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Names
Preferred IUPAC name (5R,10S,10aR,14aS,15bS)-10,10a-Dihydroxy-7-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,12,13,14,14a,15b-octahydro-5H,15H-3,4-dioxa-5a,11a,15a-triazacycloocta[lm]indeno[5,6-b]fluorene-11,15(2H)-dione
Identifiers
CAS Number	12771-72-1
3D model (JSmol)	Interactive image
ChemSpider	10405461
KEGG	C20045
PubChem CID	104862
SMILES CC(=CC1N2C3=C(C=CC(=C3)OC)C4=C2C(CC(OO1)(C)C)N5C(=O)C6CCCN6C(=O)C5(C4O)O)C
Properties
Chemical formula	C27H33N3O7
Molar mass	511.575 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Verruculogen is a mycotoxin produced by certain strains of aspergillus that belongs to a class of naturally occurring 2,5-diketopiperazines.^[1] It is an annulated analogue of cyclo(L-Trp-L-Pro) which belongs to the most abundant and structurally diverse class of tryptophan-proline 2,5-diketopiperazine natural products. It produces tremors in mice due to its neurotoxic properties. It also tested positive in a Salmonella/mammalian microsome assay and was shown to be genotoxic. It is a potent blocker of calcium-activated potassium channels.^[2]

Both verruculogen and its isoprenyl derivative fumitremorgin A belong to the only family of alkaloids with an eight-membered endoperoxide ring, and both have been synthesised involving ligand-controlled C–H borylation.^[3]

Verruculogen is classified as a tremorgenic mycotoxin due to its potent effects on the central nervous system. In animal models, particularly mice, verruculogen induces sustained muscle tremors, hyperactivity, and convulsions shortly after exposure.^[4] These tremors are characteristic of mycotoxins that affect neuronal excitability.

Toxicological databases describe verruculogen as a neurotoxin with high acute toxicity potential. Verruculogen is an inhibitor of large-conductance calcium-activated BK channels. By blocking these channels, verruculogen increases the frequency of neuronal firing, leading to tremors and convulsions. It is considered harmful if ingested and may cause long-lasting effects due to its action on potassium ion channels in nerve cells. Although no human LD₅₀ is published, verruculogen is known to exert toxicity at microgram-per-kilogram levels in mammalian species.^[5]

Verruculogen is produced naturally by several species of fungi, such as Aspergillus and Penicillium. It is associated with the Aspergillus fumigatus and Penicillium verruculosum, species most commonly, which are commonly found in soil, decaying organic matter, and stored agricultural products.^[6] It is considered to be both an airborne and foodborne toxin because of its presence in dust, soil, and fungal-infected crops.

Studies have shown that verruculogen can disrupt ion transport in human airway epithelial cells, suggesting that it also can play a role in respiratory dysfunction. There have been studies towards this pharmacological activity, using verruculogen as a molecular probe to observe epithelial barrier integrity and ion channel physiology. ^[7]