Aeruginascin

Aeruginascin
Clinical data
ATC code	none;
Legal status
Legal status	DE: NpSG (Industrial and scientific use only) ; UK: Class A ;
Identifiers
	IUPAC name [3-[2-(Trimethylazaniumyl)ethyl]-1H-indol-4-yl] hydrogen phosphate;
CAS Number	114264-95-8 ;
PubChem CID	60208479;
ChemSpider	26233970 ;
UNII	7U9WQY1P7R;
CompTox Dashboard (EPA)	DTXSID60921308 ;
Chemical and physical data
Formula	C13H20N2O4P
Molar mass	299.287 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[N+](C)(C)CCc1c[nH]c2c1c(ccc2)OP(=O)(O)[O-];
	InChI InChI=1S/C13H19N2O4P/c1-15(2,3)8-7-10-9-14-11-5-4-6-12(13(10)11)19-20(16,17)18/h4-6,9,14H,7-8H2,1-3H3,(H-,16,17,18) ; Key:OIIPFLWAQQNCHA-UHFFFAOYSA-N ;
	(verify)

Aeruginascin or N,N,N-trimethyl-4-phosphoryloxytryptamine is an indoleamine derivative which occurs naturally within the mushroom Inocybe aeruginascens[1][2][3][4][5] and Pholiotina cyanopus. Aeruginascin is the N-trimethyl analogue of psilocybin. It is closely related to the frog skin toxin bufotenidine (5-HTQ), a potent 5-HT₃ receptor agonist. The only scientific literature about the pharmacological effects of aeruginascin is from a study published by Gartz in 1989.[6] Across 23 analyzed cases of accidental hallucinogenic mushroom poisonings, people who had ingested the mushroom Inocybe aeruginascens reported only euphoric experiences. This is in contrast to the slight and in some cases extremely dysphoric experiences reported from the accidental ingestion of non aeruginascin containing mushrooms(containing solely psilocybin and psilocin).

Inocybe aeruginascens

References

Gartz J (1995). "Inocybe aeruginascens Babos". Eleusis, Journal of Psychoactive Plants & Compounds. Museo Civico di Rovereto. 3: 31–4.
Jensen N, Gartz J, Laatsch H (June 2006). "Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens" (PDF). Planta Medica. 72 (7): 665–6. doi:10.1055/s-2006-931576. PMID 16673333. Archived from the original (PDF) on 2011-05-24.
Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, Meisenheimer P (February 2020). "Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin". Journal of Natural Products. 83 (2): 461–467. doi:10.1021/acs.jnatprod.9b01061. PMID 32077284.
Servillo L, Giovane A, Balestrieri ML, Cautela D, Castaldo D (September 2012). "N-methylated tryptamine derivatives in citrus genus plants: identification of N,N,N-trimethyltryptamine in bergamot". Journal of Agricultural and Food Chemistry. 60 (37): 9512–8. doi:10.1021/jf302767e. PMID 22957740.
de Carvalho Junior AR, Oliveira Ferreira R, de Souza Passos M, da Silva Boeno SI, Glória das Virgens LL, Ventura TL, et al. (March 2019). "Psychotria nuda (Cham. & Schltdl.) Wawra". Molecules. 24 (6): 1026. doi:10.3390/molecules24061026. PMC 6471101. PMID 30875889.
Gartz J (January 1989). "Analysis of Aeruginascin in Fruit Bodies of the Mushroom Inocybe aeruginascens". International Journal of Crude Drug Research. 27 (3): 141–144. doi:10.3109/13880208909053954. ISSN 0167-7314.

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[MCR-1] Gartz J (1995). "Inocybe aeruginascens Babos". Eleusis, Journal of Psychoactive Plants & Compounds. Museo Civico di Rovereto. 3: 31–4.

[2] Jensen N, Gartz J, Laatsch H (June 2006). "Aeruginascin, a trimethylammonium analogue of psilocybin from the hallucinogenic mushroom Inocybe aeruginascens" (PDF). Planta Medica. 72 (7): 665–6. doi:10.1055/s-2006-931576. PMID 16673333. Archived from the original (PDF) on 2011-05-24.

[3] Sherwood AM, Halberstadt AL, Klein AK, McCorvy JD, Kaylo KW, Kargbo RB, Meisenheimer P (February 2020). "Synthesis and Biological Evaluation of Tryptamines Found in Hallucinogenic Mushrooms: Norbaeocystin, Baeocystin, Norpsilocin, and Aeruginascin". Journal of Natural Products. 83 (2): 461–467. doi:10.1021/acs.jnatprod.9b01061. PMID 32077284.

[4] Servillo L, Giovane A, Balestrieri ML, Cautela D, Castaldo D (September 2012). "N-methylated tryptamine derivatives in citrus genus plants: identification of N,N,N-trimethyltryptamine in bergamot". Journal of Agricultural and Food Chemistry. 60 (37): 9512–8. doi:10.1021/jf302767e. PMID 22957740.

[5] Carvalho Junior AR, Oliveira Ferreira R, de Souza Passos M, da Silva Boeno SI, Glória das Virgens LL, Ventura TL, et al. (March 2019). "Psychotria nuda (Cham. & Schltdl.) Wawra". Molecules. 24 (6): 1026. doi:10.3390/molecules24061026. PMC 6471101. PMID 30875889.

[6] Gartz J (January 1989). "Analysis of Aeruginascin in Fruit Bodies of the Mushroom Inocybe aeruginascens". International Journal of Crude Drug Research. 27 (3): 141–144. doi:10.3109/13880208909053954. ISSN 0167-7314.