5-MeOT   Click here for help

GtoPdb Ligand ID: 107

Synonyms: 5-methoxytryptamine | 5-MT | mexamine
PDB Ligand
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 51.04
Molecular weight 190.11
XLogP 1.32
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NCCc1c[nH]c2c1cc(OC)cc2
Isomeric SMILES NCCc1c[nH]c2c1cc(OC)cc2
InChI InChI=1S/C11H14N2O/c1-14-9-2-3-11-10(6-9)8(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3
InChI Key JTEJPPKMYBDEMY-UHFFFAOYSA-N
References
1. Adham N, Gerald C, Schechter L, Vaysse P, Weinshank R, Branchek T. (1996)
[3H]5-hydroxytryptamine labels the agonist high affinity state of the cloned rat 5-HT4 receptor.
Eur J Pharmacol, 304 (1-3): 231-5. [PMID:8813606]
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Cloning of another human serotonin receptor (5-HT1F): a fifth 5-HT1 receptor subtype coupled to the inhibition of adenylate cyclase.
Proc Natl Acad Sci USA, 90 (2): 408-12. [PMID:8380639]
3. Bach T, Syversveen T, Kvingedal AM, Krobert KA, Brattelid T, Kaumann AJ, Levy FO. (2001)
5HT4(a) and 5-HT4(b) receptors have nearly identical pharmacology and are both expressed in human atrium and ventricle.
Naunyn Schmiedebergs Arch Pharmacol, 363 (2): 146-60. [PMID:11218067]
4. Bai F, Yin T, Johnstone EM, Su C, Varga G, Little SP, Nelson DL. (2004)
Molecular cloning and pharmacological characterization of the guinea pig 5-HT1E receptor.
Eur J Pharmacol, 484 (2-3): 127-39. [PMID:14744596]
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Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase.
J Biol Chem, 268 (31): 23422-6. [PMID:8226867]
6. Bender E, Pindon A, van Oers I, Zhang YB, Gommeren W, Verhasselt P, Jurzak M, Leysen J, Luyten W. (2000)
Structure of the human serotonin 5-HT4 receptor gene and cloning of a novel 5-HT4 splice variant.
J Neurochem, 74 (2): 478-89. [PMID:10646498]
7. Blondel O, Gastineau M, Dahmoune Y, Langlois M, Fischmeister R. (1998)
Cloning, expression, and pharmacology of four human 5-hydroxytryptamine 4 receptor isoforms produced by alternative splicing in the carboxyl terminus.
J Neurochem, 70 (6): 2252-61. [PMID:9603189]
8. 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.
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9. Boess FG, Monsma Jr FJ, Sleight AJ. (1998)
Identification of residues in transmembrane regions III and VI that contribute to the ligand binding site of the serotonin 5-HT6 receptor.
J Neurochem, 71 (5): 2169-77. [PMID:9798944]
10. Bonhaus DW, Berger J, Adham N, Branchek TA, Hsu SA, Loury DN, Leung E, Wong EH, Clark RD, Eglen RM. (1997)
[3H]RS 57639, a high affinity, selective 5-HT4 receptor partial agonist, specifically labels guinea-pig striatal and rat cloned (5-HT4S and 5-HT4L) receptors.
Neuropharmacology, 36 (4-5): 671-9. [PMID:9225293]
11. Claeysen S, Sebben M, Journot L, Bockaert J, Dumuis A. (1996)
Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor.
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12. Dukat M, Smith C, Herrick-Davis K, Teitler M, Glennon RA. (2004)
Binding of tryptamine analogs at h5-HT1E receptors: a structure-affinity investigation.
Bioorg Med Chem, 12 (10): 2545-52. [PMID:15110837]
13. Egan C, Grinde E, Dupre A, Roth BL, Hake M, Teitler M, Herrick-Davis K. (2000)
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.
Synapse, 35 (2): 144-50. [PMID:10611640]
14. Gerald C, Adham N, Kao HT, Olsen MA, Laz TM, Schechter LE, Bard JA, Vaysse PJ, Hartig PR, Branchek TA et al.. (1995)
The 5-HT4 receptor: molecular cloning and pharmacological characterization of two splice variants.
EMBO J, 14 (12): 2806-15. [PMID:7796807]
15. Hamblin MW, Metcalf MA. (1991)
Primary structure and functional characterization of a human 5-HT1D-type serotonin receptor.
Mol Pharmacol, 40 (2): 143-8. [PMID:1652050]
16. Herrick-Davis K, Egan C, Teitler M. (1997)
Activating mutations of the serotonin 5-HT2C receptor.
J Neurochem, 69 (3): 1138-44. [PMID:9282936]
17. Jasper JR, Kosaka A, To ZP, Chang DJ, Eglen RM. (1997)
Cloning, expression and pharmacology of a truncated splice variant of the human 5-HT7 receptor (h5-HT7b).
Br J Pharmacol, 122 (1): 126-32. [PMID:9298538]
18. Johnson MP, Loncharich RJ, Baez M, Nelson DL. (1994)
Species variations in transmembrane region V of the 5-hydroxytryptamine type 2A receptor alter the structure-activity relationship of certain ergolines and tryptamines.
Mol Pharmacol, 45 (2): 277-86. [PMID:8114677]
19. 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]
20. Krobert KA, Bach T, Syversveen T, Kvingedal AM, Levy FO. (2001)
The cloned human 5-HT7 receptor splice variants: a comparative characterization of their pharmacology, function and distribution.
Naunyn Schmiedebergs Arch Pharmacol, 363 (6): 620-32. [PMID:11414657]
21. Leysen JE, Gommeren W, Heylen L, Luyten WH, Van de Weyer I, Vanhoenacker P, Haegeman G, Schotte A, Van Gompel P, Wouters R et al.. (1996)
Alniditan, a new 5-hydroxytryptamine1D agonist and migraine-abortive agent: ligand-binding properties of human 5-hydroxytryptamine1D alpha, human 5-hydroxytryptamine1D beta, and calf 5-hydroxytryptamine1D receptors investigated with [3H]5-hydroxytryptamine and [3H]alniditan.
Mol Pharmacol, 50 (6): 1567-80. [PMID:8967979]
22. Mialet J, Berque-Bestel I, Eftekhari P, Gastineau M, Giner M, Dahmoune Y, Donzeau-Gouge P, Hoebeke J, Langlois M, Sicsic S et al.. (2000)
Isolation of the serotoninergic 5-HT4(e) receptor from human heart and comparative analysis of its pharmacological profile in C6-glial and CHO cell lines.
Br J Pharmacol, 129 (4): 771-81. [PMID:10683202]
23. Mialet J, Berque-Bestel I, Sicsic S, Langlois M, Fischmeister R, Lezoualc'h F. (2000)
Pharmacological characterization of the human 5-HT(4(d)) receptor splice variant stably expressed in Chinese hamster ovary cells.
Br J Pharmacol, 131 (4): 827-35. [PMID:11030734]
24. 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]
25. Parker EM, Izzarelli DG, Lewis-Higgins L, Palmer D, Shapiro RA. (1996)
Two amino acid differences in the sixth transmembrane domain are partially responsible for the pharmacological differences between the 5-HT1D beta and 5-HT1E 5-hydroxytryptamine receptors.
J Neurochem, 67 (5): 2096-103. [PMID:8863519]
26. 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]
27. Ruat M, Traiffort E, Leurs R, Tardivel-Lacombe J, Diaz J, Arrang JM, Schwartz JC. (1993)
Molecular cloning, characterization, and localization of a high-affinity serotonin receptor (5-HT7) activating cAMP formation.
Proc Natl Acad Sci USA, 90 (18): 8547-51. [PMID:8397408]
28. 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]
29. Van den Wyngaert I, Gommeren W, Verhasselt P, Jurzak M, Leysen J, Luyten W, Bender E. (1997)
Cloning and expression of a human serotonin 5-HT4 receptor cDNA.
J Neurochem, 69 (5): 1810-9. [PMID:9349523]
30. Wainscott DB, Cohen ML, Schenck KW, Audia JE, Nissen JS, Baez M, Kursar JD, Lucaites VL, Nelson DL. (1993)
Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor.
Mol Pharmacol, 43 (3): 419-26. [PMID:8450835]
31. Weinshank RL, Zgombick JM, Macchi MJ, Branchek TA, Hartig PR. (1992)
Human serotonin 1D receptor is encoded by a subfamily of two distinct genes: 5-HT1D alpha and 5-HT1D beta.
Proc Natl Acad Sci USA, 89 (8): 3630-4. [PMID:1565658]