Desipramine PubChem

1/10/2019 Desipramine | C18H22N2 - PubChem
COMPOUND SUMMARY
Desipramine
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CONTENTS
Title and Summary
1 Structures
PubChem CID: 2995
2 Names and Identifiers
3 Chemical and Physical Properties
4 Spectral Information
5 Related Records
6 Chemical Vendors
2D
7 Drug and Medication Information
Structure: 8 Pharmacology and Biochemistry
9 Use and Manufacturing
10 Identification
11 Safety and Hazards

3D
12 Toxicity
Find Similar 13 Literature
Structures
14 Patents
15 Biomolecular Interactions and Pathways
16 Biological Test Results
Irritant
Chemical Safety: Health Hazard
Environmental
Hazard
Laboratory Chemical
Safety Summary
(LCSS) Datasheet
Molecular Formula: C18H22N2
desipramine
Norimipramine
Desmethylimipramine
Desipramin
Chemical Names:
Demethylimipramine
More...
Molecular Weight: 266.4 g/mol
Dates:
https://pubchem.ncbi.nlm.nih.gov/compound/2995 1/57
Modify:
2019-09-21
Create:
2005-03-25
Desipramine is an active metabolite of imipramine, a

tertiary amine and a synthetic tricyclic derivative of the
antidepressant. Desipramine enhances monoamine
neurotransmission in certain areas of the brain by
inhibiting the re-uptake of noradrenaline and
serotonin at the noradrenergic and serotoninergic
nerve endings, respectively. It also induces sedation
through histamine 1 receptor blockage and
hypotension through beta-adrenergic blockage.
from NCIt
Desipramine is a Tricyclic Antidepressant.

from FDA Pharm Classes
Desipramine is an oral tricyclic antidepressant that

widely used in the therapy of depression. Desipramine
can cause mild and transient serum enzyme elevations
and is rare cause of clinically apparent acute cholestatic
liver injury.
from LiverTox
1 Structures
1.1 2D Structure
Find Similar Structures Get Image Download
Chemical Structure
Depiction
from PubChem
1.2 3D Conformer
Get Image Download
Interactive Chemical
Structure Model
Ball and Stick
Sticks
Wire-Frame
Space-Filling
Show Hydrogens
Animate
from PubChem
1.3 Crystal Structures
PDBe Ligand Code DSM
PDBe Structure Code 2QJU
Interactive Chemical
Structure Model
Ball and Stick
Sticks Wire-Frame
Space-Filling
Show Hydrogens
Animate
PDBe Conformer
from Protein Data Bank in Europe (PDBe)
2 Names and Identifiers
2.1 Computed Descriptors
2.1.1 IUPAC Name
3-(5,6-dihydrobenzo[b][1]benzazepin-11-yl)-N-
methylpropan-1-amine
from PubChem
2.1.2 InChI
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
from PubChem
2.1.3 InChI Key
HCYAFALTSJYZDH-UHFFFAOYSA-N
from PubChem
2.1.4 Canonical SMILES
CNCCCN1C2=CC=CC=C2CCC3=CC=CC=C31
from PubChem
2.2 Molecular Formula

C18H22N2
from PubChem
2.3 Other Identifiers
2.3.1 CAS
50-47-5
from ChemIDplus; DrugBank; EPA DSSTox; European Chemicals Agency (ECHA); HSDB; Human Metabolome Database (HMDB)
Related CAS
58-28-6 (hydrochloride)
from ChemIDplus
2.3.2 European Community (EC)

Number
200-040-0
from European Chemicals Agency (ECHA)
2.3.3 UNII
TG537D343B
from FDA/SPL Indexing Data
2.3.4 Wikipedia
Desipramine
from Wikipedia
2.4 Synonyms
2.4.1 MeSH Entry Terms
Apo Desipramine Pertofrane

Apo-Desipramine Pertrofran
Demethylimipramine Petylyl
Desipramine PMS Desipramine
Desipramine Hydrochloride PMS-Desipramine
Desmethylimipramine Ratio Desipramine
Hydrochloride, Desipramine ratio-Desipramine
Norpramin
Novo Desipramine
Novo-Desipramine
Nu Desipramine
Nu-Desipramine
Pertofran
from MeSH
2.4.2 Depositor-Supplied Synonyms
desipramine
Norimipramine
Desmethylimipramine
Desipramin
Demethylimipramine
Monodemethylimipramine
50-47-5
Desimipramine
Dimethylimipramine
Dezipramine
Methylaminopropyliminodibenzyl
3-(10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPIN-5-YL)-N-
METHYLPROPAN-1-AMINE
from PubChem
3 Chemical and Physical

Properties
3.1 Computed Properties
Property Name Property Value
Molecular Weight 266.4 g/mol
XLogP3 4.9
Hydrogen Bond Donor Count 1
Hydrogen Bond Acceptor

2
Count
Rotatable Bond Count 4
Exact Mass 266.178299 g/mol
Monoisotopic Mass 266.178299 g/mol
Topological Polar Surface Area 15.3 A^2
Heavy Atom Count 20
Formal Charge 0
Complexity 267
Isotope Atom Count 0
Defined Atom Stereocenter

0
Count
Undefined Atom Stereocenter

0
Count
Defined Bond Stereocenter

0
Count
Undefined Bond Stereocenter

0
Count
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes
from PubChem
3.2 Experimental Properties
3.2.1 Physical Description
Solid
from Human Metabolome Database (HMDB)
3.2.2 Boiling Point
172-174 DEG C @ 0.02 MM HG

Budavari, S. (ed.). The Merck Index - An Encyclopedia of
Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck
and Co., Inc., 1996., p. 494
from HSDB
3.2.3 Melting Point
214-218 °C
from DrugBank
214-218°C
3.2.4 Solubility
58.6 mg/L (at 24 °C)

YALKOWSKY,SH & DANNENFELSER,RM (1992)
from DrugBank
Water Solubility
2.20e-04 M
YALKOWSKY,SH & DANNENFELSER,RM (1992)
from EPA DSSTox
In water, 58.6 mg/l @ 24 deg C.

Yalkowsky SH, Dannenfelser RM; The AQUASOL dATAbASE of
Aqueous Solubility. Fifth ed, Tucson, AZ: Univ Az, College of
Pharmacy (1992)
from HSDB
3.96e-02 g/L
3.2.5 Octanol/Water Partition

Coefficient
4.9
HANSCH,C ET AL. (1995)
from DrugBank
4.9 (LogP)
HANSCH,C ET AL. (1995)
from EPA DSSTox
log Kow = 4.90
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic,

Electronic, and Steric Constants. Washington, DC: American
Chemical Society., 1995., p. 157
from HSDB
LogP
3.7
3.2.6 LogS
-3.66
ADME Research, USCD
from DrugBank
3.2.7 Stability/Shelf Life
UNSTABLE AFTER LONG EXPOSURE TO LIGHT, HEAT, & AIR

/HYDROGEN CHLORIDE/
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical
Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co.,
1975., p. 1030
from HSDB
3.2.8 Decomposition
When heated to decomposition it emits toxic fumes of

nitroxides.
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 9th
ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold, 1996., p.
1334
from HSDB
3.2.9 Caco2 Permeability
-4.67
ADME Research, USCD
from DrugBank
3.2.10 pKa
10.4
SANGSTER (1994)
from DrugBank
3.2.11 Kovats Retention Index
2242, 2217, 2217, 2200, 2235,

2235, 2241, 2220, 2242, 2237.5,
Standard non-polar 2231.1, 2200, 2255, 2242,
2248.7, 2254.4, 2236, 2236,
2256.5
Semi-standard non-polar 2240, 2243.2, 2204, 2233.8
from NIST
3.2.12 Other Experimental Properties
WHITE CRYSTALLINE POWDER; ODORLESS; BITTER TASTE;

MELTS WITHIN 5 DEG RANGE BETWEEN 208-218 DEG C; 1 G
IN CA 4 ML CHLOROFORM, 20 ML WATER, 20 ML ALC;
FREELY SOL IN METHANOL; INSOL IN ETHER /HCL/
1975., p. 1030
from HSDB
4 Spectral Information
4.1 Mass Spectrometry

Showing 2 of 12 View More
Intense mass spectral peaks: 44

Mass Spectrometry m/z, 71 m/z, 195 m/z, 235 m/z,
266 m/z
from HSDB
MoNA ID JP003855
MS Category Experimental
Chromatography identified as
MS Type
GC-MS
MS Level MS1
Instrument Unknown
Instrument Type EI-B
Ionization Mode positive
splash10-0544-7980000000-
Splash
e155fe1ae5cd0aa22da3
Thumbnail
Kimito Funatsu, Faculty of

Submitter
Engineering, University of Tokyo
from MassBank of North America (MoNA)
4.1.1 GC-MS
GC-MS Spectrum 12325 -

HMDB HMDB0015282
GC-MS
HMDB HMDB0015282
HMDB HMDB0015282
NIST Number 250707
Library Main library
Total Peaks 179
m/z Top Peak 234
m/z 2nd Highest 195
m/z 3rd Highest 193
Thumbnail
from NIST
4.1.2 MS-MS
MS-MS Spectrum 47835 -

HMDB HMDB0015282
HMDB HMDB0015282
HMDB HMDB0015282
MS-MS
HMDB HMDB0015282
HMDB HMDB0015282
HMDB HMDB0015282
NIST Number 1006547
Instrument Type IT/ion trap
Collision Energy 0
Spectrum Type MS2
Precursor Type [M+H]+
Precursor m/z 267.1856
Total Peaks 5
m/z Top Peak 236
m/z 2nd Highest 208
m/z 3rd Highest 196
Thumbnail
from NIST
4.1.3 EI-MS
EI-MS Spectrum 275 - HMDB

EI-MS
HMDB0015282
4.2 UV Spectra
MAX ABSORPTION: 213 NM (LOG E= 4.39); 252 NM (LOG E=
3.93)
and Co., Inc., 1996., p. 394
from HSDB
4.3 IR Spectra
4.3.1 ATR-IR Spectra
Instrument Name Bio-Rad FTS
ATR-Film (MeCl2) (DuraSamplIR

Technique
II)
Source of Spectrum Forensic Spectral Research
Source of Sample Alltech Associates, Inc., Grace
Davison Discovery Sciences
Catalog Number 1361
Lot Number 332
Copyright © 2012-2018 Bio-Rad

Copyright Laboratories, Inc. All Rights
Reserved.
Thumbnail
from SpectraBase
5 Related Records
5.1 Related Compounds with
Annotation
from PubChem
5.2 Related Compounds
Same Connectivity 6 Records
Same Parent, Connectivity 22 Records
Same Parent, Exact 14 Records
Mixtures, Components, and

50 Records
Neutralized Forms
Similar Compounds 777 Records
Similar Conformers 1,332 Records
from PubChem
5.3 Substances
5.3.1 Related Substances
All 344 Records
Same 142 Records
Mixture 202 Records
from PubChem
5.3.2 Substances by Category
from PubChem
5.4 Entrez Crosslinks
PubMed 234 Records
Protein Structures 1 Record
Taxonomy 4 Records
OMIM 19 Records
Gene 54 Records
from PubChem
5.5 Associated Chemicals

Desipramine hydrochloride;58-28-6
from HSDB
5.6 NCBI LinkOut
from NCBI
6 Chemical Vendors
from PubChem
7 Drug and Medication

Information
7.1 Drug Indication

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.
from DrugBank
FDA Label
from DrugBank
7.2 LiverTox Summary

Desipramine is an oral tricyclic antidepressant that widely
used in the therapy of depression. Desipramine can cause
mild and transient serum enzyme elevations and is rare
cause of clinically apparent acute cholestatic liver injury.
from LiverTox
7.3 Drug Classes

Antidepressants
from LiverTox
7.4 Clinical Trials
7.4.1 ClinicalTrials.gov
from ClinicalTrials.gov
7.4.2 EU Clinical Trials Register
from EU Clinical Trials Register
7.5 Therapeutic Uses

Adrenergic Uptake Inhibitors; Antidepressive Agents,
Tricyclic
National Library of Medicine's Medical Subject Headings online
file (MeSH, 1999)
from HSDB
...USED IN MANAGEMENT OF DEPRESSIVE STATES.

DESIPRAMINE IS REPORTED TO BE OF BENEFIT IN
ENDOGENOUS DEPRESSIONS SUCH AS MANIC DEPRESSIVE
REACTIONS, & REACTIVE DEPRESSIONS.
1975., p. 1030
from HSDB
...IF...GIVEN OVER PERIOD OF TIME TO DEPRESSED

PATIENTS, ELEVATION OF MOOD OCCURS. ... 2-3
WK...BEFORE THERAPEUTIC EFFECTS...EVIDENT.
/IMIPRAMINE/
Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of
Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc.,
1975., p. 175
from HSDB
ANTIDEPRESSANT
The Merck Index. 9th ed. Rahway, New Jersey: Merck & Co., Inc.,
1976., p. 383
from HSDB
... May effectively treat tic disorder, either in association with

the use of stimulants, or arising in patients with both
attention disorder and Tourette's syndrome.
Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G.
Goodman (eds.). Goodman and Gilman's The Pharmacological
Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996.,
p. 445
from HSDB
Tricyclic antidepressants are used in the prophylaxis of

vascular headache (including migraine) and mixed headache
syndrome. /NOT included in US product labeling; Tricyclic
antidepressants/
USP Convention. USPDI - Drug Information for the Health Care
Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc.,
1997. (Plus Updates)., p. 265
from HSDB
Desipramine /is/ used to reduce craving and/or prevent

depression upon withdrawal of cocaine. /NOT included in
US product labeling/
from HSDB
Desipramine /has/ been shown to be effective in controlling

the binge eating and subsequent purging of bulimia
nervosa. /NOT included in US product labeling/
from HSDB
Tricyclic antidepressants, especially desipramine /is/ used in

patients with normal or depressed mood for the
management of chronic, severe pain as in cancer; migraine
and chronic, daily muscle-contraction headaches; rheumatic
disorders; atypical facial pain; post-herpetic neuralgia; post-
traumatic neuropathy; and diabetic or other peripheral
neuropathy. /NOT included in US product labeling/
from HSDB
Tricyclic antidepressants, expecially desipramine /is/ used to

treat cataplexy associated with narcolepsy, with little or no
effect on narcoleptic sleep attacks. /NOT included in US
product labeling/
from HSDB
Desipramine /is/ used to relieve the symptoms of attention

deficit hyperactivity disorder in some children over 6 years
of age and in young adults. Tricyclic antidepressants may be
more useful than stimulants when the patient has become
withdrawn and depressed. /NOT included in US product
labeling/

from HSDB
Tricyclic antidepressants, especially desipramine /is/ used in

conjunction with psychotherapy and behavior therapy to
block the recurrence of panic attacks, with or without
phobias. /NOT included in US product labeling/
from HSDB
Desipramine /is/ indicated for the relief of symptoms of

major depressive episodes; bipolar disorder, depressed type;
dysthymia; and atypical depressions. Some conditions
associated with or accompanied by depression that are
treated with tricyclic antidepressants include alcoholism,
organic disease such as stroke or Parkinson's disease, and
agitation or anxiety. /Included in US product labeling/
from HSDB
7.6 Drug Warnings

SINCE TRICYCLIC ANTIDEPRESSANTS CAN CAUSE

ORTHOSTATIC HYPOTENSION, PRODUCE ARRHYTHMIAS, &
INTERACT IN DELETERIOUS WAYS WITH OTHER
DRUGS...GREAT CAUTION MUST BE OBSERVED IN THEIR USE
IN PT WITH SIGNIFICANT CARDIAC DISEASE. /TRICYCLIC
ANTIDEPRESSANTS/
1975., p. 177
from HSDB
SPECIAL PRECAUTIONS SHOULD BE TAKEN IN PT WITH

BENIGN PROSTATIC HYPERTROPHY. /IMIPRAMINE/
1975., p. 178
from HSDB
DESIPRAMINE HYDROCHLORIDE IS CONTRAINDICATED IN

PATIENTS ON MONOAMINE OXIDASE-INHIBITOR THERAPY.
.../IT/ SHOULD NOT BE GIVEN TO PT WITH GLAUCOMA,
URETHRAL OR URETERAL SPASM, OR THOSE WHO HAVE
HAD MYOCARDIAL INFARCTION WITHIN 3 WK. IT IS ALSO
CONTRAINDICATED IN PT WITH SEVERE CORONARY HEART

DISEASES OR WITH ACTIVE EPILEPSY. /HYDROGEN
CHLORIDE/
1975., p. 1030
from HSDB
The most common adverse effects of tricyclic

antidepressants are those which result from anticholinergic
activity. These include dry mucous membranes (occasionally
associated with sublingual adenitis), blurred vision resulting
from mydriasis and cycloplegia, increased intraocular
pressure, hyperthermia, constipation, adynamic ileus, urinary
retention, delayed micturition, and dilation of the urinary
tract. The drugs have been reported to reduce the tone of
the esophagogastric sphincter and to induce hiatal hernia in
susceptible individuals or to exacerbate the condition in
patients with preexisting hiatal hernias. Tricyclic
antidepressants should be withdrawn if symptoms of
esophageal reflux develop; if antidepressant therapy is
essential, a cautious trial of a cholinergic agent such as
bethanechol used concomitantly with the antidepressant
may be warranted. Anticholinergic effects appear to occur
most frequently in geriatric patients, but constipation is
frequent in children receiving tricyclic antidepressants for
functional enuresis. /Tricyclic antidepressants/
McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug
Information 19 98. Bethesda, MD: American Society of Health-
System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1791
from HSDB
Adverse CNS and neuromuscular effects occur frequently.

Drowsiness is the most frequent adverse reaction to tricyclic
antidepressants; weakness, lethargy, and fatigue are also
common. Conversely, agitation, excitement, nightmares,
restlessness, and insomnia have occurred. Confusion,
disturbed concentration, disorientation, delusions, and
hallucinations may occur, most commonly in geriatric
patients. Children receiving tricyclic antidepressants for
functional enuresis may experience drowsiness, anxiety,
emotional instability, nervousness, and sleep disorder.
Although effects differ among individual patients, sedative
effects are usually greatest with amitriptyline or doxepin
and least with protriptyline. /Tricyclic antidepressants/
from HSDB
Exacerbation of depression, hypomania, panic, troublesome

hostility, anxiety, or euphoria may occur in patients receiving
tricyclic antidepressants. Exacerbation of psychosis has
occurred in patients with schizophrenia or paranoid
symptoms treated with the drugs; patients with bipolar
depression may shift to the manic phase. Such psychotic

manifestations should be treated by decreasing the dose of
tricyclic antidepressant or by administering an antipsychotic
drug such as a phenothiazine with the antidepressant.
Alteration in EEG patterns and occasionally seizures have
occurred. Seizures are more common in children than in
adults. Coma also has occurred. /Tricyclic antidepressants/
from HSDB
Rarely, agranulocytosis, thrombocytopenia, eosinophilia,

leukopenia, and purpura have been reported and may be
hypersensitivity reaction. Leukocyte and differential counts
should be performed in all patients who develop symptoms
of blood dyscrasias, such as sore throat and fever, and
tricyclic antidepressants should be discontinued if evidence
of pathologic neutrophil depression is found. /Tricyclic
antidepressants/
from HSDB
Asymptomatic increases in serum aminotransferase

(transaminase) concentration, changes in serum alkaline
phosphatase concentrations, obstructive-type jaundice, and
hepatitis which appear to be allergic in nature have also
occurred during therapy with tricyclic antidepressants.
Elevated values on liver function tests indicate the need for
repeat tests; if progressive elevations occur, the drugs
should discontinued. Jaundice and hepatitis are reversible
following discontinuance of the drugs; however, deaths
resulting from hepatitis have occurred when tricyclic
antidepressants were continued. Hepatic failure has been
reported in patients receiving amitriptyline; however, a
causal relationship to the drug could not be established.
/Tricyclic antidepressants/
from HSDB
Allergic manifestations have included rash and erythema,

petechiae, urticaria, pruritus, eosinophilia, edema (general or
of face and tongue), drug fever, and photosensitivity.
Patients who demonstrate photosensitivity should avoid
exposure to sunlight. A lupus-like syndrome (migratory
arthritis,positive ANA and rheumatoid factor) has been
reported in patients receiving amitriptyline; however, a
causal relationship to the drug could not be established.
from HSDB
Adverse GI effects such as anorexia, nausea and vomiting,

diarrhea, abdominal cramps, increases in pancreatic
enzymes, epigastric distress, stomatitis, peculiar taste, and
black tongue have been reported in patients receiving
tricyclic antidepressants. Ageusia has been reported in
patients receiving amitriptyline; however, a causal
relationship to the drug could not be established. ...
Endocrine effects which have occurred in patients receiving
tricyclic antidepressants include increased or decreased
libido, impotence, testicular swelling, painful ejaculation,
breast engorgement and galactorrhea in females,
gynecomastia in males, syndrome of inappropriate
antidiuretic hormone secretion (SIADH), and elevation or
lowering of blood glucose concentrations. /Tricyclic
antidepressants/
from HSDB
Tricyclic antidepressants should be used with caution in

patients whom excess anticholinergic activity could be
harmful, such as those with benign prostatic hypertrophy, a
history of urinary retention, increased intraocular pressure,
or angle-closure glaucoma. /Tricyclic antidepressants/
from HSDB
Tricyclic antidepressants may lower the seizure threshold

and should be used with caution in patients with a history of
seizure disorders, organic brain disease, or who may be
predisposed to seizures (eg, in the acute withdrawal phase
of alcoholism). Depressed patients are especially prone to
suicidal tendencies and large quantities of tricyclic
antidepressants should not be prescribed at one time.
from HSDB
Tricyclic antidepressants are contraindicated in the acute

recovery phase following myocardial infarction. The drugs
should be used with extreme caution in patients with
preexisting cardiovascular disease because tricyclic
antidepressants may cause adverse cardiovascular effects.

from HSDB
Children are more sensitive than adults to acute overdosage,

which should be considered serious and potentially fatal.
Increasing the dose in children increases the risk of adverse
effects, such as alterations in electrocardiogram (ECG)
patterns, nervousness, sleep disorders, tiredness,
hypertension in some children, or mild gastrointestinal
problems, without necessarily enhancing the therapeutic
effect. Adolescent patients may require reduced dosage
because they are also prone to exhibit increased dose
sensitivity. /Tricyclic antidepressants/
from HSDB
Elderly patients often require lower dosage and more

gradual dose increases to avoid toxicity, because of slower
metabolic rates and/or excretion and an increased ratio of
fat to lean tissue. The elderly also exhibit increased
sensitivity to anticholinergic effects, such as urinary
retention (especially in older men with prostatic
hypertrophy), anticholinergic delirium, and increased
sedative and hypotensive effects. Increased anxiety may
result from these adverse effects, possibly leading to
unnecessary dose increases. If cardiovascular disease is
present, the risk of conduction defects, arrhythmias,
tachycardia, stroke, congestive heart failure, or myocardial
infarction is increased. /Tricyclic antidepressants/
from HSDB
The peripheral anticholinergic effects of tricyclic

antidepressants may decrease or inhibit salivary flow,
especially in middle-aged or elderly patients, thus
contributing to the development of caries, periodontal
disease, oral candidiasis, and discomfort. /Tricyclic
antidepressants/
from HSDB
The blood dyscrasia-causing effects of tricyclic

antidepressants, although rare, may be life-threatening. The
result may be an increased incidence of microbial infection,
delayed healing, and gingival bleeding. If agranulocytosis,
leukopenia, or thrombocytopenia occurs, dental work
should be deferred until blood counts have returned to
normal. Patient instruction in proper oral hygiene should
include caution in use of regular toothbrushes, dental floss,
and toothpicks. /Tricyclic antidepressants/

from HSDB
There have been reports of cardiac problems, irritability,

respiratory distress, muscle spasms, seizures, and urinary
retention in infants whose mothers received tricyclic
antidepressants immediately prior to delivery. /Tricyclic
antidepressants/
from HSDB
... IMIPRAMINE ... PRODUCES SLEEPINESS,

LIGHTHEADEDNES, A SLIGHT FALL IN BLOOD PRESSURE,
AND CERTAIN ANTICHOLINERGIC EFFECTS (E.G., DRY
MOUTH, BLURRED VISION)./IMIPRAMINE/
p. 436
from HSDB
/UNTOWARD REACTIONS INCL/ WEAKNESS &

FATIGUE...HEADACHE...& EPIGASTRIC DISTRESS. ... ANOTHER
UNDESIRABLE EFFECT... IS TRANSITION FROM DEPRESSION
TO HYPOMANIC OR MANIC EXCITEMENT IN CERTAIN
PATIENTS. ...HALLUCINATIONS & DELUSIONS MAY OCCUR.
... PERSISTENT FINE TREMOR OCCURS IN ABOUT 10% OF
THOSE RECEIVING DRUG. /IMIPRAMINE/

1975., p. 178
from HSDB
7.7 Drug Tolerance

TOLERANCE TO ANTICHOLINERGIC EFFECTS, SUCH AS DRY
MOUTH, CONSTIPATION, BLURRED VISION, &
TACHYCARDIA, TENDS TO DEVELOP WITH CONTINUED USE
OF IMIPRAMINE. /IMIPRAMINE/

1975., p. 178
from HSDB
8 Pharmacology and
Biochemistry
8.1 Pharmacology
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.
from DrugBank
Desipramine is an active metabolite of imipramine, a tertiary

amine and a synthetic tricyclic derivative of the
antidepressant. Desipramine enhances monoamine
neurotransmission in certain areas of the brain by inhibiting
the re-uptake of noradrenaline and serotonin at the
noradrenergic and serotoninergic nerve endings,
respectively. It also induces sedation through histamine 1
receptor blockage and hypotension through beta-
adrenergic blockage.
from NCIt
8.2 MeSH Pharmacological

Classification
Adrenergic Uptake Inhibitors
Drugs that block the transport of adrenergic transmitters

into axon terminals or into storage vesicles within terminals.
The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS,
TRICYCLIC) and amphetamines are among the
therapeutically important drugs that may act via inhibition
of adrenergic transport. Many of these drugs also block
transport of serotonin. (See all compounds classified as
Adrenergic Uptake Inhibitors.)
from MeSH
Antidepressive Agents, Tricyclic
Substances that contain a fused three-ring moiety and are

used in the treatment of depression. These drugs block the
uptake of norepinephrine and serotonin into axon terminals
and may block some subtypes of serotonin, adrenergic, and
histamine receptors. However the mechanism of their

antidepressant effects is not clear because the therapeutic
effects usually take weeks to develop and may reflect
compensatory changes in the central nervous system. (See
all compounds classified as Antidepressive Agents,
Tricyclic.)
from MeSH
Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such

a manner as to prevent the normal substrate-enzyme
combination and the catalytic reaction. (See all compounds
classified as Enzyme Inhibitors.)
from MeSH
8.3 FDA Pharmacological

Classification
8.3.1 FDA Pharmacology Summary
Desipramine is a Tricyclic Antidepressant.
8.3.2 Active Moiety
DESIPRAMINE
8.3.3 FDA UNII
TG537D343B
8.3.4 Pharmacological Classes
Established Pharmacologic
Tricyclic Antidepressant
Class [EPC]
8.4 ATC Code

N - Nervous system
N06 - Psychoanaleptics
N06A - Antidepressants
N06AA - Non-selective monoamine reuptake inhibitors
N06AA01 - Desipramine
from WHO ATC
8.5 Absorption, Distribution and

Excretion
Absorption
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.
from DrugBank
Route of Elimination
Desipramine is metabolized in the liver, and approximately

70% is excreted in the urine.
from DrugBank
...DESIPRAMINE /WAS GIVEN/ IN DOSE OF 25 MG EVERY 8

HR TO 15 PT. .../IT/ ACCUM IN BODY FOR PERIODS VARYING
FROM 1 TO 16 DAYS, PEAK PLASMA LEVELS RANGING
FROM 10 TO 275 UG/L...
LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug
Metabolism and Disposition. Baltimore: Williams and Wilkins,
1971., p. 336
from HSDB
IN ANIMALS, TRANSPLACENTAL PASSAGE HAS BEEN

DEMONSTRATED RECENTLY OF...DESIPRAMINE...
The Chemical Society. Foreign Compound Metabolism in
Mammals Volume 3. London: The Chemical Society, 1975., p. 637
from HSDB
AFTER IV ADMIN OF SINGLE DOSE OF

DESMETHYLIMIPRAMINE...TO DOGS, RATE OF RENAL
EXCRETION OF UNCHANGED DRUG DECR DRAMATICALLY
IN INCREASING URINARY PH, WITH LITTLE CHANGE IN
CREATININE CLEARANCE. ... URINARY EXCRETION...IN MAN
WAS ALSO SHOWN TO BE PH-DEPENDENT...
The Chemical Society. Foreign Compound Metabolism in
Mammals. Volume 1: A Review of the Literature Published
Between 1960 and 1969. London: The Chemical Society, 1970., p.
108
from HSDB
THERE IS WIDE INTERPATIENT VARIATION IN STEADY-STATE

PLASMA CONCN OF TRICYCLIC ANTIDEPRESSANTS.
...VARIATION SEEMS TO BE GENETICALLY DETERMINED...
/TRICYCLIC ANTIDEPRESSANTS/
1975., p. 178
from HSDB
IMIPRAMINE IS WELL ABSORBED FROM GI TRACT. ...

DEMETHYLATION CONVERTS DRUG TO ACTIVE
METABOLITE, DESIPRAMINE. ... PHARMACOLOGICALLY
ACTIVE METABOLITES OF IMIPRAMINE ARE HIGHLY BUT
VARIABLY BOUND TO PLASMA PROTEIN... /IMIPRAMINE/
1975., p. 178
from HSDB
Desipramine hydrochloride appears to be well absorbed

from the GI tract. Peak plasma concentrations occur within
4-6 hours after oral adminstration. /Desipramine
hydrochloride/
System Pharmacists, Inc. 1998 (Plus Supplements).
from HSDB
8.6 Metabolism/Metabolites
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.
from DrugBank
DEMETHYLIMIPRAMINE YIELDS BISDEMETHYLIMIPRAMINE,

DEMETHYL-2-HYDROXYIMIPRAMINE, DEMETHYL-10-
HYDROXYIMIPRAMINE, & IMINODIBENZYL IN MAN.
/FROM TABLE/
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic

Compounds. New York: Wiley, 1976., p. D-7
from HSDB
DEMETHYLIMIPRAMINE YIELDS IMIPRAMINE IN RABBITS

AND IN RATS. /FROM TABLE/
Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic
Compounds. New York: Wiley, 1976., p. D-7
from HSDB
8.7 Biological Half-Life

7-60+ hours; 70% eliminated renally
from DrugBank
...DESIPRAMINE /WAS GIVEN/ IN DOSE OF 25 MG EVERY 8

HR TO 15 PT. ...BIOLOGICAL HALF-LIFE...FROM A FEW HR TO
MORE THAN 2 DAYS...
LaDu, B.N., H.G. Mandel, and E.L. Way. Fundamentals of Drug
Metabolism and Disposition. Baltimore: Williams and Wilkins,
1971., p. 336
from HSDB
8.8 Mechanism of Action

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.
from DrugBank
MANNER IN WHICH IMIPRAMINE

RELIEVES...DEPRESSION...IS NOT CLEAR. .../EFFECT/
DESCRIBED AS DULLING OF DEPRESSIVE IDEATION RATHER
THAN AS EUPHORIC STIMULATION PRODUCED BY MAO
INHIBITORS...DEFINITIVELY DISCRIMINATIVE EXPT... YET TO
BE PERFORMED. ...DOES HAVE STIMULANT ACTION UNDER
CERTAIN CIRCUMSTANCES. /IMIPRAMINE/
1975., p. 175
from HSDB
ACTION OF TRICYCLIC ANTIDEPRESSANTS ON METABOLISM

OF CATECHOLAMINES & INDOLEAMINES IN BRAIN HAS
CONTRIBUTED SIGNIFICANTLY TO "BIOGENIC AMINE
HYPOTHESIS" OF DEPRESSION. ... ALL TRICYCLIC
ANTIDEPRESSANTS BLOCK RE-UPTAKE OF
NOREPINEPHRINE BY ADRENERGIC NERVE TERMINALS.
/TRICYCLIC ANTIDEPRESSANTS/
1975., p. 176
from HSDB
IMIPRAMINE SLOWS TURNOVER RATE OF 5-HT, EFFECT

NOT SHARED BY DESIPRAMINE, WHILE TURNOVER RATE OF
NOREPINEPHRINE IS INCR BY DEMETHYLATED DRUGS
NORTRIPTYLINE & DESIPRAMINE. EXACT RELATIONSHIP OF
THESE EFFECTS TO ACTIONS OF TRICYCLIC
ANTIDEPRESSANTS IN HUMAN DEPRESSION IS NOT
KNOWN.
1975., p. 176
from HSDB
8.9 Human Metabolite

Information
8.9.1 Metabolite Description
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).
8.9.2 Cellular Locations
Cytoplasm
Extracellular
Membrane
8.9.3 Metabolite Pathways
Desipramine Action Pathway

Desipramine Metabolism Pathway
Imipramine Action Pathway
Imipramine Metabolism Pathway
9 Use and Manufacturing
9.1 Uses
EPA CPDat Chemical and Product Categories
from EPA Chemical and Products Database (CPDat)
Antidepressant
and Co., Inc., 1996., p. 494
from HSDB
9.2 Methods of Manufacturing

FREE BASE & HYDROCHLORIDE: BRITISH PATENT 908,788
(1962 TO GEIGY)
and Co., Inc., 1996., p. 494
from HSDB
9.3 Formulations/Preparations
DESIPRAMINE HYDROCHLORIDE, NF: NORPRAMIN,
CAPSULES: 25, 50 MG; PERTOFRANE, TABLETS: 25, 50 MG
/HYDROGEN CHLORIDE, FROM TABLE/

1975., p. 177
from HSDB
9.4 Manufacturers
Merrell Pharmaceuticals Inc., subdidiary of Hoechst Roussel,
Inc., Kansas City, MO 64137
PDR; Physicians' Desk Reference 52nd ed 1998. Montvale,NJ:
Medical Economics Co. p. 1227 (1998)
from HSDB
9.5 General Manufacturing

Information
PREPN OF HYDROCHLORIDE: BELGIAN PATENT 614,616, CA
58 11338C (1963), (1962 TO GEIGY)
and Co., Inc., 1996., p. 494
from HSDB
10 Identification
10.1 Clinical Laboratory Methods

DETERMINATION OF IMIPRAMINE & DESIPRAMINE IN
BLOOD BY FLUORIMETRY @ EXCITATION WAVELENGTH OF
290 NM & EMISSION WAVELENGTH OF 415 NM; CURRY, A,
POISON DETECTION IN HUMAN ORGANS, 2ND ED,
CHARLES C THOMAS, SPRINGFIELD, 1969, 135.
Sunshine, Irving (ed.) Methodology for Analytical Toxicology.
Cleveland: CRC Press, Inc., 1975., p. 194
from HSDB
COLORIMETRIC DETERMINATION OF IMIPRAMINIC DRUGS

IN BLOOD & URINE.
SANTOS SRC, SZNELWAR RB; STUDY OF IMIPRAMINIC DRUGS IN
BLOOD & URINE FOR THERAPEUTIC CONTROL &
INTOXICATION DIAGNOSIS; REV FARM BIOQUIM UNIV SAO
PAULO 15 (1-2): 173-94 (1977)
from HSDB
DETERMINATION OF TRICYCLIC ANTIDEPRESSANTS &

SOME OF THEIR METABOLITES IN SERUM BY STRAIGHT
PHASE HPLC.
UGES DRA, BOUMA P; DETERMINATION OF TRICYCLIC

ANTIDEPRESSANTS & SOME OF THEIR METABOLITES IN SERUM
BY STRAIGHT PHASE HPLC; PHARM WEEKBL, SCI ED 1 (2): 417-24
(1979)
from HSDB
DETERMINATION OF DRUGS IN PLASMA BY HIGH-

PERFORMANCE TLC & QUANTITATIVE ANALYSIS OF
SEPARATED COMPONENTS BY UV REFLECTANCE
SPECTROMETRY.
FENIMORE DC ET AL; DETERMINATION OF DRUGS IN PLASMA BY
HIGH-PERFORMANCE TLC; CLIN CHEM (WINSTON-SALEM, NC)
24 (8): 1386-92 (1978)
from HSDB
QUANTITATIVE GC DETERMINATION OF DESIPRAMINE IN

SERUM.
ERVIK M ET AL; QUANTITATIVE GC DETERMINATION OF
NANOGRAM LEVELS OF DESIPRAMINE IN SERUM; ACTA PHARM
SUEC 7: 625-34 (1970)
from HSDB
MONITORING OF PSYCHOTROPIC DRUGS IN PLASMA BY

RADIOIMMUNOASSAY.
MIDHA PK ET AL; MONITORING OF THERAPEUTIC CONCN OF
PSYCHOTROPIC DRUGS IN PLASMA BY RADIOIMMUNOASSAYS; J
ANAL TOXICOL 2 (5): 185-92 (1978)
from HSDB
11 Safety and Hazards
11.1 Hazards Identification
11.1.1 GHS Classification
Irritant Health Hazard

Pictogram(s)
Environmental
Hazard
Signal Danger
GHS Hazard Statements Aggregated GHS information

provided by 3 companies from
2 notifications to the ECHA
C&L Inventory. Each
notification may be associated
with multiple companies.
H302 (66.67%): Harmful if
swallowed [Warning Acute
toxicity, oral]
H336 (66.67%): May cause
drowsiness or dizziness
[Warning Specific target organ
toxicity, single exposure;
Narcotic effects]
H370 (66.67%): Causes damage

to organs [Danger Specific
target organ toxicity, single
exposure]
H400 (33.33%): Very toxic to
aquatic life [Warning
Hazardous to the aquatic
environment, acute hazard]
Information may vary between
notifications depending on
impurities, additives, and other
factors. The percentage value
in parenthesis indicates the
notified classification ratio
from companies that provide
hazard codes. Only hazard
codes with percentage values
above 10% are shown.
P260, P261, P264, P270, P271,

P273, P301+P312, P304+P340,
P307+P311, P312, P321, P330,
P391, P403+P233, P405, and
Precautionary Statement P501
Codes
(The corresponding statement
to each P-code can be found
at the GHS Classification
page.)
from European Chemicals Agency (ECHA)
11.2 Accidental Release

Measures
11.2.1 Disposal Methods
SRP: At the time of review, criteria for land treatment or

burial (sanitary landfill) disposal practices are subject to
significant revision. Prior to implementing land disposal of
waste residue (including waste sludge), consult with
environmental regulatory agencies for guidance on
acceptable disposal practices.
from HSDB
11.3 Handling and Storage
11.3.1 Storage Conditions
Desipramine hydrochloride capsules and tablets should be

stored in tight containers at a temperature less than 40 deg
C, preferably at 15-30 deg C. /Desipramine hydrochloride/
from HSDB
11.4 Regulatory Information

1/10/2019
g y Desipramine | C18H22N2 - PubChem
11.4.1 FDA Requirements
Manufacturers, packers, and distributors of drug and drug

products for human use are responsible for complying with
the labeling, certification, and usage requirements as
prescribed by the Federal Food, Drug, and Cosmetic Act, as
amended (secs 201-902, 52 Stat. 1040 et seq., as amended;
21 U.S.C. 321-392).
21 CFR 200-299, 300-499, 820, and 860 (4/1/97)
from HSDB
12 Toxicity
12.1 Toxicological Information
12.1.1 Hepatotoxicity
Liver test abnormalities have been reported to occur in up

to 16% of patients being treated with tricyclic
antidepressants, but elevations are uncommonly above 3
times the upper limit of normal. The aminotransferase
abnormalities are usually mild, asymptomatic and transient,
reversing even with continuation of medication and without
dose adjustment. Rare instances of clinically apparent acute
liver injury have been reported due to desipramine, but far
fewer than have been reported with amitriptyline or
imipramine. The onset of jaundice is usually within 1 to 8
weeks of starting the antidepressant, and the pattern of
serum enzyme elevations can be either hepatocellular or
cholestatic. Features suggestive of hypersensitivity (fever,
rash, eosinophilia) are common, but rarely severe.
Autoantibody formation is unusual. These features are
typical of tricyclic antidepressant hepatotoxicity.
from LiverTox
12.1.2 Acute Effects
from ChemIDplus
12.1.3 Interactions
ADMIN OF TRICYCLIC ANTIDEPRESSANTS...WITH OR

SHORTLY AFTER...MAO INHIBITORS HAS RESULTED IN
SEVERE REACTIONS. ... OTHER INTERACTIONS INCL
POTENTIATION OF CENTRAL DEPRESSANT DRUGS,
BLOCKADE OF ANTIHYPERTENSIVE EFFECTS OF
GUANETHIDINE, & AUGMENTATION OF PRESSOR EFFECTS
OF SYMPATHOMIMETIC AMINES. /TRICYCLIC
ANTIDEPRESSANTS/
1975., p. 179
from HSDB
Concurrent use /of thyroid hormones/ with tricyclic

antidepressants may increase the therapeutic and toxic
effects of both medications, possibly due to increased
receptor sensitivity to catecholamines; toxic effects include
cardiac arrhythmias and CNS stimulation. /Tricyclic
antidepressants/
from HSDB
Concurrent use /of sympathomimetics/ with tricyclic

antidepressants may potentiate cardiovascular effects
possibly resulting in arrhythmias, tachycardia, or severe
hypertension or hyperpyrexia; phentolamine can control the
adverse reaction. Significant systemic absorption of
ophthalmic epinephrine may also potentiate cardiovascular
effects; also, local anesthetics with vasoconstrictors should
be avoided or a minimal amount of the vasoconstrictor
should be used with the local anesthetic. Concurrent use
with tricyclic antidepressants may decrease the pressor
effect of ephedrine and mephentermine. /Tricyclic
antidepressants/
from HSDB
If significant systemic absorption occurs, concurrent use /of

ophthalmic naphazoline, nasal or ophthalmic
oxymetazoline, nasal or ophthalmic phenylephrine, or nasal
xylometazoline/ with tricyclic antidepressants may
potentiate pressor effects of these medications. /Tricyclic
antidepressants/

from HSDB
Concurrent use /of pimozide/ with tricyclic antidepressants

may potentiate cardiac arrhythmias, which are seen on ECG
as prolongation of QT interval. /Tricyclic antidepressants/
from HSDB
Concurrent use /of monamine oxidase (MAO) inhibitors,

including furazolidone, procarbazine, and selegiline/ with
tricyclic antidepressants has resulted in an increased
incidence of hyperpyretic episodes, severe convulsions,
hypertensive crises, and death; however, recent studies have
shown that concurrent use of some tricyclic antidepressants
with MAO inhibitors can be used for refractory depression
with no adverse effects if both medications are initiated
simultaneously at lower than usual doses, with dose being
raised gradually thereafter, or if the MAO inhibitor is
gradually added to the tricyclic, also at low doses; a tricyclic
should not be added to an existing MAO inhibitor regimen;
the tricyclic antidepressants most commonly used in this
combined therapy are amitriptyline, doxepin, and
trimipramine; imipramine, desipramine, nortriptyline,
protriptyline, and clomipramine are not recommended for
use in such a regimen because of potential excessive
stimulation. /Tricyclic antidepressants/
from HSDB
Administration of intrathecal metrizamide may lower the

seizure threshold and increase the risk of seizures in patients
taking tricyclic antidepressants; it is recommended that
tricyclic antidepressants be discontinued for at least 48
hours before and at least 24 hours after myelography.
from HSDB
Concurrent use /of fluoxetine/ with tricyclic antidepressants

has produced increased plasma concentrations of the
tricyclic antidepressant, possibly due to inhibition of tricyclic
antidepressant metabolism; some clinicians recommend
dosage reductions for tricyclic antidepressants of about 50%
if used concurrently with fluoxetine. /Tricyclic
antidepressants/
from HSDB
Concurrent use /of disulfiram or ethchlorvynol/ with

tricyclics, especially amitriptyline, may result in transient
delirium. Also, CNS depressant effects may be increased
when ethchlorvynol is used concurrently with tricyclic
antidepressants. /Tricyclic antidepressants/
from HSDB
Tricyclic antidepressants do not relieve, and may exacerbate,

corticosteroid-induced mental depression. /Tricyclic
antidepressants/
from HSDB
Concurrent use /of cocaine/ with tricyclic antidepressants

may increase the risk of cardiac arrhythmias; if use of
cocaine is necessary in patients receiving tricyclics, it is
recommended that the cocaine be administered with
caution, in reduced dosage, and in conjunction with
electrocardiographic monitoring. /Tricyclic antidepressants/
from HSDB
Concurrent use of clonidine with tricyclic antidepressants

may result in potentiation of CNS depressant effects.
from HSDB
Concurrent use /of clonidine or guanadrel or guanethidine

with tricyclic antidepressants/ may decrease the hypotensive
effects of these medications. /Tricyclic antidepressants/
from HSDB
Cimetidine may inhibit tricyclic metabolism and increase

plasma concentrations, leading to toxicity; lowering the dose
of the tricyclic antidepressant by 20 to 30% may be
necessary when cimetidine is given concurrently; patient
should be closely observed for sedation, anticholinergic
effects, and orthostatic hypotension. /Tricyclic

antidepressants/
from HSDB
Plasma concentrations and therapeutic effects of tricyclic

antidepressants may be decreased during concurrent use
with barbiturates, especially phenobarbital, or
carbamazepine because of increased metabolism resulting
from induction of hepatic microsomal enzymes. /Tricyclic
antidepressants/
from HSDB
Concurrent use /of antithyroid agents/ with tricyclic

antidepressants may increase the risk of agranulocytosis.
from HSDB
Tricyclic antidepressants may enhance CNS depression,

lower the seizure threshold when taken in high doses, and
decrease the effects of the anticonvulsant medication;
dosage adjust of the anticonvulsant may be necessary to
control seizures; monitoring of serum concentrations of
both medications may be necessary to detect possible
interaction; ... . /Tricyclic antidepressants/
from HSDB
Concurrent use may potentiate the CNS depressant effects

of either antihistamines or tricyclic antidepressants. /Tricyclic
antidepressants/
from HSDB
Concurrent use /alcohol or other CNS depression-producing

medications/ with tricyclic antidepressants may result in
serious potentiation of CNS depression, respiratory
depression, and hypotensive effects; caution is
recommended, and dosage of one or both agents should be
reduced. In addition, tricyclics may increase the effects of
alcohol, especially during the first few days of tricyclic
antidepressant treatment; in patients who use alcohol
excessively, tricyclics may increase the danger inherent in

any suicide attempt. /Tricyclic antidepressants/
from HSDB
Concurrent use /of amantadine or anticholinergics or other

medications with anticholinergic activity or antidyskinetics or
antihistamines/ with tricyclic antidepressants may intensify
anticholinergic effects, especially mental confusion,
hallucinations, and nightmares, because of secondary
anticholinergic activities of tricyclic antidepressants. /Tricyclic
antidepressants/
from HSDB
12.1.4 Toxicity Summary
Male mice: LD50 = 290 mg/kg, female rats: LD50 = 320

mg/kg. Antagonism of the histamine H1 and α1 receptors
can lead to sedation and hypotension. Antimuscarinic
activity confers anticholinergic side effects such as blurred
vision, dry mouth, constipation and urine retention may
occur. Cardiotoxicity may occur with high doses of
desipramine. Cardiovascular side effects in postural
hypotension, tachycardia, hypertension, ECG changes and
congestive heart failure. Psychotoxic effects include
impaired memory and delirium. Induction of hypomanic or
manic episodes may occur in patients with a history of
bipolar disorder. Withdrawal symptoms include GI
disturbances (e.g. nausea, vomiting, abdominal pain,
diarrhea), anxiety, insomnia, nervousness, headache and
malaise.
from DrugBank
12.1.5 Human Toxicity Excerpts
MILD PARKINSONIAN SYNDROME...MAY BE SEEN IN SOME

PT, PARTICULARLY OLDER PERSONS TAKING LARGE DOSES.
...HIGH DOSES...MAY PRODUCE GRAND MAL SEIZURES EVEN
IN PT WITHOUT HISTORY OF CONVULSIONS. .../IT/ MAY
PRODUCE ALLERGIC TYPE OF OBSTRUCTIVE
JAUNDICE.../WHICH/ CLEARS WHEN DRUG IS
DISCONTINUED. /IMIPRAMINE/
1975., p. 178
from HSDB
Effects of overdosage include agitation, hallucinations,

hyperreflexia, hyperpyrexia, and convulsions. Both
hypotension and hypertension also occur.
p. 443
from HSDB
12.1.6 Non-Human Toxicity Excerpts
IN CATS UNDER ANESTHESIA IV INJECTION OF 4 TO 25 MG

OF DESIPRAMINE HAS BEEN FOUND TO REDUCE
SPONTANEOUS ACTIVITY OF RETINAL NEURONES. DOSES
OF 5 TO 20 MG/KG INCR C-WAVE IN ELECTRORETINOGRAM,
& DOSES OF 20 TO 35 MG/KG REDUCED B-WAVE...
Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles
C. Thomas Publisher, 1986., p. 309
from HSDB
DESPITE ITS CLINICAL ANTIDEPRESSANT EFFECTS,

IMIPRAMINE PRODUCES DEPRESSION OF SPONTANEOUS
MOTOR ACTIVITY IN LAB ANIMALS. ...IT ALSO...DECR BODY
TEMP, & CAUSES ATAXIA. IT IMPAIRS BOTH ACQUISITION &
PERFORMANCE OF CONDITIONED AVOIDANCE RESPONSES.
/IMIPRAMINE/
1975., p. 176
from HSDB
IMIPRAMINE LOWERS BLOOD PRESSURE IN ANESTHETIZED

DOGS & OBTUNDS VARIOUS CARDIOVASCULAR REFLEXES,
INCL CAROTID OCCLUSION REFLEX, BEZOLD-JARISCH
REFLEX, & POSTURAL RESPONSES. /IMIPRAMINE/
1975., p. 177
from HSDB
12.1.7 Non-Human Toxicity Values
LD50 Rat oral 375 mg/kg

1334
from HSDB
LD50 Rat ip 48 mg/kg

1334
from HSDB
LD50 Rat sc 183 mg/kg

1334
from HSDB
LD50 Rat iv 29 mg/kg

1334
from HSDB
LD50 Mouse oral 448 mg/kg

1334
from HSDB
LD50 Mouse ip 85 mg/kg

1334
from HSDB
LD50 Mouse sc 214 mg/kg

1334
from HSDB
LD50 Mouse iv 22 mg/kg

1334
from HSDB
12.1.8 Protein Binding
73-92% bound to plasma proteins
from DrugBank
13 Literature
13.1 Depositor Provided PubMed
Citations
from PubChem
13.2 NLM Curated PubMed

Citations
from PubChem
13.3 Synthesis References

Biel, J.H.and Judd, C.I.; US. Patent 3,454,554; July 8,1969;
assigned to Colgate Palmolive Co.
from DrugBank
13.4 Springer Nature References
from Springer Nature
13.5 Thieme References

1 item View More Details Download
Title Publication Name Publication DOI

Date
Pharmaceutical
Desipramine 2003
Substances
from Thieme Chemistry
13.6 Chemical Co-Occurrences in

Literature
Showing 3 of 25
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Chemical Evidence from All Time
2,175 articles
mention
norepinephrine Download CSV Vi
alongside
desipramine.
Enduring attenuation of norepinephrine sy

and augmentation of the pharmacological
effects of desipramine by repeated immob
Norepinephrine
PMID 28232061; Neuropharmacology 2017 May;1
CID 439260 Name matches: norepinephrine desipramine
Chronic desipramine treatment alters tyro
not norepinephrine transporter immunore
norepinephrine axons in the rat prefrontal
PMID 21208501; The international journal of neur
2011 Oct;14(9):1219-32
Name matches: norepinephrine desipramine
Desipramine selectively potentiates norep

ERK1/2 activation through the α2A adrene
PMID 22405824; Biochemical and biophysical rese
2012 Mar;420(1):161-5
Name matches: norepinephrine desipramine
Chemical Evidence from All Time
1,415 articles
mention
imipramine Download CSV Vi
alongside
desipramine.
Super paramagnetic core-shells anchored

with C(8)/NH(2) nano-particles for ultraso
magnetic solid phase extraction of imipram
Imipramine desipramine from plasma.
CID 3696 PMID 29413577; Journal of chromatography. B, A
the biomedical and life sciences 2018 Mar;?(?):52-
Name matches: imipramine desipramine
A Simple, Rapid and Reliable Method to D
Imipramine and Desipramine in Mouse Se
High-Performance Liquid Chromatography
of-Flight Mass Spectrometry.
PMID 26688563; Journal of chromatographic scien
8
The Use of In Vitro Data and Physiological

Pharmacokinetic Modeling to Predict Drug
Exposure: Desipramine Exposure in Cytoch
Extensive and Poor Metabolizers Following
Imipramine.
PMID 27440861; Drug metabolism and dispositio
chemicals 2016 Oct;44(10):1569-78
1,251 articles
mention
serotonin Download CSV Vi
alongside
desipramine.
'Compulsive' lever-pressing in rats is atten

serotonin re-uptake inhibitors paroxetine
not by the tricyclic antidepressant desipra
Serotonin anxiolytic diazepam.
CID 5202 PMID 15187582; Behavioural pharmacology 2004
Name matches: serotonin desipramine
Quantitative in vitro phosphor imaging us
radioligands: the effects of chronic desipra
serotonin 5-HT2 receptors.
PMID 15585298; Journal of neuroscience method
Name matches: serotonin desipramine
Enhancement of the serotonin-mediated a

by repeated desmethylimipramine treatme
hippocampus of freely moving rats.
PMID 10496330; Japanese journal of pharmacolog
Name matches: serotonin desmethylimipramine
from PubChem
13.7 Chemical-Disease Co-

Occurrences in Literature
from PubChem
13.8 Chemical-Gene Co-

Occurrences in Literature
from PubChem
14 Patents
14.1 Depositor-Supplied Patent
Identifiers
from PubChem
Link to all deposited patent identifiers
from PubChem
15 Biomolecular
Interactions and Pathways
15.1 Protein Bound 3-D
Structures
from PDB
View 1 protein in NCBI Structure
from PubChem
15.2 Pathways
from PubChem
15.3 DrugBank Interactions
Sodium-dependent
Target
noradrenaline transporter
Action inhibitor
PubChem Protein Target P23975
PubChem Gene Target SLC6A2
Norepinephrine:sodium
General Function
symporter activity
Amine transporter. Terminates

the action of noradrenaline by
Specific Function its high affinity sodium-
dependent reuptake into
presynaptic terminals.
Interaction References 1. Zavosh A, Schaefer J,

Ferrel A, Figlewicz DP:
Desipramine treatment
decreases 3H-nisoxetine
binding and
norepinephrine
transporter mRNA in SK-
N-SHSY5Y cells. Brain Res
Bull. 1999 Jul 1;49(4):291-
5. [PMID:10424850]
2. Weinshenker D, White SS,
Javors MA, Palmiter RD,
Szot P: Regulation of
norepinephrine
transporter abundance
by catecholamines and
desipramine in vivo. Brain
Res. 2002 Aug
16;946(2):239-46.
[PMID:12137927]
3. Bryan-Lluka LJ, Bonisch
H, Lewis RJ: chi-
Conopeptide MrIA
partially overlaps
desipramine and cocaine
binding sites on the
human norepinephrine
transporter. J Biol Chem.
2003 Oct
10;278(41):40324-9. Epub
2003 Jul 1.
[PMID:12837768]
4. Zhu MY, Kyle PB, Hume
AS, Ordway GA: The
persistent membrane
retention of desipramine
causes lasting inhibition
of norepinephrine
transporter function.
Neurochem Res. 2004
Feb;29(2):419-27.
[PMID:15002740]
5. Ordway GA, Jia W, Li J,
Zhu MY, Mandela P, Pan
J: Norepinephrine
transporter function and
desipramine: residual
drug effects versus short-
term regulation. J
Neurosci Methods. 2005
Apr 30;143(2):217-25.
Epub 2004 Dec 30.
[PMID:15814154]
6. Chen X, Ji ZL, Chen YZ:
TTD: Therapeutic Target
Database. Nucleic Acids
Res. 2002 Jan
1;30(1):412-5.
[PMID:11752352]
7. 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.
[PMID:9537821]
from DrugBank
16 Biological Test Results
16.1 BioAssay Results
from PubChem
17 Classification
17.1 Ontologies
17.1.1 MeSH Tree
Showing 1 of View in Classification Browser
1 Download
Desipramine
A tricyclic dibenzazepine compound that potentiates

neurotransmission. Desipramine selectively blocks reuptake
of norepinephrine from the neural synapse, and also
appears to impair serotonin transport. This compound also
possesses minor anticholinergic activity, through its affinity
to muscarinic receptors.
LINKED RECORDS
Compounds: 2 Substances: 106
PubMed Abstracts: 5,534
CLASSIFICATION (PARENT NODES)
MeSH Tree Chemicals And Drugs Category
Heterocyclic Compounds
Heterocyclic Compounds, Fused-Ring
Heterocyclic Compounds, 3-Ring
Dibenzazepines
from MeSH
17.1.2 ChEBI Ontology
1 Download
desipramine
A dibenzoazepine consisting of 10,11-dihydro-5H-
dibenzo[b,f]azepine substituted on nitrogen with a 3-
(methylamino)propyl group.
LINKED RECORDS
ChEBI Ontology Chemical Entity
Molecular Entity
Main Group Molecular Entity
P-Block Molecular Entity
Carbon Group Molecular Entity
Organic Molecular Entity
Organic Amino Compound
Secondary Amino Compound
from ChEBI
17.1.3 KEGG: ATC
from KEGG
17.1.4 KEGG: Target-based

Classification of Drugs
from KEGG
17.1.5 KEGG: Drug Classes
1 Download
Desipramine

Drug Classes Neuropsychiatric Agent
DG01730 Non-Selective Monoamine Reuptake Inhibitor
DG00927 Desipramine
from KEGG
17.1.6 WHO ATC Classification System
1 Download
N06AA01 - Desipramine
LINKED RECORDS
ATC Code N - Nervous System
N06 - Psychoanaleptics
N06A - Antidepressants
N06AA - Non-Selective Monoamine Reuptake Inhibitors
from WHO ATC
17.1.7 FDA Pharm Classes
17.1.8 WIPO IPC

Showing 5 of 4,098 View in Classification Browser
View More Download
A61P11/06 - Antiasthmatics
LINKED RECORDS
Compounds: 576,708 Substances: 1,184,641
Patents: 5,544
International Patent Classification
HUMAN NECESSITIES
HEALTH; LIFE-SAVING; AMUSEMENT Category
A61 - MEDICAL OR VETERINARY SCIENCE; HYGIENE
A61P - SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
A61P11/00 - Drugs For Disorders Of The Respiratory System
A61P11/08 - Bronchodilators
LINKED RECORDS
Compounds: 133,865 Substances: 242,940
Patents: 1,950
HUMAN NECESSITIES
A61P11/10 - Expectorants
LINKED RECORDS
Compounds: 13,578 Substances: 21,687 Patents: 243
HUMAN NECESSITIES
HUMAN NECESSITIES
A61P11/14 - Antitussive agents
LINKED RECORDS
HUMAN NECESSITIES
A61P11/16 - Central respiratory analeptics
LINKED RECORDS
HUMAN NECESSITIES
from WIPO
17.1.9 ChemIDplus
from ChemIDplus
17.1.10 Guide to PHARMACOLOGY

Target Classification
from IUPHAR/BPS Guide to PHARMACOLOGY
17.1.11 ChEMBL Target Tree
from ChEMBL
17.1.12 UN GHS Classification
from UN Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
17.1.13 EPA CPDat Classification
from EPA Chemical and Products Database (CPDat)
18 Information Sources
FILTER BY SOURCE ALL SOURCES
1. ChEBI
Desipramine
http://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:47781
ChEBI Ontology
http://www.ebi.ac.uk/chebi/userManualForward.do#ChEBI%20Ontolo
gy
2. DrugBank
Desipramine
http://www.drugbank.ca/drugs/DB01151
http://www.drugbank.ca/drugs/DB01151#targets
http://www.drugbank.ca/drugs/DB01151#enzymes
http://www.drugbank.ca/drugs/DB01151#transporters
http://www.drugbank.ca/drugs/DB01151#carriers
3. FDA Pharm Classes

DESIPRAMINE
https://www.accessdata.fda.gov/spl/data/9609850a-1cf0-4044-8c2b-
47dc8c3e86e1/9609850a-1cf0-4044-8c2b-47dc8c3e86e1.xml
FDA Pharmacological Classification
https://www.fda.gov/ForIndustry/DataStandards/StructuredProductLa
beling/ucm162549.htm
4. Human Metabolome Database (HMDB)

Desipramine
http://www.hmdb.ca/metabolites/HMDB0015282
5. LiverTox
Desipramine
https://livertox.nlm.nih.gov/Desipramine.htm
6. NCIt
Desipramine
https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?
dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C61700
7. ChemIDplus
Desipramine [INN:BAN]
https://chem.nlm.nih.gov/chemidplus/sid/0000050475
ChemIDplus Chemical Information Classification
https://chem.sis.nlm.nih.gov/chemidplus/
8. EPA DSSTox
Desipramine
https://comptox.epa.gov/dashboard/DTXSID6022896
9. European Chemicals Agency (ECHA)

LICENSE
Use of the information, documents and data from the ECHA
website is subject to the terms and conditions of this Legal
Notice, and subject to other binding limitations provided for
under applicable law, the information, documents and data
made available on the ECHA website may be reproduced,
distributed and/or used, totally or in part, for non-commercial
purposes provided that ECHA is acknowledged as the source:
"Source: European Chemicals Agency, http://echa.europa.eu/".
Such acknowledgement must be included in each copy of the
material. ECHA permits and encourages organisations and
individuals to create links to the ECHA website under the
following cumulative conditions: Links can only be made to
webpages that provide a link to the Legal Notice page.
https://echa.europa.eu/web/guest/legal-notice
Desipramine
https://echa.europa.eu/substance-
information/-/substanceinfo/100.000.037
Desipramine
https://echa.europa.eu/information-on-chemicals/cl-inventory-
database/-/discli/details/11421
10. HSDB
DESIPRAMINE
https://toxnet.nlm.nih.gov/cgi-bin/sis/search/r?
dbs+hsdb:@term+@rn+@rel+50-47-5
11. ClinicalTrials.gov
LICENSE
The ClinicalTrials.gov data carry an international copyright
outside the United States and its Territories or Possessions.
Some ClinicalTrials.gov data may be subject to the copyright of
third parties; you should consult these entities for any
additional terms of use.
https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
Desipramine
https://clinicaltrials.gov/
12. EPA Chemical and Products Database

(CPDat)
LICENSE
https://www.epa.gov/privacy/privacy-act-laws-policies-and-
resources
desipramine
https://comptox.epa.gov/dashboard/DTXSID6022896#exposure
EPA CPDat Classification
https://www.epa.gov/chemical-research/chemical-and-products-
database-cpdat
13. EU Clinical Trials Register

https://www.clinicaltrialsregister.eu/
14. FDA/SPL Indexing Data

TG537D343B
https://www.fda.gov/ForIndustry/DataStandards/SubstanceRegistrati
onSystem-UniqueIngredientIdentifierUNII/
15. MassBank of North America (MoNA)

DESIPRAMINE
http://mona.fiehnlab.ucdavis.edu/spectra/browse?
inchikey=HCYAFALTSJYZDH-UHFFFAOYSA-N
16. SpectraBase
https://spectrabase.com/spectrum/9nzKfppeScn
https://spectrabase.com/spectrum/E8yknsr9AQA
https://spectrabase.com/spectrum/6MjZabfxWfY
https://spectrabase.com/spectrum/IZ2HXLGCQti
https://spectrabase.com/spectrum/HLblkac5aoP
https://spectrabase.com/spectrum/EtIGs54ouqU
https://spectrabase.com/spectrum/GDe8TyQ1Meb
17. NIST
Desipramine
http://www.nist.gov/srd/nist1a.cfm
18. PDB
http://www.rcsb.org/ligand/DSM
19. Protein Data Bank in Europe (PDBe)

http://www.ebi.ac.uk/pdbe-
srv/pdbechem/chemicalCompound/show/DSM
20. Springer Nature
21. Thieme Chemistry

LICENSE
The Thieme Chemistry contribution within PubChem is provided
under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
https://creativecommons.org/licenses/by-nc-nd/4.0/
22. WHO ATC

https://www.whocc.no/atc/
ATC Code
https://www.whocc.no/atc_ddd_index/
23. Wikipedia
desipramine
https://en.wikipedia.org/wiki/Desipramine
24. MeSH
Desipramine
https://www.ncbi.nlm.nih.gov/mesh/68003891
MeSH Tree
http://www.nlm.nih.gov/mesh/meshhome.html
Adrenergic Uptake Inhibitors
Antidepressive Agents, Tricyclic

Enzyme Inhibitors
25. PubChem
https://pubchem.ncbi.nlm.nih.gov
26. KEGG
Anatomical Therapeutic Chemical (ATC) classification
http://www.genome.jp/kegg-bin/get_htext?br08303.keg
Target-based classification of drugs

Drug Classes
27. WIPO
http://www.wipo.int/classifications/ipc/
28. UN Globally Harmonized System of

Classification and Labelling of
Chemicals (GHS)
GHS Classification Tree
http://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
29. ChEMBL
Target Tree
https://www.ebi.ac.uk/chembl/target/browser
30. IUPHAR/BPS Guide to PHARMACOLOGY

Target Classification
http://www.guidetopharmacology.org/
31. NCBI
https://www.ncbi.nlm.nih.gov/projects/linkout

Desipramine PubChem

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1/10/2019 Desipramine | C18H22N2 - PubChem

Title and Summary

3 Chemical and Physical Properties

Structure: 8 Pharmacology and Biochemistry

9 Use and Manufacturing

11 Safety and Hazards

15 Biomolecular Interactions and Pathways

16 Biological Test Results

Chemical Safety: Health Hazard

Molecular Formula: C18H22N2

Molecular Weight: 266.4 g/mol

Desipramine is an active metabolite of imipramine, a

Desipramine is a Tricyclic Antidepressant.

Desipramine is an oral tricyclic antidepressant that

Get Image Download

Ball and Stick

1.3 Crystal Structures

PDBe Ligand Code DSM

PDBe Structure Code 2QJU

Ball and Stick

from Protein Data Bank in Europe (PDBe)

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2.1.3 InChI Key

2.1.4 Canonical SMILES

2.2 Molecular Formula

2.3 Other Identifiers

2.3.2 European Community (EC)

from European Chemicals Agency (ECHA)

from FDA/SPL Indexing Data

2.4.1 MeSH Entry Terms

Apo Desipramine Pertofrane

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical

3.1 Computed Properties

Property Name Property Value

Molecular Weight 266.4 g/mol

Hydrogen Bond Donor Count 1

Hydrogen Bond Acceptor

Rotatable Bond Count 4

Exact Mass 266.178299 g/mol

Monoisotopic Mass 266.178299 g/mol

Topological Polar Surface Area 15.3 A^2

Heavy Atom Count 20

Isotope Atom Count 0

Defined Atom Stereocenter

Undefined Atom Stereocenter

Defined Bond Stereocenter

Undefined Bond Stereocenter

Covalently-Bonded Unit Count 1

Compound Is Canonicalized Yes

3.2 Experimental Properties

3.2.1 Physical Description

from Human Metabolome Database (HMDB)

3.2.2 Boiling Point

172-174 DEG C @ 0.02 MM HG

3.2.3 Melting Point

from Human Metabolome Database (HMDB)

58.6 mg/L (at 24 °C)

from EPA DSSTox

In water, 58.6 mg/l @ 24 deg C.

from Human Metabolome Database (HMDB)

3.2.5 Octanol/Water Partition