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| ImageFile=Allylglycine.png
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| ImageSize=180px
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| IUPACName=2-Aminopent-4-enoic acid
| PIN = 2-Aminopent-4-enoic acid
| OtherNames=
| OtherNames=
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|Section3={{Chembox Hazards
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| MainHazards=Irritant
| MainHazards=[[Convulsant]]
| LD50=147-195 mg/kg (mice, intraperitoneal)<ref>{{cite journal|journal=Clinical and Experimental Pharmacology and Physiology|volume=4|issue=3|pages=263–6|doi=10.1111/j.1440-1681.1977.tb02623.x|pmid=891041|year=1977|last1=Piepho|first1=R. W|title=Chronopharmacology of Strychnine and Allylglycine in the Mouse|last2=Friedman|first2=A. H|s2cid=25088608}}</ref>
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'''Allylglycine''' is a [[glycine]] derivative. It is an inhibitor of the [[enzyme]] [[glutamate decarboxylase]].<ref name="pmid3205383">{{cite journal |author =Abshire VM, Hankins KD, Roehr KE, DiMicco JA |title=Injection of L-allylglycine into the posterior hypothalamus in rats causes decreases in local GABA which correlate with increases in heart rate |journal=Neuropharmacology |volume=27 |issue=11 |pages=1171–7 |date=November 1988 |pmid=3205383 |doi= 10.1016/0028-3908(88)90013-5|url= }}</ref> Inhibition of glutamate decarboxylase blocks [[GABA]] [[biosynthesis]], leading to lower levels of the [[neurotransmitter]].<ref name="pmid18308797">{{cite journal |author =Sajdyk T, Johnson P, Fitz S, Shekhar A |title=Chronic inhibition of GABA synthesis in the bed nucleus of the stria terminalis elicits anxiety-like behavior |journal=J. Psychopharmacol. (Oxford) |volume=22 |issue=6 |pages=633–41 |date=August 2008 |pmid=18308797 |doi=10.1177/0269881107082902 |url=http://jop.sagepub.com/cgi/pmidlookup?view=long&pmid=18308797 |pmc=3065212}}</ref> Allylglycine is known to induce [[seizure]]s in animals studies, presumably due to this GDC-inhibiting activity.<ref name="pmid1654571">{{cite journal |author =Thomas J, Yang YC |title=Allylglycine induced seizures in male and female rats |journal=Physiol Behav. |volume=49 |issue=6 |pages=1181-3 |date=June 1991 |pmid=1654571 |url=http://www.ncbi.nlm.nih.gov/pubmed/1654571}}</ref>
'''Allylglycine''' is a [[glycine]] derivative. It is an [[Enzyme inhibitor|inhibitor]] of [[glutamate decarboxylase]].<ref name="pmid3205383">{{cite journal |vauthors =Abshire VM, Hankins KD, Roehr KE, DiMicco JA |title=Injection of L-allylglycine into the posterior hypothalamus in rats causes decreases in local GABA which correlate with increases in heart rate |journal=Neuropharmacology |volume=27 |issue=11 |pages=1171–7 |date=November 1988 |pmid=3205383 |doi= 10.1016/0028-3908(88)90013-5|s2cid=32655173 }}</ref> Inhibition of glutamate decarboxylase blocks [[GABA]] [[biosynthesis]], leading to lower levels of the [[neurotransmitter]].<ref name="pmid18308797">{{cite journal |vauthors =Sajdyk T, Johnson P, Fitz S, Shekhar A |title=Chronic inhibition of GABA synthesis in the bed nucleus of the stria terminalis elicits anxiety-like behavior |journal=J. Psychopharmacol. (Oxford) |volume=22 |issue=6 |pages=633–41 |date=August 2008 |pmid=18308797 |doi=10.1177/0269881107082902 |pmc=3065212}}</ref> Allylglycine is known to induce [[seizure]]s in animals studies, presumably due to this GDC-inhibiting activity.<ref name="pmid1654571">{{cite journal |vauthors =Thomas J, Yang YC |title=Allylglycine induced seizures in male and female rats |journal=Physiol. Behav. |volume=49 |issue=6 |pages=1181–3 |date=June 1991 |pmid=1654571|doi=10.1016/0031-9384(91)90348-R |s2cid=10506822 }}</ref>

==See also==
*[[3-Mercaptopropionic acid]]


==References==
==References==
{{Reflist|2}}
{{Reflist|2}}


{{GABA receptor modulators}}
{{Glutamate metabolism and transport modulators}}
{{Convulsants}}


⚫
[[Category:Alpha-Amino acids]]
{{GABAergics}}

⚫
[[Category:Amino acids]]
[[Category:Convulsants]]
[[Category:Convulsants]]
[[Category:Glutamate decarboxylase inhibitors]]
[[Category:Glutamate decarboxylase inhibitors]]
[[Category:Enzyme inhibitors]]
[[Category:Allyl compounds]]




Latest revision as of 15:46, 17 September 2023

Allylglycine
Names
Preferred IUPAC name
2-Aminopent-4-enoic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.028.809 Edit this at Wikidata
  • 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
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):
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 ?)

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[edit]

References[edit]

  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.


source: https://en.wikipedia.org/w/index.php?title=Allylglycine&diff=1175809144&oldid=720260673

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