Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C8H9NO4 |
| Molecular Weight | 183.1614 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(C(O)=O)C1=CC(O)=CC(O)=C1
InChI
InChIKey=HOOWCUZPEFNHDT-UHFFFAOYSA-N
InChI=1S/C8H9NO4/c9-7(8(12)13)4-1-5(10)3-6(11)2-4/h1-3,7,10-11H,9H2,(H,12,13)
| Molecular Formula | C8H9NO4 |
| Molecular Weight | 183.1614 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
3,5-dihydroxyphenylglycine (3,5-DHPG) was the first agonist shown to be specific to the group I metabotropic glutamate receptors, mGluR1 and mGluR5 with its agonist effects residing exclusively in the S-isomer. Some studies suggested a therapeutic role for (S)-3,5-DHPG in neuronal injury, regulation of intestinal motility and secretion, learning and memory processes and in the cardiovascular system. (S)-3,5-DHPG may be useful as a cognitive enhancing agent in memory impairment associated with ischemia or hypoxia.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q13255|||Q9NU10 Gene ID: 2911.0 Gene Symbol: GRM1 Target Organism: Homo sapiens (Human) |
|||
Target ID: P41594 Gene ID: 2915.0 Gene Symbol: GRM5 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Brain-derived neurotrophic factor controls cannabinoid CB1 receptor function in the striatum. | 2010-06-16 |
|
| Abnormal mGlu 5 receptor/endocannabinoid coupling in mice lacking FMRP and BC1 RNA. | 2010-06 |
|
| Mechanisms of glutamate receptor induced proliferation of astrocytes. | 2006-12-18 |
|
| The effect of mGlu5 receptor positive allosteric modulators on signaling molecules in brain slices. | 2006-05-01 |
|
| A novel selective positive allosteric modulator of metabotropic glutamate receptor subtype 5 has in vivo activity and antipsychotic-like effects in rat behavioral models. | 2005-04 |
|
| Chronic exposure to ammonia alters the modulation of phosphorylation of microtubule-associated protein 2 by metabotropic glutamate receptors 1 and 5 in cerebellar neurons in culture. | 2005 |
|
| In vivo modulation of extracellular hippocampal glutamate and GABA levels and limbic seizures by group I and II metabotropic glutamate receptor ligands. | 2004-03 |
|
| Involvement of transient receptor potential-like channels in responses to mGluR-I activation in midbrain dopamine neurons. | 2003-10 |
|
| [3H]R214127: a novel high-affinity radioligand for the mGlu1 receptor reveals a common binding site shared by multiple allosteric antagonists. | 2003-05 |
|
| Characterization of [(3)H]Quisqualate binding to recombinant rat metabotropic glutamate 1a and 5a receptors and to rat and human brain sections. | 2000-12 |
|
| Induction or protection of limbic seizures in mice by mGluR subtype selective agonists. | 1995-08 |
Patents
Sample Use Guides
Administered i.c.v. to mice, (S)-3,5-dihydroxyphenyl-glycine ((S)-3,5-DHPG) produced a behavioral syndrome consisting of scratching and/or facial grooming, tremors, slow forelimb clonus, rearing, and falling that increased over the dose range of 10-400 nmol.
Route of Administration:
Other
In Vitro Use Guide
Curator's Comment: 3,5-dihydroxyphenylglycine was potent and effective in increasing phosphoinositide hydrolysis in both adult and neonatal hippocampus but unlike the other mGluR agonists did not inhibit forskolin-stimulated cAMP formation (in the adult) or substantially enhance basal cAMP formation (in the neonate).
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:43:57 GMT 2025
by
admin
on
Mon Mar 31 22:43:57 GMT 2025
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| Record UNII |
5YR2N37E6D
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| Record Status |
Validated (UNII)
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| Record Version |
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DTXSID901311536
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146255-66-5
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5YR2N37E6D
Created by
admin on Mon Mar 31 22:43:57 GMT 2025 , Edited by admin on Mon Mar 31 22:43:57 GMT 2025
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PRIMARY |