(1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-14-oxo-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-4-ium iodide

• ChemBase ID: 131785
• Molecular Formular: C20H24INO4
• Molecular Mass: 469.31333
• Monoisotopic Mass: 469.07500625
• SMILES: C[N+]1(CC[C@]23c4c5ccc(c4O[C@H]2C(=O)CC[C@]3([C@H]1C5)O)O)CC=C.[I-]
• Canonical SMILES: C=CC[N+]1(C)CC[C@@]23[C@@]4([C@H]1Cc1c3c(O[C@H]2C(=O)CC4)c(cc1)O)O.[I-]
• InChI: InChI=1S/C20H23NO4.HI/c1-3-9-21(2)10-8-19-16-12-4-5-13(22)17(16)25-18(19)14(23)6-7-20(19,24)15(21)11-12;/h3-5,15,18,24H,1,6-11H2,2H3;1H/t15-,18+,19+,20-,21?;/m1./s1
• InChIKey: ICONPJDAXITIPI-UXYWFNEESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-14-oxo-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-4-ium iodide
• IUPAC Traditional name: (1S,5R,13R,17S)-10,17-dihydroxy-4-methyl-14-oxo-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-4-ium iodide
• Synonyms: (5α,17R)-4,5-Epoxy-3,14-dihydroxy-17-methyl-6-oxo-17-(2-propenyl)-morphinanium iodide; N-Methylnaloxonium iodide; Naloxone methiodide

Database IDs

• CAS Number: 93302-47-7
• MDL Number: MFCD00078592
• PubChem SID: 162226062; 24897480
• PubChem CID: 16219719

CALCULATED PROPERTIES

• Acid pKa: 9.903247
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.539887
• LogD (pH = 7.4): -2.3936982
• Log P: -2.5421154
• Molar Refractivity: 104.6358 cm^3
• Polarizability: 36.31935 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: white to tan solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - N129

Biochem/physiol Actions
Quaternary salt of naloxone that, like the parent compound, is a nonselective antagonist at opioid receptors. It does not cross the blood-brain barrier.