Name | 5-Amino-1-methylquinolinium chloride |
CAS number | 42464-96-0 |
Description | 5-Amino-1-methylquinolinium chloride, identified by the Chemical Abstracts Service Registry Number 42464-96-0, is a synthetic quaternary ammonium compound derived from the quinoline heterocyclic ring system. |
Structural formula | |
Molecular Formula | C10H11N2.I |
Molecular Weight | 286.11 g/mol |
Appearance | White powder |
Quality Standard | 99% |
Storage Condition | Cool dry place( away from the light) |
Shelf Life | >2 years if stored properly |
Sample package | Aluminium foil bag |
Commercial package | Aluminium Tin, Fiber drum |
Origin | China |
5-Amino-1-methylquinolinium chloride More Info
5-Amino-1-methylquinolinium chloride, identified by the Chemical Abstracts Service Registry Number 42464-96-0, is a synthetic quaternary ammonium compound derived from the quinoline heterocyclic ring system. The molecule consists of a quinolinium core with an amino group at the fifth position and a methyl group attached to the ring nitrogen, bearing a positive charge that is balanced by a chloride counterion. Its molecular formula is C₁₀H₁₁ClN₂, with a molecular weight of approximately 194.6 grams per mole for the chloride salt form, though the compound is also commonly encountered as the iodide salt, which has a molecular weight of 286.11 grams per mole. The IUPAC name for this compound is 5-amino-1-methylquinolin-1-ium chloride, and it is frequently referred to by the synonymous names 5-amino-1MQ and NNMTi. In its physical form, the compound appears as a brown to reddish-brown solid with a reported melting point between 213 and 214 degrees Celsius. It is soluble in organic solvents such as dimethyl sulfoxide and demonstrates stability when stored at temperatures of negative twenty degrees Celsius or below.
The primary biological significance of 5-amino-1-methylquinolinium chloride lies in its function as a potent and selective inhibitor of nicotinamide N-methyltransferase, an enzyme that catalyzes the transfer of a methyl group from S-adenosyl methionine to nicotinamide, producing 1-methylnicotinamide and S-adenosyl homocysteine. The compound exhibits an inhibitory concentration fifty value of 1.2 micromolar under standard assay conditions, indicating potent enzyme inhibition at relatively low concentrations. Importantly, it selectively targets the substrate binding site of NNMT without affecting related methyltransferases or enzymes involved in the NAD+ salvage pathway, a specificity profile that distinguishes it from broader-acting methyltransferase inhibitors. This selective inhibition has significant implications for cellular metabolism, as NNMT plays a critical role in regulating the availability of nicotinamide precursors required for NAD+ biosynthesis, thereby linking the activity of this enzyme to the metabolic status of the cell, methylation balance, and cellular energy homeostasis.
The research applications of this compound have been most extensively explored in the context of skeletal muscle biology and age-related degenerative conditions. NNMT expression has been shown to increase progressively with aging in muscle tissues and is considered a dominant component of the gene expression signature associated with sarcopenia, the age-related decline in muscle mass, strength, and function. Overexpression of NNMT leads to significantly reduced levels of NAD+ within muscle cells, which in turn impairs the activity of sirtuin1 and other NAD+-dependent enzymes that regulate cellular stress resistance, metabolic function, and mitochondrial health. In preclinical studies using aged mice, treatment with 5-amino-1-methylquinolinium chloride at doses of 5 and 10 milligrams per kilogram enhanced the proliferation, fusion, and regenerative capacity of muscle stem cells following acute muscle injury. Treated animals demonstrated approximately seventy percent greater peak torque in the injured muscle and nearly two-fold larger myofiber cross-sectional area compared to control animals, indicating both structural and functional improvements in muscle regeneration.
Beyond its applications in musculoskeletal research, this compound has been investigated for its metabolic effects in adipose tissue and liver. Studies have demonstrated that NNMT inhibition can reduce adipogenesis and decrease 1-methylnicotinamide levels in adipocytes, with an effective concentration fifty value of 2.3 micromolar for the latter effect. When combined with dietary interventions, NNMT inhibitor treatment accelerated body weight and fat loss, increased the ratio of lean mass to body weight, reduced liver and epididymal white adipose tissue weights, decreased liver adiposity, and improved hepatic steatosis compared to dietary intervention alone. These findings have generated interest in the compound as a potential therapeutic agent for metabolic disorders including obesity, fatty liver disease, and diabetes, though all current evidence remains at the preclinical stage. The compound also promotes myoblast differentiation in vitro, with studies on C2C12 myoblast cells showing a forty-five percent increase in the extent of differentiation when treated with 30 micromolar of the compound over ninety-six hours.
From a safety and regulatory perspective, 5-amino-1-methylquinolinium chloride is currently classified as a research chemical and is not approved for human therapeutic use by any major regulatory authority, including the United States Food and Drug Administration or the European Medicines Agency. Preclinical toxicology studies in mice have indicated that daily subcutaneous administration of the compound at 10 milligrams per kilogram for one week produced no systemic toxicity, with no significant differences observed in glucose, cholesterol, plasma proteins, or electrolyte levels between treated and control animals. However, hazard classification for the compound includes warnings for potential harm if swallowed, skin irritation, serious eye irritation, and respiratory tract irritation, necessitating appropriate handling precautions in laboratory settings. The compound is commercially available from multiple suppliers for research purposes only, with purity specifications typically exceeding ninety-eight percent as determined by high-performance liquid chromatography, and it is supplied as a solid powder or as a 10 millimolar solution in dimethyl sulfoxide. Storage recommendations emphasize the importance of maintaining the compound at low temperatures, protection from light and moisture, and proper disposal in accordance with institutional and regulatory guidelines for chemical waste.
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