6,16-diazatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),10,12,14-tetraene

• ChemBase ID: 169844
• Molecular Formular: C14H16N2
• Molecular Mass: 212.29024
• Monoisotopic Mass: 212.13134852
• SMILES: c1ccc2c(c1)c1c([nH]2)C2N(CC1)CCC2
• Canonical SMILES: C1CN2C(C1)c1[nH]c3c(c1CC2)cccc3
• InChI: InChI=1S/C14H16N2/c1-2-5-12-10(4-1)11-7-9-16-8-3-6-13(16)14(11)15-12/h1-2,4-5,13,15H,3,6-9H2
• InChIKey: LXJWBHIVLXMHDZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,16-diazatetracyclo[7.7.0.0^2,^6.0^1^0,^1^5]hexadeca-1(9),10,12,14-tetraene
• IUPAC Traditional name: 6,16-diazatetracyclo[7.7.0.0^2,^6.0^1^0,^1^5]hexadeca-1(9),10,12,14-tetraene
• Synonyms: 2,3,5,6,11,11b-Hexahydro-1H-indolizino[8,7-b]indole; (+/-)-Harmicine; Harmicine

Database IDs

• CAS Number: 885-40-5
• PubChem SID: 162263976
• PubChem CID: 372331

CALCULATED PROPERTIES

• Acid pKa: 16.375172
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.42923325
• LogD (pH = 7.4): 1.3234956
• Log P: 2.4388587
• Molar Refractivity: 66.0855 cm^3
• Polarizability: 26.657877 Å^3
• Polar Surface Area: 19.03 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H105200

Harmicine is a tetracyclic β-carboline alkaloid as potent α2-adrenoceptor antagonist.

REFERENCES

• Cheng, Y., et al.: Biochem. Pharmacol., 22, 3099 (1973)
• Kassack, M., et al.: J. Biomol. Screen, 7, 233 (1973)
• Wittig, T., et al.: J. Med. Chem., 47, 4155 (1973)