(1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one hydrochloride

• ChemBase ID: 174933
• Molecular Formular: C19H22ClNO4
• Molecular Mass: 363.83528
• Monoisotopic Mass: 363.12373587
• SMILES: c12[C@]34[C@@]5([C@@H](Cc1ccc(c2O[C@H]3C(=O)CC5)O)N(CC=C)CC4)O.Cl
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O.Cl
• InChI: InChI=1S/C19H21NO4.ClH/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11;/h2-4,14,17,21,23H,1,5-10H2;1H/t14-,17+,18+,19-;/m1./s1
• InChIKey: RGPDIGOSVORSAK-STHHAXOLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-trien-14-one hydrochloride; (1S,5R,13R,17S)-10,17-dihydroxy-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18)-trien-14-one hydrochloride
• IUPAC Traditional name: naloxone hydrochloride
• Synonyms: (5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one Hydrochloride; 17-Allyl-4,5α-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride; Nalone; Narcan; Narcanti; EN-15304; Naloxone Hydrochloride

Database IDs

• CAS Number: 357-08-4
• PubChem SID: 164230843
• PubChem CID: 5464092

CALCULATED PROPERTIES

• Acid pKa: 10.066371
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.6951441
• LogD (pH = 7.4): 1.0430377
• Log P: 1.6202211
• Molar Refractivity: 88.7222 cm^3
• Polarizability: 34.542297 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 202-205°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Product Information

• Salt Data: HCl
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Toronto Research Chemicals - N285000

Specific opioid antagonist. Narcotic antagonist.

REFERENCES

• Jasinski, D.R., et al.: J. Pharmacol. Exp. Ther., 157, 420 (1967)
• McNicholas, L.F., et al.: Drugs, 27, 81 (1967)
• Hasson, M.M.A., et al.: Anal. Profiles Drug Subs., 14, 453 (1967)
• Stowe, C., et al.: Ann. Pharmacother., 27, 447 (1967)