(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 dihydrate hydrochloride

• ChemBase ID: 133745
• Molecular Formular: C19H26ClNO6
• Molecular Mass: 399.86584
• Monoisotopic Mass: 399.14486524
• SMILES: C=CCN1CC[C@]23c4c5ccc(c4O[C@H]2C(=O)CC[C@]3([C@@H]1C5)O)O.O.O.Cl
• Canonical SMILES: C=CCN1CC[C@@]23[C@@]4([C@@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O.O.O.Cl
• InChI: InChI=1S/C19H21NO4.ClH.2H2O/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;2*1H2/t14-,17+,18+,19-;;;/m1.../s1
• InChIKey: TXMZWEASFRBVKY-IOQDSZRYSA-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 dihydrate 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 dihydrate hydrochloride
• IUPAC Traditional name: naloxone dihydrate hydrochloride
• Synonyms: Naloxone hydrochloride dihydrate

Database IDs

• CAS Number: 51481-60-8
• MDL Number: MFCD00150901
• Beilstein Number: 6260807
• PubChem SID: 162228022; 24278050
• PubChem CID: 20112022

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: ethanol: soluble3.3 mg/mL (stable for several months refrigerated if protected from light.); H2O: soluble50 mg/mL (stable for several months refrigerated if protected from light.)
• Apperance: white to off-white powder
• Optical Rotation: [α]25/D -178.6°, c = 2.5 in H2O(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... OPRD1(4985), OPRK1(4986), OPRM1(4988), OPRS1(10280)

Product Information

• Purity: ≥98% (TLC and titration)
• Salt Data: 2 H2O, HCl
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - N7758

Biochem/physiol Actions
Competitive antagonist for μ, κ, δ, and σ opioid receptors; blocks the action of σ-agonists at opioid sites.
Caution
Light sensitive.