AMITRIPTYLINE

Search structure
Synonyms:
Status: Approved (1961)
Entry Type: Small molecule
Molecule Category: Parent
ATC: N06AA09
UNII: 1806D8D52K

Structure
InChI Key KRMDCWKBEZIMAB-UHFFFAOYSA-N
Smile CN(C)CCC=C1c2ccccc2CCc2ccccc21
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

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H23N
Molecular Weight 277.41
AlogP 4.17
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 3.24
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 21.0

Pharmacology

Primary Target
H1 receptor
M1 receptor
M2 receptor
M3 receptor
M4 receptor
M5 receptor
NET
SERT
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Trk family
86000 60000 - - -
Ion channel Ligand-gated ion channel 5HT3 receptor
- 44 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 3000-10000 - - 98
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 3750-23200 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 1000-7000 - - 74
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Acetylcholine receptor
- 300 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Adrenergic receptor
- 0 - - -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Dopamine receptor
- - - 170 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Histamine receptor
- 0 - 1 -
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Monoamine receptor Serotonin receptor
- 44 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC06 neurotransmitter transporter family
- 12589 - 4-141 -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 11
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- 16900 - - 79

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Depressive Disorder 4 D003866 ClinicalTrials
Migraine Disorders 3 D008881 ClinicalTrials
Pain 3 D010146 ClinicalTrials
Neuralgia 3 D009437 ClinicalTrials
Schizophrenia 3 D012559 ClinicalTrials
Sleep Initiation and Maintenance Disorders 3 D007319 ClinicalTrials
Anxiety 3 D001007 ClinicalTrials
Fibromyalgia 3 D005356 ClinicalTrials
Dementia 3 D003704 ClinicalTrials
Headache 3 D006261 ClinicalTrials
Cystitis, Interstitial 3 D018856 ClinicalTrials
Depressive Disorder, Major 3 D003865 ClinicalTrials
Peripheral Nervous System Diseases 2 D010523 ClinicalTrials
Intervertebral Disc Displacement 2 D007405 ClinicalTrials
Paget Disease, Extramammary 2 D010145 ClinicalTrials
Digestive System Diseases 2 D004066 ClinicalTrials
Diabetes Mellitus 2 D003920 ClinicalTrials
Biliary Dyskinesia 2 D001657 ClinicalTrials
Bursitis 2 D002062 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt

Cross References

Resources Reference
CAS NUMBER 50-48-6
ChEBI 2666
ChEMBL CHEMBL629
DrugBank DB00321
DrugCentral 180
EPA CompTox DTXSID7022594
FDA SRS 1806D8D52K
Human Metabolome Database HMDB0014466
Guide to Pharmacology 200
KEGG C06824
PDB TP0
PharmGKB PA448385
PubChem 2160
SureChEMBL SCHEMBL7824
ZINC ZINC000000968257
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