(1S,5R,13R,14S,17S)-4-[cyclobutyl(2H2)methyl](14-2H)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-10,14,17-triol

• ChemBase ID: 174913
• Molecular Formular: C21H27NO4
• Molecular Mass: 357.44338
• Monoisotopic Mass: 357.19400835
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H]([C@H](CC4)O)O2)CCN1CC1CCC1)O)O
• Canonical SMILES: O[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC2CCC2)ccc1O)O
• InChI: InChI=1S/C21H27NO4/c23-14-5-4-13-10-16-21(25)7-6-15(24)19-20(21,17(13)18(14)26-19)8-9-22(16)11-12-2-1-3-12/h4-5,12,15-16,19,23-25H,1-3,6-11H2/t15-,16+,19-,20-,21+/m0/s1
• InChIKey: NETZHAKZCGBWSS-CEDHKZHLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17S)-4-[cyclobutyl(^2H₂)methyl](14-^2H)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-triene-10,14,17-triol
• IUPAC Traditional name: (1S,5R,13R,14S,17S)-4-[cyclobutyl(^2H₂)methyl](14-^2H)-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10-triene-10,14,17-triol
• Synonyms: (5α,6α)-17-(Cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol-d3; N-Cyclobutylmethyl-14-hydroxydihydronormorphine-d3; Nalbuphine-d3

Database IDs

• PubChem SID: 164230823
• PubChem CID: 71750895

CALCULATED PROPERTIES

• Acid pKa: 10.392419
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.743254
• LogD (pH = 7.4): -0.7291438
• Log P: 1.1929245
• Molar Refractivity: 96.9999 cm^3
• Polarizability: 38.206432 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 222-223°C

Safety Information

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

DETAILS

Toronto Research Chemicals - N232502

Labelled Nalbuphine (N232500). Nalbuphine is a mixed opioid agonist-antagonist. Nalbuphine is an analgesic (narcotic).

REFERENCES

• Holtzman, S.G., et al.: J. Pharmacol. Exp. Ther., 201, 55 (1977)
• Errick, J.K., et al.: Drugs, 26, 191 (1977)