2-Chloromescaline

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2-Chloromescaline
2-Chloromescaline.svg
Clinical data
Other names2-CM; 2-Cl-M; 2-Chloro-3,4,5-trimethoxyphenethylamine
Drug class Serotonin receptor modulator
ATC code
  • None
Identifiers
  • 2-(2-chloro-3,4,5-trimethoxyphenyl)ethan-1-amine
Chemical and physical data
Formula C11H16ClNO3
Molar mass 245.70 g·mol−1
3D model (JSmol)
  • NCCc1cc(OC)c(c(c1Cl)OC)OC
  • InChI=1S/C11H16ClNO3/c1-14-8-6-7(4-5-13)9(12)11(16-3)10(8)15-2/h6H,4-5,13H2,1-3H3
  • Key:LNEOIKLZQLPCLZ-UHFFFAOYSA-N

2-Chloromescaline (2-CM or 2-Cl-M), also known as 2-chloro-3,4,5-trimethoxyphenethylamine, is a serotonin receptor modulator of the scaline family related to mescaline. [1] [2] [3] It has been encountered as an artifact in the isolation of mescaline from the Trichocereus peruvianus (San Pedro/Peruvian torch) cactus with a chlorinated solvent. [1] [2] [3]

Contents

Pharmacology

Pharmacodynamics

The drug shows affinity for serotonin receptors, including the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors (Ki = 465 nM, 826 nM, and 726 nM, respectively). [1] Its affinities for these receptors were 6.4-fold, 5.5-fold, and 10.7-fold higher than those of mescaline, respectively. [1] The drug is not known to have been tested in animals or humans. [1] [2]

History

2-Chloromescaline was first described in the scientific literature by J. H. Pardanani and colleagues in 1977. [3] [2] It was described in greater detail by Daniel Trachsel and colleagues in 2013, who cited personal communication with David E. Nichols as the source for its serotonin receptor affinities. [1]

See also

References

  1. 1 2 3 4 5 6 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. p. 907. ISBN   978-3-03788-700-4. OCLC   858805226. Archived from the original on 21 August 2025.
  2. 1 2 3 4 Shulgin A, Manning T, Daley P (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds . Vol. 1. Berkeley: Transform Press. ISBN   978-0-9630096-3-0. (1) 2-CM is an artifact in the isolation of mescaline from Trichocereus peruvianus with a chlorinated solvent (Pardanani et al., 1977).
  3. 1 2 3 Pardanani JH, McLaughlin JL, Kondrat RW, Cooks RG (1977). "Cactus alkaloids. XXXVI. Mescaline and related compounds from Trichocereus peruvianus". Lloydia. 40 (6): 585–590. PMID   600028.
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