Conessine

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 327756587

| ImageFile = Conessine.svg

| ImageSize = 220px

| PIN = (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

| OtherNames = Neriine; Roquessine; Wrightine; Conessinum; (3β)-N,N-Dimethyl-con-5-enin-3-amine

| Section1 = {{Chembox Identifiers

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = EZ38J9BBDF

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=546-06-5

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 27965

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 191703

| PubChem = 441082

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 389885

| SMILES = 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

| 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

| InChIKey = GPLGAQQQNWMVMM-MYAJQUOBBK

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = GPLGAQQQNWMVMM-MYAJQUOBSA-N

| MeSHName=Conessine

}}

| Section2 = {{Chembox Properties

| C=24 | H=40 | N=2

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

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| Section3 = {{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

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Conessine is a steroidal alkaloid found in a number of plant species from the family Apocynaceae, including Holarrhena floribunda,{{cite journal | pmid=3445993| year=1987| last1=Duez| first1=P| title=Changes in conessine in stem bark of Holarrhena floribunda in Burkina Faso| journal=Annales pharmaceutiques françaises| volume=45| issue=4| pages=307–13| last2=Chamart| first2=S| last3=Lejoly| first3=J| last4=Hanocq| first4=M| last5=Zeba| first5=B| last6=Sawadogo| first6=M| last7=Guissou| first7=P| last8=Molle| first8=L}} Holarrhena antidysenterica{{cite journal | pmid=17541193| year=2007| last1=Kumar| first1=N| title=Steroidal alkaloids from Holarrhena antidysenterica (L.) WALL| journal=Chemical & Pharmaceutical Bulletin| volume=55| issue=6| pages=912–4| last2=Singh| first2=B| last3=Bhandari| first3=P| last4=Gupta| first4=A. P.| last5=Kaul| first5=V. K.| doi=10.1248/cpb.55.912| doi-access=free}} and Funtumia elastica.{{cite journal | pmid=15863333| year=2005| last1=Zirihi| first1=G. N.| title=Isolation, characterization and antiplasmodial activity of steroidal alkaloids from Funtumia elastica (Preuss) Stapf| journal=Bioorganic & Medicinal Chemistry Letters| volume=15| issue=10| pages=2637–40| last2=Grellier| first2=P| last3=Guédé-Guina| first3=F| last4=Bodo| first4=B| last5=Mambu| first5=L| doi=10.1016/j.bmcl.2005.03.021}} It acts as a histamine antagonist, selective for the H₃ subtype (with an affinity of pK_i = 8.27; K_i = ~5 nM).{{cite journal | pmid=18194865| year=2008| last1=Santora| first1=V. J.| title=A new family of H3 receptor antagonists based on the natural product Conessine| journal=Bioorganic & Medicinal Chemistry Letters| volume=18| issue=4| pages=1490–4| last2=Covel| first2=J. A.| last3=Hayashi| first3=R| last4=Hofilena| first4=B. J.| last5=Ibarra| first5=J. B.| last6=Pulley| first6=M. D.| last7=Weinhouse| first7=M. I.| last8=Sengupta| first8=D| last9=Duffield| first9=J. J.| last10=Semple| first10=G| last11=Webb| first11=R. R.| last12=Sage| first12=C| last13=Ren| first13=A| last14=Pereira| first14=G| last15=Knudsen| first15=J| last16=Edwards| first16=J. E.| last17=Suarez| first17=M| last18=Frazer| first18=J| last19=Thomsen| first19=W| last20=Hauser| first20=E| last21=Whelan| first21=K| last22=Grottick| first22=A. J.| doi=10.1016/j.bmcl.2007.12.059}} It was also found to have long CNS clearance times, high blood–brain barrier penetration and high affinity for the adrenergic receptors.{{cite journal | doi=10.1021/jm8003625| pmid=18683917| title=The Alkaloid Conessine and Analogues as Potent Histamine H3Receptor Antagonists| journal=Journal of Medicinal Chemistry| volume=51| issue=17| pages=5423–30| year=2008| last1=Zhao| first1=Chen| last2=Sun| first2=Minghua| last3=Bennani| first3=Youssef L.| last4=Gopalakrishnan| first4=Sujatha M.| last5=Witte| first5=David G.| last6=Miller| first6=Thomas R.| last7=Krueger| first7=Kathleen M.| last8=Browman| first8=Kaitlin E.| last9=Thiffault| first9=Christine| last10=Wetter| first10=Jill| last11=Marsh| first11=Kennan C.| last12=Hancock| first12=Arthur A.| last13=Esbenshade| first13=Timothy A.| last14=Cowart| first14=Marlon D.}}