BIBN 99

BIBN 99
Names
IUPAC name
N-[3-[1-[2-(8-chloro-6-oxo-5H-pyrido[2,3-b][1,4]benzodiazepin-11-yl)-2-oxoethyl]piperidin-4-yl]propyl]-N-ethyl-2,2-dimethylpentanamide
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • Key: LUPAFPUKESJDMZ-UHFFFAOYSA-N
  • InChI=1S/C31H42ClN5O3/c1-5-15-31(3,4)30(40)36(6-2)17-8-9-22-13-18-35(19-14-22)21-27(38)37-26-12-11-23(32)20-24(26)29(39)34-25-10-7-16-33-28(25)37/h7,10-12,16,20,22H,5-6,8-9,13-15,17-19,21H2,1-4H3,(H,34,39)
  • CCCC(C)(C)C(=O)N(CC)CCCC1CCN(CC1)CC(=O)N2C3=C(C=C(C=C3)Cl)C(=O)NC4=C2N=CC=C4
Properties
C31H42ClN5O3
Molar mass 568.16 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

BIBN 99 is an antagonist of mACh receptors. Specifically, it is selective for the M2 type, and was prototypical for this class of selective compounds. BIBN 99 is lipophilic, it crosses the blood-brain barrier and is a competitive antagonist of the M2 receptor with 30-fold selectivity over M1 receptors.

Effects

During research, it was observed that BIBN 99 was able to diminish the cognitive deficits caused by injury. Another also came to the conclusion that the compound could provide cognitive improvements. The cognitive effects could possibly be caused by the increased release of acetylcholine, a neurotransmitter.

References

  1. 1 2 Doods, H.; Entzeroth, M.; Ziegler, H.; Schiavi, G.; Engel, W.; Mihm, G.; Rudolf, K.; Eberlein, W. (21 September 1993). "Characterization of BIBN 99: a lipophilic and selective muscarinic M2 receptor antagonist". European Journal of Pharmacology. 242 (1): 23–30. doi:10.1016/0014-2999(93)90005-3. ISSN 0014-2999. PMID 8223934.
  2. ↑ Doods, H.N.; Quirion, R.; Mihm, G.; Engel, W.; Rudolf, K.; Entzeroth, M.; Schiavi, G.B.; Ladinsky, H.; Bechtel, W.D.; Ensinger, H.A.; Mendla, K.D.; Eberlein, W. (1993). "Therapeutic potential of CNS-active M2 antagonists: Novel structures and pharmacology". Life Sciences. 52 (5–6): 497–503. doi:10.1016/0024-3205(93)90307-o. PMID 8441330.
  3. ↑ Pike, B. R.; Hamm, R. J. (17 July 1995). "Post-injury administration of BIBN 99, a selective muscarinic M2 receptor antagonist, improves cognitive performance following traumatic brain injury in rats". Brain Research. 686 (1): 37–43. doi:10.1016/0006-8993(95)00448-y. ISSN 0006-8993. PMID 7583269.
  4. ↑ Rowe, W. B.; O'Donnell, J.-P.; Pearson, D.; Rose, G. M.; Meaney, M. J.; Quirion, R. (17 October 2003). "Long-term effects of BIBN-99, a selective muscarinic M2 receptor antagonist, on improving spatial memory performance in aged cognitively impaired rats". Behavioural Brain Research. 145 (1–2): 171–178. doi:10.1016/s0166-4328(03)00116-5. ISSN 0166-4328. PMID 14529815.
  5. ↑ Quirion, R.; Wilson, A.; Rowe, W.; Aubert, I.; Richard, J.; Doods, H.; Parent, A.; White, N.; Meaney, M. J. (February 1995). "Facilitation of acetylcholine release and cognitive performance by an M(2)-muscarinic receptor antagonist in aged memory-impaired". The Journal of Neuroscience. 15 (2): 1455–1462. doi:10.1523/JNEUROSCI.15-02-01455.1995. ISSN 0270-6474. PMC 6577836. PMID 7869110.