16676-29-2

Basic information

• Product Name: Naltrexone hydrochloride
• Synonyms: 17-(cyclopropylmethyl)-4,5-alpha-epoxy-3,14-dihydroxy-morphinan-6-onehydroch;17-(cyclopropylmethyl)-4,5-alpha-epoxy-3,14-dihydroxy-morphinan-6-onhydr;17-(cyclopropylmethyl)-4,5-alpha-oxy-3,14-dihydoxy-morphinan-6-onhydrochlo;17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-morphinan-6-onhydrochlor;en1639a;n-cyclopropylmethyl-noroxymorphonehydrochloride;nih8503;N-CYCLOPROPYLMETHYL-14-HYDROXYDI-HYDROMORPHINONE HYDROCHLORIDE
• CAS NO: 16676-29-2
• Molecular Formula: C₂₀H₂₃NO₄*ClH
• Molecular Weight: 377.86
• EINECS: 240-723-0
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Antagonists;Opioids;Pharmacologicals;Enzyme Inhibitors;Enzyme Inhibitors by Type;Other;Opioid receptor and opioid-like receptor;Chiral Reagents
• Mol File: 16676-29-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 274-2760C
• Boiling Point: 558.1 °C at 760 mmHg
• Flash Point: 291.4 °C
• Appearance: white crystalline powder
• Density: 1.47 g/cm3
• Vapor Pressure: 2.71E-13mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: H2O: 50 mg/mL, clear, colorless
• Water Solubility: Soluble in water at 50mg/ml.
• Sensitive: Light Sensitive
• Merck: 13,6389
• BRN: 3580333
• CAS DataBase Reference: Naltrexone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Naltrexone hydrochloride(16676-29-2)
• EPA Substance Registry System: Naltrexone hydrochloride(16676-29-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-36
• WGK Germany: 3
• RTECS: QD2160000
• F: 8-10
• Hazardous Substances Data: 16676-29-2(Hazardous Substances Data)

Usage

Description

Naltrexone hydrochloride, a potent, long-acting, and orally-effective narcotic antagonist, is a white crystalline powder. It is a congener of naloxone and is used in the management of narcotic addiction. Branded as TREXAN, this compound is a nonselective opioid receptor antagonist.

Uses

Used in Pharmaceutical Industry:
Naltrexone hydrochloride is used as a narcotic antagonist for the treatment of alcoholism. It helps in managing narcotic addiction by blocking the effects of opioids in the brain, thus reducing the desire for alcohol or other drugs.
Used in Research and Development:
Naltrexone hydrochloride is used as an opioid antagonist in research to analyze its effect on ethanol preference using Caenorhabditis elegans as a model. It is also utilized to determine its effectiveness in reducing the preference for substances of abuse (SOA) like nicotine and cocaine using the same model organism.
Used in Drug Development for Specific Diseases:
In the preparation of combinatorial drug PXT3003, Naltrexone hydrochloride is used for treating Charcot-Marie-Tooth disease 1A (CMT1A) transgenic rat model Pmp22. This application highlights its potential in developing novel therapies for specific medical conditions.
Used in Ophthalmology:
Naltrexone hydrochloride is used as a sulfonamide, carbonic anhydrase inhibitor, and anti-glaucoma agent. Its application in this field aids in the management of glaucoma by reducing intraocular pressure.

Originator

Endo (USA)

Biological Activity

Opioid antagonist.

Biochem/physiol Actions

Competitive antagonist for μ, κ, δ, and σ-opioid receptors; has greater oral efficacy and longer duration of action than naloxone.

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.

Metabolism

Naltrexone is well absorbed from the gastrointestinal tract but is subject to considerable first-pass metabolism and may undergo enterohepatic recycling. It is extensively metabolised in the liver and the major metabolite, 6-β-naltrexol, may also possess weak opioid antagonist activity. It is excreted mainly in the urine, <5% is excreted in the faeces. The renal clearance for naltrexone ranges from 30-127 mL/min and suggests that renal elimination is primarily by glomerular filtration

Purification Methods

This narcotic antagonist has been purified by recrystallisation from MeOH and dried in air. The free base has m 168-170o after recrystallisation from Me2CO. [Cone et al. J Pharm Sci 64 618 1975, Gold et al. Med Res Rev 2 211 1982.]

InChI:InChI=1/C20H23NO4.ClH/c22-13-4-3-12-9-15-20(24)6-5-14(23)18-19(20,16(12)17(13)25-18)7-8-21(15)10-11-1-2-11;/h3-4,11,15,18,22,24H,1-2,5-10H2;1H/t15-,18+,19+,20-;/m1./s1

Upstream product

• 1489-69-6 Cyclopropanecarboxaldehyde 
• 64643-76-1 4,5α-epoxy-3,14-diacetoxy-6-oxo-17-methylmorphinan 
• 33522-95-1 noroxymorphone 
• 115-37-7 thebaine 
• 76-42-6 Oxycodone 
• 76-41-5 oxymorphone 
• 16590-41-3 Naltrexone 

Downstream Products

• 111555-53-4 naltrindole 
• 111469-81-9 naltrindole hydrochloride 
• 111555-57-8 N-Methylnaltrindole 
• 105618-27-7 Binaltorphimine dihydrochloride 
• 111555-58-9 naltriben 
• 105618-26-6 norbinaltorphimine 
• 105618-26-6 nor-binaltorphimine dihydrochloride 
• 121962-99-0 14-Acetoxy-17-(cyclopropylmethyl)-3-hydroxy-6-oxo-4,5α-epoxymorphinan 
• 129468-29-7 C₄₇H₅₀N₂O₈ 
• 129468-28-6 7-benzylidene-7-dehydronaltrexonee 
• 153611-34-8 (E)-7-benzylidenenaltrexone 
• 155732-90-4 17-cyclopropylmethyl-4,5α-epoxy-14β-hydroxy-3-[(1-phenyl-1H-tetrazol-5-yl)oxy]-morphinan-6-one 
• 153567-11-4 2,2,2-trichloroethyl (4'R,7a'R,12b'S)-9'-(benzyloxy)-1',2',4',6'-tetrahydro-3'H,7a'Hspiro[[1,3]dioxolane-2,7'-[4,12]methanobenzofuro[3,2-e]isoquinoline]-3'-carboxylate 

Related news

Design of controlled release inert matrices of Naltrexone hydrochloride (cas 16676-29-2) based on percolation concepts09/27/2019

The percolation theory is a statistical theory able to study chaotic or disordered systems that has been applied in the pharmaceutical field since 1987. Through the application of this theory, the design of controlled release inert matrices has been improved. The aim of the present paper is to e...detailed

Research ArticlesStructural characterization of anhydrous naloxone‐ and Naltrexone hydrochloride (cas 16676-29-2) by high resolution laboratory X‐ray powder diffraction and thermal analysis09/24/2019

ABSTRACTThe crystal structures of the analgesic compounds anhydrous naloxone and naltrexone hydrochloride were determined ab initio from high resolution laboratory X‐ray powder diffraction data. Both compounds crystallize in the orthorhombic space group P212121 with lattice parameters of a = 14...detailed

Pharmaceutics, Preformulation and Drug DeliveryDesign and Evaluation of Controlled-Release Niosomes and Discomes for Naltrexone hydrochloride (cas 16676-29-2) Ocular Delivery09/07/2019

ABSTRACT:This study aimed at preparing and evaluating Span 60-based niosomes for ocular delivery of naltrexone hydrochloride (NTX). Selected charged lipids [dicetyl phosphate (DCP) and stearyl amine (STA)] and surfactants [poly-24-oxyethylene cholesteryl ether (C24) and sodium cholate (CH)] were...detailed

In-vivo study of Naltrexone hydrochloride (cas 16676-29-2) release from an in-situ forming PLGA-PEG-PLGA system in the rabbit09/06/2019

A thermosensitive hydrogel of PLGA-PEG-PLGA triblock synthesized via ring opening polymerization using microwave irradiation method was used to control the release of naltrexone HCl drug. In the present work, the injectable prepared hydrogel was dissolved in phosphate buffer with different amoun...detailed

Relevant articles and documents

AN IMPROVED PROCESS FOR THE PREPARATION OF MORPHINANE ANALOGUES

The present invention relates to an improved process for preparing morphinane analogues of formula (1) wherein the substituents R1, R2, R2a, R3, R4, R5 and Y have the meanings as defined in the specifications.

Transdermal delivery of naltrexone hydrochloride, naltrexol hydrochloride, and bis(hydroxy-methyl)propionyl-3-0 ester naltrexone using microneedles

The present invention provides methods for transdermal delivery of a therapeutically effective amount of Naltrexone Hydrochloride, Naltrexol Hydrochloride, and/or Naltrexone Diol Ester using microneedles. The invention also provides methods for treatment of narcotic dependence, alcohol abuse, and/or alcoholism. Preferably, the Naltrexone Hydrochloride, Naltrexol Hydrochloride, and/or Naltrexone Diol Ester is administered by creating a microneedle-treated site in the skin of a subject by inserting microneedles, followed by applying the Naltrexone Hydrochloride, Naltrexol Hydrochloride, and/or Naltrexone Diol Ester to the microneedle-treated site.

PREPARATION OF OPIATE ANALGESICS BY REDUCTIVE ALKYLATION

A process for preparing a compound of formula (A), (B) or (C): wherein P is H, CH3 or a hydroxyl protecting group; X is O, a protected ketone, OH, a protected hydroxyl group or H; Y is OH, a protected hydroxyl group or H; W is C(CH3)2OH, C(CH3)(C(CH3)3)OH or COCH3; Z is C2-C10 alkyl or C2-C10 arylalkyl; and ′ is a. single bond or a double bond, is disclosed. The process is a reductive alkylation in the presence of hydrogen and a reductive alkylation catalyst.