(S)-3,5-DHPG - ≥99%, high purity , CAS No.162870-29-3

  • ≥99%
Item Number
D274696
Grouped product items
SKUSizeAvailabilityPrice Qty
D274696-5mg
5mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$325.90
D274696-10mg
10mg
Available within 8-12 weeks(?)
Production requires sourcing of materials. We appreciate your patience and understanding.
$586.90

Selective group I mGlu agonist

Basic Description

Synonyms(2r)-Amino(3,5-Dihydroxyphenyl)Acetic Acid | (S)-3,5-DHPG | HMS3411L21 | (S)-3,5-Dihydroxyphenylglycine hydrate | HB0045 | NCGC00024800-01 | NCGC00024800-04 | BDBM50079183 | J516.528H | NCGC00015338-02 | (S)-3,5-Dihydroxyphenylglycine | EN300-3004820 | Q2
Specifications & Purity≥99%
Biochemical and Physiological MechanismsSelective group I mGlu agonist. Also available in simple stock solutions - add 1 ml of water to get an exact, ready-to-use concentration.
Storage TempProtected from light,Store at -20°C,Desiccated
Shipped InIce chest + Ice pads
NoteThis compound is also unstable in alkaline solution when it rapidly forms a brown colouration it is therefore recommended that alkaline is not used to dissolve this compound. We recommend stock solutions are made up in water, aliquoted immediately and stored at -20°C. They should be used within one week. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.
Product Description

Store at -20°C. Store In the Dark. Store under desiccating conditions. This product is air and light sensitive and impurities can occur as a result of air oxidation or due to metabolism by microbes.

Associated Targets(Human)

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DRD1 Tclin Dopamine D1 receptor (9720 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRM4 Tchem Metabotropic glutamate receptor 4 (2320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRM1 Tchem Metabotropic glutamate receptor 1 (2309 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GRM5 Tchem Metabotropic glutamate receptor 5 (5733 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLCB1 Tbio Phospholipase C-beta-1 (15 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LMNA Tbio Prelamin-A/C (36751 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RECQL Tbio ATP-dependent DNA helicase Q1 (5575 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BLM Tchem Bloom syndrome protein (4248 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Grm2 Metabotropic glutamate receptor 2 (1326 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grm8 Metabotropic glutamate receptor 8 (169 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hdac6 Histone deacetylase 6 (222 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grm7 Metabotropic glutamate receptor 7 (580 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Saccharomyces cerevisiae (19171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GCN5 Histone acetyltransferase GCN5 (89 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Npsr1 Neuropeptide S receptor (260 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
rep Replicase polyprotein 1ab (378 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hippocampus (57 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mapt Microtubule-associated protein tau (6 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NS1 Nonstructural protein 1 (33327 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Grm5 Metabotropic glutamate receptor (9 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Names and Identifiers

IUPAC Name (2S)-2-amino-2-(3,5-dihydroxyphenyl)acetic acid
INCHI 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)/t7-/m0/s1
InChi Key HOOWCUZPEFNHDT-ZETCQYMHSA-N
Canonical SMILES C1=C(C=C(C=C1O)O)C(C(=O)O)N
Isomeric SMILES C1=C(C=C(C=C1O)O)[C@@H](C(=O)O)N
PubChem CID 443586
Molecular Weight 183.16

Certificates

Certificate of Analysis(COA)

Enter Lot Number to search for COA:

Chemical and Physical Properties

SolubilitySoluble in water to 50 mM
Sensitivityair and light sensitive

Related Documents

References

1. Cho HP, Garcia-Barrantes PM, Brogan JT, Hopkins CR, Niswender CM, Rodriguez AL, Venable DF, Morrison RD, Bubser M, Daniels JS et al..  (2014)  Chemical modulation of mutant mGlu1 receptors derived from deleterious GRM1 mutations found in schizophrenics..  ACS Chem Biol,  (10): (2334-46).  [PMID:25137254] [10.1021/op500134e]
2. Noetzel MJ, Rook JM, Vinson PN, Cho HP, Days E, Zhou Y, Rodriguez AL, Lavreysen H, Stauffer SR, Niswender CM et al..  (2012)  Functional impact of allosteric agonist activity of selective positive allosteric modulators of metabotropic glutamate receptor subtype 5 in regulating central nervous system function..  Mol Pharmacol,  81  (2): (120-33).  [PMID:22021324] [10.1021/op500134e]
3. Redolfi N et al..  (2021)  A New Transgenic Mouse Line for Imaging Mitochondrial Calcium Signals..  Function (Oxf),  (3): (zqab012).  [PMID:35330679]
4. Topolnik L et al..  (2009)  Activity-dependent compartmentalized regulation of dendritic Ca2+ signaling in hippocampal interneurons..  J Neurosci,  29  (14): (4658-63).  [PMID:19357290]
5. Aloisi E et al..  (2017)  Altered surface mGluR5 dynamics provoke synaptic NMDAR dysfunction and cognitive defects in Fmr1 knockout mice..  Nat Commun,  (1103).  [PMID:29062097]
6. Bridges TM et al..  (2013)  Biotransformation of a novel positive allosteric modulator of metabotropic glutamate receptor subtype 5 contributes to seizure-like adverse events in rats involving a receptor agonism-dependent mechanism..  Drug Metab Dispos,  41  (9): (1703-14).  [PMID:23821185]
7. Serra I et al..  (2022)  Ca2+-modulated photoactivatable imaging reveals neuron-astrocyte glutamatergic circuitries within the nucleus accumbens..  Nat Commun,  13  (5272).  [PMID:36071061]
8. Fernandes G et al..  (2021)  Correction of amygdalar dysfunction in a rat model of fragile X syndrome..  Cell Rep,  37  (2): (109805).  [PMID:34644573]
9. Kalmbach BE et al..  (2013)  Dendritic generation of mGluR-mediated slow afterdepolarization in layer 5 neurons of prefrontal cortex..  J Neurosci,  33  (33): (13518-32).  [PMID:23946410]
10. Shin JH et al..  (2009)  Depolarization-induced slow current in cerebellar Purkinje cells does not require metabotropic glutamate receptor 1..  Neuroscience,  162  (3): (688-93).  [PMID:19409231]
11. Bragina L et al..  (2015)  Differential expression of metabotropic glutamate and GABA receptors at neocortical glutamatergic and GABAergic axon terminals..  Front Cell Neurosci,  (345).  [PMID:26388733]
12. Li Y et al..  (2012)  Epileptic stimulus increases Homer 1a expression to modulate endocannabinoid signaling in cultured hippocampal neurons..  Neuropharmacology,  63  (6): (1140-9).  [PMID:22814532]
13. Niculescu D et al..  (2013)  Erg potassium currents of neonatal mouse Purkinje cells exhibit fast gating kinetics and are inhibited by mGluR1 activation..  J Neurosci,  33  (42): (16729-40).  [PMID:24133274]
14. Chanda S & Xu-Friedman MA.  (2011)  Excitatory modulation in the cochlear nucleus through group I metabotropic glutamate receptor activation..  J Neurosci,  31  (20): (7450-5).  [PMID:21593328]
15. Špirková A et al..  (2022)  Glutamate can act as a signaling molecule in mouse preimplantation embryos†..  Biol Reprod,  107  (4): (916-927).  [PMID:35746896]
16. Roloff AM et al..  (2010)  Homer 1a gates the induction mechanism for endocannabinoid-mediated synaptic plasticity..  J Neurosci,  30  (8): (3072-81).  [PMID:20181604]
17. Li DP & Pan HL.  (2010)  Increased group I metabotropic glutamate receptor activity in paraventricular nucleus supports elevated sympathetic vasomotor tone in hypertension..  Am J Physiol Regul Integr Comp Physiol,  299  (2): (R552-61).  [PMID:20519363]
18. Gan J et al..  (2011)  Indirect modulation of neuronal excitability and synaptic transmission in the hippocampus by activation of proteinase-activated receptor-2..  Br J Pharmacol,  163  (5): (984-94).  [PMID:21366553]
19. Colavita M et al..  (2016)  Layer-specific potentiation of network GABAergic inhibition in the CA1 area of the hippocampus..  Sci Rep,  (28454).  [PMID:27345695]
20. Trovò L et al..  (2013)  Low hippocampal PI(4,5)P2 contributes to reduced cognition in old mice as a result of loss of MARCKS..  Nat Neurosci,  16  (4): (449-55).  [PMID:23434911]
21. Cosgrove KE & Maccaferri G.  (2012)  mGlu1a-dependent recruitment of excitatory GABAergic input to neocortical Cajal-Retzius cells..  Neuropharmacology,  63  (3): (486-93).  [PMID:22579657]
22. Wagner W et al..  (2019)  Myosin VI Drives Clathrin-Mediated AMPA Receptor Endocytosis to Facilitate Cerebellar Long-Term Depression..  Cell Rep,  28  (11-20.e9).  [PMID:31269433]
23. Quattrocolo G & Maccaferri G.  (2013)  Novel GABAergic circuits mediating excitation/inhibition of Cajal-Retzius cells in the developing hippocampus..  J Neurosci,  33  (13): (5486-98).  [PMID:23536064]
24. Lafourcade CA et al..  (2009)  Novel mGluR- and CB1R-independent suppression of GABA release caused by a contaminant of the group I metabotropic glutamate receptor agonist, DHPG..  PLoS One,  (7): (e6122).  [PMID:19568435]
25. Kovacs FE et al..  (2011)  Purine receptor-mediated endocannabinoid production and retrograde synaptic signalling in the cerebellar cortex..  Br J Pharmacol,  162  (4): (974-88).  [PMID:21054344]
26. Subrahmanyam R et al..  (2021)  Reciprocal regulation of spontaneous synaptic vesicle fusion by Fragile X mental retardation protein and group I metabotropic glutamate receptors..  J Neurochem,  158  (5): (1094-1109).  [PMID:34327719]
27. Asiedu MN et al..  (2011)  Spinal protein kinase M ? underlies the maintenance mechanism of persistent nociceptive sensitization..  J Neurosci,  31  (18): (6646-53).  [PMID:21543593]
28. Cassé F & Martin S.  (2015)  Tracking the activity-dependent diffusion of synaptic proteins using restricted photoconversion of Dendra2..  Front Cell Neurosci,  (367).  [PMID:26441538]

Solution Calculators