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739-71-9 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}-2-methylpropyl)dimethylamine

ChemBase ID: 607
Molecular Formular: C20H26N2
Molecular Mass: 294.43384
Monoisotopic Mass: 294.20959884
SMILES and InChIs

SMILES:
N1(CC(CN(C)C)C)c2c(CCc3c1cccc3)cccc2
Canonical SMILES:
CN(CC(CN1c2ccccc2CCc2c1cccc2)C)C
InChI:
InChI=1S/C20H26N2/c1-16(14-21(2)3)15-22-19-10-6-4-8-17(19)12-13-18-9-5-7-11-20(18)22/h4-11,16H,12-15H2,1-3H3
InChIKey:
ZSCDBOWYZJWBIY-UHFFFAOYSA-N

Cite this record

CBID:607 http://www.chembase.cn/molecule-607.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}-2-methylpropyl)dimethylamine
(3-{2-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-yl}-2-methylpropyl)dimethylamine
IUPAC Traditional name
trimipramine
Brand Name
Sapilent
Surmontil
Surmontyl
Temaril
Synonyms
Trimipramina [INN-Spanish]
Trimeprimine
Trimeprimina [Italian]
beta-Methylimipramine
Trimipraminum [INN-Latin]
Trimipramine
CAS Number
739-71-9
PubChem SID
46507121
160964070
PubChem CID
5584
CHEBI ID
9738
ATC CODE
N06AA10
CHEMBL
644
Chemspider ID
5382
DrugBank ID
DB00726
KEGG ID
D00394
Unique Ingredient Identifier
6S082C9NDT
Wikipedia Title
Trimipramine
Medline Plus
a602010

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) 1.3963908  LogD (pH = 7.4) 2.746556 
Log P 4.757892  Molar Refractivity 95.022 cm3
Polarizability 36.51729 Å3 Polar Surface Area 6.48 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 4.67  LOG S -4.05 
Solubility (Water) 2.60e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
Slightly soluble expand Show data source
Hydrophobicity(logP)
4.2 expand Show data source
Admin Routes
Oral, IM, IV expand Show data source
Bioavailability
40% expand Show data source
Excretion
Renal expand Show data source
Half Life
11-23 hours expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
C expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00726 external link
Item Information
Drug Groups approved
Description Tricyclic antidepressant similar to imipramine, but with more antihistaminic and sedative properties. [PubChem]
Indication For the treatment of depression and depression accompanied by anxiety, agitation or sleep disturbance
Pharmacology Trimipramine is a tricyclic antidepressant. It was thought that tricyclic antidepressants work by inhibiting the re-uptake of the neurotransmitters norepinephrine and serotonin by nerve cells. However, this response occurs immediately, yet mood does not lift for around two weeks. It is now thought that changes occur in receptor sensitivity in the cerebral cortex and hippocampus. The hippocampus is part of the limbic system, a part of the brain involved in emotions. Presynaptic receptors are affected: a1 and b1 receptors are sensitized, a2 receptors are desensitised (leading to increased noradrenaline production). Tricyclics are also known as effective analgesics for different types of pain, especially neuropathic or neuralgic pain. A precise mechanism for their analgesic action is unknown, but it is thought that they modulate anti-pain opioid systems in the CNS via an indirect serotonergic route. They are also effective in migraine prophylaxis, but not in abortion of acute migraine attack. The mechanism of their anti-migraine action is also thought to be serotonergic.
Toxicity Side effects include agitation, coma, confusion, convulsions, dilated pupils, disturbed concentration, drowsiness, hallucinations, high fever, irregular heart rate, low body temperature, muscle rigidity, overactive reflexes, severely low blood pressure, stupor, vomiting
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Rapid absorption
Half Life 11-18 hrs
Protein Binding 93%-96% (to plasma proteins)
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

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PATENTS

PATENTS

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