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| Other names | 6-(Phenylcarbamoyl)-6-nor-LSD; 9,10-Didehydro-N,N-diethyl-6-(phenylcarbamoyl)ergoline-8β-carboxamide |
| Drug class | Chemokine CXCR3 receptor antagonist |
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| Formula | C26H28N4O2 |
| Molar mass | 428.536 g·mol−1 |
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NIBR2130, also known as 6-(phenylcarbamoyl)-6-nor-LSD, is a small-molecule chemokine CXCR3 receptor antagonist which has been used in scientific research.[1][2][3] It is a lysergamide and is a derivative of the psychedelic drug lysergic acid diethylamide (LSD).[1]
In contrast to LSD, NIBR2130 shows profoundly reduced affinities for monoamine receptors (IC50 = 750–>10,000nM).[1] Instead, it was surprisingly found to act as a selective and highly potent chemokine CXCR3 receptor antagonist, with an affinity (IC50) of 54nM and an inhibitory potency (IC50) of 18 to 74nM.[1] Unlike NIBR2130, LSD itself is completely inactive at the chemokine CXCR3 receptor.[1] NIBR2130 can fully block the chemokine CXCR3 receptor in rodents in vivo.[3]
Various analogues of NIBR2130 have also been studied and described, with some of them substantially more potent as chemokine CXCR3 receptor antagonists and some of them acting as highly potent histamine H3 receptor antagonists with potential applications in treatment of narcolepsy.[1][4][5]
NIBR2130 was first described in the scientific literature by 2008.[3][1][2]
See also
[edit]References
[edit]- ^ a b c d e f g Thoma G, Baenteli R, Lewis I, Wagner T, Oberer L, Blum W, et al. (November 2009). "Special ergolines are highly selective, potent antagonists of the chemokine receptor CXCR3: discovery, characterization and preliminary SAR of a promising lead". Bioorganic & Medicinal Chemistry Letters. 19 (21): 6185–6188. doi:10.1016/j.bmcl.2009.09.002. PMID 19783143.
- ^ a b Christen S, Holdener M, Beerli C, Thoma G, Bayer M, Pfeilschifter JM, et al. (September 2011). "Small molecule CXCR3 antagonist NIBR2130 has only a limited impact on type 1 diabetes in a virus-induced mouse model". Clinical and Experimental Immunology. 165 (3): 318–328. doi:10.1111/j.1365-2249.2011.04426.x. PMC 3170981. PMID 21649647.
- ^ a b c Zerwes HG, Li J, Kovarik J, Streiff M, Hofmann M, Roth L, et al. (August 2008). "The chemokine receptor Cxcr3 is not essential for acute cardiac allograft rejection in mice and rats". American Journal of Transplantation. 8 (8): 1604–1613. doi:10.1111/j.1600-6143.2008.02309.x. PMID 18557719.
- ^ Thoma G, Baenteli R, Lewis I, Jones D, Kovarik J, Streiff MB, et al. (August 2011). "Special ergolines efficiently inhibit the chemokine receptor CXCR3 in blood". Bioorganic & Medicinal Chemistry Letters. 21 (16): 4745–4749. doi:10.1016/j.bmcl.2011.06.070. PMID 21764306.
- ^ Auberson YP, Troxler T, Zhang X, Yang CR, Fendt M, Feuerbach D, et al. (August 2014). "Ergoline-derived inverse agonists of the human h3 receptor for the treatment of narcolepsy". ChemMedChem. 9 (8): 1683–1696. doi:10.1002/cmdc.201402055. PMID 24850792.