Actinidine

{{cs1 config|name-list-style=vanc}}

{{distinguish|Actinidin|Actinide|Actinium}}

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477241564

| Name = Actinidine

| ImageFile = Structural formula of actinidine.svg

| ImageSize = 180

| ImageName = Structural formula of actinidine

| ImageFile1 = Actinidine Space-Filling.png

| ImageSize1 =

| ImageName1 = Space-filling

| PIN = (7S)-4,7-Dimethyl-6,7-dihydro-5H-cyclopenta[c]pyridine

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 61533

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C09910

| Beilstein = 81308

| PubChem = 68231

| InChI = 1/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1

| InChIKey = ZHQQRIUYLMXDPP-ZETCQYMHBZ

| SMILES1 = n1cc(c2c(c1)[C@H](CC2)C)C

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

| StdInChI = 1S/C10H13N/c1-7-3-4-9-8(2)5-11-6-10(7)9/h5-7H,3-4H2,1-2H3/t7-/m0/s1

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

| StdInChIKey = ZHQQRIUYLMXDPP-ZETCQYMHSA-N

| CASNo_Ref = {{cascite|changed|??}}

| CASNo = 524-03-8

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

| UNII = VWU976C78Y

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

| ChEBI = 2443

| SMILES = C[C@@H](CC1)C2=C1C(C)=CN=C2

}}

|Section2={{Chembox Properties

| C=10 | H=13 | N=1

| Density =

| MeltingPt=<

| MeltingPtC =25

| BoilingPtC = 100 to 103

| BoilingPt_notes = at 9 mmHg{{cite journal|last=Sakan |first=Takeo |title=On the Structure of Actinidine and Matatabilactone, the Effective Components of Actinidia polygama |journal=Bulletin of the Chemical Society of Japan |date=1959 |volume=32 |issue=3 |pages=315–316|doi=10.1246/bcsj.32.315 }}

}}

}}

Actinidine is an iridoid produced in nature by a wide variety of plants and animals. It was the first cyclopentanoid monoterpene alkaloid to be discovered.{{cite journal|last1=Tsutsui|first1=Minoru|last2=Tsutsui|first2=Ethel Ashworth|title=Diterpenoids|journal=Chemical Reviews|volume=59|issue=6|pages=1031–1075|year=1959|doi=10.1021/cr50030a003|jstor=|url=https://pubs.acs.org/doi/10.1021/cr50030a003}} It is one of several compounds that may be extracted from the valerian (Valeriana officinalis) root{{cite journal| vauthors = Janot MM, Guilhem J, Contz O, Venera G, Cionga E | year = 1979| title = Contribution to the study of valerian alcaloids (Valeriana officinalis L.): actinidine and naphthyridylmethylketone, a new alkaloid |lang=French| journal = Ann. Pharm. Fr.| volume = 37| issue = 9–10| pages = 413–20| pmid = 547813}} and silver vine (Actinidia polygama), as well as several types of insects in the larval and imaginal stages.{{cite journal| vauthors = Weibel DB, Oldham NJ, Feld B, Glombitza G, Dettner K, Boland W| year = 2001| title = Iridoid biosynthesis in staphylinid rove beetles (Coleoptera: Staphylinidae, Philonthinae)| journal = Insect Biochemistry and Molecular Biology| volume = 31| issue = 6–7| pages = 583–591| doi = 10.1016/s0965-1748(00)00163-6| pmid = 11267897}} Actinidine is a cat attractant, with effects like those of nepetalactone, the active compound found in catnip.{{cite journal|last1=Lichman|first1=Benjamin R.|last2=Godden|first2=Grant T.|last3=Hamilton|first3=John P.|last4=Palmer|first4=Lira|last5=Kamileen|first5=Mohamed O.|last6=Zhao|first6=Dongyan|last7=Vaillancourt|first7=Brieanne|last8=Wood|first8=Joshua C.|last9=Sun|first9=Miao|last10=Kinser|first10=Taliesin J.|last11=Henry|first11=Laura K.|date=2020-05-01|title=The evolutionary origins of the cat attractant nepetalactone in catnip|journal=Science Advances|language=en|volume=6|issue=20|pages=eaba0721|doi=10.1126/sciadv.aba0721|pmid=32426505|pmc=7220310|bibcode=2020SciA....6..721L |issn=2375-2548|doi-access=free}}

Certain species of stick insects, including Megacrania batesii and Megacrania tsudai, possess a chemical defense mechanism which involves the secretion of an actinidine-containing substance from the prothoracic glands, when threatened by a predator.{{cite journal|title=Life cycles, phenology and genetic structure of endangered Megacrania tsudai Shiraki (Phasmatodea: Phasmatidae): Male individuals from a geographic parthenogenesis species|journal=Entomological Science|volume=23|issue=2|pages=183–192|year=2020|doi=10.1111/ens.12410|jstor=|url=https://www.researchgate.net/publication/340179816|last1=Wu|first1=I-Hsin|last2=Liu|first2=Hsui-Huei|last3=Chen|first3=Yu-Yen|last4=Tsai|first4=Cheng-Lung|last5=Yu|first5=Yi-Ching|last6=Hsiao|first6=Chung-Yi|last7=Yeh|first7=Wen-Bin|s2cid=216322536}}