(2Z)-but-2-enedioic acid; (4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide

• ChemBase ID: 133555
• Molecular Formular: C24H29N3O6
• Molecular Mass: 455.50356
• Monoisotopic Mass: 455.20563566
• SMILES: CC[C@@H](CO)NC(=O)[C@H]1CN([C@@H]2Cc3c[nH]c4c3c(ccc4)C2=C1)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)c[nH]3)CO
• InChI: InChI=1S/C20H25N3O2.C4H4O4/c1-3-14(11-24)22-20(25)13-7-16-15-5-4-6-17-19(15)12(9-21-17)8-18(16)23(2)10-13;5-3(6)1-2-4(7)8/h4-7,9,13-14,18,21,24H,3,8,10-11H2,1-2H3,(H,22,25);1-2H,(H,5,6)(H,7,8)/b;2-1-/t13-,14+,18-;/m1./s1
• InChIKey: NOFOWWRHEPHDCY-DAUURJMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-but-2-enedioic acid; (4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,9,12(16),13-pentaene-4-carboxamide; (2Z)-but-2-enedioic acid; (4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
• IUPAC Traditional name: maleic acid; methylergonovine
• Synonyms: 9,10-Didehydro-N-[(S)-1-(hydroxymethyl)propyl]-6-methylergoline-8β-carboxamide maleate salt; Methergine maleate salt; Methylergonovine maleate salt; (8β)-9,10-Didehydro-N-[(1S)-1-(hydroxymethyl)propyl]-6-methyl-ergoline-8-carbox-amide Maleate; N-[α-(Hydroxymethyl)propyl]-D-lysergamide Maleate; Basofortina; Erezin; Metenarin; Methergin; Methergine; Methylergobasine Maleate; Methylergometrine Maleate; Methyl Ergonovine Maleate Salt

Database IDs

• CAS Number: 57432-61-8
• EC Number: 260-734-4
• MDL Number: MFCD00078588
• PubChem SID: 162227832; 24278543
• PubChem CID: 5281072

CALCULATED PROPERTIES

• Acid pKa: 14.997192
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.80055475
• LogD (pH = 7.4): 0.95344526
• Log P: 1.5932183
• Molar Refractivity: 99.5759 cm^3
• Polarizability: 39.292522 Å^3
• Polar Surface Area: 68.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble; ethanol: slightly soluble; H2O: soluble25 mg/mL; Sparingly soluble in Ethanol; Water
• Apperance: Light Brown Solid; white
• Melting Point: 192-194°C (dec)

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: KE5500000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25-62
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331-H361
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 3

Pharmacology Properties

• Gene Information: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - M2776

Biochem/physiol Actions
Ergot alkaloid which interacts with serotonergic, dopaminergic and α-adrenergic systems. Dopamine antagonist.

Toronto Research Chemicals - M304600

A metabolite of Methysergide. Semisynthetic ergot alkaloid. Oxytocic.

REFERENCES

• Mueller, L., et al.: Headache, 37, 437 (1997)
• de Groot, A.N., et al.: Drugs, 56, 523 (1997)