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N,N-Diformylmescaline

From Wikipedia, the free encyclopedia

Pharmaceutical compound
N,N-Diformylmescaline
Clinical data
Other namesDiformylmescaline;N,N-Diformyl-3,4,5-trimethoxyphenethylamine;N,N-Diformyl-3,4,5-TMPEA
Drug classSerotonergic psychedelic;Hallucinogen
ATC code
  • None
Identifiers
  • N-formyl-N-[2-(3,4,5-trimethoxyphenyl)ethyl]formamide
PubChemCID
ChemSpider
Chemical and physical data
FormulaC13H17NO5
Molar mass267.281 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1OC)OC)CCN(C=O)C=O
  • InChI=1S/C13H17NO5/c1-17-11-6-10(4-5-14(8-15)9-16)7-12(18-2)13(11)19-3/h6-9H,4-5H2,1-3H3
  • Key:ONCGKRHDZQPRFG-UHFFFAOYSA-N

N,N-Diformylmescaline, also known asN,N-diformyl-3,4,5-trimethoxyphenethylamine, is a possiblepsychedelic drug of thephenethylamine andscaline families related tomescaline.[1][2][3] It is theN,N-diformylderivative of mescaline.[1][2][3] The compound has been found to bechemically unstable underacidic orbasic conditions, breaking down intoN-formylmescaline and then into mescaline.[1][2][3] Relatedly, it is thought thatN,N-diformylmescaline may act as aprodrug of mescalinein vivo.[1][2][3] Thechemical synthesis of the compound has been described.[2][3] It was encountered as a possible noveldesigner drug in 2020 and this was reported in 2022.[1][2][3]N,N-Diformylmescaline itself is not known to benaturally occurring, butN-formylmescaline is known to occur naturally in trace amounts inpeyote.[2][3][4][5][6]

See also

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References

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  1. ^abcdePonce JD (2024)."The use of prodrugs as drugs of abuse".WIREs Forensic Science.6 (3) e1514.doi:10.1002/wfs2.1514.ISSN 2573-9468.In January 2020, Australian authorities seized a powder suspected of being cocaine. After analysis by GC–MS, NMR and IR, the compound was identified as N,N-diformylmescaline. Under exposure to acid and basic conditions, the structure degraded to N-formylmescaline, a naturally occurring compound in Peyote, and further to mescaline (Gallagher et al., 2023).
  2. ^abcdefgGallagher R, McLaughlin MG, Blakey K, Wermuth UD, Boyd S, McGowan J (February 2023). "N,N-Diformylmescaline: A novel analogue of mescaline detected in Queensland".Drug Testing and Analysis.15 (2):204–212.doi:10.1002/dta.3390.hdl:10072/422047.PMID 36245421.
  3. ^abcdefg"Мескалин 2FORM" [N,N-Diformylmescaline].АИПСИН [ASPIN] (in Russian). Retrieved31 October 2025.
  4. ^Elks J (2014)."Mescaline".The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 774.ISBN 978-1-4757-2085-3. Retrieved31 October 2025.
  5. ^Lundström J (1989)."β-Phenethylamines and ephedrines of plant origin.". In Brossi A (ed.).The Alkaloids: Chemistry and Pharmacology. Vol. 35. Academic Press. pp. 77-154 (111).ISBN 978-0-08-086559-1. Retrieved31 October 2025.
  6. ^"N-Formylmescaline".Trout’s Notes. Isomer Design.

External links

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