3,3-diethyl-1-[(2R,4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),9,12(16),13-tetraen-4-yl]urea

• ChemBase编号: 132219
• 分子式: C20H28N4O
• 平均质量: 340.46252
• 单一同位素质量: 340.22631154
• SMILES: CCN(CC)C(=O)N[C@H]1C[C@@H]2c3cccc4c3c(c[nH]4)C[C@H]2N(C1)C
• Canonical SMILES: CCN(C(=O)N[C@@H]1CN(C)[C@H]2[C@H](C1)c1cccc3c1c(C2)c[nH]3)CC
• InChI: InChI=1S/C20H28N4O/c1-4-24(5-2)20(25)22-14-10-16-15-7-6-8-17-19(15)13(11-21-17)9-18(16)23(3)12-14/h6-8,11,14,16,18,21H,4-5,9-10,12H2,1-3H3,(H,22,25)/t14-,16+,18+/m0/s1
• InChIKey: JOAHPSVPXZTVEP-YXJHDRRASA-N

名称和登记号

名称

• IUPAC标准名: 3,3-diethyl-1-[(2R,4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraen-4-yl]urea; 3,3-diethyl-1-[(2R,4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]urea
• IUPAC传统名: 3,3-diethyl-1-[(2R,4S,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),9,12(16),13-tetraen-4-yl]urea; terguride
• 别名: S(+)-N,N-Diethyl-N′([8α]-6-methylergolin-8-yl)urea; S(+)-Terguride (5R, 8S, 10R); S(+)-Terguride; N,N-Diethyl-N'-[(8α)-6-methylergolin-8-yl]urea; (+)-(5R,8S,10R)-Terguride; (+)-Terguride; (5R,8S,10R)-Terguride; 6-Methyl-8α-(diethylcarbamoylamino)ergoline; 9,10α-Dihydrolisuride; N,N-Diethyl-N'-(D-6-methyl-10α-isoergolin-8-yl)urea; TDHL; Tergurid; Terguride; trans-Dihydrolisuride; trans-Dihydro Lisuride

登记号

• CAS号: 37686-84-3
• EC号: 253-624-2
• MDL号: MFCD00242729
• PubChem SID: 24278800; 162226496
• PubChem CID: 443951

理论计算性质

• Acid pKa: 15.539188
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 0.20163696
• LogD (pH = 7.4): 1.8428042
• Log P: 2.2022138
• 摩尔折射率: 101.1931 cm^3
• 极化性: 39.982605 Å^3
• 极化表面积: 51.37 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: soluble; ethanol: soluble; H2O: insoluble
• 外观: white
• 比旋光度: [α]20/D +28°, c = 0.2 in pyridine(lit.)

安全信息

• RTECS编号: YS9378700
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 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): 2
• 危险公开号: 23/24/25
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H311-H331
• GHS警示性声明: P261-P280-P301 + P310-P311
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

药理学性质

• 相关基因信息: human ... DRD2(1813)rat ... Drd2(24318)

详细说明

Sigma Aldrich - T165

Biochem/physiol Actions
Ergot derivative; dehydrogenated analog of lisuride; D2 dopamine receptor partial agonist.

Toronto Research Chemicals - D449495

An ergot alkaloid derivative that acts as a partial dopamine D2-receptor agonist. An anti-hyperprolactinemia agent.

参考文献

• Spealman, R.D.: Pharmacol. Biochem. Behav., 51, 661 (1995)
• McDougall, S. et al.: Psychopharmacol., 178, 431 (1995)
• Yamada, Y. et al.: Yakug. Zas., 123, 255 (1995)