73232-52-7 Usage
Description
Naltrexone methylbromide, also known as methylnaltrexone bromide, is a quaternary derivative of naltrexone, an opioid antagonist. It is created by the methylation of the amine group of naltrexone, which increases its polarity and reduces its lipid solubility, preventing it from crossing the blood-brain barrier. This modification results in a peripherally acting antagonist with a decreased potency but maintains its effectiveness in antagonizing opioid binding at mu-opioid receptors.
Used in Pharmaceutical Industry:
Naltrexone methylbromide is used as a peripherally acting mu-opioid receptor antagonist for the treatment of opioid-induced constipation in patients with advanced illness receiving palliative care. Its inability to cross the blood-brain barrier allows it to reduce the peripherally-mediated side effects of opioids without affecting their pain-relieving properties in the central nervous system.
Used in Research Applications:
Naltrexone methylbromide is used as a tool in drug research for measuring plasma protein binding, permeability, and the membrane coefficient to predict the penetration of the blood-brain barrier. Additionally, it serves as a mu-opioid receptor antagonist to counteract morphine tolerance and opioid-induced hyperalgesia, providing valuable insights into the development of new treatments for opioid-related issues.
Originator
University of Chicago (United States)
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 73232-52-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,3,2,3 and 2 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 73232-52:
(7*7)+(6*3)+(5*2)+(4*3)+(3*2)+(2*5)+(1*2)=107
107 % 10 = 7
So 73232-52-7 is a valid CAS Registry Number.
InChI:InChI=1/C21H25NO4.BrH/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13;/h4-5,12,16,19,25H,2-3,6-11H2,1H3;1H/t16-,19+,20+,21-,22?;/m1./s1
73232-52-7Relevant articles and documents
Preparation method of methylnaltrexone bromide
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Paragraph 0068-0069, (2017/02/02)
The invention discloses a preparation method of methylnaltrexone bromide. Naltrexone is used as an initial raw material, methylation is carried out by bromomethane, and a methylnaltrexone bromide crude product is obtained; and salt forming, acidifying and purification are carried out in order to prepare methylnaltrexone bromide. The method has the advantages of simple technological operation, scientific and reasonable processes, and high purity and yield of the product.
Brominated morphinan quaternary ammonium salt preparation method
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Paragraph 0091-0093, (2016/10/08)
Disclosed is a preparation method for a morphinan bromide quaternary ammonium salt as represented by Formula (I). The method comprises: transforming a compound as represented by Formula (II) in a compound as represented by Formula (I) by an ion-exchange using a brominated strongly basic anion-exchange resin. The definitions of A, R1, R1 and X- found in Formula (I) and Formula (II) are as presented in the description.
Process for the preparation of quaternary n-alkyl morphinan alkaloid salts
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Page/Page column 29-30, (2010/02/17)
An improved process for the N-alkylation of tertiary morphinan alkaloid bases to form the corresponding quaternary morphinan alkaloid derivatives.