N-Methyl Naltrexone Glucuronide

CAS: 1067644-15-8

Ref. TR-M493190

Product Information

• Name: N-Methyl Naltrexone Glucuronide
• Synonyms: (2S,3S,4S,5R,6S)-6-[[(3R,4R,4aS,12bS)-3-(cyclopropylmethyl)-4a-hydroxy-3-methyl-7-oxo-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-9-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Description

Applications N-Methyl Naltrexone Glucuronide is metabolite of Naltrexone (N285750). Methylnaltrexone (MNTX; M320350), a selective μ-opioid receptor (MOR) antagonist, functions as a peripherally acting receptor antagonist in tissues of the gastrointestinal tract. When opiates activate μ-opioid receptors (MORs) they trigger signaling pathways that lead to tolerance and hyperalgesia. Methylnaltrexone (M320350) is positively charged and therefore does not cross the blood brain barier. Mice given morphine with methylnaltrexone experienced pain relief without degeloping tolerance.
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 (2007); Chem. and Eng. News p.4 Jan. 23, (2017)

• Brand: TRC

Chemical properties

• Molecular weight: 532.56
• Formula: C₂₇H₃₄NO₁₀
• Color/Form: Neat
• InChI: InChI=1S/C27H33NO10/c1-28(11-12-2-3-12)9-8-26-17-13-4-5-15(36-25-20(32)18(30)19(31)22(38-25)24(33)34)21(17)37-23(26)14(29)6-7-27(26,35)16(28)10-13/h4-5,12,16,18-20,22-23,25,30-32,35H,2-3,6-11H2,1H3/p+1/t16-,18+,19+,20-,22+,23?,25-,26+,27-,28-/m1/s1
• SMILES: C[N@+]1(CC2CC2)CC[C@]23c4c5ccc(O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O)c4OC2C(=O)CC[C@@]3(O)[C@H]1C5