| Identification | More | [Name]
Naloxone hydrochloride | [CAS]
357-08-4 | [Synonyms]
4,5alpha-epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one hydrochloride
(5ALPHA)-4,5-EPOXY-3,14-DIHYDRO-17-(2-PROPENYL)MORPHINAN-6-ONE HYDROCHLORIDE
NALOXONE HCL
NALOXONE HYDROCHLORIDE
17-allyl-4,5-alpha-epoxy-3,14-dihydroxymorphinan-6-onehydrochloride
17-allyl-4,5-alpha-epoxy-3,14-dihydroxy-morphinan-6-onhydrochloride
en1530
l-n-allyl-14-hydroxynordihydromorphinonehydrochloride
morphinan-6-one,4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-,hydrochloride,(5-a
nalonee
narcan
nih7890
(5alpha)-17-allyl-4,5-epoxy-3,14-dihydroxymorphinan-6-one hydrochloride
NALOXONE HYDROCHLORIDE OPIOID ANTAGONIST
NALOXONE HYDROCHLORIDE CRYSTALLINE
(5a)-4,5-Epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one Hydrochloride
17-Allyl-4,5a-epoxy-3,14-dihydroxymorphinan-6-one Hydrochloride
EN-15304
Nalone
Narcanti | [EINECS(EC#)]
206-611-0 | [Molecular Formula]
C19H22ClNO4 | [MDL Number]
MFCD00069322 | [Molecular Weight]
363.84 | [MOL File]
357-08-4.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
200-2050C | [RTECS ]
QD2275000 | [storage temp. ]
2-8°C
| [solubility ]
ethanol: 3.3 mg/mL stable for several months refrigerated if protected from light.
| [form ]
powder
| [color ]
white to off-white
| [Water Solubility ]
Soluble in water (73 mg/ml), ethanol (3.3 mg/ml), methanol (50 mg/ml) and dimethyl sulfoxide (73 mg/ml). Insoluble in ether | [Usage]
Specific opioid antagonist. Narcotic antagonist | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 2 months. | [CAS DataBase Reference]
357-08-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
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| Hazard Information | Back Directory | [Description]
Naloxone (hydrochloride) (CRM) (Item No. ISO60191) is a certified reference material categorized as an opioid antagonist.1 Formulations containing naloxone have been used as antidotes for opioid overdose and the prevention of overdose.2,3 They have also been used in combination with buprenorphine (Item Nos. ISO60178 | 14025) in the treatment of opiate addiction and in pain management.4,5 This product is intended for research and forensic applications. | [Chemical Properties]
Crystalline Solid | [Originator]
Narcan,Du Pont,US,1971 | [Uses]
A nonspecific opiate receptor antagonist that displays anitnociceptive effects | [Uses]
Opioate antidote; | [Uses]
Specific opioid antagonist. Narcotic antagonist | [Definition]
ChEBI: A hydrochloride resulting from the formal reaction of equimolar amounts of naloxone and hydrogen chloride. A specific opioid antagonist, it is used to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known
r suspected opioid overdose. | [Manufacturing Process]
10 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 name]
Narcan (Bristol-Myers Squibb); Narcan (Endo). | [Therapeutic Function]
Narcotic antagonist | [Biological Activity]
Opioid antagonist. | [Clinical Use]
#N/A | [Veterinary Drugs and Treatments]
Naloxone is used in veterinary medicine almost exclusively for its
opiate reversal effects, but the drug is being investigated for treating
other conditions (e.g., septic, hypovolemic or cardiogenic
shock). Naloxone may also be employed as a test drug to see if
endogenous opiate blockade will result in diminished tail chasing
or other self-mutilating behaviors. It, potentially, could be useful
for treating overdoses of clonidine or the CNS effects of benzodiazepines
(ivermectin?), but more research is necessary before recommending
its use. | [Drug interactions]
Potentially hazardous interactions with other drugs
None known | [Metabolism]
Naloxone hydrochloride is rapidly metabolised in the
liver, mainly by conjugation with glucuronic acid to
naloxone-3-glucuronide, which is excreted in the urine | [storage]
Store at 2-8°C | [References]
1) Le Bourdonnec?et al., (2008),?Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as mu opioid receptor antagonists with improved opioid receptor selectivity profiles: Bioorg. Med. Chem. Lett..?18?2006
2) Boyer?et al.?(2012),?Management of opioid analgesic overdose; New Engl. J. Med.?367?146
3) Wang?et al.?(2017),?Opioids and opioid receptors orchestrate wound repair;?Transl. Res.?185?13
4) Wright and Rodgers (2013),?Low dose naloxone attenuates the pruritic but not anorectic response to rimonabant in male rats; Psychopharmacology (Berl.)?226?415 |
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