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N-Formylmescaline

From Wikipedia, the free encyclopedia

Pharmaceutical compound
N-Formylmescaline
Clinical data
Other namesFormylmescaline;N-Formyl-3,4,5-trimethoxyphenethylamine;N-Formyl-3,4,5-TMPEA
Drug classSerotonergic psychedelic;Hallucinogen
ATC code
  • None
Identifiers
  • N-[2-(3,4,5-trimethoxyphenyl)ethyl]formamide
PubChemCID
Chemical and physical data
FormulaC12H17NO4
Molar mass239.271 g·mol−1
3D model (JSmol)
  • COC1=CC(=CC(=C1OC)OC)CCNC=O
  • InChI=1S/C12H17NO4/c1-15-10-6-9(4-5-13-8-14)7-11(16-2)12(10)17-3/h6-8H,4-5H2,1-3H3,(H,13,14)
  • Key:BESRMWQCUXKEMP-UHFFFAOYSA-N

N-Formylmescaline, also known asN-formyl-3,4,5-trimethoxyphenethylamine, is analkaloid and possiblepsychedelic drug of thephenethylamine andscaline families related tomescaline.[1][2][3] It is theN-formylderivative of mescaline.[1][2][3]N,N-Diformylmescaline has been found to bechemically unstable underacidic orbasic conditions, breaking down intoN-formylmescaline, which then further degrades into mescaline.[1][2][3] Relatedly, it is thought thatN-formylmescaline andN,N-diformylmescaline may act asprodrugs of mescalinein vivo.[1][2][3]N-Formylmescaline is known to occur naturally in trace amounts inpeyote.[2][3][4][5][6]

See also

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References

[edit]
  1. ^abcdPonce 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. ^abcdeGallagher 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. ^abcde"N,N-Diformylmescaline (Мескалин 2FORM)".АИПСИН (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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