(3S)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide

• ChemBase ID: 169463
• Molecular Formular: C14H17N3O
• Molecular Mass: 243.30428
• Monoisotopic Mass: 243.13716218
• SMILES: c1(ccc2c(c1)c1c([nH]2)CC[C@@H](C1)NC)C(=O)N
• Canonical SMILES: CN[C@@H]1Cc2c(CC1)[nH]c1c2cc(cc1)C(=O)N
• InChI: InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m0/s1
• InChIKey: XPSQPHWEGNHMSK-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide
• IUPAC Traditional name: (6S)-6-(methylamino)-6,7,8,9-tetrahydro-5H-carbazole-3-carboxamide
• Synonyms: (3S)-2,3,4,9-Tetrahydro-3-(methylamino)-1H-carbazole-6-carboxamide; (S)-Frovatriptan; ent-Frovatriptan

Database IDs

• CAS Number: 158930-18-8
• PubChem SID: 162263595
• PubChem CID: 6336426

CALCULATED PROPERTIES

• Acid pKa: 14.536194
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): -2.1550536
• LogD (pH = 7.4): -1.739132
• Log P: 1.077976
• Molar Refractivity: 71.8382 cm^3
• Polarizability: 28.223196 Å^3
• Polar Surface Area: 70.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F768505

Serotonin 5-HT1B/1D receptor agonist. It is a triptan drug for the treatment of migraine headaches. Frovatriptan causes vasoconstriction of arteries and veins that supply blood to the head.

REFERENCES

• Parsons, A.A., et al.: J. Cardiovasc. Pharmacol., 30, 136 (1997)
• Siow, C.H., et al.: Cephalalgia, 24, 1045 (1997)
• Poolsup, N., et al.: J. Clin. Pharm. Ther., 30, 521 (1997)