Isovaline
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| Names | |
|---|---|
| IUPAC name
2-Amino-2-methylbutanoic acid | |
| Other names
2-Amino-2-methylbutyric acid; 2-Ethylalanine; α-Ethylalanine | |
| Identifiers | |
595-39-1  3059-97-0 (R) 595-40-4 (S) | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 85483 |
| PubChem | 6971275 |
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| |
| Properties | |
| C5H11NO2 | |
| Molar mass | 117.15 g·mol−1 |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Isovaline is a rare amino acid transported to earth by the Murchison meteorite, which landed in Australia in 1969. The discovery of isovaline in the biosphere demonstrates an extraterrestrial origin of amino acids and has been linked to the homochirality of life on earth [1] suggesting a role in the origin of life.[2]
The structure of isovaline is similar to the amino acids GABA and glycine, the chief inhibitory neurotransmitters in the mammalian central nervous system. Isovaline acts as an analgesic in mice [3][4] by activating peripheral GABAB receptors.[4][5] In a mouse model of osteoarthritis isovaline restored mobility, suggesting inhibition of nociception by isovaline in the synovial membrane of the mouse knee.[4]
Isovaline does not cross the blood-brain barrier[4] and does not enter into the brain or spinal cord. Drugs such as opioids cross the blood-brain barrier to produce analgesia but often produce confusion, sedation and addiction.
Isovaline acts downstream to the cyclooxygenase system that NSAIDs inhibit, suggesting a means to avoid adverse effects such as irritation of the gastrointestinal system.
This novel first-in-class compound has potential for treatment of acute and chronic pain, without the negative side effects associated with other commonly used analgesics.
See also
References
- ↑ J.R. Cronin; S. Pizzarello (1999). "Amino acid enantiomer excesses in meteorites". origin and significanca Adv. Space Rex. 23 (2): 293–299. doi:10.1016/s0273-1177(99)00050-2.
- ↑ Mindy Levine; Craig Scott Kenesky; Daniel Mazori; Ronald Breslow (2008). "Enantioselective Synthesis and Enantiomeric Amplification of Amino Acids". Prebiotic Conditions Organic Letters. 10 (12): 2433–2436. doi:10.1021/ol8007099.
- ↑ Macleod BA. Wang JT. Chung CC. Ries CR. Schwarz SK. Puil E. (Apr 2010). "Analgesic properties of the novel amino acid, isovaline". Anesthesia & Analgesia. 110 (4): 1206–14. doi:10.1213/ane.0b013e3181d27da2.
- 1 2 3 4 Whitehead RA. Puil E. Ries CR. Schwarz SK. Wall RA. Cooke JE. Putrenko I. Sallam NA. Macleod BA. (Jun 28, 2012). "GABA(B) receptor-mediated selective peripheral analgesia by the non-proteinogenic amino acid, isovaline.". Neuroscience. 213: 154–60. doi:10.1016/j.neuroscience.2012.04.026.
- ↑ Cooke JE. Mathers DA. Puil E. (Jan 2010). "R-Isovaline: a subtype-specific agonist at GABA(B)-receptors?". Neuroscience. 201: 85–95. doi:10.1016/j.neuroscience.2011.10.049.