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1668-19-5 molecular structure
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dimethyl(3-{9-oxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine

ChemBase ID: 1013
Molecular Formular: C19H21NO
Molecular Mass: 279.37614
Monoisotopic Mass: 279.1623143
SMILES and InChIs

SMILES:
O1Cc2c(/C(=C\CCN(C)C)/c3c1cccc3)cccc2
Canonical SMILES:
CN(CC/C=C\1/c2ccccc2OCc2c1cccc2)C
InChI:
InChI=1S/C19H21NO/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19/h3-6,8-12H,7,13-14H2,1-2H3/b17-11+
InChIKey:
ODQWQRRAPPTVAG-GZTJUZNOSA-N

Cite this record

CBID:1013 http://www.chembase.cn/molecule-1013.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
dimethyl(3-{9-oxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine
dimethyl({3-[(2E)-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
IUPAC Traditional name
dimethyl(3-{9-oxatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}propyl)amine
dimethyl({3-[(2E)-9-oxatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene]propyl})amine
Brand Name
Sinequan, Zonalon
Adapin
Aponal
Curatin
Quitaxon
Triadapin
Zonalon
Synonyms
Doxepin, Hydrochloride
Doxepin Hcl
Doxepina [INN-Spanish]
Doxepine
Doxepinum [INN-Latin]
Doxepin
CAS Number
1668-19-5
PubChem SID
160964476
PubChem CID
667477
3158
CHEBI ID
4710
ATC CODE
N06AA12
CHEMBL
101740
Chemspider ID
3046
DrugBank ID
DB01142
IUPHAR ligand ID
1225
KEGG ID
D07875
Unique Ingredient Identifier
5ASJ6HUZ7D
Wikipedia Title
Doxepin
Medline Plus
a682390

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 Donor LogD (pH = 5.5) 0.40824065 
LogD (pH = 7.4) 1.5076776  Log P 3.8399742 
Molar Refractivity 98.2448 cm3 Polarizability 34.1806 Å3
Polar Surface Area 12.47 Å2 Rotatable Bonds
Lipinski's Rule of Five true  H Acceptors
Log P 4.08  LOG S -3.94 
Solubility (Water) 3.19e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
4.9 mg/L expand Show data source
Hydrophobicity(logP)
4 expand Show data source
Admin Routes
Oral, IM, IV expand Show data source
Bioavailability
Absolute: 25%
When main metabolite desmethyldoxepin is included: 31%
expand Show data source
Excretion
Renal expand Show data source
Half Life
Doxepin 17 hours, main metabolite Desmethyldoxepin 51 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C (Australia) expand Show data source
Not recommended.
Animal studies have shown embryotoxic properties.
expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB01142 external link
Item Information
Drug Groups approved
Description Doxepin hydrochloride is a dibenzoxepin-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, doxepin does not affect mood or arousal, but may cause sedation. In depressed individuals, doxepin exerts a positive effect on mood. TCAs are potent inhibitors of serotonin and norepinephrine reuptake. Tertiary amine TCAs, such as doxepin 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. Doxepin has less sedative and anticholinergic effects than amitriptyline. See toxicity section below for a complete listing of side effects. Doxepin may be used to treat depression and insomnia. Unlabeled indications include chronic and neuropathic pain, and anxiety. Doxepin may also be used as a second line agent to treat idiopathic urticaria.
Indication Labeled indications: depression and insomnia. Unlabeled indications: chronic and neuropathic pain, anxiety, idiopathic urticaria.
Pharmacology Doxepin, a tricyclic antidepressant of the dibenzoxepin type, is used to treat depression and anxiety and, topically, pruritus associated with eczema. Doxepin has substantial anticholinergic and sedative effects.
Toxicity LD50=26 (mg/kg) (in mice, iv); LD50=16 (mg/kg) (in rats, iv); Cardiac dysrhythmias, severe hypotension, convulsions, and CNS depression, including coma. Changes in the electrocardiogram, particularly in QRS axis or width, are clinically significant indicators of tricyclic antidepressant toxicity.
Side effects include: sedation, hypotension, blurred vision, dry mouth, constipation, urinary retention, postural hypotension, tachycardia, hypertension, ECG changes, heart failure, impaired memory and delirium, and precipitation of hypomanic or manic episodes in bipolar depression.
Withdrawal symptoms include gastrointestinal disturbances, anxiety, and insomnia.
Affected Organisms
Humans and other mammals
Biotransformation Extensively metabolized in the liver via the same pathways as other TCAs. N-demethylation produces an active metabolite, N-desmethyldoxepin.
Absorption Well-absorbed from the GI tract. Peak plasma concentrations occur within 2 hours of oral administration.
Half Life 6 - 24.5 hours
Protein Binding Highly bound to plasma proteins.
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

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