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50-47-5 molecular structure
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(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)(methyl)amine

ChemBase ID: 1022
Molecular Formular: C18H22N2
Molecular Mass: 266.38068
Monoisotopic Mass: 266.17829871
SMILES and InChIs

SMILES:
N1(c2c(CCc3c1cccc3)cccc2)CCCNC
Canonical SMILES:
CNCCCN1c2ccccc2CCc2c1cccc2
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
InChIKey:
HCYAFALTSJYZDH-UHFFFAOYSA-N

Cite this record

CBID:1022 http://www.chembase.cn/molecule-1022.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)(methyl)amine
(3-{2-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-2-yl}propyl)(methyl)amine
(3-{2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)(methyl)amine
IUPAC Traditional name
desipramine
Brand Name
Pentofran
Pertofran
Pertrofane
Sertofran
Norpramin
Synonyms
DMI
Demethylimipramine
Desimipramine
Desimpramine
Desipramin
Desipramine Hcl
Desmethylimipramine
Dezipramine
Dimethylimipramine
Methylaminopropyliminodibenzyl
Monodemethylimipramine
Norimipramine
Norpramine
Desipramine
3-(10,11-DIHYDRO-5H-DIBENZO[B,F]AZEPIN-5-YL)-N-METHYLPROPAN-1-AMINE
CAS Number
50-47-5
PubChem SID
160964485
46504624
PubChem CID
2995
CHEBI ID
47781
ATC CODE
N06AA01
CHEMBL
72
Chemspider ID
2888
DrugBank ID
DB01151
IUPHAR ligand ID
2399
KEGG ID
D07791
Unique Ingredient Identifier
TG537D343B
Wikipedia Title
Desipramine
Medline Plus
a682387

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.67586446  LogD (pH = 7.4) 1.3685079 
Log P 3.895521  Molar Refractivity 85.3109 cm3
Polarizability 32.823364 Å3 Polar Surface Area 15.27 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.02  LOG S -3.83 
Solubility (Water) 3.96e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
0.0586 mg/mL at 24 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] expand Show data source
Hydrophobicity(logP)
3.7 expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
73-92% expand Show data source
Excretion
Renal expand Show data source
Half Life
21-23 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB01151 external link
Item Information
Drug Groups approved
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).
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.
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.
Toxicity 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.
Affected Organisms
Humans and other mammals
Biotransformation 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.
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.
Half Life 7-60+ hours; 70% eliminated renally
Protein Binding 73-92% bound to plasma proteins
Elimination Desipramine is metabolized in the liver, and approximately 70% is excreted in the urine.
External Links
Wikipedia
RxList
Drugs.com
DrugBank - DB07682 external link
Drug information: experimental

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