Ryanodine

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464384841

| ImageFile = Ryanodine.svg

| ImageSize = 240px

| PIN = (1S,2R,2aS,2a¹R,3S,3aS,6S,7R,7aR,9S,9aS)-1,2a,2a¹,3a,7,9-Hexahydroxy-3,6,9a-trimethyl-1-(propan-2-yl)dodecahydro-3,9-methanobenzo[1,2]pentaleno[1,6-bc]furan-2-yl 1H-pyrrole-2-carboxylate

| OtherNames =

|Section1={{Chembox Identifiers

| IUPHAR_ligand = 4303

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 16736002

| InChI = 1/C25H35NO9/c1-12(2)22(31)17(34-16(28)14-7-6-10-26-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)8-9-20(18,24)29/h6-7,10,12-13,15,17,26-27,29-33H,8-9,11H2,1-5H3/t13-,15+,17+,18-,19+,20-,21-,22+,23+,24+,25+/m0/s1

| InChIKey = JJSYXNQGLHBRRK-SFEDZAPPBA

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C25H35NO9/c1-12(2)22(31)17(34-16(28)14-7-6-10-26-14)23(32)18(4)11-21(30)19(22,5)25(23,33)24(35-21)15(27)13(3)8-9-20(18,24)29/h6-7,10,12-13,15,17,26-27,29-33H,8-9,11H2,1-5H3/t13-,15+,17+,18-,19+,20-,21-,22+,23+,24+,25+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = JJSYXNQGLHBRRK-SFEDZAPPSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 15662-33-6

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 37H6ATE4SA

| PubChem = 5114

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

| ChEMBL = 612231

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 8925

| SMILES = C[C@H]1CC[C@@]2([C@@]3(C[C@]4([C@@]5([C@]([C@H]([C@@]3([C@]5([C@]2([C@@H]1O)O4)O)O)OC(=O)c6ccc[nH]6)(C(C)C)O)C)O)C)O

| MeSHName = Ryanodine

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C08705

}}

|Section2={{Chembox Properties

| C=25 | H=35 | N=1 | O=9

| Appearance =

| Density =

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| BoilingPt =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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Ryanodine is a poisonous diterpenoid found in the South American plant Ryania speciosa (Salicaceae). It was originally used as an insecticide.

The compound has extremely high affinity to the open-form ryanodine receptor, a group of calcium channels found in skeletal muscle, smooth muscle, and heart muscle cells.{{cite journal|last1=Santulli|first1=Gaetano|last2=Marks|first2=Andrew|title=Essential Roles of Intracellular Calcium Release Channels in Muscle, Brain, Metabolism, and Aging|journal=Current Molecular Pharmacology|volume=8|issue=2|year=2015|pages=206–222|issn=1874-4672|doi=10.2174/1874467208666150507105105|pmid=25966694}} It binds with such high affinity to the receptor that it was used as a label for the first purification of that class of ion channels and gave its name to it.

At nanomolar concentrations, ryanodine locks the receptor in a half-open state, whereas it fully closes them at micromolar concentration. The effect of the nanomolar-level binding is that ryanodine causes release of calcium from calcium stores as the sarcoplasmic reticulum in the cytoplasm, leading to massive muscle contractions. The effect of micromolar-level binding is paralysis. This is true for both mammals and insects.{{cite journal | last1 = Van Petegem | first1 = F | year = 2012 | title = Ryanodine receptors: structure and function | journal = The Journal of Biological Chemistry | volume = 287 | issue = 38| pages = 31624–32 | doi = 10.1074/jbc.r112.349068 | pmid = 22822064 | pmc = 3442496 | doi-access = free }}