(1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-4-methyl-14-oxo-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-4-ium bromide

• ChemBase ID: 173912
• Molecular Formular: C21H26BrNO4
• Molecular Mass: 436.33944
• Monoisotopic Mass: 435.10452032
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@]4([C@@]3([C@H](C(=O)CC4)O2)CC[N+]1(CC1CC1)C)O)O.[Br-]
• Canonical SMILES: O=C1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2[N+](CC3)(C)CC2CC2)ccc1O)O.[Br-]
• InChI: InChI=1S/C21H25NO4.BrH/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13;/h4-5,12,16,19,25H,2-3,6-11H2,1H3;1H/t16-,19+,20+,21-,22?;/m1./s1
• InChIKey: IFGIYSGOEZJNBE-KNLJMPJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,17S)-4-(cyclopropylmethyl)-10,17-dihydroxy-4-methyl-14-oxo-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 bromide
• IUPAC Traditional name: methylnaltrexone bromide
• Synonyms: (5α)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxomorphinanium Bromide; Methylnaltrexone; Methylnaltrexone Bromide; N-Cyclopropylmethyl-noroxymorphone Methobromide; N-Methylnaltrexone Bromide; Naltrexone Methyl Bromide; Naltrexone Methobromide; Relistor; MRZ 2663BR; N-Methyl Naltrexone Bromide

Database IDs

• CAS Number: 73232-52-7
• PubChem SID: 164229822
• PubChem CID: 5361917

CALCULATED PROPERTIES

• Acid pKa: 9.903289
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.4905596
• LogD (pH = 7.4): -2.3443832
• Log P: -2.492788
• Molar Refractivity: 107.4151 cm^3
• Polarizability: 37.679363 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Pink Solid
• Melting Point: 237-239°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M320350

A metabolite of Naltrexone (N285750). Methylnaltrexone (MNTX), a selective μ-opioid receptor antagonist, functions as a peripherally acting receptor antagonist in tissues of the gastrointestinal tract.

REFERENCES

• Wall, M., et al.: Drug Metab. Dispos., 12, 677 (1984)
• Jones, D., et al.: .: Bioorg. Med. Chem., 13, 6727 ( 2005), Chen, T., et al.: Drugs Future, 32, 771 (1984)