Conessine

Last updated
Conessine
Conessine.svg
Names
Preferred IUPAC name
(3S,3aS,5aS,5bR,9S,11aR,11bS,13aR)-N,N,2,3,11a-Pentamethyl-2,3,3a,4,5,5a,5b,6,8,9,10,11,11a,11b,12,13-hexadecahydro-1H-naphtho[2′,1′:4,5]indeno[1,7a-c]pyrrol-9-amine
Other names
Neriine; Roquessine; Wrightine; Conessinum; (3β)-N,N-Dimethyl-con-5-enin-3-amine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.089 OOjs UI icon edit-ltr-progressive.svg
MeSH Conessine
PubChem CID
UNII
  • InChI=1S/C24H40N2/c1-16-20-8-9-22-19-7-6-17-14-18(25(3)4)10-12-23(17,2)21(19)11-13-24(20,22)15-26(16)5/h6,16,18-22H,7-15H2,1-5H3/t16-,18-,19+,20+,21-,22-,23-,24-/m0/s1 X mark.svgN
    Key: GPLGAQQQNWMVMM-MYAJQUOBSA-N X mark.svgN
  • InChI=1/C24H40N2/c1-16-20-8-9-22-19-7-6-17-14-18(25(3)4)10-12-23(17,2)21(19)11-13-24(20,22)15-26(16)5/h6,16,18-22H,7-15H2,1-5H3/t16-,18-,19+,20+,21-,22-,23-,24-/m0/s1
    Key: GPLGAQQQNWMVMM-MYAJQUOBBK
  • C[C@H]1[C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4(CC[C@@H](C5)N(C)C)C)CN1C
Properties
C24H40N2
Molar mass 356.598 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Conessine is a steroidal alkaloid found in a number of plant species from the family Apocynaceae, including Holarrhena floribunda , [1] Holarrhena antidysenterica [2] and Funtumia elastica . [3] It acts as a histamine antagonist, selective for the H3 subtype (with an affinity of pKi = 8.27; Ki = ~5 nM). [4] It was also found to have long CNS clearance times, high blood–brain barrier penetration and high affinity for the adrenergic receptors. [5]

References

  1. ↑ Duez, P; Chamart, S; Lejoly, J; Hanocq, M; Zeba, B; Sawadogo, M; Guissou, P; Molle, L (1987). "Changes in conessine in stem bark of Holarrhena floribunda in Burkina Faso". Annales pharmaceutiques françaises. 45 (4): 307–13. PMID   3445993.
  2. ↑ Kumar, N; Singh, B; Bhandari, P; Gupta, A. P.; Kaul, V. K. (2007). "Steroidal alkaloids from Holarrhena antidysenterica (L.) WALL". Chemical & Pharmaceutical Bulletin. 55 (6): 912–4. doi: 10.1248/cpb.55.912 . PMID   17541193.
  3. ↑ Zirihi, G. N.; Grellier, P; Guédé-Guina, F; Bodo, B; Mambu, L (2005). "Isolation, characterization and antiplasmodial activity of steroidal alkaloids from Funtumia elastica (Preuss) Stapf". Bioorganic & Medicinal Chemistry Letters. 15 (10): 2637–40. doi:10.1016/j.bmcl.2005.03.021. PMID   15863333.
  4. ↑ Santora, V. J.; Covel, J. A.; Hayashi, R; Hofilena, B. J.; Ibarra, J. B.; Pulley, M. D.; Weinhouse, M. I.; Sengupta, D; Duffield, J. J.; Semple, G; Webb, R. R.; Sage, C; Ren, A; Pereira, G; Knudsen, J; Edwards, J. E.; Suarez, M; Frazer, J; Thomsen, W; Hauser, E; Whelan, K; Grottick, A. J. (2008). "A new family of H3 receptor antagonists based on the natural product Conessine". Bioorganic & Medicinal Chemistry Letters. 18 (4): 1490–4. doi:10.1016/j.bmcl.2007.12.059. PMID   18194865.
  5. ↑ Zhao, Chen; Sun, Minghua; Bennani, Youssef L.; Gopalakrishnan, Sujatha M.; Witte, David G.; Miller, Thomas R.; Krueger, Kathleen M.; Browman, Kaitlin E.; Thiffault, Christine; Wetter, Jill; Marsh, Kennan C.; Hancock, Arthur A.; Esbenshade, Timothy A.; Cowart, Marlon D. (2008). "The Alkaloid Conessine and Analogues as Potent Histamine H3Receptor Antagonists". Journal of Medicinal Chemistry. 51 (17): 5423–30. doi:10.1021/jm8003625. PMID   18683917.
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