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

• ChemBase ID: 175030
• 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-;/m1./s1
• InChIKey: NNEACMQMRLNNIL-CTHHTMFSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,10bR)-4-propyl-2H,3H,4H,4aH,5H,6H,10bH-naphtho[1,2-b]morpholin-9-ol hydrochloride
• IUPAC Traditional name: (4aR,10bR)-4-propyl-2H,3H,4aH,5H,6H,10bH-naphtho[1,2-b]morpholin-9-ol hydrochloride
• Synonyms: (4aR-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; L 647339; MK 458; (+)-PHNO Hydrochloride; Dopazinol Hydrochloride; Nazagolide HCl; Naxagolide Hydrochloride

Database IDs

• CAS Number: 99705-65-4
• PubChem SID: 164230940
• PubChem CID: 57532

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: Ethanol; Methanol; Water
• Apperance: Off-White to Tan Solid
• Melting Point: 296-298°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - N379800

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