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    Chemistry

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    Also known as: L-glutamic acid, 56-86-0, (2s)-2-aminopentanedioic acid, (s)-2-aminopentanedioic acid, Glutamidex, Glutaminol
    Molecular Formula
    C5H9NO4
    Molecular Weight
    147.13  g/mol
    InChI Key
    WHUUTDBJXJRKMK-VKHMYHEASA-N
    FDA UNII
    3KX376GY7L
    L-Glutamic Acid
    A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.
    1 2D Structure

    L-Glutamic Acid

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (2S)-2-aminopentanedioic acid
    2.1.2 InChI
    InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
    2.1.3 InChI Key
    WHUUTDBJXJRKMK-VKHMYHEASA-N
    2.1.4 Canonical SMILES
    C(CC(=O)O)C(C(=O)O)N
    2.1.5 Isomeric SMILES
    C(CC(=O)O)[C@@H](C(=O)O)N
    2.2 Other Identifiers
    2.2.1 UNII
    3KX376GY7L
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Aluminum L Glutamate

    2. Aluminum L-glutamate

    3. D Glutamate

    4. D-glutamate

    5. Glutamate

    6. Glutamate, Potassium

    7. Glutamic Acid, (d)-isomer

    8. L Glutamate

    9. L Glutamic Acid

    10. L-glutamate

    11. L-glutamate, Aluminum

    12. L-glutamic Acid

    13. Potassium Glutamate

    2.3.2 Depositor-Supplied Synonyms

    1. L-glutamic Acid

    2. 56-86-0

    3. (2s)-2-aminopentanedioic Acid

    4. (s)-2-aminopentanedioic Acid

    5. Glutamidex

    6. Glutaminol

    7. H-glu-oh

    8. L-glutamate

    9. Glutacid

    10. Glutaton

    11. Aciglut

    12. L-glutaminic Acid

    13. Glutamicol

    14. Glusate

    15. (s)-glutamic Acid

    16. L-glu

    17. D-glutamiensuur

    18. L-(+)-glutamic Acid

    19. Acidum Glutamicum

    20. Glutaminic Acid

    21. Alpha-aminoglutaric Acid

    22. Glutamic Acid, L-

    23. Poly-l-glutamate

    24. (s)-(+)-glutamic Acid

    25. Acido Glutamico

    26. Acide Glutamique

    27. Fema No. 3285

    28. Glut

    29. Glutamate

    30. L-alpha-aminoglutaric Acid

    31. Alpha-glutamic Acid

    32. Polyglutamic Acid

    33. Glu

    34. Pentanedioic Acid, 2-amino-, (s)-

    35. 2-aminoglutaric Acid

    36. Ccris 7314

    37. Glutamic Acid (l-glutamic Acid)

    38. 1-aminopropane-1,3-dicarboxylic Acid

    39. L-2-aminoglutaric Acid

    40. Acidum Glutaminicum

    41. Ai3-18472

    42. 25513-46-6

    43. Epa Pesticide Chemical Code 374350

    44. Nsc 143503

    45. Glutamic Acid (van)

    46. Glutamic Acid (h-3)

    47. Glutaminic Acid (van)

    48. Gamma-l-glutamic Acid

    49. Glutamate, L-

    50. Glutamic Acid [usan:inn]

    51. Alpha-poly-l-glutamic Acid

    52. L(+)-glutamic Acid

    53. L-2-amino-pentanedioic Acid

    54. Acide Glutamique [inn-french]

    55. Acido Glutamico [inn-spanish]

    56. Acidum Glutamicum [inn-latin]

    57. Glutamic Acid, (s)-

    58. Alpha-aminoglutaric Acid (van)

    59. 3kx376gy7l

    60. Ins No.620

    61. E 620

    62. Chebi:16015

    63. Ins-620

    64. Nsc-143503

    65. 2-aminopentanedioic Acid, (s)-

    66. Ncgc00024502-03

    67. E620

    68. Glutamic Acid Polymer

    69. A-glutamic Acid

    70. E-620

    71. 55443-55-5

    72. A-aminoglutaric Acid

    73. Poly(alpha-l-glutamic Acid)

    74. Alpha-l-glutamic Acid Polymer

    75. L-a-aminoglutaric Acid

    76. (2s)-2-aminopentanedioate

    77. L-glutaminsaeure

    78. L-acido Glutamico

    79. .alpha.-glutamic Acid

    80. Glt

    81. L(+)-monosodium Glutamate Monohydrate

    82. 1-amino-propane-1,3-dicarboxylic Acid

    83. Glutamic Acid [usan]

    84. 6106-04-3

    85. Einecs 200-293-7

    86. L-glutamic Acid (9ci)

    87. Mfcd00002634

    88. Aminoglutarate

    89. Unii-3kx376gy7l

    90. Alpha-glutamate

    91. A-glutamate

    92. L-gluatmate

    93. A-aminoglutarate

    94. L-glutamic-acid

    95. L-glutamic Adid

    96. 2-aminoglutarate

    97. Aminoglutaric Acid

    98. 1ftj

    99. 1xff

    100. (s)-glutamate

    101. L-a-aminoglutarate

    102. Alpha-aminoglutarate

    103. Ggl

    104. (l)-glutamic Acid

    105. H-glu

    106. L-glutamic,(s)

    107. L-(+)-glutamate

    108. Poly(l-glutamicacid)

    109. L-alpha-aminoglutarate

    110. Glutamic Acid (usp)

    111. Poly(l-glutamic Acid)

    112. Tocris-0218

    113. [3h]-l-glutamic Acid

    114. 1ii5

    115. (+)-l-glutamic Acid

    116. (s)-(+)-glutamate

    117. (s)-glu

    118. Dsstox_cid_659

    119. L-[14c(u)]glutamate

    120. (s)-2-aminopentanedioate

    121. Biomol-nt_000170

    122. Ec 200-293-7

    123. Glutamic Acid [mi]

    124. L-glutamic Acid (jp17)

    125. Schembl2202

    126. Dsstox_rid_75716

    127. Gamma-poly(l-glutamic Acid)

    128. Glutamic Acid [inn]

    129. H-glu-2-chlorotrityl Resin

    130. L-glutamic Acid-[13c5]

    131. Dsstox_gsid_20659

    132. L-glutamic Acid, 98.5%

    133. Lopac0_000529

    134. S)-2-aminopentanedioic Acid

    135. Glutamic Acid [inci]

    136. Glutamic Acid [vandf]

    137. L-glutamic Acid [fcc]

    138. L-glutamic Acid [jan]

    139. Bpbio1_001132

    140. Chembl575060

    141. Gtpl1369

    142. Hsdb 490

    143. Glutamic Acid [usp-rs]

    144. Glutamic Acid [who-dd]

    145. L-glutamic Acid [fhfi]

    146. L-glutamic Acid, 99%, Fcc

    147. Dtxsid5020659

    148. Bdbm17657

    149. Chebi:53374

    150. 1-aminopropane-1,3-dicarboxylate

    151. Glutamic Acid, L- (7ci,8ci)

    152. L (+)-glutamic Acid, Alpha-form

    153. 1-amino-propane-1,3-dicarboxylate

    154. 6899-05-4

    155. L-glutamic Acid, Non-animal Source

    156. Zinc1482113

    157. Tox21_113053

    158. Glutamic Acid [ep Monograph]

    159. Hsci1_000269

    160. Pdsp1_000128

    161. Pdsp1_001539

    162. Pdsp2_000127

    163. Pdsp2_001523

    164. S6266

    165. Akos006238837

    166. Akos015854087

    167. Am81690

    168. Ccg-204619

    169. Db00142

    170. Sdccgsbi-0050512.p002

    171. Cas-56-86-0

    172. Alanine Impurity B [ep Impurity]

    173. Ncgc00024502-01

    174. Ncgc00024502-02

    175. Ncgc00024502-04

    176. Ncgc00024502-07

    177. (2s)-2-aminopentanedioic Acid;h-glu-oh

    178. Ac-11294

    179. Ds-13284

    180. Gamma-poly(l-glutamic Acid) Macromolecule

    181. Hy-14608

    182. (s)-1-aminopropane-1,3-dicarboxylic Acid

    183. (s)-2-amino-1,5-pentanedioic Acid

    184. A6810

    185. Cs-0003473

    186. G0059

    187. L-glutamic Acid, Bioultra, >=99.5% (nt)

    188. L-glutamic Acid, Tested According To Ph.eur.

    189. C00025

    190. D00007

    191. L-glutamic Acid, Nist(r)rm 8573, Usgs40

    192. Lysine Acetate Impurity B [ep Impurity]

    193. M02979

    194. M03872

    195. L-glutamic Acid, Jis Special Grade, >=99.0%

    196. L-glutamic Acid, Nist(r) Rm 8574, Usgs41

    197. 002g634

    198. A831210

    199. Sr-01000597730

    200. J-502415

    201. L-glutamic Acid, Reagentplus(r), >=99% (hplc)

    202. L-glutamic Acid, Vetec(tm) Reagent Grade, >=99%

    203. Sr-01000597730-1

    204. L-glutamic Acid, >=99%, Fcc, Natural Sourced, Fg

    205. Q26995161

    206. F8889-8668

    207. Z1250208666

    208. 27322e29-9696-49c1-b541-86bef72de2f3

    209. Glutamic Acid, European Pharmacopoeia (ep) Reference Standard

    210. L-glutamic Acid, Certified Reference Material, Tracecert(r)

    211. Glutamic Acid, United States Pharmacopeia (usp) Reference Standard

    212. L-glutamic Acid, From Non-animal Source, Meets Ep Testing Specifications, Suitable For Cell Culture, 98.5-100.5%

    213. L-glutamic Acid, Pharmagrade, Ajinomoto, Ep, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production, Suitable For Cell Culture

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 147.13 g/mol
    Molecular Formula C5H9NO4
    XLogP3-3.7
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count4
    Exact Mass147.05315777 g/mol
    Monoisotopic Mass147.05315777 g/mol
    Topological Polar Surface Area101 Ų
    Heavy Atom Count10
    Formal Charge0
    Complexity145
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Considered to be nature's "Brain food" by improving mental capacities; helps speed the healing of ulcers; gives a "lift" from fatigue; helps control alcoholism, schizophrenia and the craving for sugar.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    In addition to being one of the building blocks in protein synthesis, it is the most widespread neurotransmitter in brain function, as an excitatory neurotransmitter and as a precursor for the synthesis of GABA in GABAergic neurons.

    5.2 Absorption, Distribution and Excretion

    Absorption

    Absorbed from the lumen of the small intestine into the enterocytes.Absorption is efficient and occurs by an active transport mechanism.

    /MILK/ Previous short observational studies on the free amino acid (FAA) content of human milk have shown that glutamine and glutamic acid increase in the first 4 to 6 weeks of life. Changes in human milk content of free amino acids (FAAs) was determined at colostrum, 1 month, and 3 months of lactation in 16 healthy lactating women after delivery of full-term infants. Milk was collected at the end of each feeding (hindmilk) during 24 hours. Glutamic acid and taurine were the most abundant FAAs at colostrum. Although taurine remained stable throughout lactation, glutamic acid (the prevalent FAA) and glutamine increased approximately 2.5 and 20 times, respectively, with progressing lactation representing more than 50% of total FAA at 3 months. The content of essential FAA was also stable, so the change in total FAA content was almost entirely due to the changes in glutamic acid and glutamine. Breast-fed infants are supplied with progressively increasing amounts of glutamine and glutamic acid throughout lactation. The increasing intake of glutamic acid and glutamine could benefit breast-fed infants with molecules that are likely to protect the enteral mucosa and act as neurotransmitters and as a source of nitrogen.

    PMID:11144435 Agostoni C et al; J Pediatr Gastroenterol Nutr. 31 (5): 508-12 (2000)

    In this report, (13)N -labeled L-glutamine and L-glutamic acid was synthesized by an enzymatic method ... . Organ distribution studies and whole body scans in mongrel dogs demonstrated low myocardial uptake of glutamine and glutamic acid and that the liver demonstrated a greater uptake of glutamine than glutamic acid or ammonia.

    Gelbard A et al; Radiology; 116:127-132 (1975)

    The measurement of the intestinal metabolism of the nitrogen moiety of glutamic acid has been investigated by oral ingestion of l-[(15)N]glutamic acid and sampling of arterialized blood. Measurements have been made in six normal adults weighing an average of 72.8 kg ingesting 100 mg of l-[(15)N]glutamic acid after an overnight fast. Measurement of the enrichment of arterial glutamic acid, glutamine and alanine was by gas chromatography-mass spectrometry. Isotopic enrichment of the amino acids was followed for 150 min after the ingestion of the amino acid. Arterialized venous blood amino acid concentrations, measured by HPLC, demonstrated no significant changes during the course of the experiment. From the observed appearance of label in arterialized glutamic acid, alanine and glutamine, little luminal glutamic acid reaches the extracellular pool. The majority of the administered nitrogen label appears in the arterial alanine and glutamine components.

    PMID:2908193 Johnson AW et al; Clin Sci (Lond). 75 (5): 499-502 (1988)

    5.3 Metabolism/Metabolites

    Hepatic

    Cortical excitability reflects a balance between excitation and inhibition. Glutamate is the main excitatory and GABA the main inhibitory neurotransmitter in the mammalian cortex. Changes in glutamate and GABA metabolism may play important roles in the control of cortical excitability. Glutamate is the metabolic precursor of GABA, which can be recycled through the tricarboxylic acid cycle to synthesize glutamate. GABA synthesis is unique among neurotransmitters, having two separate isoforms of the rate-controlling enzyme, glutamic acid decarboxylase. The need for two separate genes on two chromosomes to control GABA synthesis is unexplained. Two metabolites of GABA are present in uniquely high concentrations in the human brain. Homocarnosine and pyrrolidinone have a major impact on GABA metabolism in the human brain. Both of these GABA metabolites have anticonvulsant properties and can have a major impact on cortical excitability. /Glutamate, GABA/

    PMID:12467378 Petroff OA; Neuroscientist. 8 (6): 562-73 (2002)

    The measurement of the intestinal metabolism of the nitrogen moiety of glutamic acid has been investigated by oral ingestion of l-[(15)N]glutamic acid and sampling of arterialized blood. Measurements have been made in six normal adults weighing an average of 72.8 kg ingesting 100 mg of l-[(15)N]glutamic acid after an overnight fast. Measurement of the enrichment of arterial glutamic acid, glutamine and alanine was by gas chromatography-mass spectrometry. Isotopic enrichment of the amino acids was followed for 150 min after the ingestion of the amino acid. Arterialized venous blood amino acid concentrations, measured by HPLC, demonstrated no significant changes during the course of the experiment. From the observed appearance of label in arterialized glutamic acid, alanine and glutamine, little luminal glutamic acid reaches the extracellular pool. The majority of the administered nitrogen label appears in the arterial alanine and glutamine components.

    PMID:2908193 Johnson AW et al; Clin Sci (Lond). 75 (5): 499-502 (1988)

    5.4 Mechanism of Action

    Glutamate activates both ionotropic and metabotropic glutamate receptors. The ionotropic ones being non-NMDA (AMPA and kainate) and NMDA receptors. Free glutamic acid cannot cross the blood-brain barrier in appreciable quantities; instead it is converted into L-glutamine, which the brain uses for fuel and protein synthesis. It is conjectured that glutamate is involved in cognitive functions like learning and memory in the brain, though excessive amounts may cause neuronal damage associated in diseases like amyotrophic lateral sclerosis, lathyrism, and Alzheimer's disease. Also, the drug phencyclidine (more commonly known as PCP) antagonizes glutamate at the NMDA receptor, causing behavior reminiscent of schizophrenia. Glutamate in action is extremely difficult to study due to its transient nature.

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    15-Feb-2021
    17-Sep-2024
    KGS
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