(4aS,10bS)-4-propyl-2H,3H,4H,4aH,5H,6H,10bH-naphtho[1,2-b]morpholin-9-ol hydrochloride

• ChemBase ID: 175032
• Molecular Formular: C15H22ClNO2
• Molecular Mass: 283.79368
• Monoisotopic Mass: 283.13390663
• SMILES: c1(ccc2c(c1)[C@H]1[C@H](CC2)N(CCO1)CCC)O.Cl
• Canonical SMILES: CCCN1CCO[C@@H]2[C@@H]1CCc1c2cc(cc1)O.Cl
• InChI: InChI=1S/C15H21NO2.ClH/c1-2-7-16-8-9-18-15-13-10-12(17)5-3-11(13)4-6-14(15)16;/h3,5,10,14-15,17H,2,4,6-9H2,1H3;1H/t14-,15-;/m0./s1
• InChIKey: NNEACMQMRLNNIL-YYLIZZNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aS,10bS)-4-propyl-2H,3H,4H,4aH,5H,6H,10bH-naphtho[1,2-b]morpholin-9-ol hydrochloride
• IUPAC Traditional name: (4aS,10bS)-4-propyl-2H,3H,4aH,5H,6H,10bH-naphtho[1,2-b]morpholin-9-ol hydrochloride
• Synonyms: (4aS-trans)-3,4,4a,5,6,10b-Hexahydro-4-propyl-2H-naphth[1,2-b]-1,4-oxazin-9-ol Hydrochloride; (-)-Propyl-9-hydroxynaphthoxazine Hydrochloride; (-)-PHNO; ent-Naxagolide Hydrochloride

Database IDs

• CAS Number: 100935-99-7
• PubChem SID: 164230942
• PubChem CID: 46782460

CALCULATED PROPERTIES

• Acid pKa: 9.678521
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.7821642
• LogD (pH = 7.4): 2.4567008
• Log P: 2.8758984
• Molar Refractivity: 72.1797 cm^3
• Polarizability: 28.183266 Å^3
• Polar Surface Area: 32.7 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White to Light Beige Solid
• Melting Point: 273-275°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N379805

A dopamine D2-receptor agonist. Used for treatment of extrapyramidal disorders. Antiparkinsonian drug.

REFERENCES

• Fujita, N., et al.: Brain Res., 333, 231 (1985)
• Weiss, F., et al.: Eur. J, Pharmacol., 337, 219 (1985)
• Wilson, A., et al.: J. Med. Chem., 48, 4153 (1985)
• Ginovart, N., et al.: J. Neurochem., 97, 1089 (1985)
• Willeit, M., et al.: Biol. Psychiatry, 59, 3