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

• ChemBase ID: 174238
• Molecular Formular: C17H22N2S
• Molecular Mass: 286.43498
• Monoisotopic Mass: 286.15036971
• SMILES: C1[C@H]2[C@H](N(C[C@@H]1CSC)C)Cc1c3c2cccc3[nH]c1
• Canonical SMILES: CSC[C@H]1CN(C)[C@H]2[C@H](C1)c1cccc3c1c(C2)c[nH]3
• InChI: InChI=1S/C17H22N2S/c1-19-9-11(10-20-2)6-14-13-4-3-5-15-17(13)12(8-18-15)7-16(14)19/h3-5,8,11,14,16,18H,6-7,9-10H2,1-2H3/t11-,14-,16-/m1/s1
• InChIKey: HEZLHSNBFOCKCQ-DJSGYFEHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,7R)-6-methyl-4-[(methylsulfanyl)methyl]-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene
• IUPAC Traditional name: (2R,4R,7R)-6-methyl-4-[(methylsulfanyl)methyl]-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]hexadeca-1(16),9,12,14-tetraene
• Synonyms: (8β)-6-Methyl-8-[(methylthio)methyl]ergoline; LY 062; LY 116467; 6-Methyl Pergolide

Database IDs

• CAS Number: 57202-76-3
• PubChem SID: 164230148
• PubChem CID: 21154394

CALCULATED PROPERTIES

• Acid pKa: 17.350536
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.18418153
• LogD (pH = 7.4): 1.8107537
• Log P: 3.3459594
• Molar Refractivity: 87.7441 cm^3
• Polarizability: 35.153633 Å^3
• Polar Surface Area: 19.03 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethylformamide; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >256°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M326070

Potent antagonist of 5-HT2A and 5-HT2B receptors on porcine cardiac valves, it also activates brain dopaminergic receptors and lowers cranial DOPAC levels in rats.

REFERENCES

• Fuller, R.W., et al.: Neuroendocrinol., 36, 285 (1983)
• Goernemann, T., et al.: J. Pharmacol. Exp. Ther., 324, 1136 (1983)