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N-Methyl-2C-I

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N-Methyl-2C-I
Clinical data
Other names25I-NMe; N-Methyl-4-iodo-2,5-dimethoxyphenethylamine
Drug classSerotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-(4-iodo-2,5-dimethoxyphenyl)-N-methylethan-1-amine
Chemical and physical data
FormulaC11H16INO2
Molar mass321.158 g·mol−1
3D model (JSmol)
  • CNCCc1cc(OC)c(cc1OC)I
  • InChI=1S/C11H16INO2/c1-13-5-4-8-6-11(15-3)9(12)7-10(8)14-2/h6-7,13H,4-5H2,1-3H3
  • Key:VKPKTPYPZITMRK-UHFFFAOYSA-N

N-Methyl-2C-I, also known as 25I-NMe or as N-methyl-4-iodo-2,5-dimethoxyphenethylamine, is a serotonin receptor modulator of the phenethylamine and 2C families related to the psychedelic drug 2C-I.[1][2] It is specifically the N-methyl analogue of 2C-I.[1][2]

The drug shows more than 2,500-fold reduced affinity for the serotonin 5-HT2A receptor compared to 2C-I.[1][2] In addition, N-methyl-2C-I showed around 170-fold lower affinity for the serotonin 5-HT2C receptor relative to 2C-I.[1][2] These results are in accordance with general findings that N-alkylation of psychedelic phenethylamines results in dramatic or complete losses of psychedelic and related activities.[1][2] In contrast to simple N-alkylation however, the N-benzyl derivative of 2C-I, 25I-NB (N-benzyl-2C-I), showed similar affinity for the serotonin 5-HT2A receptor compared to 2C-I itself.[1][2][3] Relatedly, the N-(2-methoxybenzyl) derivatives, such as 25I-NBOMe, have not only retained but greatly enhanced activity and constitute the extremely potent NBOMe family of psychedelics.[1][4][5]

N-Methyl-2C-I was first described in the scientific literature by at least 2012.[2]

See also

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References

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  1. ^ a b c d e f g Nichols DE (2018). "Chemistry and Structure-Activity Relationships of Psychedelics". Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
  2. ^ a b c d e f g Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT 2A agonists" (PDF). Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X.
  3. ^ Braden MR, Parrish JC, Naylor JC, Nichols DE (December 2006). "Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists". Molecular Pharmacology. 70 (6): 1956–1964. doi:10.1124/mol.106.028720. PMID 17000863.
  4. ^ Poulie CB, Jensen AA, Halberstadt AL, Kristensen JL (December 2020). "DARK Classics in Chemical Neuroscience: NBOMes". ACS Chemical Neuroscience. 11 (23): 3860–3869. doi:10.1021/acschemneuro.9b00528. PMC 9191638. PMID 31657895.
  5. ^ Halberstadt AL (2017). "Pharmacology and Toxicology of N-Benzylphenethylamine ("NBOMe") Hallucinogens". In Baumann M, Glennon R, Wiley J (eds.). Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. Cham: Springer. pp. 283–311. doi:10.1007/7854_2016_64. ISBN 978-3-319-52444-3. PMID 28097528.
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