6beta-Naltrexol

Base Information

• Chemical Name: 6beta-Naltrexol
• CAS No.: 49625-89-0
• Deprecated CAS: 163713-44-8
• Molecular Formula: C20H25 N O4
• Molecular Weight: 343.423
• European Community (EC) Number: 803-959-0
• UNII: J0W963M37T
• DSSTox Substance ID: DTXSID80197942
• Nikkaji Number: J291.598G
• Wikipedia: 6%CE%B2-Naltrexol
• Wikidata: Q19598102
• Pharos Ligand ID: MTXB3Q73XKSP
• ChEMBL ID: CHEMBL140278
• Mol file: 49625-89-0.mol

Synonyms:6 alpha-hydroxynaltrexone;6 alpha-naltrexol;6 beta-hydroxynaltrexone;6 beta-hydroxynaltrexone, hydrochloride;6 beta-naltrexol;6,beta-naltrexol;6alpha-hydroxynaltrexone;beta-naltrexol;N-cyclopropylmethyl-7,8-dihydro-14-hydroxynorisomorphine;naltrexol

Chemical Property of 6beta-Naltrexol

Chemical Property:

• Vapor Pressure: 2.9E-13mmHg at 25°C
• Melting Point: 90-96?C
• Boiling Point: 557.5°Cat760mmHg
• PKA: 9.39±0.60(Predicted)
• Flash Point: 291°C
• PSA: 73.16000
• Density: 1.48g/cm³
• LogP: 1.25510
• Storage Temp.: Refrigerator
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 343.17835828
• Heavy Atom Count: 25
• Complexity: 582

Purity/Quality:

98%,99%, ^*data from raw suppliers

6β-Naltrexol solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC1CN2CCC34C5C(CCC3(C2CC6=C4C(=C(C=C6)O)O5)O)O
• Isomeric SMILES: C1C[C@]2([C@H]3CC4=C5[C@@]2(CCN3CC6CC6)[C@H]([C@@H]1O)OC5=C(C=C4)O)O
• Recent ClinicalTrials: Evaluation of Intranasal Naltrexone and Naloxone
• General Description: 6β-Naltrexol HCl, also known as 6β-hydroxynaltrexone or β-naltrexol, is a derivative of naltrexone with a hydroxyl group at the 6β-position, enhancing its potential for further functionalization. It retains high affinity for μ-opioid receptors due to its morphinan core, 4,5α-epoxy group, and 3,14-dihydroxy moieties. The 6β-position is structurally versatile, accommodating various electrophilic groups without substantial loss of binding affinity, making it a promising scaffold for developing selective and potent opioid receptor ligands. The findings highlight the flexibility of the receptor binding site near the 6β-substituent, enabling diverse modifications for improved pharmacological properties.

Technology Process of 6beta-Naltrexol

There total 11 articles about 6beta-Naltrexol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.7%

Naltrexone (16590-41-3) → β-naltrexol (49625-89-0)

Guidance literature:

With Aminoiminomethanesulfinic acid; sodium hydroxide; In water monomer; at 80 ℃; for 1.5h;

DOI:10.1016/j.bmcl.2014.09.072

Reference yield: 90.0%

naltrexone Hydrochloride (16676-29-2) → β-naltrexol (49625-89-0)

Guidance literature:

With sodium hydroxide; Aminoiminomethanesulfinic acid; In water; at 20 - 85 ℃; for 2.41667h;

Reference yield: 90.0%

C29H30N2O8 → β-naltrexol (49625-89-0)

Guidance literature:

With potassium hydroxide; In ethanol; for 0.166667h; Heating;

DOI:10.1016/S0040-4020(01)85541-1

upstream raw materials:

Naltrexone

17-cyclopropylmethyl-4,5α-epoxy-3-methoxymorphinan-6β,14β-diol

C₃₅H₃₉ClN₂O₈

3-acetoxy-6α,14-dihydroxy-17-(cyclopropylmethyl)-4,5α-epoxymorphinan

Downstream raw materials:

C₃₅H₃₉ClN₂O₈

17-(cyclopropylmethyl)-3-(triphenylmethoxy)-4,5α-epoxy-6β,14-dihydroxymorphinan

3-(benzyloxy)-4,5α-epoxy-6β,14-dihydroxy-17-(cyclopropylmethyl)morphinan

17-(cyclopropylmethyl)-3-(triphenylmethoxy)-6β-(9-antracylmethoxy)-4,5α-epoxy-14-hydroxymorphinan

Refernces

Electrophilic opioid ligands. Oxygen tethered α-methylene-γ-lactone, acrylate, isothiocyanate, and epoxide derivatives of 6β-naltrexol

10.1021/jm00091a005

6β-Naltrexol is a derivative of naltrexone, an opioid receptor antagonist known for its high affinity and selectivity for μ-opioid receptors. The addition of an ethoxy group at the 6β-position of naltrexone forms 6β-naltrexol. This modification allows for further functionalization with electrophilic groups, which are the focus of this study. The chemical structure of 6β-naltrexol includes a morphinan core with a 4,5α-epoxy group, a 3,14-dihydroxy moiety, and an ethoxy group at the 6β-position. The research concludes that the 6β-position of naltrexol can accommodate a variety of electrophilic groups without significant loss of binding affinity. The study provides insights into the structural requirements for high-affinity binding and irreversibility at opioid receptors, which could be valuable for designing more selective and potent opioid receptor ligands. The findings suggest that the region of the binding site accommodating the 6β-substituent is quite large, allowing for significant structural variation.