5-Chloro-DMT

5-Chloro-DMT
Identifiers
	IUPAC name 2-(5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine;
CAS Number	22120-32-7 ;
PubChem CID	2762739;
ChemSpider	2043437 ;
CompTox Dashboard (EPA)	DTXSID90376408 ;
Chemical and physical data
Formula	C12H15ClN2
Molar mass	222.72 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References[]

^ 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.
^ 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.
^ 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.
^ "Analytical Report: 5-Cl-DMT" (PDF). Slovenia: Nacionalni Forenzični Laboratorij. July 2020.

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[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.

[Ibrahim_2017-2] 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.

[Dong_2021-3] 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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[2]

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[4]

Identifiers

IUPAC name 2-(5-chloro-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number	22120-32-7^Y
PubChem CID	2762739
ChemSpider	2043437^Y
CompTox Dashboard (EPA)	DTXSID90376408
Chemical and physical data
Formula	C₁₂H₁₅ClN₂
Molar mass	222.72 g·mol⁻¹
3D model (JSmol)	Interactive image
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

5-Chloro-DMT

See also[]

References[]