Isovaline

Isovaline

Names
IUPAC name 2-Amino-2-methylbutanoic acid
Other names 2-Amino-2-methylbutyric acid; 2-Ethylalanine; α-Ethylalanine
Identifiers
CAS Number	595-39-1 Y 3059-97-0 (R) Y 595-40-4 (S) Y
ChemSpider	85483
Jmol 3D model	Interactive image
PubChem	6971275
InChI InChI=1S/C5H11NO2/c1-3-5(2,6)4(7)8/h3,6H2,1-2H3,(H,7,8) Key: GCHPUFAZSONQIV-UHFFFAOYSA-N
SMILES O=C(O)C(N)(C)CC
Properties
Chemical formula	C5H11NO2
Molar mass	117.15 g·mol−1
Vapor pressure	{{{value}}}
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 suggesting a role in the origin of life.

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 by activating peripheral GABA_B receptors. In a mouse model of osteoarthritis isovaline restored mobility, suggesting inhibition of nociception by isovaline in the synovial membrane of the mouse knee.

Isovaline does not cross the blood-brain barrier 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

• Valine
• Norvaline