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.

References

^ Gartz J (1995). "Inocybe aeruginascens Babos". Eleusis, journal of psychoactive plants & compounds. 3. Museo Civico di Rovereto: 31–4.
^ Jensen, Niels; Gartz, Jochen; Laatsch, Hartmut (June 2006). "Aeruginascin, a Trimethylammonium Analogue of Psilocybin from the Hallucinogenic Mushroom Inocybe aeruginascens" (PDF). Planta Medica. 72 (07): 665–666. doi:10.1055/s-2006-931576. ISSN 1439-0221. PMID 16673333. Archived from the original (PDF) on 2011-05-24.
^ Sherwood, Alexander M.; Halberstadt, Adam L.; Klein, Adam K.; McCorvy, John D.; Kaylo, Kristi W.; Kargbo, Robert B.; Meisenheimer, Poncho (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. ISSN 0163-3864. PMID 32077284.
^ Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Cautela, Domenico; Castaldo, Domenico (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): 9512–9518. doi:10.1021/jf302767e. ISSN 0021-8561. PMID 22957740.
^ de Carvalho Junior, Almir Ribeiro; Oliveira Ferreira, Rafaela; de Souza Passos, Michel; da Silva Boeno, Samyra Imad; Glória das Virgens, Lorena de Lima; Ventura, Thatiana Lopes Biá; Calixto, Sanderson Dias; Lassounskaia, Elena; de Carvalho, Mario Geraldo; Braz-Filho, Raimundo; Curcino Vieira, Ivo Jose (March 2019). "Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra". Molecules. 24 (6): 1026. doi:10.3390/molecules24061026. PMC 6471101. PMID 30875889.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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[MCR-1] Gartz J (1995). "Inocybe aeruginascens Babos". Eleusis, journal of psychoactive plants & compounds. 3. Museo Civico di Rovereto: 31–4.

[2] Jensen, Niels; Gartz, Jochen; Laatsch, Hartmut (June 2006). "Aeruginascin, a Trimethylammonium Analogue of Psilocybin from the Hallucinogenic Mushroom Inocybe aeruginascens" (PDF). Planta Medica. 72 (07): 665–666. doi:10.1055/s-2006-931576. ISSN 1439-0221. PMID 16673333. Archived from the original (PDF) on 2011-05-24.

[3] Sherwood, Alexander M.; Halberstadt, Adam L.; Klein, Adam K.; McCorvy, John D.; Kaylo, Kristi W.; Kargbo, Robert B.; Meisenheimer, Poncho (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. ISSN 0163-3864. PMID 32077284.

[4] Servillo, Luigi; Giovane, Alfonso; Balestrieri, Maria Luisa; Cautela, Domenico; Castaldo, Domenico (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): 9512–9518. doi:10.1021/jf302767e. ISSN 0021-8561. PMID 22957740.

[5] Carvalho Junior, Almir Ribeiro; Oliveira Ferreira, Rafaela; de Souza Passos, Michel; da Silva Boeno, Samyra Imad; Glória das Virgens, Lorena de Lima; Ventura, Thatiana Lopes Biá; Calixto, Sanderson Dias; Lassounskaia, Elena; de Carvalho, Mario Geraldo; Braz-Filho, Raimundo; Curcino Vieira, Ivo Jose (March 2019). "Antimycobacterial and Nitric Oxide Production Inhibitory Activities of Triterpenes and Alkaloids from Psychotria nuda (Cham. & Schltdl.) Wawra". Molecules. 24 (6): 1026. doi:10.3390/molecules24061026. PMC 6471101. PMID 30875889.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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