5-AMINO-1MQ

5-Amino-1MQ (5-amino-1-methylquinolinium) is a small-molecule inhibitor of nicotinamide N-methyltransferase (NNMT), the cytosolic enzyme that methylates nicotinamide using S-adenosylmethionine (SAM) as the methyl donor. It comes from a quinolinium inhibitor series developed through structure-activity screening and docking to the enzyme’s nicotinamide-binding site. Researchers have studied this NNMT inhibitor in cultured adipocytes, diet-induced obese mice and rat pharmacokinetic work, measuring NAD+, SAM, lipogenesis and liver pathology. Research Market supplies 5-Amino-1MQ as the iodide salt, with purity and identity data for each lot reported on its certificate of analysis. It is sold strictly for laboratory research use.

Chemical structure and identification

• Molecular formula: C₁₀H₁₁IN₂
• Molecular weight: 286.11 g/mol
• CAS number: 42464-96-0
• PubChem CID: 66522933
• Active cation: 5-amino-1-methylquinolinium, C₁₀H₁₁N₂⁺, 159.21 g/mol (PubChem CID 950107)
• Synonyms: 5-amino-1-methylquinolinium iodide, NNMTi
• Form: Powder
• Analytical methods: HPLC for purity and mass spectrometry for identity, reported on the batch certificate of analysis

Research applications

• Inhibitor design: Screening of N-methylated quinolinium, isoquinolinium, pyridinium and benzimidazolium/benzothiazolium analogues identified quinoliniums as a scaffold with NNMT IC₅₀ values near 1 µM, with docking scores that correlated with measured IC₅₀ [1]
• Permeability and selectivity: Methylquinolinium analogues with primary amine substitutions crossed membranes in PAMPA and Caco-2 assays, did not inhibit related SAM-dependent methyltransferases or NAD⁺ salvage enzymes, and in adipocytes reduced 1-methylnicotinamide, raised NAD⁺ and SAM and suppressed lipogenesis [2]
• NNMT as a target: Nnmt knockdown in white adipose tissue and liver of mice increased energy expenditure, and NNMT inhibition raised adipose SAM and NAD⁺ and altered polyamine flux and histone H3K4 methylation [3]
• Liver and glucose measures: In diet-induced obese mice given 5A1MQ daily for 28 days, researchers reported improved oral glucose tolerance, less hepatic steatosis and macrophage infiltration, and distribution of the compound to adipose tissue, muscle and liver [4]
• Bioanalysis and pharmacokinetics: A validated LC-MS/MS assay quantified 5-amino-1-methylquinolinium in rat plasma and urine; in rats it showed a terminal half-life of 3.8 h intravenously and 6.9 h orally, with 38.4% oral bioavailability [5]

Reference citations

1. Neelakantan H. et al. (2017). Structure-activity relationship for small molecule inhibitors of nicotinamide N-methyltransferase. J Med Chem, 60(12):5015–5028. PMID 28548833 · DOI
2. Neelakantan H. et al. (2018). Selective and membrane-permeable small molecule inhibitors of nicotinamide N-methyltransferase reverse high fat diet-induced obesity in mice. Biochem Pharmacol, 147:141–152. PMID 29155147 · DOI
3. Kraus D. et al. (2014). Nicotinamide N-methyltransferase knockdown protects against diet-induced obesity. Nature, 508(7495):258–262. PMID 24717514 · DOI
4. Babula J.J. et al. (2024). Nicotinamide N-methyltransferase inhibition mitigates obesity-related metabolic dysfunction. Diabetes Obes Metab, 26(11):5272–5282. PMID 39161060 · DOI
5. Awosemo O. et al. (2021). Development & validation of LC-MS/MS assay for 5-amino-1-methyl quinolinium in rat plasma: application to pharmacokinetic and oral bioavailability studies. J Pharm Biomed Anal, 204:114255. PMID 34304009 · DOI

Compound data from PubChem CID 66522933. Literature summaries describe published preclinical research and are not claims about this product’s effects in humans or animals.