(1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-triene-10,14,17-triol hydrate hydrochloride

• ChemBase ID: 132833
• Molecular Formular: C21H30ClNO5
• Molecular Mass: 411.9196
• Monoisotopic Mass: 411.18125075
• SMILES: c1cc(c2c3c1C[C@H]1[C@]4([C@]3(CCN1CC1CCC1)[C@@H](O2)[C@H](CC4)O)O)O.O.Cl
• Canonical SMILES: O[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@@H]2N(CC3)CC2CCC2)ccc1O)O.O.Cl
• InChI: InChI=1S/C21H27NO4.ClH.H2O/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;1H;1H2/t15-,16+,19-,20-,21+;;/m0../s1
• InChIKey: IUGXDRGXUYNFHK-XSFMULHUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17S)-4-(cyclobutylmethyl)-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 hydrate hydrochloride
• IUPAC Traditional name: nalbuphine hydrate hydrochloride
• Synonyms: 17-(Cyclobutylmethyl)-4,5-epoxymorphinan-3,6,14-triol hydrochloride hydrate; Nalbuphine hydrochloride hydrate

Database IDs

• CAS Number: 23277-43-2(anhydrous)
• EC Number: 245-549-9
• PubChem SID: 24278052; 162227110
• PubChem CID: 16219750

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: 38.206367 Å^3
• Polar Surface Area: 73.16 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble; H2O: soluble

Safety Information

• RTECS: QD3181000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Drug Control: regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Gene Information: human ... OPRK1(4986), OPRM1(4988)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - N4396

Biochem/physiol Actions
Partial agonist for μ and κ opioid receptors.