2-Me-IAA is a non-proteinogenic amino acid derivative related to indole-3-acetic acid (IAA) in which a methyl substituent is present at the 2-position of the indole ring, while the molecule retains the characteristic amino-acid-like framework bearing an amino group and a carboxyl group. The indole heteroaromatic side-chain provides a planar, conjugated aromatic system that can participate in noncovalent interactions, and the amino and carboxyl functional groups allow it to exist as a zwitterionic species under appropriate conditions, supporting salt formation and controlled reactivity in chemical transformations. 2-Me-IAA is typically used in chemical biology and structure-activity or labeling studies where modified indole-containing amino acid analogues are needed to probe effects of ring substitution on conjugation, binding assays, or analytical detection of IAA-like motifs.
CAT No: CP25510
CAS No:1912-43-2
Synonyms/Alias:2-Methylindole-3-aceticacid;1912-43-2;(2-Methyl-1H-indol-3-yl)aceticacid;2-Methyl-3-indoleaceticacid;2-(2-methyl-1H-indol-3-yl)aceticacid;QJNNHJVSQUUHHE-UHFFFAOYSA-N;2-(2-methylindol-3-yl)aceticacid;PubChem7229;SMR000036607;ACMC-209euw;AC1LBU9M;AC1Q2EZJ;AC1Q2EZK;2-methylindole-3aceticacid;Oprea1_079937;KSC174C7R;MLS000039417;SCHEMBL379103;333301_ALDRICH;CHEMBL312858;CTK0H4178;(2-methyl-3-indolyl)aceticacid;MolPort-000-877-527;BB_SC-1381;HMS2462J09
Chemical Name:2-Methylindole-3-acetic acid, 99%
2-Me-IAA is a substituted indole-3-acetic acid (IAA) analog featuring a methyl substituent at the 2-position of the indole ring, retaining the acetic acid side chain that is commonly leveraged in auxin-related chemical biology. As a non-proteinogenic amino acid-like small molecule, it is typically used as a defined structural probe to interrogate auxin receptor recognition, signaling pathway responses, and structure-activity relationships in controlled experimental systems. Researchers also employ 2-Me-IAA as a chemically characterized standard or reference compound when benchmarking auxin-analog performance in binding, uptake, and downstream readouts.
1. Auxin Signaling Probing
2-Me-IAA is used in chemical biology studies designed to probe auxin/indole-3-acetic acid recognition and downstream signaling behavior using structurally defined analogs. Investigators commonly incorporate this compound into receptor-binding assays, cell-based reporter workflows, and pathway interrogation experiments to assess how indole-ring substitution patterns influence auxin-like activity profiles. The 2-methyl substitution provides a practical handle for SAR work because it directly perturbs the indole microenvironment while keeping the acetic acid motif consistent with IAA-like recognition elements.
2. Structure-Activity Relationship Studies
2-Me-IAA supports medicinal chemistry and plant-growth regulation research programs focused on structure-activity relationship (SAR) mapping of auxin analogs. Teams developing new indoleacetic acid mimetics use it as a reference scaffold to compare how ring substitution affects physicochemical behavior and experimental outcomes across a panel of analogs. Because 2-Me-IAA is a single, well-defined analog rather than a mixture, it is also frequently used for head-to-head comparisons in screening follow-ups and for interpreting trends when correlating structural changes with assay readouts.
3. Analytical Reference Compound
2-Me-IAA is frequently selected as an analytical standard or calibration/reference material for quantifying auxin-analog chemistry in research samples. Analytical method developers use it to support LC-MS workflows, targeted quantitation, and identity confirmation when monitoring indoleacetic acid analogs in extracts or reaction mixtures. The defined substitution pattern helps distinguish it from native IAA and other analogs in chromatographic and mass-based separations, making it useful for method validation, internal benchmarking, and data normalization in auxin-related studies.
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