 | |
| Names | |
|---|---|
| IUPAC name 2-Acetamidobutanedioic acid[1] | |
| Identifiers | |
3D model (JSmol) | |
| 1726198S | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.012.403 |
| EC Number |
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| KEGG |
|
| MeSH | N-acetylaspartate |
| RTECS number |
|
| UNII | |
| |
| |
| Properties | |
| C6H9NO5 | |
| Molar mass | 175.140 g·mol−1 |
| Appearance | Colourless, transparent crystals |
| Melting point | 137 to 140 °C (279 to 284 °F; 410 to 413 K) |
| Boiling point | 141 to 144 °C (286 to 291 °F; 414 to 417 K) |
| logP | −2.209 |
| Acidity (pKa) | 3.142 |
| Basicity (pKb) | 10.855 |
| Hazards | |
| GHS labelling: | |
 | |
| Warning | |
| H315,H319,H335 | |
| P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P362,P403+P233,P405,P501 | |
| Related compounds | |
Related alkanoic acids | |
Related compounds | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
N-Acetylaspartic acid, orN-acetylaspartate (NAA), is a derivative ofaspartic acid with a formula of C6H9NO5 and a molecular weight of 175.139.
NAA is the second-most-concentratedmolecule in thebrain after theamino acidglutamate. It is detected in the adult brain inneurons,[2]oligodendrocytes andmyelin[3] and is synthesized in themitochondria from the amino acidaspartic acid andacetyl-coenzyme A.[4]
The various functions served by NAA are under investigation, but the primary proposed functions include:
In the brain, NAA was thought to be present predominantly in neuronal cell bodies, where it acts as a neuronal marker,[5] but it is also free to diffuse throughout neuronal fibers.[6]
However, the recent discovery of a higher concentration of NAA in myelin and oligodendrocytes than in neurons raises questions about the validity of the use of NAA as a neuronal marker.[3] NAA gives off the largest signal inmagnetic resonance spectroscopy of the human brain. The levels measured there are decreased in numerous neuropathological conditions ranging from brain injury tostroke toAlzheimer's disease. This fact makes NAA a potential diagnostic molecule for doctors treating patients with brain damage or disease.
NAA may be a marker of creativity.[7] High NAA levels in thehippocampus are related to betterworking memory performance in humans.[8] Whole-brain levels of NAA have also been found to be positively correlated with educational attainment in adults.[9]
NAA may function as aneurotransmitter in the brain by acting onmetabotropic glutamate receptors.[10]
