CHEBI:2666 - amitriptyline

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ChEBI Name amitriptyline
ChEBI ID CHEBI:2666
Definition An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H23N
Net Charge 0
Average Mass 277.40336
Monoisotopic Mass 277.183
InChI InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3
InChIKey KRMDCWKBEZIMAB-UHFFFAOYSA-N
SMILES CN(C)CCC=C1c2ccccc2CCc2ccccc12
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants 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.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): antidepressant
Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants 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.
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ChEBI Ontology
Outgoing amitriptyline (CHEBI:2666) has parent hydride dibenzo[a,d][7]annulene (CHEBI:35642)
amitriptyline (CHEBI:2666) has role adrenergic uptake inhibitor (CHEBI:35640)
amitriptyline (CHEBI:2666) has role antidepressant (CHEBI:35469)
amitriptyline (CHEBI:2666) has role environmental contaminant (CHEBI:78298)
amitriptyline (CHEBI:2666) has role xenobiotic (CHEBI:35703)
amitriptyline (CHEBI:2666) is a organic tricyclic compound (CHEBI:51959)
amitriptyline (CHEBI:2666) is a tertiary amine (CHEBI:32876)
Incoming nortriptyline (CHEBI:7640) has functional parent amitriptyline (CHEBI:2666)
IUPAC Name
3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine
Synonyms Sources
10,11-dihydro-5-(γ-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene NIST Chemistry WebBook
10,11-dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-Δ5,γ-propylamine NIST Chemistry WebBook
3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine NIST Chemistry WebBook
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethylpropan-1-amine ChEBI
5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptatriene NIST Chemistry WebBook
5-(3-dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene NIST Chemistry WebBook
5-(γ-dimethylaminopropylidene)-5H-dibenzo[a,d][1,4]cycloheptadiene NIST Chemistry WebBook
Amitriptylin ChemIDplus
Amitriptyline KEGG COMPOUND
Database Links Databases
180 DrugCentral
Amitriptyline Wikipedia
C06824 KEGG COMPOUND
CN101780063 Patent
D07448 KEGG DRUG
DB00321 DrugBank
HMDB14466 HMDB
LSM-3190 LINCS
WO2011089289 Patent
View more database links
Registry Numbers Types Sources
2217885 Reaxys Registry Number Reaxys
2217885 Beilstein Registry Number Beilstein
50-48-6 CAS Registry Number KEGG COMPOUND
50-48-6 CAS Registry Number NIST Chemistry WebBook
50-48-6 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15554244 PubMed citation Europe PMC
18359012 PubMed citation Europe PMC
24447704 PubMed citation Europe PMC
Last Modified
22 February 2017
General Comment
2014-10-29 Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag