Synonym
2PCCA; 2 PCCA; 2-PCCA
IUPAC/Chemical Name
(1R,2R)-N-[(2S,3S)-2-Amino-3-methylpentyl]-N-(4'-propyl[1,1'-biphenyl]-4-yl)-2-(2-pyridinyl)-cyclopropanecarboxamide
InChi Key
OBGKRTYDTRUMGO-RFNYNIMXSA-N
InChi Code
InChI=1S/C30H37N3O/c1-4-8-22-10-12-23(13-11-22)24-14-16-25(17-15-24)33(20-28(31)21(3)5-2)30(34)27-19-26(27)29-9-6-7-18-32-29/h6-7,9-18,21,26-28H,4-5,8,19-20,31H2,1-3H3/t21-,26+,27+,28+/m0/s1
SMILES Code
O=C([C@H]1[C@H](C2=NC=CC=C2)C1)N(C[C@@H](N)[C@@H](C)CC)C3=CC=C(C4=CC=C(CCC)C=C4)C=C3
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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
455.65
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.
| 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 |
1: Li JX, Thorn DA, Jin C. The GPR88 receptor agonist 2-PCCA does not alter the behavioral effects of methamphetamine in rats. Eur J Pharmacol. 2013 Jan 5;698(1-3):272-7. doi: 10.1016/j.ejphar.2012.10.037. Epub 2012 Nov 2. PubMed PMID: 23123351.
2: Jin C, Decker AM, Huang XP, Gilmour BP, Blough BE, Roth BL, Hu Y, Gill JB, Zhang XP. Synthesis, pharmacological characterization, and structure-activity relationship studies of small molecular agonists for the orphan GPR88 receptor. ACS Chem Neurosci. 2014 Jul 16;5(7):576-87. doi: 10.1021/cn500082p. Epub 2014 May 14. PubMed PMID: 24793972; PubMed Central PMCID: PMC4102971.
3: Jin C, Decker AM, Harris DL, Blough BE. Effect of Substitution on the Aniline Moiety of the GPR88 Agonist 2-PCCA: Synthesis, Structure-Activity Relationships, and Molecular Modeling Studies. ACS Chem Neurosci. 2016 Oct 19;7(10):1418-1432. Epub 2016 Aug 16. PubMed PMID: 27499251; PubMed Central PMCID: PMC5071162.
4: Jin C, Decker AM, Langston TL. Design, synthesis and pharmacological evaluation of 4-hydroxyphenylglycine and 4-hydroxyphenylglycinol derivatives as GPR88 agonists. Bioorg Med Chem. 2017 Jan 15;25(2):805-812. doi: 10.1016/j.bmc.2016.11.058. Epub 2016 Dec 1. PubMed PMID: 27956039; PubMed Central PMCID: PMC5218591.
5: Decker AM, Gay EA, Mathews KM, Rosa TC, Langston TL, Maitra R, Jin C. Development and validation of a high-throughput calcium mobilization assay for the orphan receptor GPR88. J Biomed Sci. 2017 Mar 27;24(1):23. doi: 10.1186/s12929-017-0330-3. PubMed PMID: 28347302; PubMed Central PMCID: PMC5369193.
6: Jin C, Decker AM, Makhijani VH, Besheer J, Darcq E, Kieffer BL, Maitra R. Discovery of a Potent, Selective, and Brain-Penetrant Small Molecule that Activates the Orphan Receptor GPR88 and Reduces Alcohol Intake. J Med Chem. 2018 Aug 9;61(15):6748-6758. doi: 10.1021/acs.jmedchem.8b00566. Epub 2018 Jul 30. PubMed PMID: 30011199; PubMed Central PMCID: PMC6108082.
7: Ye N, Li B, Mao Q, Wold EA, Tian S, Allen JA, Zhou J. Orphan Receptor GPR88 as an Emerging Neurotherapeutic Target. ACS Chem Neurosci. 2018 Dec 12. doi: 10.1021/acschemneuro.8b00572. [Epub ahead of print] PubMed PMID: 30540906.
