
Role of brain dopaminergic system in the adrenomedullin-induced diuresis and natriuresis.
2003 Nov
Effects of electroconvulsive seizures and antidepressant drugs on brain-derived neurotrophic factor protein in rat brain.
2003 Oct 1
[Effects of neurotensin microinjected into ventral tegmental area on spontaneous motor activity in neonatal 6-hydroxydopamine-treated rats].
2004 Apr
Ethnic differences in substance abuse treatment retention, compliance, and outcome from two clinical trials.
2004 Feb
Discovering modes of action for therapeutic compounds using a genome-wide screen of yeast heterozygotes.
2004 Jan 9
Clinical implications of genetic polymorphism of CYP2D6 in Mexican Americans.
2004 Jun 1
NO induced apoptosis of vascular smooth muscle cells accompanied by ceramide increase.
2004 May
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Coadministration of histone deacetylase inhibitors and perifosine synergistically induces apoptosis in human leukemia cells through Akt and ERK1/2 inactivation and the generation of ceramide and reactive oxygen species.
2005 Mar 15
Brugada syndrome precipitated by a tricyclic antidepressant.
2005 May
Selective cortical VGLUT1 increase as a marker for antidepressant activity.
2005 Nov
Response to SSRI-induced enuresis: a case report.
2006 Feb
Enhanced neurally evoked responses and inhibition of norepinephrine reuptake in rat mesenteric arteries after spinal transection.
2006 Jan
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations].
2006 Jun
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Down-regulation of norepinephrine transporter function induced by chronic administration of desipramine linking to the alteration of sensitivity of local-anesthetics-induced convulsions and the counteraction by co-administration with local anesthetics.
2006 Jun 22
Desipramine activated Bcl-2 expression and inhibited lipopolysaccharide-induced apoptosis in hippocampus-derived adult neural stem cells.
2007 May
Anti-inflammatory properties of desipramine and fluoxetine.
2007 May 3
The role of NMDA receptor antagonists in nicotine tolerance, sensitization, and physical dependence: a preclinical review.
2008 Apr 30
Do desipramine [10,11-dihydro-5-[3-(methylamino) propyl]-5H-dibenz[b,f]azepine monohydrochloride] and fluoxetine [N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-propan-1-amine] ameliorate the extent of colonic damage induced by acetic acid in rats?
2008 Dec
The 5-hydroxytryptamine2A receptor antagonist R-(+)-alpha-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl-4-piperidinemethanol (M100907) attenuates impulsivity after both drug-induced disruption (dizocilpine) and enhancement (antidepressant drugs) of differential-reinforcement-of-low-rate 72-s behavior in the rat.
2008 Dec
A novel approach for predicting antidepressant-induced sexual dysfunction in rats.
2008 Jan
Photophysics and photochemistry of imipramine, desimipramine, and clomipramine in several solvents: a fluorescence, 266 nm laser flash, and theoretical study.
2008 Jan 10
D-161, a novel pyran-based triple monoamine transporter blocker: behavioral pharmacological evidence for antidepressant-like action.
2008 Jul 28
Narcolepsy: current treatment options and future approaches.
2008 Jun
Impaired parasympathetic function increases susceptibility to inflammatory bowel disease in a mouse model of depression.
2008 Jun
Community-based randomised controlled trial evaluating falls and osteoporosis risk management strategies.
2008 Nov 4
Assessing the neuronal serotonergic target-based antidepressant stratagem: impact of in vivo interaction studies and knockout models.
2008 Sep
Tetrabenazine as anti-chorea therapy in Huntington disease: an open-label continuation study. Huntington Study Group/TETRA-HD Investigators.
2009 Dec 18
Reactivation of inflammatory bowel disease in a mouse model of depression.
2009 Jun
Association of changes in norepinephrine and serotonin transporter expression with the long-term behavioral effects of antidepressant drugs.
2009 May
Patents

Sample Use Guides

Usual Adult Dose for Depression
Route of Administration: Oral
Neuronal uptake 1 inhibitor desipramine (100 nM) decreased NE in 60-min hypothermic ischemia in isolated perfused guinea pig hearts.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:09:22 UTC 2021
Edited
by admin
on Sat Jun 26 12:09:22 UTC 2021
Record UNII
TG537D343B
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESIPRAMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
10,11-DIHYDRO-5-(3-(METHYLAMINO)PROPYL)-5H-DIBENZ(B,F)AZEPINE
Systematic Name English
N-DESMETHYLIMIPRAMINE
Common Name English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 10,11-DIHYDRO-N-METHYL-
Systematic Name English
DESIPRAMINE [VANDF]
Common Name English
DESIPRAMINE [WHO-DD]
Common Name English
DESIPRAMINE [HSDB]
Common Name English
IMIPRAMINE, DEMETHYL-
Common Name English
MONODEMETHYLIMIPRAMINE
Common Name English
IMIPRAMINE HYDROCHLORIDE IMPURITY A [EP]
Common Name English
DESIPRAMINE [INN]
Common Name English
NORIMIPRAMINE
Common Name English
DESIPRAMINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94727
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
NDF-RT N0000175752
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
LIVERTOX 283
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
WHO-ATC N06AA01
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
WHO-VATC QN06AA01
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
Code System Code Type Description
CAS
50-47-5
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
ChEMBL
CHEMBL72
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
EPA CompTox
50-47-5
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
PUBCHEM
2995
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
EVMPD
SUB06995MIG
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
INN
1500
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-040-0
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
HSDB
3052
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
DRUG CENTRAL
812
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
RXCUI
3247
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB01151
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
MERCK INDEX
M4191
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY Merck Index
IUPHAR
2399
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
WIKIPEDIA
DESIPRAMINE
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
MESH
D003891
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
NCI_THESAURUS
C61700
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
FDA UNII
TG537D343B
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
LACTMED
Desipramine
Created by admin on Sat Jun 26 12:09:23 UTC 2021 , Edited by admin on Sat Jun 26 12:09:23 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> SUBSTRATE
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
Metabolizing reaction by CYP2D6: Hydroxylation
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
Pharmacological action: Tricyclic antidepressant drug (TCA)
BINDER->LIGAND
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Imipramine has activities at both the serotonin and norepeinephrine transporters with greater affinity for the serotonin transporter while desipramine and 2-hydroxydesipramine have greater affinities for the norepinephrine transporter (Owens et al., 1997).
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY