Synonym
Xanthine-amine congener, Xanthine -amine-congener, XAC; Papaxac
IUPAC/Chemical Name
N-(2-Aminoethyl)-2-[4-(2,6-dioxo-1,3-dipropyl-7H-purin-8-yl)phenoxy]acetamide
InChi Key
FIQGIOAELHTLHM-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H28N6O4/c1-3-11-26-19-17(20(29)27(12-4-2)21(26)30)24-18(25-19)14-5-7-15(8-6-14)31-13-16(28)23-10-9-22/h5-8H,3-4,9-13,22H2,1-2H3,(H,23,28)(H,24,25)
SMILES Code
O=C(NCCN)COC1=CC=C(C(N2)=NC(N(CCC)C(N3CCC)=O)=C2C3=O)C=C1
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
428.49
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: Jacobson KA, Ukena D, Kirk KL, Daly JW. [3H]xanthine amine congener of 1,3-dipropyl-8-phenylxanthine: an antagonist radioligand for adenosine receptors. Proc Natl Acad Sci U S A. 1986 Jun;83(11):4089-93. doi: 10.1073/pnas.83.11.4089. PMID: 3012550; PMCID: PMC323672.
2: Ji XD, Stiles GL, Jacobson KA. [(3)H]XAC (xanthine amine congener) is a radioligand for A(2)-adenosine receptors in rabbit striatum. Neurochem Int. 1991;18(2):207-13. doi: 10.1016/0197-0186(91)90187-i. PMID: 20504695; PMCID: PMC4827159.
3: Gao ZG, Toti KS, Campbell R, Suresh RR, Yang H, Jacobson KA. Allosteric Antagonism of the A2A Adenosine Receptor by a Series of Bitopic Ligands. Cells. 2020 May 12;9(5):1200. doi: 10.3390/cells9051200. PMID: 32408534; PMCID: PMC7290864.
4: Morgan PF, Deckert J, Jacobson KA, Marangos PJ, Daly JW. Potent convulsant actions of the adenosine receptor antagonist, xanthine amine congener (XAC). Life Sci. 1989;45(8):719-28. doi: 10.1016/0024-3205(89)90091-x. PMID: 2779359; PMCID: PMC3478950.
5: Senchina DS, Hallam JE, Kohut ML, Nguyen NA, Perera MA. Alkaloids and athlete immune function: caffeine, theophylline, gingerol, ephedrine, and their congeners. Exerc Immunol Rev. 2014;20:68-93. PMID: 24974722.
6: Barone S, Churchill PC, Jacobson KA. Adenosine receptor prodrugs: towards kidney-selective dialkylxanthines. J Pharmacol Exp Ther. 1989 Jul;250(1):79-85. PMID: 2746513; PMCID: PMC3476460.
7: Sawmiller DR, Linden J, Berne RM. Effects of xanthine amine congener on hypoxic coronary resistance and venous and epicardial adenosine concentrations. Cardiovasc Res. 1994 May;28(5):604-9. doi: 10.1093/cvr/28.5.604. PMID: 8025903.
8: Al-Khadhra RS. The determination of common anabolic steroid and stimulants in nutritional supplements by HPLC-DAD and LC-MS. J Chromatogr Sci. 2020 Apr 23;58(4):355-361. doi: 10.1093/chromsci/bmz121. PMID: 32099999.
9: Ukena D, Jacobson KA, Kirk KL, Daly JW. A [3H]amine congener of 1,3-dipropyl-8-phenylxanthine. A new radioligand for A2 adenosine receptors of human platelets. FEBS Lett. 1986 Apr 21;199(2):269-74. doi: 10.1016/0014-5793(86)80493-8. PMID: 3009222; PMCID: PMC4351550.
10: Deckert J, Morgan PF, Bisserbe JC, Jacobson KA, Kirk KL, Daly JW, Marangos PJ. Autoradiographic localization of mouse brain adenosine receptors with an antagonist ([3H]xanthine amine congener) ligand probe. Neurosci Lett. 1988 Mar 31;86(2):121-6. doi: 10.1016/0304-3940(88)90557-5. PMID: 3368115; PMCID: PMC6231418.
