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Merck
CN

A8378

DL-2-Allylglycine

Synonym(s):

(±)-2-Amino-4-pentenoic acid, DL-C-Allylglycine

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About This Item

Linear Formula:
H2C=CHCH2CH(NH2)CO2H
CAS Number:
7685-44-1
Molecular Weight:
115.13
NACRES:
NA.26
PubChem Substance ID:
24891336
eCl@ss:
32160406
UNSPSC Code:
12352200
EC Number:
231-689-8
MDL number:
MFCD00063103
Beilstein/REAXYS Number:
1748645

Key Documents

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InChI key

WNNNWFKQCKFSDK-UHFFFAOYSA-N

InChI

1S/C5H9NO2/c1-2-3-4(6)5(7)8/h2,4H,1,3,6H2,(H,7,8)

SMILES string

NC(CC=C)C(O)=O

assay

≥98% (TLC)

form

powder

color

white

mp

258-260 °C (lit.)

application(s)

peptide synthesis

storage temp.

−20°C

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Biochem/physiol Actions

DL-2-Allylglycine is a racemic mixture of L- and D-allylglycine. D-allylglycine is the enantiomer of L-allylglycine, a glutamate decarboxylase (GAD) inhibitor used in GABA research. D-allylglycine may be used as a control supplement versus L-allylglycine in GABA research. D-allylglycine is used in the organic synthesis of cyclic opioid peptide agonists and antagonists.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBQ1153V
018K5103
067K2614
067K2611
086K5004

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S Moyanova et al.
Acta physiologica et pharmacologica Bulgarica, 15(1), 47-53 (1989-01-01)
The effect of DL-allylglycine (DL-AG) in two doses (40 and 60 mg/kg i.v.) was studied on cats under acute conditions. DL-AG provoked the appearance of epileptiform EEG patterns either spontaneous or in response to intermittent light stimulation with a frequency
Non-centrosymmetric racemates: space-group frequencies and conformational similarities between crystallographically independent molecules.
Dalhus B, Gorbitz CH.
Acta Physiologica Et Pharmacologica Bulgarica, 56, 715-719 (2000)
Pl Johnson et al.
Journal of psychopharmacology (Oxford, England), 22(6), 642-652 (2008-03-01)
Panic patients are vulnerable to induction of panic attacks by sub-threshold interoceptive stimuli such as intravenous (i.v.) sodium lactate infusions. Facilitation of serotonergic signaling with selective serotonin reuptake inhibitors can suppress anxiety and panic-like responses, but the mechanisms involved are
Irena Berezowska et al.
Chemical biology & drug design, 74(4), 329-334 (2009-08-22)
The opioid peptide H-Tyr-c[D-Cys-Phe-Phe-Cys]NH(2) cyclized via a methylene dithiother is a potent and selective mu opioid agonist (Przydial M.J. et al., J Peptide Res, 66, 2005, 255). Dicarba analogues of this peptide with Tyr, 2',6'-dimethyltyrosine (Dmt), 3-[2,6-dimethyl-4-hydroxyphenyl)propanoic acid (Dhp) or
Tadashi Saigusa et al.
Neuropharmacology, 62(2), 907-913 (2011-10-04)
GABA released from accumbal GABAergic interneurons plays an inhibitory role in the regulation of dopamine efflux through GABA(B) and GABA(A) receptors located on accumbal dopaminergic nerve endings. The cytosolic newly synthesised GABA alters vesicular GABA levels and, accordingly, the amount
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