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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 transported to Earth by theMurchison meteorite[citation needed], 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,[1] suggesting a role in the origin of life.[2]
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[3][4] by activating peripheralGABAB receptors.[4][5] In a mouse model ofosteoarthritis isovaline restored mobility, suggesting inhibition of nociception by isovaline in the synovial membrane of the mouse knee.[4]
Isovaline does not cross theblood–brain barrier[4] and does not enter into the brain or spinal cord. Drugs such asopioids cross the blood–brain barrier to produce analgesia but often produce in addition confusion, sedation, andaddiction.
Isovaline acts downstream to thecyclooxygenase system thatNSAIDs inhibit, suggesting a means to avoid adverse effects such as irritation of thegastrointestinal system.
