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

• ChemBase ID: 172449
• Molecular Formular: C16H16N2O2
• Molecular Mass: 268.31044
• Monoisotopic Mass: 268.12117776
• SMILES: c1cc2[nH]cc3C[C@@H]4C(=C[C@@H](CN4C)C(=O)O)c(c1)c23
• Canonical SMILES: CN1C[C@H](C=C2[C@H]1Cc1c[nH]c3c1c2ccc3)C(=O)O
• InChI: InChI=1S/C16H16N2O2/c1-18-8-10(16(19)20)5-12-11-3-2-4-13-15(11)9(7-17-13)6-14(12)18/h2-5,7,10,14,17H,6,8H2,1H3,(H,19,20)/t10-,14+/m0/s1
• InChIKey: ZAGRKAFMISFKIO-IINYFYTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,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-carboxylic acid
• IUPAC Traditional name: (4S,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-carboxylic acid
• Synonyms: (8β)-9,10-Didehydro-6-methylergoline-8-carboxylic Acid; (+)-Lysergic Acid; D(+)-Lysergic Acid; D-Lysergic Acid; Lysergic Acid

Database IDs

• CAS Number: 82-58-6
• PubChem SID: 164228359
• PubChem CID: 15559956

CALCULATED PROPERTIES

• Acid pKa: 3.6504738
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.7862347
• LogD (pH = 7.4): -0.8272867
• Log P: -0.7841139
• Molar Refractivity: 77.6219 cm^3
• Polarizability: 30.602657 Å^3
• Polar Surface Area: 56.33 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Pyrridine
• Apperance: Light Brown Solid
• Melting Point: >170°C (dec.)

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - L488000

Lysergic acid and iso-lysergic acid are the main cleavage products formed on alkaline hydrolysis of the alkaloids which are characteristic of ergot. Potent hallucinogen; non-selective serotonin receptor agonist.Controlled substance.

REFERENCES

• Keller, U., et al.: Biochemistry, 27, 6164 (1988)
• Mey, G., et al.: Mol. Microbiol., 46, 305 (1988)
• Steiner, U., et al.: Planta, 224, 533 (1988)