Naltrexone hydrochloride

Base Information

• Chemical Name: Naltrexone hydrochloride
• CAS No.: 16676-29-2
• Molecular Formula: C20H23NO4^.HCl
• Molecular Weight: 377.868
• European Community (EC) Number: 240-723-0
• UNII: Z6375YW9SF
• DSSTox Substance ID: DTXSID50937236
• Wikidata: Q27096434
• NCI Thesaurus Code: C679
• RXCUI: 105069
• ChEMBL ID: CHEMBL1201149
• Mol file: 16676-29-2.mol

Synonyms:Antaxone;Celupan;EN 1639A;EN-1639A;EN1639A;Nalorex;Naltrexone;Naltrexone Hydrochloride;Nemexin;ReVia;Trexan

Chemical Property of Naltrexone hydrochloride

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 2.71E-13mmHg at 25°C
• Melting Point: 274-276 °C
• Boiling Point: 558.1 °C at 760 mmHg
• Flash Point: 291.4 °C
• PSA: 70.00000
• Density: 1.47 g/cm3
• LogP: 2.26530
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: 50 mg/mL, clear, colorless
• Water Solubility.: Soluble in water at 50mg/ml.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 377.1393859
• Heavy Atom Count: 26
• Complexity: 621

Purity/Quality:

99% ^*data from raw suppliers

Naltrexone hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1CC1CN2CCC34C5C(=O)CCC3(C2CC6=C4C(=C(C=C6)O)O5)O.Cl
• Isomeric SMILES: C1CC1CN2CC[C@]34[C@@H]5C(=O)CC[C@]3([C@H]2CC6=C4C(=C(C=C6)O)O5)O.Cl
• Recent ClinicalTrials: Harm Reduction With Pharmacotherapy (HaRP)
• Recent EU Clinical Trials: To evaluate the effect of low-dose naltrexone (LDN) on pain perception and quality of life in women
• Description: Naltrexone hydrochloride is a potent, long-acting, orally-effective narcotic antagonist useful in the management of narcotic addiction.
• Uses: Nonselective opioid receptor antagonist; congener of naloxone Naltrexone hydrochloride has been used:as an opioid antagonist, to analyse its effect on ethanol preference using Caenorhabditis elegans as a model.to determine its effectiveness in reducing the preference for substance of abuse (SOA) like nicotine and cocaine using Caenorhabditis elegans as a model.in the preparation of combinatorial drug, PXT3003 for treating Charcot-Marie-Tooth disease 1A (CMT1A) transgenic rat model Pmp22. sulfonamide, carbonic anhydrase inhibitor, anti-glaucoma agent Narcotic antagonist, In treatment of?alcoholism
• Clinical Use: Opioid antagonist: Adjunctive prophylactic treatment in patient’s previously opioid dependant Treatment of alcohol dependence
• Drug interactions: Potentially hazardous interactions with other drugs Opioids: Avoid concomitant use.

Technology Process of Naltrexone hydrochloride

There total 10 articles about Naltrexone hydrochloride 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: 83.0%

nor-14-hydroxymorphinone + Cyclopropanecarboxaldehyde (1489-69-6) → naltrexone Hydrochloride (16676-29-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; platinum on activated charcoal; In 1-methyl-pyrrolidin-2-one; methanol; at 50 ℃; for 2h; under 2068.65 Torr; Product distribution / selectivity;

Reference yield: 74.0%

noroxymorphone (33522-95-1) + Cyclopropanecarboxaldehyde (1489-69-6) → naltrexone Hydrochloride (16676-29-2)

Guidance literature:

noroxymorphone; Cyclopropanecarboxaldehyde; With hydrogen; platinum on activated charcoal; In 1-methyl-pyrrolidin-2-one; methanol; at 50 ℃; for 1h; under 2068.65 Torr;

With hydrogenchloride; In ethanol; water; pH=< 4; Product distribution / selectivity;

Reference yield:

Naltrexone (16590-41-3) → naltrexone Hydrochloride (16676-29-2)

Guidance literature:

With hydrogenchloride; In water; acetonitrile;

upstream raw materials:

Cyclopropanecarboxaldehyde

Naltrexone

noroxymorphone

oxymorphone

Downstream raw materials:

C₃₂H₃₀N₂O₃*ClH

naltrindole

naltrindole hydrochloride

N-Methylnaltrindole

Refernces

Fischer indole synthesis in water: Simple, efficient preparation of naltrindole, naltriben and analogs

10.1039/b920864j

The research presents an environmentally friendly method for synthesizing naltrindole (NTI), naltriben (NTB), and their analogs using Fischer indole synthesis under mildly acidic, purely aqueous conditions. The study explores the preparation of these compounds, which are valuable tools for opioid receptor pharmacology studies, using hydrochloride salts of naltrexone and various phenylhydrazines in boiling water, achieving good to excellent yields and high purities without the need for organic solvents or harsh acids. The chemicals that played a crucial role in this research include naltrexone hydrochloride (NTX·HCl), phenylhydrazine hydrochloride, and other substituted phenylhydrazines such as 1-methyl-1-phenylhydrazine, o-chlorophenylhydrazine, o-fluorophenylhydrazine, and o-nitrophenylhydrazine. The study also utilized dilute hydrochloric acid (HCl) to facilitate the synthesis, and in some cases, sulfuric acid (H?SO?) for comparison. The products were obtained through simple filtration or centrifugation, highlighting the simplicity and efficiency of the aqueous Fischer synthesis method.