amitriptyline   Click here for help

GtoPdb Ligand ID: 200

Synonyms: amitryptiline | Elavil® | Endep®
Approved drug PDB Ligand
amitriptyline is an approved drug (FDA (1961))
Compound class: Synthetic organic
Comment: Amitriptyline is a tricyclic antidepressant (TCA).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 3.24
Molecular weight 277.18
XLogP 4.93
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CN(CCC=C1c2ccccc2CCc2c1cccc2)C
Isomeric SMILES CN(CCC=C1c2ccccc2CCc2c1cccc2)C
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
InChI Key KRMDCWKBEZIMAB-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
H1 receptor Primary target of this compound Hs Antagonist Antagonist 9.3 pKi - 5
pKi 9.3 (Ki 5x10-10 M) [5]
Description: Antagonism of [3H]mepyramine binding
α1A-adrenoceptor Hs Antagonist Antagonist 8.2 pKi - 12
pKi 8.2 [12]
5-HT2A receptor Rn Antagonist Antagonist 8.0 – 8.4 pKi - 10,15
pKi 8.4 [10]
pKi 8.0 (Ki 1.1x10-8 M) [15]
M4 receptor Primary target of this compound Hs Antagonist Antagonist 8.1 pKi - 14
pKi 8.1 (Ki 7.2x10-9 M) [14]
5-HT2C receptor Rn Antagonist Antagonist 8.1 pKi - 15
pKi 8.1 (Ki 8x10-9 M) [15]
M2 receptor Primary target of this compound Hs Antagonist Antagonist 7.9 pKi - 14
pKi 7.9 (Ki 1.18x10-8 M) [14]
M3 receptor Primary target of this compound Hs Antagonist Antagonist 7.9 pKi - 14
pKi 7.9 (Ki 1.28x10-8 M) [14]
M1 receptor Primary target of this compound Hs Antagonist Antagonist 7.8 pKi - 14
pKi 7.8 (Ki 1.47x10-8 M) [14]
M5 receptor Primary target of this compound Hs Antagonist Antagonist 7.8 pKi - 14
pKi 7.8 (Ki 1.57x10-8 M) [14]
5-HT6 receptor Hs Antagonist Antagonist 6.9 – 7.2 pKi - 2,4,7
pKi 6.9 – 7.2 [2,4,7]
5-HT7 receptor Rn Antagonist Antagonist 6.9 – 7.0 pKi - 13
pKi 6.9 – 7.0 [13]
5-HT6 receptor Rn Antagonist Antagonist 6.5 – 7.2 pKi - 3-4,8
pKi 6.5 – 7.2 [3-4,8]
5-HT7 receptor Mm Antagonist Antagonist 6.4 pKi - 11
pKi 6.4 [11]
LPA1 receptor Hs Antagonist Antagonist ~6.2 pIC50 - 9
pIC50 ~6.2 (IC50 ~6x10-7 M) [9]
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Kir3.2 Mm Channel blocker Antagonist 4.0 pIC50 - 6
pIC50 4.0 [6]
Voltage: -70.0 mV
Kir3.4 Mm Channel blocker Antagonist 3.6 pIC50 - 6
pIC50 3.6 [6]
Voltage: -70.0 mV
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
SERT Primary target of this compound Hs Inhibitor Inhibition 6.8 pKi - 1
pKi 6.8 (Ki 1.41x10-7 M) [1]
NET Primary target of this compound Hs Inhibitor Inhibition 6.5 pKi - 1
pKi 6.5 (Ki 3.33x10-7 M) [1]
Ligand mentioned in the following text fields