79250-80-9

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
MSMA is utilized as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new and improved products in these fields.
Used as a Protecting Group in Organic Synthesis:
The trimethylsilyl group in MSMA makes it a useful protecting group for amines during organic synthesis, allowing for selective reactions and the synthesis of complex organic molecules.
Used in the Preparation of Functionalized Amine Derivatives:
MSMA serves as a reagent in the preparation of functionalized amine derivatives, which are important building blocks in the synthesis of various organic compounds.
Used as a Corrosion Inhibitor:
MSMA is employed as a corrosion inhibitor, helping to prevent the degradation of materials and extending their service life in various industrial applications.
Used in the Production of Specialty Chemicals:
MSMA is utilized as a chemical intermediate in the production of specialty chemicals, contributing to the development of unique and high-value products in the chemical industry.

InChI:InChI=1/C8H21NSi/c1-8(2,3)9-7-10(4,5)6/h9H,7H2,1-6H3

Upstream product

• 75-64-9 tert-butylamine 
• 1135084-10-4 C₈H₂₁NSi*ClH 
• 2344-80-1 Chloromethyltrimethylsilane 
• 4206-67-1 iodo(trimethylsilyl)methane 

Downstream Products

• 455957-73-0 methyl (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)-pyrrolidine-3-carboxylate 
• 455957-72-9 methyl (3R,4S)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate 
• 111267-95-9 N-tert-butyl-N-<(trimethylsilyl)methyl>benzylamine 

Relevant academic research and scientific papers

CHEMISTRY OF ORGANOSILICON COMPOUNDS. CLXXXIII. AN ESR STUDY ON β-TRIMETHYLSILYLAMINE- AND RELATED AMINE-N-OXYLS. UNUSUAL CONFORMATIONAL PREFERENCE OF THE β-SILYL GROUP

Fifteen β-trimethylsilylamine- and related amine-N-oxyls were generated by oxidation of the parent amines with m-chloroperoxybenzoic acid.Studies on the preferred conformation of the radicals by ESR spectroscopy indicate that the β-trimethylsilyl group exerts a strong influence favouring the conformation in which the trimethylsilyl group lies in the same plane as the N-O bond.The ESR spectra of related alkyl radicals, as well as results of unrestricted CNDO/2 calculations on the silylmethylamine-N-oxyls, are discussed.

Single electron transfer promoted photoaddition reactions of α-trimethylsilyl substituted secondary N-alkylamines with fullerene C60

Single electron transfer (SET) promoted photoaddition reactions of secondary N-α-trimethylsilyl-N-alkylamines to C60 were explored to gain a deeper understanding of the mechanistic pathways followed and to expand the library of novel types of organofullerenes that can be generated using this approach. The results show that photoreactions of 10% EtOH-toluene solutions containing C60 and N-α-trimethylsilyl-N-alkylamines produce either aminomethyl-1,2-dihydrofullerenes or symmetric fulleropyrrolidines as major products depending on the nature of alkyl substituents. In contrast, photoreactions of 10% EtOH-ODCB solutions of these amines with C60 mainly lead to the formation of symmetric fulleropyrrolidines. Based on the analysis of product distributions and the results of earlier studies, two feasible mechanistic pathways are proposed for these processes. One route is initiated by SET from the amine substrates to the triplet-excited state of C60 to form the corresponding aminium radicals and C60 anion radicals. EtOH-promoted desilylation of the aminium radicals then takes place to produce aminomethyl radicals which can either add to C60 or couple with the C60 radical anions to form respective radicals or anion precursors of aminomethyl-1,2-dihydrofullerene products. The competing pathway leading to the generation of symmetric fulleropyrrolidines also involves the formation of aminomethyl radicals by using the sequential SET-desilylation process. In this route, the aminomethyl radicals are oxidized by SET to C60 to form iminium ions, which are then transformed to azomethine ylides by a pathway involving a second molecule of the secondary amine. Dipolar cycloaddition of the azomethine ylides to C60 forms the symmetric fulleropyrrolidine cycloadducts. Importantly, the observation that symmetric fulleropyrrolidines are the sole products formed in photoreactions between N-α-trimethylsilyl-N-alkylamines and C60 in 10% EtOH-ODCB has synthetic significance.

Stereo-, Regio-, and Chemoselective [3 + 2]-Cycloaddition of (2E,4E)-Ethyl 5-(Phenylsulfonyl)penta-2,4-dienoate with Various Azomethine Ylides, Nitrones, and Nitrile Oxides: Synthesis of Pyrrolidine, Isoxazolidine, and Isoxazoline Derivatives and a Computational Study

One-pot chemo-, regio-, and stereoselective synthesis of series of heterocyclic and spiroheterocyclic compounds was accomplished through mono- and bis[3 + 2]-cycloaddition reactions of (2E,4E)-ethyl 5-(phenylsulfonyl)penta-2,4-dienoate as a dipolarophile with azomethine ylides, nitrones, and nitrile oxides in good yields. The structures of the products were established by spectroscopic techniques as well as by single-crystal XRD study, and DFT calculations were performed to further understand the mechanism of this [3 + 2]-cycloaddition reaction.

Discovery of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans

The relevance of the melanocortin system to sexual activity is well established, and nonselective peptide agonists of the melanocortin receptors have shown evidence of efficacy in human sexual dysfunction. The role of the MC4 receptor subtype has received particular scrutiny, but the sufficiency of its selective activation in potentiating sexual response has remained uncertain owing to conflicting data from studies in preclinical species. We describe here the discovery of a novel series of small-molecule MC4 receptor agonists derived from library hit 2. The addition of methyl substituents at C3 and C5 of the 4-phenylpiperidin-4-ol ring was found to be markedly potency-enhancing, enabling the combination of low nanomolar potencies with full rule-of-five compliance. In general, the series shows only micromolar activity at other melanocortin receptors. Our preferred compound 40a provided significant systemic exposure in humans on both sublingual and oral administration and was safe and well tolerated up to the maximum tested dose. In a pilot clinical study of male erectile dysfunction, the highest dose of 40a tested (200 mg) provided a similar level of efficacy to sildenafil.

Use of Mc4 Receptor Agonist Compounds

This invention relates to the use of an MC4 receptor agonist compound for the manufacture of a medicament for the treatment of lower urinary tract dysfunction.

PIPERIDINOYL-PYRROLIDINE AND PIPERIDINOYL-PIPERIDINE COMPOUNDS

The present invention relates to a class of compounds of general formula (I) and the salts, hydrates, solvates, polymorphs and prodrugs wherein n, R6, R7 and R10 are as defined herein and especially to MCR4 agonist compounds of formula (I), to their use in medicine, particularly in the treatment of sexual dysfunction and obesity, to intermediates useful in their synthesis and to compositions containing them.

ACYLATED SPIROPIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR MODULATORS

Certain novel N-acylated spiropiperidine derivatives are ligands of the human melanocortin receptor(s) and, in particular, are selective ligands of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of MC-4R, such as obesity, diabetes, nicotine addiction, alcoholism, sexual dysfunction, including erectile dysfunction and female sexual dysfunction.

Pharmaceutically active compounds

The present invention relates to a class of melanocortin MCR4 agonists of general formula (I) wherein R1, R2, R3, R4 and R5 are as defined herein and especially to selective MCR4 agonist compounds, to

PIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS

Certain novel piperidine derivatives are agonists of the human melanocortin receptor(s) and, in particular, are selective agonists of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the activation of MC-4R, such as obesity, diabetes, sexual dysfunction, including erectile dysfunction and female sexual dysfunction.

BICYCLIC PIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS

Certain novel bicyclic N-acylated piperidine derivatives are agonists of the human melanocortin receptor(s) and, in particular, are selective agonists of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or p