Naloxone hydrochloride CAS 357-08-4
Introduction：Basic information about Naloxone hydrochloride CAS 357-08-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Naloxone hydrochloride Basic information
| Product Name: | Naloxone hydrochloride |
| Synonyms: | NALOXONE HCL;NALOXONE HYDROCHLORIDE;(5ALPHA)-4,5-EPOXY-3,14-DIHYDRO-17-(2-PROPENYL)MORPHINAN-6-ONE HYDROCHLORIDE;17-allyl-4,5-alpha-epoxy-3,14-dihydroxymorphinan-6-onehydrochloride;4,5alpha-epoxy-3,14-dihydroxy-17-(2-propenyl)morphinan-6-one hydrochloride;en1530;l-n-allyl-14-hydroxynordihydromorphinonehydrochloride;morphinan-6-one,4,5-epoxy-3,14-dihydroxy-17-(2-propenyl)-,hydrochloride,(5-a |
| CAS: | 357-08-4 |
| MF: | C19H22ClNO4 |
| MW: | 363.84 |
| EINECS: | 206-611-0 |
| Product Categories: | API;Chiral Reagents;Drug Analogues;Intermediates & Fine Chemicals;Pharmaceuticals;Opioid receptor and opioid-like receptor;Opioids |
| Mol File: | 357-08-4.mol |
Naloxone hydrochloride Chemical Properties
| 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 |
| 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. |
| InChI | InChI=1/C19H21NO4.ClH/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;1H/t14-,17+,18+,19-;/s3 |
| InChIKey | RGPDIGOSVORSAK-ASLVLMPBNA-N |
| SMILES | [C@@]123CCN(CC=C)[C@@H]4CC5=CC=C(O)C(O[C@H]1C(CC[C@]24O)=O)=C35.Cl |&1:0,7,16,20,r| |
| CAS DataBase Reference | 357-08-4(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 22-24/25-26-36/37/39-36 |
| WGK Germany | 3 |
| Description | Naloxone (hydrochloride) (CRM) (Item No. ISO60191) is a certified reference material categorized as an opioid antagonist. Formulations containing naloxone have been used as antidotes for opioid overdose and the prevention of overdose. They have also been used in combination with buprenorphine (Item Nos. ISO60178 | 14025) in the treatment of opiate addiction and in pain management. This product is intended for research and forensic applications. |
| Chemical Properties | Crystalline Solid |
| Originator | Narcan,Du Pont,US,1971 |
| Uses | Opioate antidote; |
| Uses | A nonspecific opiate receptor antagonist that displays anitnociceptive effects |
| Uses | Naloxone Hydrochloride is a 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 convertedinto its diacetate by warming it on the steam bath with 80 cc of aceticanhydride for about 2 hours. The acetic anhydride was removed on the waterbath under a vacuum of about 30 mm absolute pressure. The melting point ofthe residue was 220°C. The residue was taken up in 100 cc of chloroform. Anequal amount by weight of cyanogen bromide was added and the mixture wasrefluxed at about 60°C for about 5 hours. After refluxing, the mixture waswashed with 100 cc of a 5% aqueous hydrochloric acid solution, dried oversodium sulfate and the chloroform removed by evaporation under a vacuum ofabout 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 with300 cc of 20% aqueous hydrochloric acid solution, and treated with a smallamount, e.g., 1 gram of charcoal. The hydrochloric acid was then removedunder a vacuum of 15 mm, the residue dissolved in 30 cc of water andprecipitated by the addition of 2.4 cc of concentrated aqueous ammonia. Theprecipitate 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 ethylalcohol, half its weight of sodium bicarbonate and half its weight of allylbromide added and the resulting mixture was refluxed at about 75°C for 48hours. The solution was cooled, e.g., to 10°C and filtered and the alcoholremoved under a vacuum of 30 mm. The residue was dissolved in chloroformand filtered. The chloroform was removed under a vacuum of 30 mm and theresidue was crystallized from ethylacetate. The crystallized product, N-allyl-1,4-hydroxydihydronormorphinone, has a melting point of 184°C, is soluble inchloroform and insoluble in petroleum ether. The yield amounts to 20% basedon the weight of the reacted 14-hydroxydihydromorphinone. |
| Brand name | Narcan (Bristol-Myers Squibb); Narcan (Endo). |
| Therapeutic Function | Narcotic antagonist |
| Biological Activity | Opioid antagonist. |
| Veterinary Drugs and Treatments | Naloxone is used in veterinary medicine almost exclusively for itsopiate reversal effects, but the drug is being investigated for treatingother conditions (e.g., septic, hypovolemic or cardiogenicshock). Naloxone may also be employed as a test drug to see ifendogenous opiate blockade will result in diminished tail chasingor other self-mutilating behaviors. It, potentially, could be usefulfor treating overdoses of clonidine or the CNS effects of benzodiazepines(ivermectin?), but more research is necessary before recommendingits use. |
| 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 | Room temperature |
| References | [1] BERTRAND LE BOURDONNEC . Novel trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidines as μ opioid receptor antagonists with improved opioid receptor selectivity profiles[J]. Bioorganic & Medicinal Chemistry Letters, 2008, 18 6: Pages 2006-2012. DOI:10.1016/j.bmcl.2008.01.106 [2] EDOARDO PICETTI M L C Ilaria Rossi. Management of opioid analgesic overdose.[J]. New England Journal of Medicine, 2012, 367 14: 1372; author reply 1372-3. DOI:10.1056/nejmc1209707 [3] YING WANG . Opioids and opioid receptors orchestrate wound repair[J]. Translational Research, 2017, 185: Pages 13-23. DOI:10.1016/j.trsl.2017.05.003 [4] F L WRIGHT R J R. Low dose naloxone attenuates the pruritic but not anorectic response to rimonabant in male rats.[J]. Psychopharmacology, 2013, 226 2: 415-431. DOI:10.1007/s00213-012-2916-5 |
Naloxone hydrochloride Preparation Products And Raw materials
| Raw materials | Acetic anhydride-->OXYMORPHONE-->Hydrochloric acid-->Cyanogen bromide-->Allyl bromide |
| Preparation Products | Naltrexone 3-Methyl Ether-->Naloxone |
