(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编号: 133555
• 分子式: C24H29N3O6
• 平均质量: 455.50356
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (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传统名: maleic acid; methylergonovine
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 14.997192
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): -0.80055475
• LogD (pH = 7.4): 0.95344526
• Log P: 1.5932183
• 摩尔折射率: 99.5759 cm^3
• 极化性: 39.292522 Å^3
• 极化表面积: 68.36 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: 0.1 M HCl: soluble; ethanol: slightly soluble; H2O: soluble25 mg/mL; Sparingly soluble in Ethanol; Water
• 外观: Light Brown Solid; white
• 熔点: 192-194°C (dec)

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: KE5500000
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 1544
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 23/24/25-62
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H311-H331-H361
• GHS警示性声明: P261-P280-P301 + P310-P311
• 个人保护装置: 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

药理学性质

• 相关基因信息: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)

产品相关信息

• 纯度: ≥98% (TLC)

详细说明

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.

参考文献

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