6-Alpha Naloxol

• CAT Number: I002576
• CAS Number: 20410-95-1
• Molecular Formula: C19H23NO4
• Molecular Weight: 329.40 g/mol
• Purity: ≥95%
• Synonyms: (5α,6α)-4,5-
• Target: opioid antagonist
• Solubility: 10 mM in DMSO
• Storage: -20°C
• IUPAC Name: (4R,4aS,7S,7aR,12bS)-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7,9-triol
• InChI: 1S/C19H23NO4/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/h2-4,13-14,17,21-23H,1,5-10H2/t13-,14+,17-,18-,19+/m0/s1
• InChIKey: HMWHERQFMBEHNG-AQQQZIQISA-N
• SMILES: C=CCN1CC[C@]23[C@@H]4[C@H](CC[C@]2([C@H]1CC5=C3C(=C(C=C5)O)O4)O)O

6-Alpha Naloxol (Cat No.: I002576) is a biologically active metabolite of naloxone, an opioid antagonist used to counteract opioid overdose. It exhibits partial opioid receptor activity, primarily interacting with the mu-opioid receptor. While it retains some antagonist properties, it has reduced potency compared to naloxone. Research suggests its potential role in modulating opioid effects and withdrawal symptoms. As a naloxone derivative, 6-alpha naloxol is of interest in pharmacological studies related to opioid receptor interactions, addiction treatment, and pain management strategies.

Reference

[1]. Weinstein SH, et al. Metabolites of naloxone in human urine. J Pharm Sci. 1971 Oct;60(10):1567-8.

[2]. Csaba Simon, et al. Stereoselective synthesis of β-naltrexol, β-naloxol β-naloxamine, β-naltrexamine and related compounds by the application of the mitsunobu reac. Tetrahedron
Volume 50, Issue 32, 1994, Pages 9757–9768.

[3]. Schulteis G, et al. Relative potency of the opioid antagonists naloxone and 6-alpha-naloxol to precipitate withdrawal from acute morphine dependence varies with time post-antagonist. Pharmacol Biochem Behav. 2009 Mar;92(1):157-63.