Methysergide

Chemical Properties

SMILES CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3C)CO
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Molecular weight 353.2

Drug Properties

Type Small molecule
Endogenous No
Approved Yes
InChIKey KPJZHOPZRAFDTN-ZRGWGRIASA-N

Database Connections

External Links
Structure pdb 6DRZ
Ligand site mutations 5-HT1B 5-HT2A 5-HT2B 5-HT2C 5-HT6


Bioactivity

Receptor Experimental Data Source
GTP Uniprot Species Family Class Type Min Avg Max Database
5-HT1B 5HT1B Human 5-Hydroxytryptamine A pKi 6.6 7.1 7.6 Guide to Pharmacology
5-HT1D 5HT1D Human 5-Hydroxytryptamine A pKi 8.4 8.65 8.9 Guide to Pharmacology
5-HT1E 5HT1E Human 5-Hydroxytryptamine A pKi 6.5 6.65 6.8 Guide to Pharmacology
5-HT1F 5HT1F Human 5-Hydroxytryptamine A pKi 8.2 8.2 8.2 Guide to Pharmacology
5-HT1F 5HT1F Rat 5-Hydroxytryptamine A pIC50 7.8 7.8 7.8 Guide to Pharmacology
5-HT2A 5HT2A Rat 5-Hydroxytryptamine A pKi 8.4 8.38 9.5 Guide to Pharmacology
5-HT2A 5HT2A Human 5-Hydroxytryptamine A pKi 8.4 8.4 8.4 Guide to Pharmacology
5-HT2B 5HT2B Human 5-Hydroxytryptamine A pKi 8.0 8.7 9.4 Guide to Pharmacology
5-HT2B 5HT2B Rat 5-Hydroxytryptamine A pKi 8.2 8.2 8.2 Guide to Pharmacology
5-HT2C 5HT2C Rat 5-Hydroxytryptamine A pKi 9.0 9.0 9.0 Guide to Pharmacology
5-HT2C 5HT2C Human 5-Hydroxytryptamine A pKi 8.6 8.85 9.1 Guide to Pharmacology
5-HT5A 5HT5A Mouse 5-Hydroxytryptamine A pKi 6.3 6.75 7.2 Guide to Pharmacology
5-HT5A 5HT5A Human 5-Hydroxytryptamine A pKi 7.0 7.0 7.0 Guide to Pharmacology
5-HT5A 5HT5A Rat 5-Hydroxytryptamine A pKi 6.7 6.7 6.7 Guide to Pharmacology
5-HT6 5HT6R Rat 5-Hydroxytryptamine A pKi 6.4 6.5 6.6 Guide to Pharmacology
5-HT6 5HT6R Human 5-Hydroxytryptamine A pKi 6.5 6.65 6.8 Guide to Pharmacology
5-HT7 5HT7R Rat 5-Hydroxytryptamine A pKi 7.9 7.9 7.9 Guide to Pharmacology
5-HT7 5HT7R Human 5-Hydroxytryptamine A pKi 7.1 7.45 7.8 Guide to Pharmacology
5-HT7 5HT7R Mouse 5-Hydroxytryptamine A pKi 7.9 7.9 7.9 Guide to Pharmacology
5-HT1B 5HT1B Rat 5-Hydroxytryptamine A pIC50 6.75 6.75 6.75 ChEMBL
5-HT1B 5HT1B Rat 5-Hydroxytryptamine A pKi 6.97 6.97 6.97 ChEMBL
α2B ADA2B Human Adrenoceptors A pIC50 5.32 5.32 5.32 ChEMBL
α2B ADA2B Human Adrenoceptors A pKi 5.66 5.66 5.66 ChEMBL
α2A ADA2A Human Adrenoceptors A pIC50 5.79 5.79 5.79 ChEMBL
α2A ADA2A Human Adrenoceptors A pKi 6.21 6.21 6.21 ChEMBL
5-HT2B 5HT2B Human 5-Hydroxytryptamine A pIC50 9.25 9.25 9.25 ChEMBL
5-HT2B 5HT2B Human 5-Hydroxytryptamine A pKi 8.12 8.6 9.45 ChEMBL
D1 DRD1 Human Dopamine A pIC50 6.03 6.03 6.03 ChEMBL
D1 DRD1 Human Dopamine A pKi 6.33 6.33 6.33 ChEMBL
5-HT1A 5HT1A Rat 5-Hydroxytryptamine A pIC50 7.27 7.27 7.27 ChEMBL
5-HT1A 5HT1A Rat 5-Hydroxytryptamine A pKi 7.51 7.51 7.51 ChEMBL
5-HT6 5HT6R Human 5-Hydroxytryptamine A pIC50 6.79 6.79 6.79 ChEMBL
5-HT6 5HT6R Human 5-Hydroxytryptamine A pKi 7.12 7.12 7.12 ChEMBL
5-HT2C 5HT2C Human 5-Hydroxytryptamine A pKi 8.6 8.89 9.1 ChEMBL
5-HT2C 5HT2C Human 5-Hydroxytryptamine A pIC50 8.68 8.68 8.68 ChEMBL
5-HT1A 5HT1A Human 5-Hydroxytryptamine A pKi 7.77 7.77 7.77 ChEMBL
5-HT2A 5HT2A Human 5-Hydroxytryptamine A pKi 8.0 8.21 8.42 ChEMBL
5-HT2A 5HT2A Human 5-Hydroxytryptamine A pIC50 7.89 7.89 7.89 ChEMBL
D3 DRD3 Human Dopamine A pIC50 6.76 6.76 6.76 ChEMBL
D3 DRD3 Human Dopamine A pKi 7.23 7.23 7.23 ChEMBL
D2 DRD2 Human Dopamine A pIC50 6.09 6.09 6.09 ChEMBL
D2 DRD2 Human Dopamine A pKi 6.57 6.57 6.57 ChEMBL
5-HT1A 5HT1A Rat 5-Hydroxytryptamine A pKi 4.33 5.94 6.67 PDSP KiDatabase
5-HT1A A0A4X1UTF5 Pig 5-Hydroxytryptamine A pKi 6.63 6.63 6.63 PDSP KiDatabase
5-HT1A A0A4W2HQH6 Hybrid cattle 5-Hydroxytryptamine A pKi 6.4 6.4 6.4 PDSP KiDatabase
5-HT2C A0A4X1VZZ6 Pig 5-Hydroxytryptamine A pKi 7.49 7.65 7.9 PDSP KiDatabase
5-HT1D F1MMU1 Bovine 5-Hydroxytryptamine A pKi 5.92 7.15 7.42 PDSP KiDatabase
5-HT1D 5HT1D Human 5-Hydroxytryptamine A pKi 6.03 6.49 7.44 PDSP KiDatabase
5-HT1D 5HT1D Rat 5-Hydroxytryptamine A pKi 6.0 6.2 6.39 PDSP KiDatabase
5-HT1B 5HT1B Rat 5-Hydroxytryptamine A pKi 4.74 5.19 5.51 PDSP KiDatabase
5-HT2A 5HT2A Rat 5-Hydroxytryptamine A pKi 6.82 7.61 8.38 PDSP KiDatabase
5-HT2A 5HT2A Human 5-Hydroxytryptamine A pKi 5.98 7.16 7.8 PDSP KiDatabase
5-HT2A 5HT2A Pig 5-Hydroxytryptamine A pKi 6.58 6.58 6.58 PDSP KiDatabase
5-HT5A 5HT5A Mouse 5-Hydroxytryptamine A pKi 5.3 6.0 6.2 PDSP KiDatabase
5-HT6 5HT6R Rat 5-Hydroxytryptamine A pKi 5.4 5.47 5.59 PDSP KiDatabase
5-HT7 5HT7R Rat 5-Hydroxytryptamine A pKi 5.4 6.67 6.9 PDSP KiDatabase
5-HT6 5HT6R Human 5-Hydroxytryptamine A pKi 5.43 6.0 6.52 PDSP KiDatabase
5-HT1B 5HT1B Human 5-Hydroxytryptamine A pKi 5.79 7.02 7.6 PDSP KiDatabase
5-HT2C 5HT2C Rat 5-Hydroxytryptamine A pKi 7.7 7.92 8.1 PDSP KiDatabase
5-HT2B 5HT2B Human 5-Hydroxytryptamine A pKi 5.82 7.65 9.0 PDSP KiDatabase
5-HT2C 5HT2C Human 5-Hydroxytryptamine A pKi 7.35 7.72 8.02 PDSP KiDatabase
5-HT5A 5HT5A Rat 5-Hydroxytryptamine A pKi 5.0 5.36 5.71 PDSP KiDatabase
5-HT2B 5HT2B Rat 5-Hydroxytryptamine A pKi 6.06 6.97 7.2 PDSP KiDatabase
5-HT7 5HT7R Guinea pig 5-Hydroxytryptamine A pKi 6.03 6.36 6.65 PDSP KiDatabase
5-HT7 5HT7R Human 5-Hydroxytryptamine A pKi 6.08 6.19 6.52 PDSP KiDatabase
5-HT6 5HT6R Mouse 5-Hydroxytryptamine A pKi 6.9 6.9 6.9 PDSP KiDatabase
5-HT1E 5HT1E Human 5-Hydroxytryptamine A pKi 5.49 5.7 6.23 PDSP KiDatabase
5-HT1F 5HT1F Human 5-Hydroxytryptamine A pKi 6.47 6.47 6.47 PDSP KiDatabase
H1 HRH1 Rat Histamine A pKi 3.48 3.74 4.0 PDSP KiDatabase
D1 DRD1 Rat Dopamine A pKi 5.66 5.66 5.66 PDSP KiDatabase
D2 DRD2 Rat Dopamine A pKi 5.94 5.94 5.94 PDSP KiDatabase
D1 DRD1 Bovine Dopamine A pKi 4.8 5.17 5.54 PDSP KiDatabase
5-HT1A 5HT1A Human 5-Hydroxytryptamine A pKi 6.6 6.73 6.85 PDSP KiDatabase
5-HT1D 5HT1D Dog 5-Hydroxytryptamine A pKi 7.11 7.11 7.11 PDSP KiDatabase
5-HT1F 5HT1F Mouse 5-Hydroxytryptamine A pKi 7.2 7.2 7.2 PDSP KiDatabase
5-HT1F 5HT1F Rat 5-Hydroxytryptamine A pKi 6.87 6.87 6.87 PDSP KiDatabase
5-HT2B 5HT2B Mouse 5-Hydroxytryptamine A pKi 6.9 6.9 6.9 PDSP KiDatabase
5-HT7 5HT7R Mouse 5-Hydroxytryptamine A pKi 6.9 6.9 6.9 PDSP KiDatabase
D2 DRD2 Bovine Dopamine A pKi 5.8 5.8 5.8 PDSP KiDatabase
5-HT2A 5HT2A Mouse 5-Hydroxytryptamine A pKi 7.24 7.24 7.24 PDSP KiDatabase
5-HT1B 5HT1B Guinea pig 5-Hydroxytryptamine A pKi 5.73 5.73 5.73 PDSP KiDatabase
5-HT5A 5HT5A Human 5-Hydroxytryptamine A pKi 4.0 4.0 4.0 PDSP KiDatabase
D1 DRD1 Human Dopamine A pKi 4.0 4.0 4.0 PDSP KiDatabase
D2 DRD2 Human Dopamine A pKi 4.0 4.0 4.0 PDSP KiDatabase
D3 DRD3 Rat Dopamine A pKi 4.0 4.0 4.0 PDSP KiDatabase
H1 HRH1 Human Histamine A pKi 4.0 4.19 4.52 PDSP KiDatabase
D4 DRD4 Human Dopamine A pKi 4.0 4.0 4.0 PDSP KiDatabase
D5 DRD5 Human Dopamine A pKi 4.0 4.0 4.0 PDSP KiDatabase
α1B ADA1B Human Adrenoceptors A pKi 4.0 4.0 4.0 PDSP KiDatabase
α2A ADA2A Human Adrenoceptors A pKi 5.77 5.77 5.77 PDSP KiDatabase
α2B ADA2B Human Adrenoceptors A pKi 5.97 5.97 5.97 PDSP KiDatabase
β1 ADRB1 Human Adrenoceptors A pKi 4.0 4.0 4.0 PDSP KiDatabase
β2 ADRB2 Human Adrenoceptors A pKi 4.0 4.0 4.0 PDSP KiDatabase
M1 ACM1 Human Acetylcholine (muscarinic) A pKi 4.26 4.26 4.26 PDSP KiDatabase
M2 ACM2 Human Acetylcholine (muscarinic) A pKi 4.21 4.21 4.21 PDSP KiDatabase
M3 ACM3 Human Acetylcholine (muscarinic) A pKi 4.33 4.33 4.33 PDSP KiDatabase
α1A ADA1A Human Adrenoceptors A pKi 4.0 4.0 4.0 PDSP KiDatabase
α2C ADA2C Human Adrenoceptors A pKi 6.05 6.05 6.05 PDSP KiDatabase
M4 ACM4 Human Acetylcholine (muscarinic) A pKi 4.0 4.0 4.0 PDSP KiDatabase
EP3 PE2R3 Human Prostanoid A pKi 4.0 4.0 4.0 PDSP KiDatabase
EP4 PE2R4 Human Prostanoid A pKi 4.0 4.0 4.0 PDSP KiDatabase
H2 HRH2 Human Histamine A pKi 4.0 4.0 4.0 PDSP KiDatabase
M5 ACM5 Human Acetylcholine (muscarinic) A pKi 4.0 4.0 4.0 PDSP KiDatabase
CB1 CNR1 Rat Cannabinoid A pKi 4.0 4.0 4.0 PDSP KiDatabase
mGlu1 GRM1 Rat Metabotropic glutamate C pKi 4.0 4.0 4.0 PDSP KiDatabase
mGlu5 GRM5 Rat Metabotropic glutamate C pKi 4.0 4.0 4.0 PDSP KiDatabase
mGlu2 GRM2 Rat Metabotropic glutamate C pKi 4.0 4.0 4.0 PDSP KiDatabase
mGlu4 GRM4 Rat Metabotropic glutamate C pKi 4.0 4.0 4.0 PDSP KiDatabase
mGlu8 GRM8 Rat Metabotropic glutamate C pKi 4.0 4.0 4.0 PDSP KiDatabase
H1 HRH1 Guinea pig Histamine A pKi 4.52 4.52 4.52 PDSP KiDatabase