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913839 Sigma-Aldrich

2-Methylnicotinic acid imidazolide


Synonym: (1H-imidazol-1-yl)(2-methylpyridin-3-yl)methanone, 1H-Imidazol-1-yl(2-methyl-3-pyridinyl)methanone, 3-(1H-imidazole-1-carbonyl)-2-methylpyridine, NAI, RNA SHAPE probe, RNA structure probe, mNAI




2-Methylnicotinic acid imidazolide (NAI or mNAI) is an RNA SHAPE probe for live-cell RNA structure profiling. SHAPE -- or selective 2′-hydroxyl acylation analyzed by primer extension -- uses small, electrophilic chemical probes to react with the 2′-hydroxyl group and provides insight to RNA structure and its dynamics in varied cells states or in cells with gene knockouts. It has also been extended to the SHALiPE approach, selective 2′-hydroxyl acylation with lithium ion-based primer extension.

Other Notes

Conditional control of RNA-guided nucleic acid cleavage and gene editing

Guidelines for SHAPE Reagent Choice and Detection Strategy for RNA Structure Probing Studies

SnapShot: RNA Structure Probing Technologies

Structural Analysis using SHALiPE to Reveal RNA G-Quadruplex Formation in Human Precursor MicroRNA

Determination of in vivo RNA structure in low-abundance transcripts

Safety & Documentation

Safety Information

WGK Germany 
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


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03-310 In Vivo SHAPE Reagent for Live Cell RNA Structure Analysis, In Vivo SHAPE Reagent contains 2-methylnicotinic acid imidazolide (NAI). This reagent has very low toxicity and permits the analysis of RNA structure in living cells using Selective 2’-Hydroxyl Acylation and Primer Extension (SHAPE).
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