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

• ChemBase ID: 127281
• Molecular Formular: C16H17N3O
• Molecular Mass: 267.32568
• Monoisotopic Mass: 267.13716218
• SMILES: O=C(N)[C@@H]1C=C2c3cccc4c3c(c[nH]4)C[C@H]2N(C1)C
• Canonical SMILES: CN1C[C@@H](C=C2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)N
• InChI: InChI=1S/C16H17N3O/c1-19-8-10(16(17)20)5-12-11-3-2-4-13-15(11)9(7-18-13)6-14(12)19/h2-5,7,10,14,18H,6,8H2,1H3,(H2,17,20)/t10-,14-/m1/s1
• InChIKey: GENAHGKEFJLNJB-QMTHXVAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,7R)-6-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: (+)-lysergamide
• Synonyms: and LA-111; Ergine; LSA; d-lysergic acid amidA; d-lysergamidA; ErginA; (8β)-9,10-Didehydro-6-methylergoline-8-carboxamide; (+)-Lysergamide; D-Lysergic Acid Amide; Ergine; Lysergic Acid Amide; Lysergamide

Database IDs

• CAS Number: 478-94-4
• PubChem SID: 162221602
• PubChem CID: 442072
• CHEBI ID: 4819
• CHEMBL: 227213
• Chemspider ID: 390611
• Wikipedia Title: Ergine

CALCULATED PROPERTIES

• Acid pKa: 16.337584
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.3876082
• LogD (pH = 7.4): 0.3807116
• Log P: 1.1205469
• Molar Refractivity: 79.4441 cm^3
• Polarizability: 31.31988 Å^3
• Polar Surface Area: 62.12 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Brown Solid
• Melting Point: >200°C (dec.)

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

Pharmacology Properties

• Admin Routes: Oral, Intramuscular
• Excretion: renal
• Metabolism: hepatic
• Legal Status: Class A (UK); Schedule III (US)
• Pregnancy Category: X

DETAILS

Toronto Research Chemicals - L487990

An alkaloid in abundance in tall fescue, resulted in vasoconstriction similar to that previously shown for the ergot alkaloids ergonovine and ergotamine.

REFERENCES

• Knaus, H., et al.: Biochemistry, 33, 5819 (1994)
• Bennett, J., et al.: Clin. Microbiol. Rev., 16, 497 (1994)
• Sulyok, M., et al.: Anal. Bioanal. Chem., 389, 1505 (1994)
• Imlach, W., et al.: J. Pharmacol. Exp. Ther., 327, 657 (1994)