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Details

Stereochemistry ACHIRAL
Molecular Formula C18H22N2.ClH
Molecular Weight 302.842
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DESIPRAMINE HYDROCHLORIDE

SMILES

Cl.CNCCCN1C2=CC=CC=C2CCC3=CC=CC=C13

InChI

InChIKey=XAEWZDYWZHIUCT-UHFFFAOYSA-N
InChI=1S/C18H22N2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H22N2
Molecular Weight 266.3807
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NORPRAMIN

Approved Use

Desipramine hydrochloride tablets are indicated for the treatment of depression.

Launch Date

1964
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
Ascending catecholamine pathways and amphetamine-induced locomotor activity: importance of dopamine and apparent non-involvement of norepinephrine.
1975 Aug 15
Low dose tricyclic tachycardia.
1991 Jan
Repeated administration of desmethylimipramine blocks the reserpine-induced increase in tyrosine hydroxylase mRNA in locus coeruleus neurons of the rat.
1991 Jul
Regulation of serotonin type 2 (5-HT2) and beta-adrenergic receptors in rat cerebral cortex following novel and classical antidepressant treatment.
1991 Nov
Desipramine-induced oral-pharyngeal disturbances: stuttering and jaw myoclonus.
1992 Dec
Increased pulse and blood pressure associated with desipramine treatment of bulimia nervosa.
1992 Jun
Oral contraceptives and panic disorder.
1992 May
Trazodone induction of migraine headache through mCPP.
1992 May
Activity of phenothiazines against antibiotic-resistant Mycobacterium tuberculosis: a review supporting further studies that may elucidate the potential use of thioridazine as anti-tuberculosis therapy.
2001 May
Microheterogeneity of myocardial blood flow.
2001 Nov
Antidepressants reduce phosphoinositide-specific phospholipase C (PI-PLC) activity and the mRNA and protein expression of selective PLC beta 1 isozyme in rat brain.
2002 Dec
Acute treatment with the cyclic antidepressant desipramine, but not fluoxetine, increases membrane-associated G protein-coupled receptor kinases 2/3 in rat brain.
2002 Dec
Effects of catecholamine uptake blockers in the caudate-putamen and subregions of the medial prefrontal cortex of the rat.
2002 May 17
Chronic inhibition of the norepinephrine transporter in the brain participates in seizure sensitization to cocaine and local anesthetics.
2003 Feb 21
Desipramine and contingency management for cocaine and opiate dependence in buprenorphine maintained patients.
2003 Jun 5
NO induced apoptosis of vascular smooth muscle cells accompanied by ceramide increase.
2004 May
Norepinephrine-deficient mice lack responses to antidepressant drugs, including selective serotonin reuptake inhibitors.
2004 May 25
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Desipramine treatment for cocaine dependence in buprenorphine- or methadone-treated patients: baseline urine results as predictor of response.
2005 Jan-Feb
Brugada syndrome precipitated by a tricyclic antidepressant.
2005 May
Desipramine treatment of cocaine-dependent patients with depression: a placebo-controlled trial.
2005 Nov 1
Nigrostriatal damage with 6-OHDA: validation of routinely applied procedures.
2006 Aug
Response to SSRI-induced enuresis: a case report.
2006 Feb
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Reduced evoked fos expression in activity-related brain regions in animal models of behavioral depression.
2007 Aug 15
Desipramine activated Bcl-2 expression and inhibited lipopolysaccharide-induced apoptosis in hippocampus-derived adult neural stem cells.
2007 May
Desipramine induces apoptotic cell death through nonmitochondrial and mitochondrial pathways in different types of human colon carcinoma cells.
2008
The role of NMDA receptor antagonists in nicotine tolerance, sensitization, and physical dependence: a preclinical review.
2008 Apr 30
Desipramine-induced apoptosis in human PC3 prostate cancer cells: activation of JNK kinase and caspase-3 pathways and a protective role of [Ca2+]i elevation.
2008 Aug 19
Comparison of the effects of desmethylimipramine on behavior in the forced swim test in peripubertal and adult rats.
2008 Feb
Evaluation of the repeated open-space swim model of depression in the mouse.
2008 Nov
Desipramine potentiation of the acute depressant effects of ethanol: modulation by alpha2-adrenoreceptors and stress.
2008 Oct
Neuronal damage and protection in the pathophysiology and treatment of psychiatric illness: stress and depression.
2009
Tetrabenazine as anti-chorea therapy in Huntington disease: an open-label continuation study. Huntington Study Group/TETRA-HD Investigators.
2009 Dec 18
Behavioral sensitization to cocaine: cooperation between glucocorticoids and epinephrine.
2009 Jul
Reactivation of inflammatory bowel disease in a mouse model of depression.
2009 Jun
Transient supersensitivity to alpha-adrenoceptor agonists, and distinct hyper-reactivity to vasopressin and angiotensin II after denervation of rat tail artery.
2010 Jan
Patents

Sample Use Guides

Usual Adult Dose for Depression 100 to 200 mg orally per day Maximum dose: 300 mg orally per day Comments: -Dosage should be initiated at a lower level and increased according to tolerance and clinical response. -In severely ill patients, dosage may be further increased to 300 mg per day if needed. -Treatment of patients requiring as much as 300 mg should generally be initiated in hospitals. Usual Geriatric Dose for Depression 25 to 100 mg orally per day Maximum dose: 150 mg orally per day
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 Mon Mar 31 17:52:51 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:51 GMT 2025
Record UNII
1Y58DO4MY1
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DESIPRAMINE HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
NORPRAMIN
Preferred Name English
DESIPRAMINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
RMI 9,384A
Code English
RMI-9384A
Code English
5H-DIBENZ(B,F)AZEPINE-5-PROPANAMINE, 10,11-DIHYDRO-N-METHYL-, MONOHYDROCHLORIDE
Common Name English
JB-8181
Code English
Desipramine hydrochloride [WHO-DD]
Common Name English
EX-4355
Code English
DESIPRAMINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
PERTOFRANE
Brand Name English
EX 4355
Code English
DESIPRAMINE HYDROCHLORIDE [MI]
Common Name English
NSC-114901
Code English
DESIPRAMINE HCL
Common Name English
DESIPRAMINE HYDROCHLORIDE [USP-RS]
Common Name English
DESIPRAMINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
G-35020
Code English
10,11-DIHYDRO-5-(3-(METHYLAMINO)PROPYL)-5H-DIBENZ(B,F)AZEPINE MONOHYDROCHLORIDE
Systematic Name English
DESIPRAMINE HYDROCHLORIDE [MART.]
Common Name English
DMI
Common Name English
DESIPRAMINE HYDROCHLORIDE [USAN]
Common Name English
DESIPRAMINE HYDROCHLORIDE [VANDF]
Common Name English
DESIPRAMINE HYDROCHLORIDE [JAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94727
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
Code System Code Type Description
CHEBI
4449
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
CAS
58-28-6
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
NCI_THESAURUS
C28979
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
RXCUI
203174
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY RxNorm
NSC
114901
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
EVMPD
SUB01595MIG
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
SMS_ID
100000092164
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
MERCK INDEX
m4191
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY Merck Index
DAILYMED
1Y58DO4MY1
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
DRUG BANK
DBSALT000042
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
EPA CompTox
DTXSID9046942
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
PUBCHEM
65327
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
ChEMBL
CHEMBL72
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
RS_ITEM_NUM
1172006
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
FDA UNII
1Y58DO4MY1
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-373-1
Created by admin on Mon Mar 31 17:52:51 GMT 2025 , Edited by admin on Mon Mar 31 17:52:51 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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ACTIVE MOIETY