Catalog Number: 1490
Alternate Names: 4-Methoxy-7-nitroindolinyl-caged-L-glutamate, MNI glutamate
Chemical Name: (S)-α-Amino-2,3-dihydro-4-methoxy-7-nitro-δ-oxo-1H-indole-1-pentanoic acid
Biological Activity
MNI-caged glutamate that rapidly and efficiently releases glutamate (Cat. No. 0218) when photolysed (300 - 380 nm excitation). Water-soluble, highly resistant to hydrolysis, stable at neutral pH, and pharmacologically inactive at neuronal glutamate receptors (up to mM concentrations). 2.5-fold more efficient at releasing L-glutamate than NI-caged L-glutamate.
Technical Data
  • M.Wt:
  • Formula:
  • Solubility:
    Soluble to 50 mM in water with gentle warming
  • Purity:
  • Storage:
    Store at -20°C
  • CAS No:
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis. All Tocris products are intended for laboratory research use only.
Additional Information
Licensing Caveats:
Sold under license from the Medical Research Council
Other Product-Specific Information:
Background References
  1. Photochemical and pharmacological evaluation of 7-nitroindolinyl- and 4-methoxy-7-nitroindolinyl-amino acids as novel, fast caged neurotransmitters.
    Canepari et al.
    J.Neurosci.Methods, 2001;112:29
  2. Dendritic spine geometry is critical for AMPA receptor expression in hippocampal CA1 pyramidal neurons.
    Matsuzaki et al.
    Nat.Neurosci., 2001;4:1086
  3. New caged neurotransmitter analogs selective for glutamate receptor sub-types based on methoxynitroindoline and nitrophenylethoxycarbonyl caging groups.
    Palma-Cerda et al.
    Neuropharmacology., 2012;63:624
  4. Comparative analysis of inhibitory effects of caged ligands for the NMDA receptor.
    Maier et al.
    J.Neurosci.Methods, 2005;142:1
  5. Effects of aromatic substitutions on the photocleavage of 1-acyl-7-nitroindolines.
    Papageorgiou and Corrie
    Tetrahedron, 2000;56:8197

The citations listed below are publications that use Tocris products. Selected citations for MNI-caged-L-glutamate include:

Showing Results 1 - 10 of 41

  1. Stereotyped initiation of retinal waves by bipolar cells via presynaptic NMDA autoreceptors.
    Authors: Zhang Et al.
  2. The Shaping of Two Distinct Dendritic Spikes by A-Type Voltage-Gated K(+) Channels.
    Authors: Yang Et al.
    J Neurosci
  3. Highly differentiated cellular and circuit properties of infralimbic pyramidal neurons projecting to the periaqueductal gray and amygdala.
    Authors: Ferreira Et al.
    Nat Commun
  4. Optical control of NMDA receptors with a diffusible photoswitch.
    Authors: Laprell Et al.
    PLoS One
  5. Distribution and function of HCN channels in the apical dendritic tuft of neocortical pyramidal neurons.
    Authors: Harnett Et al.
    PLoS One
  6. Melanoma brain colonization involves the emergence of a brain-adaptive phenotype.
    Authors: Nygaard Et al.
    J Neurosci
  7. The Functional Organization of Neocortical Networks Investigated in Slices with Local Field Recordings and Laser Scanning Photostimulation.
    Authors: Erlandson Et al.
    Front Cell Neurosci
  8. Fast Decay of CaMKII FRET Sensor Signal in Spines after LTP Induction Is Not Due to Its Dephosphorylation.
    Authors: Otmakhov Et al.
    Front Cell Neurosci
  9. Spatially reciprocal inhibition of inhibition within a stimulus selection network in the avian midbrain.
    Authors: Goddard Et al.
    PLoS One
  10. Input integration around the dendritic branches in hippocampal dentate granule cells.
    Authors: Kamijo Et al.
    Cogn Neurodyn
  11. Adult neurogenesis modifies excitability of the dentate gyrus.
    Authors: Ikrar Et al.
    Front Neural Circuits
  12. Plasticity of binocularity and visual acuity are differentially limited by nogo receptor.
    Authors: Stephany Et al.
    J Neurosci
  13. Directional summation in non-direction selective retinal ganglion cells.
    Authors: Abbas Et al.
    PLoS Comput Biol
  14. Four-dimensional multi-site photolysis of caged neurotransmitters.
    Authors: Go Et al.
    Front Cell Neurosci
  15. Rapid, activity-independent turnover of vesicular transmitter content at a mixed glycine/GABA synapse.
    Authors: Apostolides and Trussell
    J Neurosci
  16. Molecular layer perforant path-associated cells contribute to feed-forward inhibition in the adult dentate gyrus.
    Authors: Li Et al.
    Proc Natl Acad Sci U S A
  17. Intrinsic connections in the anterior part of the bed nucleus of the stria terminalis.
    Authors: Turesson Et al.
    J Neurophysiol
  18. Withdrawal from cocaine self-administration alters NMDA receptor-mediated Ca2+ entry in nucleus accumbens dendritic spines.
    Authors: Ferrario Et al.
    PLoS One
  19. Mechanism of inhibition of the glutamate transporter EAAC1 by the conformationally constrained glutamate analogue (+)-HIP-B.
    Authors: Callender Et al.
  20. Alteration of synaptic network dynamics by the intellectual disability protein PAK3.
    Authors: Dubos Et al.
    J Neurosci
  21. Increased excitatory synaptic input to granule cells from hilar and CA3 regions in a rat model of temporal lobe epilepsy.
    Authors: Zhang Et al.
    J Neurosci
  22. Neural circuit mechanisms for pattern detection and feature combination in olfactory cortex.
    Authors: Davison and Ehlers
  23. Oligodendrocytes as regulators of neuronal networks during early postnatal development.
    Authors: Doretto Et al.
    PLoS One
  24. Water and urea permeation pathways of the human excitatory amino acid transporter EAAT1.
    Authors: Vandenberg Et al.
    Biochem J
  25. NMDA receptor signaling in oligodendrocyte progenitors is not required for oligodendrogenesis and myelination.
    Authors: Biase Et al.
  26. Hetero-oligomerization of neuronal glutamate transporters.
    Authors: Nothmann Et al.
    J Neurosci
  27. Dysregulation of presynaptic calcium and synaptic plasticity in a mouse model of 22q11 deletion syndrome.
    Authors: Earls Et al.
    J Biol Chem
  28. Mechanism of cation binding to the glutamate transporter EAAC1 probed with mutation of the conserved amino acid residue Thr101.
    Authors: Tao Et al.
    J Biol Chem
  29. Discovery of a Novel Chemical Class of mGlu(5) Allosteric Ligands with Distinct Modes of Pharmacology.
    Authors: Hammond Et al.
    ACS Chem Neurosci
  30. High precision and fast functional mapping of cortical circuitry through a novel combination of voltage sensitive dye imaging and laser scanning photostimulation.
    Authors: Xu Et al.
    J Neurophysiol
  31. SLM Microscopy: Scanless Two-Photon Imaging and Photostimulation with Spatial Light Modulators.
    Authors: Nikolenko Et al.
    Front Neural Circuits
  32. Robust short-latency perisomatic inhibition onto neocortical pyramidal cells detected by laser-scanning photostimulation.
    Authors: Brill and Huguenard
    J Neurosci
  33. Synaptic circuit abnormalities of motor-frontal layer 2/3 pyramidal neurons in an RNA interference model of methyl-CpG-binding protein 2 deficiency.
    Authors: Wood Et al.
    Proc Natl Acad Sci U S A
  34. Differential distribution of endoplasmic reticulum controls metabotropic signaling and plasticity at hippocampal synapses.
    Authors: Holbro Et al.
    Proc Natl Acad Sci U S A
  35. Sequential changes in AMPA receptor targeting in the developing neocortical excitatory circuit.
    Authors: Brill and Huguenard
    J Reprod Dev
  36. Natural oligomers of the Alzheimer amyloid-beta protein induce reversible synapse loss by modulating an NMDA-type glutamate receptor-dependent signaling pathway.
    Authors: Shankar Et al.
    J Neurosci
  37. Neutralization of the aspartic acid residue Asp-367, but not Asp-454, inhibits binding of Na+ to the glutamate-free form and cycling of the glutamate transporter EAAC1.
    Authors: Tao Et al.
    J Biol Chem
  38. Blockade of mGluR1 receptor results in analgesia and disruption of motor and cognitive performances: effects of A-841720, a novel non-competitive mGluR1 receptor antagonist.
    Authors: El-Kouhen Et al.
    Br J Pharmacol
  39. Dendritic spines linearize the summation of excitatory potentials.
    Authors: Araya Et al.
    Proc Natl Acad Sci U S A
  40. The spine neck filters membrane potentials.
    Authors: Araya Et al.
    J Neurosci
  41. Astrocyte glutamate transporters regulate metabotropic glutamate receptor-mediated excitation of hippocampal interneurons.
    Authors: Huang Et al.
    J Neurosci
Expand to show all
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