(4R,7R)-N,N-diethyl-9-hydroxy-6-methyl-10-oxo-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,12(16),13-tetraene-4-carboxamide

• ChemBase ID: 167715
• Molecular Formular: C20H25N3O3
• Molecular Mass: 355.4308
• Monoisotopic Mass: 355.18959168
• SMILES: c1cc2NC(=O)C3(C[C@@H]4C(=C[C@H](CN4C)C(=O)N(CC)CC)c(c1)c23)O
• Canonical SMILES: CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1C(C2)(O)C(=O)N3)CC
• InChI: InChI=1S/C20H25N3O3/c1-4-23(5-2)18(24)12-9-14-13-7-6-8-15-17(13)20(26,19(25)21-15)10-16(14)22(3)11-12/h6-9,12,16,26H,4-5,10-11H2,1-3H3,(H,21,25)/t12-,16-,20?/m1/s1
• InChIKey: YSZSHHCNLVHCNV-VRORWYBRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N,N-diethyl-9-hydroxy-6-methyl-10-oxo-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,12(16),13-tetraene-4-carboxamide
• IUPAC Traditional name: (4R,7R)-N,N-diethyl-9-hydroxy-6-methyl-10-oxo-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(15),2,12(16),13-tetraene-4-carboxamide
• Synonyms: N,N-Diethyl-2,3-dihydro-3-hydroxy-2-oxo-lysergamide; (8β)-9,10-Didehydro-N,N-diethyl-2,3-dihydro-3-hydroxy-6-methyl-2-oxoergoline-8-carboxamide; 2-Oxo-3-hydroxy-LSD; 2-Oxo-3-hydroxy Lysergic Acid Diethylamide; 2,3-Dihydro-3-hydroxy-2-oxo Lysergide

Database IDs

• CAS Number: 111295-09-1
• PubChem SID: 162261848
• PubChem CID: 10155149

CALCULATED PROPERTIES

• Acid pKa: 11.563037
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.2035837
• LogD (pH = 7.4): -0.43066922
• Log P: 0.49090308
• Molar Refractivity: 102.0648 cm^3
• Polarizability: 38.300793 Å^3
• Polar Surface Area: 72.88 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449560

2,3-Dihydro-3-hydroxy-2-oxo Lysergide is a major metabolite of Lysergide (L488010). Controlled Substance.

REFERENCES

• Reuschel, S.A. et al.: J. Anal. Toxicol., 23, 306 (1999)
• Klette, K.L. et al.: J. Anal. Toxicol., 24, 550 (1999)