(2R,4R,7R)-N-[3-(dimethylamino)propyl]-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene-4-carboxamide

• ChemBase ID: 166159
• Molecular Formular: C23H32N4O
• Molecular Mass: 380.52638
• Monoisotopic Mass: 380.25761166
• SMILES: C1[C@H]2[C@H](N(C[C@@H]1C(=O)NCCCN(C)C)CC=C)Cc1c3c2cccc3[nH]c1
• Canonical SMILES: C=CCN1C[C@@H](C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)NCCCN(C)C
• InChI: InChI=1S/C23H32N4O/c1-4-10-27-15-17(23(28)24-9-6-11-26(2)3)12-19-18-7-5-8-20-22(18)16(14-25-20)13-21(19)27/h4-5,7-8,14,17,19,21,25H,1,6,9-13,15H2,2-3H3,(H,24,28)/t17-,19-,21-/m1/s1
• InChIKey: JJTHJEHDIBAMMM-YFVAEKQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,7R)-N-[3-(dimethylamino)propyl]-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
• IUPAC Traditional name: (2R,4R,7R)-N-[3-(dimethylamino)propyl]-6-(prop-2-en-1-yl)-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene-4-carboxamide
• Synonyms: N-[3-(Dimethylamino)propyl]-6-(2-propen-1-yl)-(8β)-ergoline-8-carboxamide; (5R,8R,10R)-6-Allyl-N-[3-(dimethylamino)propyl]ergoline-8-carboxamide; FCE 21590; Desethylcarbamoyl Cabergoline

Database IDs

• CAS Number: 85329-86-8
• PubChem SID: 162260292
• PubChem CID: 10927015

CALCULATED PROPERTIES

• Acid pKa: 16.104643
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.6705093
• LogD (pH = 7.4): -0.46616268
• Log P: 2.3429694
• Molar Refractivity: 115.615 cm^3
• Polarizability: 45.687744 Å^3
• Polar Surface Area: 51.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Tan Solid
• Melting Point: 188-190°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D288860

A metabolite of Cabergoline, having affinity for D1 and D2 dopamine receptors in rat striatum

REFERENCES

• Battaglia, R., et al.: Xenobiotica, 23, 1377 (1993)
• Miyagi, M., et al.: Biol. Pharm. Bull., 19, 1210 (1993)