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 ID: 132219
• Molecular Formular: C20H28N4O
• Molecular Mass: 340.46252
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 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
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 15.539188
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 0.20163696
• LogD (pH = 7.4): 1.8428042
• Log P: 2.2022138
• Molar Refractivity: 101.1931 cm^3
• Polarizability: 39.982605 Å^3
• Polar Surface Area: 51.37 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble; H2O: insoluble
• Apperance: white
• Optical Rotation: [α]20/D +28°, c = 0.2 in pyridine(lit.)

Safety Information

• RTECS: YS9378700
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 23/24/25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2

Pharmacology Properties

• Gene Information: human ... DRD2(1813)rat ... Drd2(24318)

DETAILS

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.

REFERENCES

• 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)