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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

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 Formula	C₅H₉NO₄
Molecular Weight	147.13 g/mol
XLogP3	-3.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	4
Exact Mass	147.05315777 g/mol
Monoisotopic Mass	147.05315777 g/mol
Topological Polar Surface Area	101 Å²
Heavy Atom Count	10
Formal Charge	0
Complexity	145
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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)

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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