Naltrexone methylbromide

ChemicalBook > CAS DataBase List > Naltrexone methylbromide

Naltrexone methylbromide

Product Name: Naltrexone methylbromide
CAS No.: 73232-52-7
Chemical Name: Naltrexone methylbromide
Synonyms: MNTX;Moa-728;Relistor;Unii-rfo6il3D3m;Adamantane Impurity 52;Naltrexone methobromide;Methylnaltrexone bromide;Naltrexone methylbromide;Methyhaaltrexone broMide;N-Methyl Naltrexone BroMide
CBNumber: CB11105859
Molecular Formula: C21H26BrNO4
Formula Weight: 436.35
MOL File: 73232-52-7.mol

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Naltrexone methylbromide Property

Melting point:: 237-239°C
storage temp.: -20°C
solubility: H2O: ≥5mg/mL
form: powder
color: white to beige
Stability:: Hygroscopic

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Safety

Hazard Codes: T,N
Risk Statements: 25-50
Safety Statements: 45-61
RIDADR: UN 2811 6.1 / PGIII
WGK Germany: 3
RTECS: QD0188550
HS Code: 2934990002

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H400Very toxic to aquatic life

Precautionary statements

P273Avoid release to the environment.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0277
Product name: Methylnaltrexone bromide
Purity: ≥97% (HPLC)
Packaging: 5mg
Price: $110
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1430735
Product name: Methylnaltrexone bromide
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 100mg
Price: $1940
Updated: 2024/03/01

Cayman Chemical

Product number: 24072
Product name: Methylnaltrexone (bromide)
Purity: ≥95%
Packaging: 1mg
Price: $32
Updated: 2024/03/01

Cayman Chemical

Product number: 24072
Product name: Methylnaltrexone (bromide)
Purity: ≥95%
Packaging: 5mg
Price: $100
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0277
Product name: Methylnaltrexone bromide
Purity: ≥97% (HPLC)
Packaging: 25mg
Price: $600
Updated: 2024/03/01

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Naltrexone methylbromide Chemical Properties,Usage,Production

Description

The widespread efficacy of opioids in treating patients with moderate to severe acute and chronic pain is often accompanied by untoward side effects. In particular, opioid-induced bowel dysfunction is one of the more common and debilitating consequences afflicting up to 50% of patients. To counteract the peripherally-mediated adverse effects, opioid antagonists such as naloxone, naltrexone, and nalmephene are sometimes prescribed. The latest market entry exploits a strategic modification of naltrexone to lower its lipid solubility and increase its polarity: quaternization of the amine of naltrexone by methylation (methyl bromide) prevents crossing of the blood–brain barrier thereby creating an effective peripheral antagonist. Despite a loss of potency upon methylation, methylnaltrexone antagonizes opioid binding at m-opioid receptors with an IC₅₀ of 70 nM. Its affinity for k-opioid receptors is approximately eightfold less (IC₅₀＝ 575 nM) with no significant binding to d-opioid, orphanin, or non-opioid receptors. Methylnaltrexone bromide has been approved for the treatment of opioid-induced constipation in patients with advanced illness receiving palliative care.Regarding metabolism, methylnaltrexone bromide is eliminated primarily as intact drug (85% based on administered radioactivity) by slightly more renal than hepatic clearance.
The most common adverse events were abdominal pain and flatulence followed by nausea, dizziness, and diarrhea.

Chemical Properties

Pale Pink Solid

Originator

University of Chicago (United States)

Uses

Methylnaltrexone bromide has been used as a drug to measure plasma protein binding (PPB), permeability (Pm) and the membrane coefficient (KIAM) for the prediction of blood brain barrier (BBB) penetration. It is also used as a mu-opioid receptor (MOR) antagonist to abrogate morphine tolerance and opioid-induced hyperalgesia (OIH).

Uses

A metabolite of Naltrexone (N285750). Methylnaltrexone (MNTX), a selective μ-opioid receptor antagonist, functions as a peripherally acting receptor antagonist in tissues of the gastrointestinal tract.

brand name

Relistor

General Description

Methylnaltrexone does not cross blood brain barrier and does not affect the opioid effects in the brain, such as analgesia. It is used to treat opioid-induced constipation (OIC).

Biochem/physiol Actions

Methylnaltrexone bromide is a narcotic antagonist. It is a peripheral mu-opiod receptor antagonist that cannot cross the blood-brain barrier. It reverses many opioid side-effects without interfering with pain relief.

Clinical Use

N-Methylnaltrexone is the polar derivative of naltrexone, which does not reach the central nervous system but can block intestinal opioid receptors. The compound is under development to counteract opioid induced bowel dysfunction such as constipation and megacolon .

Synthesis

The synthesis of methylnaltrexone bromide proceeds in a straightforward manner via the alkylation of naltrexone 90 in the following scheme. Naltrexone 90 was reacted with methyl bromide in 1-methyl-2-pyrrolidinone at 60 ??C. The resulting crude product was treated with sodium methoxide in methanol/ water at 55 ??C to remove any undesired phenolic (Oalkylated) side-products. The resulting crude sodium salt was treated with hydrobromic acid in methanol/water and upon crystallization gave methylnaltrexone bromide (XII) in 35% overall yield.

storage

Store at -20°C

Naltrexone methylbromide Preparation Products And Raw materials

Raw materials

Preparation Products

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73232-52-7, Naltrexone methylbromideRelated Search:

17S-Naltrexone Methobromide HOE 140 Naltrexone

Naltrexone methobromide

Naltrexone methylbromide

Moa-728

Morphinanium, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxo-, bromide, (5alpha)-

Relistor

Unii-rfo6il3D3m

Methylnaltrexone bromide

(5alpha)-17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxomorphinanium bromide

N-Methyl Naltrexone BroMide

(5α)-17-(CyclopropylMethyl)-4,5-epoxy-3,14-dihydroxy-17-Methyl-6-oxoMorphinaniuM BroMide

N-CyclopropylMethyl-noroxyMorphone MethobroMide

Methyhaaltrexone broMide

17-(CyclopropylMethyl)-4,5-epoxy-3,14-dihydroxy-17-Methyl-6-oxoMorphinaniuM broMide

MNTX

Quaternary ammonium naltrexone

17-(Cyclopropylmethyl)-4,5A-Epoxy-3,14-Dihydroxy-17-Methyl-6-Oxomorphinanium Bromide

Methylnaltrexone Peak Identification Mixture Cll

(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7-one,bromide

Methylnaltrexone iodide salt

N-Methyl Naltrexone Bromide (1.0mg/ml in DMSO)

Methylnaltrexone Bromide (1430735)

inhibit,Opioid Receptor,suppression,gastrointestinal,Methylnaltrexone bromide,blood-brain,tract,peripheral,barrier,analgesia,Inhibitor

Adamantane Impurity 52

73232-52-7

C21H26NO4Br

Aromatics

Heterocycles

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