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MedKoo Cat#: 563212 | Name: MMPIP HCl
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Description:

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

MMPIP HCl is an allosteric mGlu7-selective receptor antagonist.

Chemical Structure

MMPIP HCl
CAS#1215566-78-1

Theoretical Analysis

MedKoo Cat#: 563212

Name: MMPIP HCl

CAS#: 1215566-78-1

Chemical Formula: C19H16ClN3O3

Exact Mass: 369.0880

Molecular Weight: 369.81

Elemental Analysis: C, 61.71; H, 4.36; Cl, 9.59; N, 11.36; O, 12.98

Price and Availability

Size Price Availability Quantity
5mg USD 315.00 2 weeks
25mg USD 985.00 2 weeks
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Related CAS #
479077-02-6
Synonym
MMPIP Hydrochloride; MMPIP HCl;
IUPAC/Chemical Name
6-(4-Methoxyphenyl)-5-methyl-3-(4-pyridinyl)-isoxazolo[4,5-c]pyridin-4(5H)-one Hydrochloride
InChi Key
HXHQNERSIJXMTQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H15N3O3.ClH/c1-22-15(12-3-5-14(24-2)6-4-12)11-16-17(19(22)23)18(21-25-16)13-7-9-20-10-8-13;/h3-11H,1-2H3;1H
SMILES Code
O=C1C2=C(ON=C2C3=CC=NC=C3)C=C(C4=CC=C(OC)C=C4)N1C.[H]Cl
Appearance
Solid powder
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
MMPIP hydrochloride is a potent allosteric mGlu7-selective receptor antagonist.
In vitro activity:
MMPIP was able to antagonize an allosteric agonist, the N,N'-dibenzhydryl-ethane-1,2-diamine dihydrochloride (AMN082)-induced inhibition of cAMP accumulation. In the absence of these agonists, MMPIP caused a further increase in forskolin-stimulated cAMP levels in CHO cells expressing mGluR7, whereas a competitive antagonist, LY341495, did not. This result indicates that MMPIP has an inverse agonistic activity. The intrinsic activity of MMPIP was pertussis toxin-sensitive and mGluR7-dependent. MMPIP at concentrations of at least 1 microM had no significant effect on mGluR1, mGluR2, mGluR3, mGluR4, mGluR5, and mGluR8. Reference: J Pharmacol Exp Ther. 2007 Oct;323(1):147-56. https://pubmed.ncbi.nlm.nih.gov/17609420/
In vivo activity:
This study investigated the effects of a single administration of 6-(4-methoxyphenyl)-5-methyl-3-pyridinyl-4-isoxazolo[4,5-c]pyridin-4(5H)-one (MMPIP), a negative allosteric modulator (NAM) of metabotropic glutamate receptor 7 (mGluR7), on pain and on affective and cognitive behavior in neuropathic mice. MMPIP increased thermal and mechanical thresholds and open-arm choice. It reduced the immobility in the tail suspension test and the number of marbles buried and of digging events in the marble burying test. MMPIP also improved cognitive performance and restored the balance between excitatory and inhibitory responses of PLC neurons in SNI mice. Reference: Pain. 2015 Jun;156(6):1060-1073. https://pubmed.ncbi.nlm.nih.gov/25760470/

Preparing Stock Solutions

The following data is based on the product molecular weight 369.81 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
Formulation protocol:
1. Niswender CM, Johnson KA, Miller NR, Ayala JE, Luo Q, Williams R, Saleh S, Orton D, Weaver CD, Conn PJ. Context-dependent pharmacology exhibited by negative allosteric modulators of metabotropic glutamate receptor 7. Mol Pharmacol. 2010 Mar;77(3):459-68. doi: 10.1124/mol.109.058768. Epub 2009 Dec 21. PMID: 20026717; PMCID: PMC2835423. 2. Suzuki G, Tsukamoto N, Fushiki H, Kawagishi A, Nakamura M, Kurihara H, Mitsuya M, Ohkubo M, Ohta H. In vitro pharmacological characterization of novel isoxazolopyridone derivatives as allosteric metabotropic glutamate receptor 7 antagonists. J Pharmacol Exp Ther. 2007 Oct;323(1):147-56. doi: 10.1124/jpet.107.124701. Epub 2007 Jul 3. PMID: 17609420. 3. Palazzo E, Romano R, Luongo L, Boccella S, De Gregorio D, Giordano ME, Rossi F, Marabese I, Scafuro MA, de Novellis V, Maione S. MMPIP, an mGluR7-selective negative allosteric modulator, alleviates pain and normalizes affective and cognitive behavior in neuropathic mice. Pain. 2015 Jun;156(6):1060-1073. doi: 10.1097/j.pain.0000000000000150. PMID: 25760470. 4. Pałucha-Poniewiera A, Pilc A. A selective mGlu7 receptor antagonist MMPIP reversed antidepressant-like effects of AMN082 in rats. Behav Brain Res. 2013 Feb 1;238:109-12. doi: 10.1016/j.bbr.2012.10.004. Epub 2012 Oct 17. PMID: 23085340.
In vitro protocol:
1. Niswender CM, Johnson KA, Miller NR, Ayala JE, Luo Q, Williams R, Saleh S, Orton D, Weaver CD, Conn PJ. Context-dependent pharmacology exhibited by negative allosteric modulators of metabotropic glutamate receptor 7. Mol Pharmacol. 2010 Mar;77(3):459-68. doi: 10.1124/mol.109.058768. Epub 2009 Dec 21. PMID: 20026717; PMCID: PMC2835423. 2. Suzuki G, Tsukamoto N, Fushiki H, Kawagishi A, Nakamura M, Kurihara H, Mitsuya M, Ohkubo M, Ohta H. In vitro pharmacological characterization of novel isoxazolopyridone derivatives as allosteric metabotropic glutamate receptor 7 antagonists. J Pharmacol Exp Ther. 2007 Oct;323(1):147-56. doi: 10.1124/jpet.107.124701. Epub 2007 Jul 3. PMID: 17609420.
In vivo protocol:
1. Palazzo E, Romano R, Luongo L, Boccella S, De Gregorio D, Giordano ME, Rossi F, Marabese I, Scafuro MA, de Novellis V, Maione S. MMPIP, an mGluR7-selective negative allosteric modulator, alleviates pain and normalizes affective and cognitive behavior in neuropathic mice. Pain. 2015 Jun;156(6):1060-1073. doi: 10.1097/j.pain.0000000000000150. PMID: 25760470. 2. Pałucha-Poniewiera A, Pilc A. A selective mGlu7 receptor antagonist MMPIP reversed antidepressant-like effects of AMN082 in rats. Behav Brain Res. 2013 Feb 1;238:109-12. doi: 10.1016/j.bbr.2012.10.004. Epub 2012 Oct 17. PMID: 23085340.
1: Palazzo E, Romano R, Luongo L, Boccella S, De Gregorio D, Giordano ME, Rossi F, Marabese I, Scafuro MA, de Novellis V, Maione S. MMPIP, an mGluR7-selective negative allosteric modulator, alleviates pain and normalizes affective and cognitive behavior in neuropathic mice. Pain. 2015 Jun;156(6):1060-73. doi: 10.1097/j.pain.0000000000000150. PubMed PMID: 25760470.