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| Names | |
|---|---|
| IUPAC name 2-Amino-2-methylbutanoic acid | |
| Other names 2-Amino-2-methylbutyric acid; 2-Ethylalanine; α-Ethylalanine | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| UNII |
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| Properties | |
| C5H11NO2 | |
| Molar mass | 117.148 g·mol−1 |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Isovaline is a rareamino acid found in theMurchison meteorite,[1] which landed inAustralia in 1969. The discovery of isovaline in thebiosphere demonstrates an extraterrestrial origin of amino acids and has been linked to thehomochirality of life on Earth,[2] suggesting a role in the origin of life.[3]
Isovaline is anisomer of the common amino acidvaline, with the position of one methyl group shifted slightly (from position 3 to position 2). The structure of isovaline is also somewhat similar to the amino acidsGABA andglycine, the chief inhibitoryneurotransmitters in themammaliancentral nervous system. Isovaline acts as an analgesic in mice[4][5] by activating peripheralGABAB receptors.[5][6] In a mouse model ofosteoarthritis isovaline restored mobility, suggesting inhibition of nociception by isovaline in the synovial membrane of the mouse knee.[5]
Isovaline does not cross theblood–brain barrier[5] and does not enter into the brain or spinal cord.
Isovaline acts downstream to thecyclooxygenase system thatNSAIDs inhibit, suggesting a means to avoid adverse effects such as irritation of thegastrointestinal system.[citation needed]
