Naloxone

Naloxone Basic information
Product Name:Naloxone
Synonyms:12-allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-4ah-8,9c-iminoethanophenanthro(4,5;12-allyl-7,7a,8,9-tetrahydro-3,7a-dihydroxy-4ah-8,9c-iminoethanophenanthro[4,5;17-allyl-4,5alpha-epoxy-3,14-dihydroxy-morphinan-6-on;17-allyl-4,5-alpha-epoxy-3,14-dihydroxymorphinan-6-one;17-allyl-4,5alpha-epoxy-3,14-dihydroxymorphinan-6-one;1-n-allyl-14-hydroxynordihydromorphinone;1-n-allyl-7,8-dihydro-14-hydroxynormorphinone;4,5-alpha-epoxy-3,14-dihydroxy-17-(2-propenyl)-morphinan-6-on
CAS:465-65-6
MF:C19H21NO4
MW:327.37
EINECS:207-365-7
Product Categories:Isotopically Labeled Pharmaceutical Reference Standard;AMPLIMEXON
Mol File:465-65-6.mol
Naloxone Structure
Naloxone Chemical Properties
Melting point 184° (Lewenstein), 177-178° (Sankyo Co.)
alpha D20 -194.5° (c = 0.93 in CHCl3)
Boiling point 465.27°C (rough estimate)
density 1.2223 (rough estimate)
refractive index 1.5000 (estimate)
Fp 9℃
storage temp. 2-8°C
solubility Chloroform (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly),
form Solid
pkapKa 7.94/7.82(H2O,t =20/37,I<0.01) (Uncertain)
color White to Off-White
InChIKeyUZHSEJADLWPNLE-GRGSLBFTSA-N
EPA Substance Registry SystemMorphinan-6-one, 4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-, (5.alpha.)- (465-65-6)
Safety Information
Hazard Codes F,T
Risk Statements 11-23/24/25-39/23/24/25
Safety Statements 7-16-36/37-45
RIDADR UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany 3
HS Code 2939190000
Hazardous Substances Data465-65-6(Hazardous Substances Data)
ToxicityAn opiate antagonist devoid of agonist activity except for mild, specific effects at very high doses. Naloxone displays a high affinity for the μ-opioid receptor, a lesser affinity for the kopioid receptor and has some affinity for δ-opioid receptor subtypes. Naloxone produces a rapid and profound reversal of the effects of opioid administration (e.g., 1 mg, i.v., blocks the effects of 25 mg of heroin). Naloxone also antagonizes the analgesia induced by placebo, acupuncture, and stress, and in animals the hypotension due to hypovolemia or spinal cord injury. Naloxone has a short half-life (about 1 h in plasma) and is not administered orally because of rapid, “first-pass” metabolism.
MSDS Information
Naloxone Usage And Synthesis
DescriptionIt 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.
OriginatorNarcan,Du Pont,US,1971
Usesantineoplastic
UsesNaloxone is a specific opioid antagonist. Narcotic antagonist.
DefinitionChEBI: 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.
Manufacturing Process10 grams of 14-hydroxydihydromorphinone (oxymorphone) was converted into its diacetate by warming it on the steam bath with 80 cc of acetic anhydride for about 2 hours. The acetic anhydride was removed on the water bath under a vacuum of about 30 mm absolute pressure. The melting point of the residue was 220°C. The residue was taken up in 100 cc of chloroform. An equal amount by weight of cyanogen bromide was added and the mixture was refluxed at about 60°C for about 5 hours. After refluxing, the mixture was washed with 100 cc of a 5% aqueous hydrochloric acid solution, dried over sodium sulfate and the chloroform removed by evaporation under a vacuum of about 30 mm. The residue had a melting point of 240°C.
The residue was then heated at about 90°C for 16 hours on a steam bath with 300 cc of 20% aqueous hydrochloric acid solution, and treated with a small amount, e.g., 1 gram of charcoal. The hydrochloric acid was then removed under a vacuum of 15 mm, the residue dissolved in 30 cc of water and precipitated by the addition of 2.4 cc of concentrated aqueous ammonia. The precipitate was filtered off and dried. It consists of 14- hydroxydihydronormorphinone. It is soluble in ethanol.
The 14-hydroxydihydronormorphinone was suspended in 200 cc of pure ethyl alcohol, half its weight of sodium bicarbonate and half its weight of allyl bromide added and the resulting mixture was refluxed at about 75°C for 48 hours. The solution was cooled, e.g., to 10°C and filtered and the alcohol removed under a vacuum of 30 mm. The residue was dissolved in chloroform and filtered. The chloroform was removed under a vacuum of 30 mm and the residue was crystallized from ethylacetate. The crystallized product, N-allyl- 1,4-hydroxydihydronormorphinone, has a melting point of 184°C, is soluble in chloroform and insoluble in petroleum ether. The yield amounts to 20% based on the weight of the reacted 14-hydroxydihydromorphinone.

Brand nameNarcan (Bristol-Myers Squibb); Narcan (Endo).
Therapeutic FunctionNarcotic antagonist
Biological FunctionsBecause 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 DescriptionNaloxone (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.

SynthesisNaloxone, (-)-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¨C58].

Synthesis_465-65-6

NALOXONE HYDROCHLORIDE,NALOXONE HCL,NALOXONE HYDROCHLORIDE OPIOID ANTAGONIST,NALOXONE HYDROCHLORIDE CRYSTALLINE,l-Naloxone hydrochloride NALOXONE FLUORESCEIN NALOXONE HYDROCHLORIDE ASSAY STANDARD BP(CRM STANDARD) ETHYLENE OXIDE Phenolic epoxy resin NALOXONE-3-GLUCURONIDE Nalmexonum NALOXONE, [N-ALLY-2,3-3H]-,NALOXONE, [N-ALLYL 2,3-3H] NALOXONE IMPURITY A4,5-ALPHA-EPOXY-3,14-DIHYDROXYMORPHINAN-6-ONE (NOROXYMORPHONE) EPN(CRM STANDARD) Naloxone NALOXONE HYDROCHLORIDE BP STANDARD(CRM STANDARD) naloxone-6-spirohydantoin Naloxone hydrochloride dihydrate Epoxy coating of terrace NALOXONE BENZOYLHYDRAZONE NALOXONE METHIODIDE Epichlorohydrin Propylene oxide

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