(1S,5R,13R,17S)-10,17-dihydroxy-4-[(2H5)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

• ChemBase ID: 174934
• Molecular Formular: C19H21NO4
• Molecular Mass: 327.37434
• Monoisotopic Mass: 327.14705816
• SMILES: c12[C@]34[C@@]5([C@@H](Cc1ccc(c2O[C@H]3C(=O)CC5)O)N(CC=C)CC4)O
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O
• InChI: InChI=1S/C19H21NO4/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/t14-,17+,18+,19-/m1/s1
• InChIKey: UZHSEJADLWPNLE-GRGSLBFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-10,17-dihydroxy-4-[(^2H₅)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
• IUPAC Traditional name: (1S,5R,13R,17S)-10,17-dihydroxy-4-[(^2H₅)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
• Synonyms: 5α)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl-d5)morphinan-6-one Hydrochloride; 17-Allyl-4,5α-epoxy-3,14-dihydroxymorphinan-6-one-d5 Hydrochloride; Nalone-d5; Narcan-d5; Narcanti-d5; EN-15304-d5; Naloxone-d5

Database IDs

• PubChem SID: 164230844
• PubChem CID: 71750914

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: 34.5423 Å^3
• Polar Surface Area: 70.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: >155°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N285002

Labelled 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)