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

• ChemBase ID: 138330
• Molecular Formular: C16H20N2O
• Molecular Mass: 256.3428
• Monoisotopic Mass: 256.15756327
• SMILES: CN1C[C@@H](C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3)CO
• Canonical SMILES: OC[C@H]1CN(C)[C@H]2[C@H](C1)c1cccc3c1c(C2)c[nH]3
• InChI: InChI=1S/C16H20N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-4,7,10,13,15,17,19H,5-6,8-9H2,1H3/t10-,13-,15-/m1/s1
• InChIKey: UFKTZIXVYHGAES-WDBKCZKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol
• IUPAC Traditional name: [(2R,4R,7R)-6-methyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraen-4-yl]methanol
• Synonyms: 6-Methylergoline-8β-methanol; 9,10-Dihydrolysergol; 6-Methyl-ergoline-8-methanol; α-Dihydro-lysergol; α-Dihydrolysergol; 8α,9-Dihydroelymoclavine; Dihydrolysergol I; LY 60722; 9,10-Dihydrolysergol; 6-甲基麦角灵-8β-甲醇; 9,10-二氢麦角醇

Database IDs

• CAS Number: 18051-16-6
• MDL Number: MFCD00134437
• PubChem SID: 162232586
• PubChem CID: 5274124

CALCULATED PROPERTIES

• Acid pKa: 15.4252
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.2352178
• LogD (pH = 7.4): 0.49929196
• Log P: 1.7075809
• Molar Refractivity: 77.0645 cm^3
• Polarizability: 30.833406 Å^3
• Polar Surface Area: 39.26 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Ethanol (hot); Methanol (hot)
• Apperance: White to Off-White Solid
• Melting Point: >265°C (dec)

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%
• Empirical Formula (Hill Notation): C16H20N2O
• Classification: Genuine Natural Compounds

DETAILS

Toronto Research Chemicals - D449150

A O-acylated derivative of Lysergol and Dehydrolysergol-I; partial agonist and antagonist at 5-HT2A, 5-HT2C and 5-HT1B receptors, and at α1-andrenergic receptors.

REFERENCES

• Pertz, H.H., et al.: J. Pharm. Pharmacol., 51, 319 (1999)