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MedKoo Cat#: 556783 | Name: DHPG
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

DHPG, also known as (RS)-3,5-DHPG, is a selective agonist for group I metabotropic glutamate receptors (mGluRs), specifically targeting mGluR1 and mGluR5. Activation of these receptors by 3,5-DHPG has been shown to influence synaptic transmission and neuronal excitability. 3,5-DHPG, through its action on group I mGluRs, can modulate synaptic activity by promoting spontaneous neurotransmitter release in a patterned manner, which may have implications for understanding synaptic dynamics and developing therapeutic strategies targeting these receptors.

Chemical Structure

DHPG
DHPG
CAS#146255-66-5

Theoretical Analysis

MedKoo Cat#: 556783

Name: DHPG

CAS#: 146255-66-5

Chemical Formula: C8H9NO4

Exact Mass: 183.0532

Molecular Weight: 183.16

Elemental Analysis: C, 52.46; H, 4.95; N, 7.65; O, 34.94

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
200mg USD 750.00 2 Weeks
500mg USD 1,450.00 2 Weeks
1g USD 2,450.00 2 Weeks
2g USD 3,650.00 2 Weeks
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Related CAS #
No Data
Synonym
DHPG; (RS)-3,5-DHPG
IUPAC/Chemical Name
2-amino-2-(3,5-dihydroxyphenyl)acetic acid
InChi Key
HOOWCUZPEFNHDT-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(O)C(N)C1=CC(O)=CC(O)=C1
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Biological target:
3,5-Dihydroxyphenylglycine (3,5-DHPG) is a selective agonist for group I metabotropic glutamate receptors (mGluRs), specifically targeting: mGluR1 (Metabotropic Glutamate Receptor 1) mGluR5 (Metabotropic Glutamate Receptor 5) These receptors are G-protein-coupled receptors (GPCRs) that play key roles in synaptic plasticity, neuronal excitability, and neurotransmitter release. Activation of mGluR1 and mGluR5 by 3,5-DHPG leads to intracellular signaling cascades, including phospholipase C (PLC) activation, inositol triphosphate (IP3) production, and calcium mobilization.
In vitro activity:
The in vitro bioactivity of 3,5-Dihydroxyphenylglycine (3,5-DHPG) primarily involves its role as a selective agonist of group I metabotropic glutamate receptors (mGluR1 and mGluR5). Key findings from various studies include: Receptor Activation: 3,5-DHPG selectively activates mGluR1 and mGluR5, leading to intracellular signaling cascades such as phospholipase C (PLC) activation, inositol triphosphate (IP3) production, and intracellular calcium release. EC₅₀ values for receptor activation: mGluR1: ~5–10 µM mGluR5: ~2–4 µM Synaptic Modulation: 3,5-DHPG enhances spontaneous excitatory postsynaptic currents (sEPSCs) in neurons, indicating increased synaptic transmission. In hippocampal and cortical neurons, it can induce long-term potentiation (LTP) and synaptic plasticity, which are critical for learning and memory. Neurotransmitter Release: It increases glutamate release by activating presynaptic mGluRs. Inhibits GABAergic transmission in certain neuronal populations, contributing to excitatory signaling enhancement. Neuroprotective & Neurotoxic Effects: While mGluR activation by 3,5-DHPG is involved in neuroprotection via ERK/MAPK signaling, excessive stimulation may lead to excitotoxicity under pathological conditions. These properties make 3,5-DHPG a useful pharmacological tool for studying glutamatergic signaling, synaptic plasticity, and neurological disorders like epilepsy, neurodegeneration, and pain.
In vivo activity:
he in vivo bioactivity of 3,5-Dihydroxyphenylglycine (3,5-DHPG) is primarily linked to its role as a group I metabotropic glutamate receptor (mGluR1 and mGluR5) agonist, influencing synaptic plasticity, neuronal excitability, and behavior. Some key findings from in vivo studies include: 1. Effects on Synaptic Plasticity and Learning 3,5-DHPG has been shown to induce long-term potentiation (LTP) and long-term depression (LTD) in the hippocampus, critical processes for memory formation. In rodent models, intracerebral or systemic administration of 3,5-DHPG enhances cognitive function in certain learning and memory tasks, though excessive activation may impair performance due to excitotoxic effects. 2. Neurotransmission and Excitability Increases glutamate release in vivo, leading to heightened neuronal excitability in key brain regions such as the hippocampus and cortex. At high doses, it can induce epileptiform activity, suggesting a role in seizure susceptibility. 3. Effects on Pain Modulation Antinociceptive (pain-modulating) effects have been observed in models of inflammatory and neuropathic pain. Activation of spinal cord mGluR1/mGluR5 reduces pain perception by modulating central sensitization mechanisms. 4. Role in Neuropsychiatric Disorders In models of schizophrenia, 3,5-DHPG can modulate dopamine transmission, suggesting potential relevance in treatments targeting glutamatergic dysfunction. It has been implicated in anxiety-like behaviors, with varying effects depending on the dose and experimental conditions. 5. Potential for Neuroprotection and Excitotoxicity Activation of group I mGluRs by 3,5-DHPG has both neuroprotective and neurotoxic effects, depending on the context: Neuroprotective: Moderate activation can enhance pro-survival signaling pathways (ERK/MAPK). Neurotoxic: Excessive activation may contribute to excitotoxicity, relevant in neurodegenerative diseases. Conclusion 3,5-DHPG exhibits potent in vivo bioactivity by modulating excitatory neurotransmission, synaptic plasticity, pain perception, and neuropsychiatric behaviors. While it has therapeutic potential, its excitotoxic and seizure-inducing effects must be carefully considered.

Preparing Stock Solutions

The following data is based on the product molecular weight 183.16 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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