(4R,7R)-N,N-diethyl-6-(2H3)methyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

• ChemBase ID: 172452
• Molecular Formular: C20H25N3O
• Molecular Mass: 323.432
• Monoisotopic Mass: 323.19976244
• SMILES: c1cc2[nH]cc3C[C@@H]4C(=C[C@H](CN4C)C(=O)N(CC)CC)c(c1)c23
• Canonical SMILES: CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC
• InChI: InChI=1S/C20H25N3O/c1-4-23(5-2)20(24)14-9-16-15-7-6-8-17-19(15)13(11-21-17)10-18(16)22(3)12-14/h6-9,11,14,18,21H,4-5,10,12H2,1-3H3/t14-,18-/m1/s1
• InChIKey: VAYOSLLFUXYJDT-RDTXWAMCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-N,N-diethyl-6-(^2H₃)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 Traditional name: (4R,7R)-N,N-diethyl-6-(^2H₃)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
• Synonyms: (8β)-9,10-Didehydro-N,N-diethyl-6-(methyl-d3)ergoline-8-carboxamide; (+)-LSD-d3; Lysergic Acid-d3 Diethylamide; Delysid-d3; Dextrolysergic Acid-d3 Diethylamide; LSD-d3; N,N-Diethyl-(+)-lysergamide-d3; N,N-Diethyllysergamide-d3; d-LSD-d3; Lysergide-d3

Database IDs

• CAS Number: 136765-38-3
• PubChem SID: 164228362
• PubChem CID: 46782093

CALCULATED PROPERTIES

• Acid pKa: 17.018362
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.15770875
• LogD (pH = 7.4): 1.6029848
• Log P: 2.281515
• Molar Refractivity: 98.7347 cm^3
• Polarizability: 38.70497 Å^3
• Polar Surface Area: 39.34 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L488012

Labelled Lysergide (L488010). Potent hallucinogen; non-selective serotonin receptor agonist. Has been used experimentally as adjunct in study and treatment of mental disorders.Controlled substance.

REFERENCES

• Hoffer, et al.: Clin. Pharmacol. Ther., 6, 183 (1965)
• Keller, U., et al.: Biochemistry, 27, 6164 (1965)
• Mey, G., et al.: Mol. Microbiol., 46, 305 (1965)
• Steiner, U., et al.: Planta, 224, 533 (1965)