76-41-5 Usage
Chemical Properties
Crystalline Solid
Originator
Numorphan,Endo, US ,1959
Manufacturing Process
Thebaine is dissolved in aqueous formic acid and treated with 30% H2O2; neutralization with aqueous ammonia gives 14-hydroxycodeinone. It is hydrogenated to give oxycodone. 90 ml of concentrated hydrobromic acid are heated to 90°C. 9 grams of 14-hydroxydihydrocodeinone (oxycodone) are then added under stirring and the mixture is quickly heated to 116°C and kept at this temperature under reflux condenser for 20 minutes, with continued stirring. The resulting brown solution is diluted with about 90 ml of water and chilled with ice. Aqueous 10% sodium hydroxide solution is now added to alkaline reaction and the liquid is extracted 3 times with 100 cc portions of chloroform. The layers are separated and the aqueous phase is filtered and acidified by the addition of concentrated aqueous hydrochloric acid, treated with charcoal and filtered.
The filtrate is treated with concentrated aqueous ammonia until the mixture gives a pink color on phenolphthalein paper. The liquid is extracted seven times with 100 cc portions of chloroform, the extracts are combined, dried with anhydrous sodium sulfate and evaporated. The residue is dissolved in ethanol by refluxing and the ethanol evaporated nearly to dryness. 100 cc of benzene are then added, the mixture is refluxed for ? hour and set aside for crystallization. After cooling, the desired compound is collected by filtration, 2.3 grams of a white crystalline powder are obtained; MP 245° to 247°C. This powder consisting of 14-hydroxydihydromorphinone can be purified by recrystallization from benzene, ethylacetate or ethanol. From benzene it generally forms diamond shaped platelets, while needles are obtained from ethylacetate.
On heating, the crystals are discolored from about 200°C on, and melt at 246° to 247°C to a black liquid, which decomposes with strong volume increase if the temperature is raised further by a few degrees.
Biological Functions
Oxymorphone is 10 times as potent as morphine,
with actions similar to those of hydromorphone.
Oxymorphone, however, has little antitussive activity,
and as such is a useful analgesic in patients with pulmonary
disease who need to retain the ability to cough.
General Description
Oxymorphone is the 14 beta-hydroxyl version of hydromorphone,analogous to the hydrocodone, oxycodone pair discussedabove. Although the addition of the 14 beta-hydroxylgroup to hydrocodone (30 mg) yielded oxycodone (20 mg),a more potent drug, the opposite is true for the conversion ofhydromorphone (7.5 mg) to oxymorphone (10 mg). The reasonfor this is that the oral bioavailability of oxymorphone(10%) is lower than that of hydromorphone (35%) becauseof decreased absorption and increased first-pass metabolism.Presumably, the addition of the OH group does increaseits binding affinity at the receptor as the injectableform of oxymorphone (1 mg) is more potent than injectablehydromorphone (1.5 mg).Oxymorphone is available as a suppository (5 mg), an injection(1 mg/mL), an immediate-release tablet (5 mg, 10mg), and in 2003 the FDA approved a sustained release formulation(Opana ER 5 mg, 10 mg, 20 mg, and 40 mg). The12-hour coverage of the extended release tablet provides anotheroption for those patients suffering from chronic pain.The side effect profile of the extended release formulationsof morphine, oxycodone, and oxymorphone are similar, andthere appears to be no clear advantage of one over the other.
Check Digit Verification of cas no
The CAS Registry Mumber 76-41-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 76-41:
(4*7)+(3*6)+(2*4)+(1*1)=55
55 % 10 = 5
So 76-41-5 is a valid CAS Registry Number.
InChI:InChI=1S/C17H19NO4/c1-18-7-6-16-13-9-2-3-10(19)14(13)22-15(16)11(20)4-5-17(16,21)12(18)8-9/h2-3,12,15,19,21H,4-8H2,1H3
76-41-5Relevant articles and documents
An Integrated Continuous-Flow Synthesis of a Key Oxazolidine Intermediate to Noroxymorphone from Naturally Occurring Opioids
Mata, Alejandro,Cantillo, David,Kappe, C. Oliver
, p. 6505 - 6510 (2017)
A telescoped procedure for the direct preparation of an advanced intermediate towards noroxymorphone from the naturally occurring alkaloids oripavine and thebaine is presented. The reaction procedure involves an intensified continuous-flow hydroxylation, followed by a continuous solvent switch and hydrogenation in a packed-bed hydrogenator (H-Cube). The obtained reaction mixture, containing oxymorphone as intermediate in excellent yield and purity, can be then directly converted into the desired noroxymorphone oxazolidine intermediate through palladium catalyzed N-methyl oxidation.
AN IMPROVED PROCESS FOR O-DEMETHYLATING METHOXY SUBSTITUTED MORPHINAN-6-ONE DERIVATIVES USING BORON-BASED COMPLEXES
-
Page/Page column 12-19, (2020/10/09)
The present invention discloses an improved process for O-demethylation of methoxy-substituted morphinan-6-one derivatives using boron-based complex as a demethylating boron complex in an inert reaction solvent.
PROCESS FOR OBTAINING 3,14-DIACETYLOXYMORPHONE FROM ORIPAVINE
-
Page/Page column 42, (2018/01/17)
The present invention relates to a new process for obtaining 3,14-diacetyloxymorphone from oripavine, a process to transform the obtained 3,14-diacetyloxymorphone into a noroxymorphone and a process to transform said noroxymorphone into naloxone, naltrexone, nalbuphine, nalfurafine or nalmefene.
This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.