5-Chloro-DMT

5-Chloro-N,N-dimethyltryptamine (5-chloro-DMT) is a tryptamine derivative related to compounds such as 5-bromo-DMT and 5-fluoro-DMT. It acts as a serotonin receptor agonist and has primarily sedative effects in animal studies.[1][2][3] It has been sold as a designer drug.[4]

5-Chloro-DMT
Identifiers
IUPAC name
  • 2-(5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H15ClN2
Molar mass222.72 g·mol−1
3D model (JSmol)
SMILES
  • CN(C)CCC1=CNC2=C1C=C(C=C2)Cl
InChI
  • InChI=1S/C12H15ClN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3
  • Key:BXYDWQABVPBLBU-UHFFFAOYSA-N

See also

References
  1. Benington F, Morin RD, Clark LC (September 1960). "Synthesis of some 5- and 6-chloro, 5-methyl, and 5,6,7-trimethyl derivatives of tryptamine". Journal of Organic Chemistry. 25 (9): 1542–1547. doi:10.1021/jo01079a020.
  2. Ibrahim MA, El-Alfy AT, Ezel K, Radwan MO, Shilabin AG, Kochanowska-Karamyan AJ, et al. (August 2017). "Marine Inspired 2-(5-Halo-1H-indol-3-yl)-N,N-dimethylethanamines as Modulators of Serotonin Receptors: An Example Illustrating the Power of Bromine as Part of the Uniquely Marine Chemical Space". Marine Drugs. 15 (8). doi:10.3390/md15080248. PMC 5577603. PMID 28792478.
  3. Dong C, Ly C, Dunlap LE, Vargas MV, Sun J, Hwang IW, et al. (May 2021). "Psychedelic-inspired drug discovery using an engineered biosensor". Cell. 184 (10): 2779–2792.e18. doi:10.1016/j.cell.2021.03.043. PMID 33915107.
  4. "Analytical Report: 5-Cl-DMT" (PDF). Slovenia: Nacionalni Forenzični Laboratorij. July 2020.
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