(1S,5R,13R,14S,17R)-4-[(2H5)prop-2-en-1-yl]-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraene-10,14-diol hydrochloride

• ChemBase ID: 174926
• Molecular Formular: C19H22ClNO3
• Molecular Mass: 347.83588
• Monoisotopic Mass: 347.12882125
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@H]4[C@@]3([C@H]([C@H](C=C4)O)O2)CCN1CC=C)O.Cl
• Canonical SMILES: C=CCN1CC[C@@]23[C@@H]4[C@H]1Cc1c3c(O[C@H]2[C@H](C=C4)O)c(cc1)O.Cl
• InChI: InChI=1S/C19H21NO3.ClH/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20;/h2-6,12-13,15,18,21-22H,1,7-10H2;1H/t12-,13+,15-,18-,19-;/m0./s1
• InChIKey: NAHATSPWSULUAA-ZQGPYOJVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-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),8,10,15-tetraene-10,14-diol hydrochloride
• IUPAC Traditional name: (1S,5R,13R,14S,17R)-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),8,10,15-tetraene-10,14-diol hydrochloride
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-17-(2-propen-1-yl)morphinan-3,6-diol-d5 Hydrochloride; 17-Allyl-7,8-didehydro-4,5α-epoxymorphinan-3,6α-diol-d5 Hydrochloride; N-Allylnormorphine-d5 Hydrochloride; Naline-d5 Hydrochloride; Nalorphine-d5 Hydrochloride; Nalorphine-d5 Hydrochloride

Database IDs

• PubChem SID: 164230836
• PubChem CID: 71750905

CALCULATED PROPERTIES

• Acid pKa: 10.204004
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.1795136
• LogD (pH = 7.4): 0.48296607
• Log P: 1.6752604
• Molar Refractivity: 89.2851 cm^3
• Polarizability: 34.137146 Å^3
• Polar Surface Area: 52.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: >255°C (dec.)

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - N284452

Narcotic antagonist.Controlled substance.

REFERENCES

• McCawley, H., et al.: J. Pharmacol., 82, 339 (1944)
• Goldenthal, E.I., et al.: Toxicol. Appl. Pharmacol., 18, 185 (1944)
• Zubair, M.U., et al.: Anal. Profiles Drug Subs., 18, 195 (1944)