2-Iodomescaline

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2-Iodomescaline
2-Iodomescaline.svg
Clinical data
Other names2-I-M; 2-Iodo-3,4,5-trimethoxyphenethylamine
Drug class Serotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-(2-iodo-3,4,5-trimethoxyphenyl)ethanamine
PubChem CID
ChemSpider
Chemical and physical data
Formula C11H16INO3
Molar mass 337.157 g·mol−1
3D model (JSmol)
  • COC1=C(C(=C(C(=C1)CCN)I)OC)OC
  • InChI=1S/C11H16INO3/c1-14-8-6-7(4-5-13)9(12)11(16-3)10(8)15-2/h6H,4-5,13H2,1-3H3
  • Key:VMDLLVSUNOVICJ-UHFFFAOYSA-N

2-Iodomescaline (2-I-M), also known as 2-iodo-3,4,5-trimethoxyphenethylamine, is a serotonin receptor modulator of the phenethylamine and scaline families related to mescaline. [1] It is the 2-iodo derivative of mescaline. [1] The drug shows affinity for the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors (Ki = 190 nM, 376 nM, and 240 nM, respectively). [1] These affinities were 16-fold, 12-fold, and 32-fold higher than those of mescaline, respectively. [1] The drug is not known to have been tested in animals or humans. [1] The chemical synthesis of 2-iodomescaline has been described. [2] 2-Iodomescaline was first described in the scientific literature by Jose A. Sintas and colleagues by 1998. [2] Subsequently, it was described in greater detail by Daniel Trachsel and colleagues in 2013. [1] The source of the information cited by Trachsel and colleagues was personal communication with David E. Nichols in 2010. [1]

Contents

See also

References

  1. 1 2 3 4 5 6 7 Trachsel D, Lehmann D, Enzensperger C (2013). Phenethylamine: von der Struktur zur Funktion [Phenethylamines: From Structure to Function]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag. pp. 908–909. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  2. 1 2 Sintas JA, Vitale AA (1998). "Synthesis of derivatives of [I-131] phenylalkylamines for brain mapping". Journal of Labelled Compounds and Radiopharmaceuticals. 41 (1): 53–61. doi:10.1002/(SICI)1099-1344(199801)41:1<53::AID-JLCR53>3.0.CO;2-K . Retrieved 26 November 2025.
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