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50-49-7 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)dimethylamine

ChemBase ID: 341
Molecular Formular: C19H24N2
Molecular Mass: 280.40726
Monoisotopic Mass: 280.19394878
SMILES and InChIs

SMILES:
N1(CCCN(C)C)c2c(CCc3c1cccc3)cccc2
Canonical SMILES:
CN(CCCN1c2ccccc2CCc2c1cccc2)C
InChI:
InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
InChIKey:
BCGWQEUPMDMJNV-UHFFFAOYSA-N

Cite this record

CBID:341 http://www.chembase.cn/molecule-341.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)dimethylamine
(3-{2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}propyl)dimethylamine
IUPAC Traditional name
imipramine
Brand Name
Antideprin
Berkomine
Censtim
Censtin
DPID
Declomipramine
Dimipressin
Dyna-Zina
Dynaprin
Estraldine
Eupramin
IM
Imavate
Imidobenzyle
Imipramina
Imipramine Hcl
Imiprin
Imizin
Imizine
Imizinum
Impramine
Intalpram
Iramil
Irmin
Janimine
Melipramin
Melipramine
Nelipramin
Norfranil
Pramine
Prazepine
Presamine
Promiben
Psychoforin
Sk-Pramine
Surplix
Timolet
Tipramine
Tofranil, Base
Tofranil-Pm
Tofraniln A
Trimipramine Maleate
Tofranil
Synonyms
Imipramine
CAS Number
50-49-7
PubChem SID
46507351
160963804
PubChem CID
3696
CHEBI ID
47499
ATC CODE
N06AA02
CHEMBL
11
Chemspider ID
3568
DrugBank ID
DB00458
IUPHAR ligand ID
357
KEGG ID
D08070
Unique Ingredient Identifier
OGG85SX4E4
Wikipedia Title
Imipramine
Medline Plus
a682389

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) 0.9912437  LogD (pH = 7.4) 2.4832094 
Log P 4.2785687  Molar Refractivity 90.6056 cm3
Polarizability 34.670334 Å3 Polar Surface Area 6.48 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.53  LOG S -3.63 
Solubility (Water) 6.64e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
18.2 mg/L expand Show data source
Hydrophobicity(logP)
3.9 expand Show data source
Admin Routes
Oral expand Show data source
Excretion
Renal expand Show data source
Half Life
11-25 hours expand Show data source
Metabolism
Hepatic
Main active metabolite desipramine
expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category

Known risk of damage to fetus.
expand Show data source
D (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00458 external link
Item Information
Drug Groups approved
Description Imipramine, the prototypical tricyclic antidepressant (TCA), is a dibenzazepine-derivative 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, imipramine does not affect mood or arousal, but may cause sedation. In depressed individuals, imipramine exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as imipramine and amitriptyline, are more potent inhibitors of serotonin reuptake than secondary amine TCAs, such as nortriptyline and desipramine. 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. Imipramine has less sedative and anticholinergic effects than the tertiary amine TCAs, amitriptyline and clomipramine. See toxicity section below for a complete listing of side effects. Imipramine may be used to treat depression and nocturnal enuresis in children. Unlabeled indications include chronic and neuropathic pain (including diabetic neuropathy), panic disorder, attention-deficit/hyperactivity disorder (ADHD), and post-traumatic stress disorder (PTSD).
Indication For the relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older. May also be used to manage panic disorders, with or without agoraphobia, as a second line agent in ADHD, management of eating disorders, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, and for symptomatic treatment of postherpetic neuralgia.
Pharmacology Imipramine is a tricyclic antidepressant with general pharmacological properties similar to those of structurally related tricyclic antidepressant drugs such as amitriptyline and doxepin. A tertiary amine, imipramine inhibits the reuptake of serotonin more so than most secondary amine tricyclics, meaning that it blocks the reuptake of neurotransmitters serotonin and noradrenaline almost equally. With chronic use, imipramine also down-regulates cerebral cortical β-adrenergic receptors and sensitizes post-synaptic sertonergic receptors, which also contributes to increased serotonergic transmission. It takes approximately 2 - 4 weeks for antidepressants effects to occur. The onset of action may be longer, up to 8 weeks, in some individuals. It is also effective in migraine prophylaxis, but not in abortion of acute migraine attack.
Toxicity Oral, rat LD50: 355 to 682 mg/kg. Toxic signs proceed progressively from depression, irregular respiration and ataxia to convulsions and death. Antagonism of the histamine H1 and α1 receptors can lead to sedation and hypotension. Antimuscarinic and anticholinergic side effects such as blurred vision, dry mouth, constipation and urine retention may occur. Cardiotoxicity may occur with high doses of imipramine. 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 Exclusively metabolized by the liver. Imipramine is converted in the liver by various CYP isoenzymes (e.g. CYP1A2, CYP2D6, CYP3A4, CYP2C9) to active metabolites desipramine and 2-hydroxydesipramine.
Absorption Rapidly and well absorbed after oral administration. Bioavailability is approximately 43%. Peak plasma concentrations usually attained 1 - 2 hours following oral administration. Absorption is unaffected by food.
Half Life Imipramine - 8-20 hours; Desipramine (active metabolite) - up to 125 hours
Protein Binding 60-95%
Elimination Approximately 40% of an orally administered dose is eliminated in urine within 24 hours, 70% in 72 hours. Small amounts are eliminated in feces via the biliary elimination.
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

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