465-65-6 Usage
Chemical Description
Naloxone is an opioid antagonist that can reverse the effects of opioids such as morphine.
Description
Naloxone is a potent opioid antagonist that possesses antagonistic properties due to its N-allylic substitution in morphine derivatives. It is several times stronger than nalorphine as an antagonist and effectively blocks opiate receptors, thereby eliminating the central and peripheral actions of opioids, including respiratory depression. Naloxone is commonly used in cases of overdose of narcotic analgesics.
Uses
Used in Antineoplastic Applications:
Naloxone is utilized as an antineoplastic agent, indicating its potential role in cancer treatment. The specific application reason and mechanism of action in this context are not provided in the materials.
Used in Medical Industry:
Naloxone is used as a specific opioid antagonist and a narcotic antagonist in the medical industry. It is primarily employed to counteract the effects of opioid overdose, helping to restore normal respiration and counteracting the central nervous system depression caused by excessive opioid consumption.
Therapeutic Function
Narcotic antagonist
Biological Functions
Because of its fast onset (minutes), naloxone (Narcan)
administered IV is used most frequently for the reversal
of opioid overdose. However, it fails to block some
side effects of the opioids that are mediated by the δ-
receptor, such as hallucinations. The rapid offset of
naloxone makes it necessary to administer the drug repeatedly
until the opioid agonist has cleared the system
to prevent relapse into overdose. The half-life of naloxone
in plasma is 1 hour. It is rapidly metabolized via glucuronidation in the liver and cleared by the kidney.
Naloxone given orally has a large first-pass effect, which
reduces its potency significantly. Often an overshoot
will follow the administration of naloxone for overdose.
The heart rate and blood pressure of the patient may
rise significantly. The overshoot is thought to be due to
precipitation of acute withdrawal signs by naloxone.
Given alone to nonaddicts, naloxone produces no pharmacological
effects.
Naloxone is approved for use in neonates to reverse
respiratory depression induced by maternal opioid use.
In addition, naloxone has been used to improve circulation
in patients in shock, an effect related to blockade of
endogenous opioids. Other experimental and less well
documented uses for naloxone include reversal of coma
in alcohol overdose, appetite suppression, and alleviation
of dementia from schizophrenia. Side effects of
naloxone are minor.
Synthesis
Naloxone, (-)-17-(allyl)-4,5-epoxy-3,14-dihydroxymorphinan-6-one (3.1.92),
is synthesized by the alkylation of 14-hydroxydihydronormorphinane (3.1.82) by allylbromide [55–58].
Check Digit Verification of cas no
The CAS Registry Mumber 465-65-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,6 and 5 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 465-65:
(5*4)+(4*6)+(3*5)+(2*6)+(1*5)=76
76 % 10 = 6
So 465-65-6 is a valid CAS Registry Number.
InChI:InChI=1/C19H21NO4/c1-2-8-20-9-7-18-15-11-3-4-12(21)16(15)24-17(18)13(22)5-6-19(18,23)14(20)10-11/h2-4,14,17,21,23H,1,5-10H2/t14-,17+,18+,19-/m1/s1
465-65-6Relevant articles and documents
Studies of 3-O-acyl derivatives of naloxone as its potential prodrugs
Ukrainets,Tkach,Gorokhova,Turov,Linsky
, p. 405 - 416 (2009)
An efficient method has been proposed for the preparation of a series of 3-O-acyl derivatives of naloxone. The features of the steric structure and NMR spectra are discussed. Pharmaceutical investigation has shown the promise within the synthesized compou
PROCESS FOR THE PREPARATION OF MORPHINANE COMPOUNDS
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Page/Page column 9, (2019/01/21)
The invention describes the process of catalytic O-demethylation of 3-methoxy-morphinane compounds using boron tribromide. Addition of catalysts reduces the reaction time, improves reacting the substrate to give the product in very good purity and yield. The said approach can be used, for example, for the preparation of oxymorphone, naltrexone, naloxone and nalbuphine from their respective O-methyl derivatives.
REDUCTION OF ALPHA, BETA-UNSATURATED KETONE LEVELS IN MORPHINAN DERIVATIVE COMPOSITIONS
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Page/Page column 00577; 00578; 00579, (2016/04/26)
The disclosure relates to processes for reducing the amount of a compound of formula (I) or a salt or a solvate thereof present in a composition comprising compounds of formulae (I) and (II) or a salt or a solvate thereof.
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