PAOPA

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MedKoo CAT#: 563115

CAS#: 114200-31-6

Description: PAOPA is an allosteric modulator of dopamine D2 receptors.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-07-10. Prices are subject to change without notice.

PAOPA is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 563115
Name: PAOPA
CAS#: 114200-31-6
Chemical Formula: C11H18N4O3
Exact Mass: 254.1379
Molecular Weight: 254.29
Elemental Analysis: C, 51.96; H, 7.14; N, 22.03; O, 18.87


Synonym: PAOPA;

IUPAC/Chemical Name: (3R)-2-Oxo-3-[[(2S)-2-Pyrrolidinylcarbonyl]amino]-1-pyrrolidineacetamide

InChi Key: QXHVGEXNEZRSGG-JGVFFNPUSA-N

InChi Code: InChI=1S/C11H18N4O3/c12-9(16)6-15-5-3-8(11(15)18)14-10(17)7-2-1-4-13-7/h7-8,13H,1-6H2,(H2,12,16)(H,14,17)/t7-,8+/m0/s1

SMILES Code: O=C(N)CN1C([C@H](NC([C@H]2NCCC2)=O)CC1)=O


Technical Data

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


References

1: Basu D, Tian Y, Hui P, Bhandari J, Johnson RL, Mishra RK. Change in expression of vesicular protein synapsin II by chronic treatment with D2 allosteric modulator PAOPA. Peptides. 2015 Apr;66:58-62. doi: 10.1016/j.peptides.2015.01.004. Epub 2015 Feb 19. PubMed PMID: 25703303.

2: Basu D, Tian Y, Bhandari J, Jiang JR, Hui P, Johnson RL, Mishra RK. Effects of the dopamine D2 allosteric modulator, PAOPA, on the expression of GRK2, arrestin-3, ERK1/2, and on receptor internalization. PLoS One. 2013 Aug 6;8(8):e70736. doi: 10.1371/journal.pone.0070736. Print 2013. PubMed PMID: 23940634; PubMed Central PMCID: PMC3735488.

3: Tan ML, Basu D, Kwiecien JM, Johnson RL, Mishra RK. Preclinical pharmacokinetic and toxicological evaluation of MIF-1 peptidomimetic, PAOPA: examining the pharmacology of a selective dopamine D2 receptor allosteric modulator for the treatment of schizophrenia. Peptides. 2013 Apr;42:89-96. doi: 10.1016/j.peptides.2013.02.004. Epub 2013 Feb 15. PubMed PMID: 23416534.

4: Beyaert MG, Daya RP, Dyck BA, Johnson RL, Mishra RK. PAOPA, a potent dopamine D2 receptor allosteric modulator, prevents and reverses behavioral and biochemical abnormalities in an amphetamine-sensitized preclinical animal model of schizophrenia. Eur Neuropsychopharmacol. 2013 Mar;23(3):253-62. doi: 10.1016/j.euroneuro.2012.04.010. Epub 2012 May 30. PubMed PMID: 22658400.

5: Dyck B, Guest K, Sookram C, Basu D, Johnson R, Mishra RK. PAOPA, a potent analogue of Pro-Leu-glycinamide and allosteric modulator of the dopamine D2 receptor, prevents NMDA receptor antagonist (MK-801)-induced deficits in social interaction in the rat: implications for the treatment of negative symptoms in schizophrenia. Schizophr Res. 2011 Jan;125(1):88-92. doi: 10.1016/j.schres.2010.09.025. Epub 2010 Oct 30. PubMed PMID: 21036015; PubMed Central PMCID: PMC3010311.

6: Verma V, Mann A, Costain W, Pontoriero G, Castellano JM, Skoblenick K, Gupta SK, Pristupa Z, Niznik HB, Johnson RL, Nair VD, Mishra RK. Modulation of agonist binding to human dopamine receptor subtypes by L-prolyl-L-leucyl-glycinamide and a peptidomimetic analog. J Pharmacol Exp Ther. 2005 Dec;315(3):1228-36. Epub 2005 Aug 26. PubMed PMID: 16126839.

7: Dolbeare K, Pontoriero GF, Gupta SK, Mishra RK, Johnson RL. Iso-lactam and reduced amide analogues of the peptidomimetic dopamine receptor modulator 3(R)-[(2(S)-pyrrolidinylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide. Bioorg Med Chem. 2003 Sep 1;11(18):4103-12. PubMed PMID: 12927872.

8: Sharma S, Paladino P, Gabriele J, Saeedi H, Henry P, Chang M, Mishra RK, Johnson RL. Pro-Leu-glycinamide and its peptidomimetic, PAOPA, attenuate haloperidol induced vacuous chewing movements in rat: A model of human tardive dyskinesia. Peptides. 2003 Feb;24(2):313-9. PubMed PMID: 12668218.

9: Mishra RK, Makman MH, Costain WJ, Nair VD, Johnson RL. Modulation of agonist stimulated adenylyl cyclase and GTPase activity by L-pro-L-leu-glycinamide and its peptidomimetic analogue in rat striatal membranes. Neurosci Lett. 1999 Jul 2;269(1):21-4. PubMed PMID: 10821635.

10: Ott MC, Costain WJ, Mishra RK, Johnson RL. L-prolyl-l-leucyl-glycinamide and its peptidomimetic analog 3(R)-[(2(S)-pyrrolidylcarbonyl)amino]-2-oxo-1-pyrrolidineacetamide (PAOPA) attenuate haloperidol-induced c-fos expression in the striatum. Peptides. 2000 Feb;21(2):301-8. PubMed PMID: 10764960.

11: Marcotte ER, Chugh A, Mishra RK, Johnson RL. Protection against MPTP treatment by an analog of Pro-Leu-Gly-NH2 (PLG, MIF-1). Peptides. 1998;19(2):403-6. PubMed PMID: 9493876.

12: Mishra RK, Marcotte ER, Chugh A, Barlas C, Whan D, Johnson RL. Modulation of dopamine receptor agonist-induced rotational behavior in 6-OHDA-lesioned rats by a peptidomimetic analogue of Pro-Leu-Gly-NH2 (PLG). Peptides. 1997;18(8):1209-15. PubMed PMID: 9396063.

13: Baures PW, Ojala WH, Gleason WB, Mishra RK, Johnson RL. Design, synthesis, X-ray analysis, and dopamine receptor-modulating activity of mimics of the "C5" hydrogen-bonded conformation in the peptidomimetic 2-oxo-3(R)-[(2(S)-pyrrolidinylcarbonyl)amino]-1- pyrrolidineacetamide. J Med Chem. 1994 Oct 28;37(22):3677-83. PubMed PMID: 7966127.

14: Mishra RK, Srivastava LK, Johnson RL. Modulation of high-affinity CNS dopamine D2 receptor by L-pro-L-leu-glycinamide (PLG) analogue 3(R)-(N-L-prolylamino)-2-oxo-1-pyrrolidineacetamide. Prog Neuropsychopharmacol Biol Psychiatry. 1990;14(5):821-7. PubMed PMID: 1981396.