91265-75-7

Usage

Uses

Used in Pharmaceutical Industry:
3-(tert-ButyldiMethylsilyl)Morphinone is used as a protected intermediate in the synthesis of various pharmaceutical compounds. The tert-butyldimethylsilyl group provides protection to the molecule, allowing for selective reactions and modifications, which can be beneficial in the development of new drugs with improved properties.
Used in Chemical Research:
3-(tert-ButyldiMethylsilyl)Morphinone is used as a research compound in the field of organic chemistry. Its unique structure and properties make it an interesting subject for studying reaction mechanisms, synthetic routes, and the development of new methodologies.
Used in Analytical Chemistry:
3-(tert-ButyldiMethylsilyl)Morphinone can be employed as a reference compound in analytical chemistry for the development and validation of analytical methods, such as chromatography, mass spectrometry, and spectroscopy. Its distinct chemical properties can aid in the identification and quantification of related compounds in complex samples.

Upstream product

• 91265-70-2 3-(_tbutyldimethylsilyl)morphine 
• 57-27-2 MORPHIN 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 50291-32-2 morphine sodium salt 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 467-02-7 dihydromorphinone 

Downstream Products

• 467-02-7 dihydromorphinone 
• 466-99-9 hydromorphone 
• 33522-95-1 noroxymorphone 

Relevant academic research and scientific papers

Thiol-Reactive Analogues of Galanthamine, Codeine, and Morphine as Potential Probes to Interrogate Allosteric Binding within Nicotinic Acetylcholine Receptors

Alkaloids including galanthamine (1) and codeine (2) are reported to be positive allosteric modulators of nicotinic acetylcholine receptors (nAChRs), but the binding sites responsible for this activity are not known with certainty. Analogues of galanthamine (1), codeine (2), and morphine (3) with reactivity towards cysteine thiols were synthesized including conjugated enone derivatives of the three alkaloids 4-6 and two chloro-alkane derivatives of codeine 7 and 8. The stability of the enones was deemed sufficient for use in buffered aqueous solutions, and their reactivity towards thiols was assessed by determining the kinetics of reaction with a cysteine derivative. All three enone derivatives were of sufficient reactivity and stability to be used in covalent trapping, an extension of the substituted cysteine accessibility method, to elucidate the allosteric binding sites of galanthamine and codeine at nAChRs.

An improved synthesis of noroxymorphone

A brief synthesis of noroxymorphone is described which involves the oxidation of 3-O-(t)butyldimethylsilylmorphine by manganese dioxide. The initial product is the corresponding morphinone which is further oxidised to the 14-hydroxymorphinone. After hydrogenation the 7,8-dihydro-14-hydroxymorphinone is acetylated and N-demethylation of the 14-O-acetylated product is achieved using vinyl chloroformate as the reagent. The overall yield from morphine is 40-45%.

Activities of morphinone and N-(cyclopropylmethyl)normorphinone at opioid receptors

Morphinone (3) and N-(cyclopropylmethyl)normorphinone (4) were synthesized and tested on electrically stimulated smooth muscle preparations (guinea pig ileum and mouse vas deferens) and in mice. Compound 3 behaved as an agonist and 4 as an antagonist in vitro and in vivo. No pronounced nonequilibrium agonist or antagonist activity was observed with either compound.