Actinidine

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title: "Actinidine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["pyridine-alkaloids", "cat-attractants", "insect-pheromones"] topic_path: "general/pyridine-alkaloids" source: "https://en.wikipedia.org/wiki/Actinidine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | ChemSpiderID = 61533 | KEGG_Ref = | 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@HC)C | StdInChI_Ref = | 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 = | StdInChIKey = ZHQQRIUYLMXDPP-ZETCQYMHSA-N | CASNo_Ref = | CASNo = 524-03-8 | UNII_Ref = | UNII = VWU976C78Y | ChEBI_Ref = | ChEBI = 2443 | SMILES = CC@@HC2=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

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. It is one of several compounds that may be extracted from the valerian (Valeriana officinalis) root and silver vine (Actinidia polygama), as well as several types of insects in the larval and imaginal stages. Actinidine is a cat attractant, with effects like those of nepetalactone, the active compound found in catnip.

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.

Biosynthesis

A potential biosynthesis of actinidine from -citronellal is shown below.

::figure[src="https://upload.wikimedia.org/wikipedia/commons/7/75/Actinidine_pathway.gif"] ::

References

References

  1. Sakan, Takeo. (1959). "On the Structure of Actinidine and Matatabilactone, the Effective Components of Actinidia polygama". Bulletin of the Chemical Society of Japan.
  2. (1959). "Diterpenoids". Chemical Reviews.
  3. (1979). "Contribution to the study of valerian alcaloids (''Valeriana officinalis'' L.): actinidine and naphthyridylmethylketone, a new alkaloid". Ann. Pharm. Fr..
  4. (2001). "Iridoid biosynthesis in staphylinid rove beetles (Coleoptera: Staphylinidae, Philonthinae)". Insect Biochemistry and Molecular Biology.
  5. (2020-05-01). "The evolutionary origins of the cat attractant nepetalactone in catnip". Science Advances.
  6. (2020). "Life cycles, phenology and genetic structure of endangered Megacrania tsudai Shiraki (Phasmatodea: Phasmatidae): Male individuals from a geographic parthenogenesis species". Entomological Science.
  7. (2015). "Alkaloids". Academic Press.

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pyridine-alkaloidscat-attractantsinsect-pheromones