(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; but-2-enedioic acid

• ChemBase ID: 155094
• Molecular Formular: C25H31N3O6
• Molecular Mass: 469.53014
• Monoisotopic Mass: 469.22128573
• SMILES: CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2Cc3cn(c4c3c(ccc4)C2=C1)C)C.C(=C\C(=O)O)/C(=O)O
• Canonical SMILES: OC(=O)/C=C/C(=O)O.CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3C)CO
• InChI: InChI=1S/C21H27N3O2.C4H4O4/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14;5-3(6)1-2-4(7)8/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26);1-2H,(H,5,6)(H,7,8)/t14-,15+,19-;/m1./s1
• InChIKey: LWYXFDXUMVEZKS-MZAYEULESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide; but-2-enedioic acid
• IUPAC Traditional name: butenedioic acid; methysergide
• Synonyms: Methysergide maleate salt

Database IDs

• CAS Number: 129-49-7
• EC Number: 204-950-9
• MDL Number: MFCD00083185
• PubChem SID: 24278129; 162249232
• PubChem CID: 52947309

CALCULATED PROPERTIES

• Acid pKa: 15.006512
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.5095057
• LogD (pH = 7.4): 1.2321609
• Log P: 1.8168944
• Molar Refractivity: 104.4726 cm^3
• Polarizability: 41.054924 Å^3
• Polar Surface Area: 57.5 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: soluble2 mg/mL
• Apperance: white to off-white solid

Safety Information

• RTECS: KE5410000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... HTR1A(3350), HTR1B(3351), HTR1D(3352), HTR1E(3354), HTR1F(3355), HTR2A(3356), HTR2B(3357), HTR2C(3358), HTR7(3363)

Product Information

• Empirical Formula (Hill Notation): C21H27N3O2 · C4H4O4

DETAILS

Sigma Aldrich - M137

Biochem/physiol Actions
Nonselective 5-HT1, 5-HT2, and 5-HT7 serotonin receptor antagonist; antimigraine.