Allylglycine

Allylglycine
Names
Preferred IUPAC name
2-Aminopent-4-enoic acid
Identifiers
CAS Number
  • 7685-44-1 ☒N
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 13425 checkY
ECHA InfoCard 100.028.809 Edit this at Wikidata
PubChem CID
  • 14044
InChI
  • InChI=1S/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8) checkY
    Key: WNNNWFKQCKFSDK-UHFFFAOYSA-N checkY
  • InChI=1/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)
    Key: WNNNWFKQCKFSDK-UHFFFAOYAL
  • 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)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

Allylglycine is a glycine derivative. It is an inhibitor of glutamate decarboxylase.[2] Inhibition of glutamate decarboxylase blocks GABA biosynthesis, leading to lower levels of the neurotransmitter.[3] Allylglycine is known to induce seizures in animals studies, presumably due to this GDC-inhibiting activity.[4]

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.
  • v
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  • e
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
  • v
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  • e
Transporter
EAATsTooltip Excitatory amino acid transporters
vGluTsTooltip Vesicular glutamate transporters
Enzyme
GAHTooltip Glutamine aminohydrolase (glutaminase)
  • BPTES
  • CB-839
  • DON
ASTTooltip Aspartate aminotransferase
  • 2-Amino-3-butenoic acid
  • AAOA
  • AMB
  • β-DL-Methylene-aspartate
  • Hydrazinosuccinate
ALTTooltip Alanine aminotransferase
  • β-Chloro-L-alanine
  • L-Cycloserine
  • Propargylglycine
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
  • v
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  • e
GABA receptor antagonists
GABA synthesis inhibitors
Glycine receptor antagonists
Glutamate receptor agonists
Convulsant barbiturates
Other


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