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Allylglycine

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Allylglycine
Names
Preferred IUPAC name 2-Aminopent-4-enoic acid
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.028.809 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)Key: WNNNWFKQCKFSDK-UHFFFAOYSA-N
  • InChI=1/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)Key: WNNNWFKQCKFSDK-UHFFFAOYAL
SMILES
  • C=CCC(C(=O)O)N
  • O=C(O)C(N)CC=C
Properties
Chemical formula C5H9NO2
Molar mass 115.13 g/mol
Appearance white crystalline powder
Density 1.098 g/mL
Melting point 265 °C (509 °F; 538 K)
Boiling point 231 °C (448 °F; 504 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Convulsant
Lethal dose or concentration (LD, LC):
LD50 (median dose) 147-195 mg/kg (mice, intraperitoneal)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Allylglycine is a glycine derivative. It is an inhibitor of glutamate decarboxylase. Inhibition of glutamate decarboxylase blocks GABA biosynthesis, leading to lower levels of the neurotransmitter. Allylglycine is known to induce seizures in animals studies, presumably due to this GDC-inhibiting activity.

See also

References

  1. Piepho, R. W; Friedman, A. H (1977). "Chronopharmacology of Strychnine and Allylglycine in the Mouse". Clinical and Experimental Pharmacology and Physiology. 4 (3): 263–6. doi:10.1111/j.1440-1681.1977.tb02623.x. PMID 891041. S2CID 25088608.
  2. Abshire VM, Hankins KD, Roehr KE, DiMicco JA (November 1988). "Injection of L-allylglycine into the posterior hypothalamus in rats causes decreases in local GABA which correlate with increases in heart rate". Neuropharmacology. 27 (11): 1171–7. doi:10.1016/0028-3908(88)90013-5. PMID 3205383. S2CID 32655173.
  3. Sajdyk T, Johnson P, Fitz S, Shekhar A (August 2008). "Chronic inhibition of GABA synthesis in the bed nucleus of the stria terminalis elicits anxiety-like behavior". J. Psychopharmacol. (Oxford). 22 (6): 633–41. doi:10.1177/0269881107082902. PMC 3065212. PMID 18308797.
  4. Thomas J, Yang YC (June 1991). "Allylglycine induced seizures in male and female rats". Physiol. Behav. 49 (6): 1181–3. doi:10.1016/0031-9384(91)90348-R. PMID 1654571. S2CID 10506822.
GABA receptor modulators
Ionotropic
GABAATooltip γ-Aminobutyric acid A receptor
GABAA-ρTooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABABTooltip γ-Aminobutyric acid B receptor
See also
Receptor/signaling modulators
GABAA receptor positive modulators
GABA metabolism/transport modulators
Glutamate metabolism and transport modulators
Transporter
EAATsTooltip Excitatory amino acid transporters
vGluTsTooltip Vesicular glutamate transporters
Enzyme
GAHTooltip Glutamine aminohydrolase (glutaminase)
ASTTooltip Aspartate aminotransferase
ALTTooltip Alanine aminotransferase
GDHTooltip Glutamate dehydrogenase
GSTooltip Glutamine synthetase
GADTooltip Glutamate decarboxylase
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Metabotropic glutamate receptor modulators • GABA metabolism and transport modulators
Convulsants
GABA receptor antagonists
GABA synthesis inhibitors
Glycine receptor antagonists
Glutamate receptor agonists
Convulsant barbiturates
Other


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