N-Formylmescaline

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N-Formylmescaline
N-Formylmescaline.svg
Clinical data
Other namesFormylmescaline; N-Formyl-3,4,5-trimethoxyphenethylamine; N-Formyl-3,4,5-TMPEA
Drug class Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • N-[2-(3,4,5-trimethoxyphenyl)ethyl]formamide
PubChem CID
Chemical and physical data
Formula C12H17NO4
Molar mass 239.271 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 as N-formyl-3,4,5-trimethoxyphenethylamine, is an alkaloid and possible psychedelic drug of the phenethylamine and scaline families related to mescaline. [1] [2] [3] It is the N-formyl derivative of mescaline. [1] [2] [3] N,N-Diformylmescaline has been found to be chemically unstable under acidic or basic conditions, breaking down into N-formylmescaline, which then further degrades into mescaline. [1] [2] [3] Relatedly, it is thought that N-formylmescaline and N,N-diformylmescaline may act as prodrugs of mescaline in vivo . [1] [2] [3] N-Formylmescaline is known to occur naturally in trace amounts in peyote. [2] [3] [4] [5] [6]

Contents

See also

References

  1. 1 2 3 4 Ponce 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. 1 2 3 4 5 Gallagher 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. 1 2 3 4 5 "N,N-Diformylmescaline (Мескалин 2FORM)". АИПСИН (in Russian). Retrieved 31 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 . Retrieved 31 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 . Retrieved 31 October 2025.
  6. ↑ "N-Formylmescaline". Trout’s Notes. Isomer Design.
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