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Conessine

From Wikipedia, the free encyclopedia
Conessine
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 InfoCard100.008.089Edit this at Wikidata
MeSHConessine
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 ☒N
    Key: GPLGAQQQNWMVMM-MYAJQUOBSA-N ☒N
  • 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 mass356.598 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Chemical compound

Conessine is asteroidal alkaloid found in a number of plant species from the familyApocynaceae, includingHolarrhena floribunda,[1]Holarrhena antidysenterica[2] andFuntumia elastica.[3] It acts as ahistamine antagonist, selective for theH3 subtype (with an affinity of pKi = 8.27; Ki = ~5 nM).[4] It was also found to have long CNS clearance times, highblood–brain barrier penetration and high affinity for the adrenergic receptors.[5]

References

[edit]
  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.
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
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