465-65-6 Usage
Chemical Description
Naloxone is an opioid antagonist that can reverse the effects of opioids such as morphine.
Description
It is worth mentioning that N-allylic substitution in a number of morphine derivatives, as
a rule, leads to antagonistic properties. Naloxone is a few times stronger than nalorphine
as an antagonist. It blocks opiate receptors. It eliminates central and peripheral action of
opioids, including respiratory depression. Naloxone is used upon overdose of narcotic
analgesics.
Uses
Different sources of media describe the Uses of 465-65-6 differently. You can refer to the following data:
1. antineoplastic
2. Naloxone is a specific opioid antagonist. Narcotic antagonist.
Definition
ChEBI: A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an all
l group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.
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.
General Description
Naloxone (Narcan) is a pure antagonist at allopioid receptor subtypes. Structurally, it resembles oxymorphoneexcept that the methyl group on the nitrogen isreplaced by an allyl group. This minor structural change retains high binding affinity to the receptor, but no intrinsicactivity. It is used to reverse the respiratory depressant effectsof opioid overdoses.Naloxone is administered intravenously with an onset ofaction within 2 minutes. Because it is competing with theopioid for the receptor sites, the dose and frequency of administrationwill depend on the amount and type of narcoticbeing antagonized. Overdoses of long-acting opioids(methadone) may require multiple IV doses of naloxone orcontinuous infusions. Neonates born to opioid-exposedmothers may be given IV naloxone at birth to reverse the effectsof opiates.Very few metabolism studies on naloxone have beenconducted, although the major metabolite found in the urineis naloxone-3-glucuronide.
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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