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
References
1. Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S. (2013)
An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'.
Bioorg. Med. Chem. Lett., 23 (11): 3411-5. [PMID:23602445]
2. Boess FG, Monsma FJ, Meyer V, Zwingelstein C, Sleight AJ. (1997)
Interaction of tryptamine and ergoline compounds with threonine 196 in the ligand binding site of the 5-hydroxytryptamine6 receptor.
Mol Pharmacol, 52: 515-523. [PMID:9284367]
3. Boess FG, Monsma Jr FJ, Carolo C, Meyer V, Rudler A, Zwingelstein C, Sleight AJ. (1997)
Functional and radioligand binding characterization of rat 5-HT6 receptors stably expressed in HEK293 cells.
Neuropharmacology, 36 (4-5): 713-20. [PMID:9225298]
4. Boess FG, Riemer C, Bos M, Bentley J, Bourson A, Sleight AJ. (1998)
The 5-hydroxytryptamine6 receptor-selective radioligand [3H]Ro 63-0563 labels 5-hydroxytryptamine receptor binding sites in rat and porcine striatum.
Mol Pharmacol, 54: 577-583. [PMID:9730917]
5. Ghoneim OM, Legere JA, Golbraikh A, Tropsha A, Booth RG. (2006)
Novel ligands for the human histamine H1 receptor: synthesis, pharmacology, and comparative molecular field analysis studies of 2-dimethylamino-5-(6)-phenyl-1,2,3,4-tetrahydronaphthalenes.
Bioorg. Med. Chem., 14 (19): 6640-58. [PMID:16782354]
6. Kobayashi T, Washiyama K, Ikeda K. (2004)
Inhibition of G protein-activated inwardly rectifying K+ channels by various antidepressant drugs.
Neuropsychopharmacology, 29 (10): 1841-51. [PMID:15150531]
7. Kohen R, Metcalf MA, Khan N, Druck T, Huebner K, Lachowicz JE, Meltzer HY, Sibley DR, Roth BL, Hamblin MW. (1996)
Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor.
J. Neurochem., 66 (1): 47-56. [PMID:8522988]
8. Monsma Jr FJ, Shen Y, Ward RP, Hamblin MW, Sibley DR. (1993)
Cloning and expression of a novel serotonin receptor with high affinity for tricyclic psychotropic drugs.
Mol. Pharmacol., 43 (3): 320-7. [PMID:7680751]
9. Olianas MC, Dedoni S, Onali P. (2020)
Antidepressants induce profibrotic responses via the lysophosphatidic acid receptor LPA1.
Eur J Pharmacol, 873: 172963. [PMID:32007501]
10. Plassat JL, Amlaiky N, Hen R. (1993)
Molecular cloning of a mammalian serotonin receptor that activates adenylate cyclase.
Mol. Pharmacol., 44 (2): 229-36. [PMID:8394987]
11. Pälvimäki EP, Roth BL, Majasuo H, Laakso A, Kuoppamäki M, Syvälahti E, Hietala J. (1996)
Interactions of selective serotonin reuptake inhibitors with the serotonin 5-HT2c receptor.
Psychopharmacology (Berl.), 126 (3): 234-40. [PMID:8876023]
12. Shen Y, Monsma Jr FJ, Metcalf MA, Jose PA, Hamblin MW, Sibley DR. (1993)
Molecular cloning and expression of a 5-hydroxytryptamine7 serotonin receptor subtype.
J. Biol. Chem., 268 (24): 18200-4. [PMID:8394362]
13. Stanton T, Bolden-Watson C, Cusack B, Richelson E. (1993)
Antagonism of the five cloned human muscarinic cholinergic receptors expressed in CHO-K1 cells by antidepressants and antihistaminics.
Biochem. Pharmacol., 45 (11): 2352-4. [PMID:8100134]
14. Sánchez C, Hyttel J. (1999)
Comparison of the effects of antidepressants and their metabolites on reuptake of biogenic amines and on receptor binding.
Cell. Mol. Neurobiol., 19 (4): 467-89. [PMID:10379421]