5-MeO-MET

5-MeO-MET
Identifiers
	IUPAC name N-Ethyl-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine;
CAS Number	16977-53-0;
PubChem CID	6619012;
ChemSpider	5051184;
CompTox Dashboard (EPA)	DTXSID10937676 ;
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CCc1c[nH]c2c1cc(OC)cc2)C;
	InChI InChI=1S/C14H20N2O/c1-4-16(2)8-7-11-10-15-14-6-5-12(17-3)9-13(11)14/h5-6,9-10,15H,4,7-8H2,1-3H3; Key:AVECDEWGCOLCPZ-UHFFFAOYSA-N;

5-MeO-MET (5-Methoxy-N-methyl-N-ethyltryptamine) is a relatively rare designer drug from the substituted tryptamine family, related to compounds such as N-Methyl-N-ethyltryptamine and 5-MeO-DMT.^[1]^[2]^[3] It was first synthesised in the 1960s and was studied to a limited extent,^[4]^[5] but was first identified on the illicit market in June 2012 in Sweden.^[6] It was made illegal in Norway in 2013,^[7] and is controlled under analogue provisions in numerous other jurisdictions.

References

^ Schifano F, Orsolini L, Papanti D, Corkery J. NPS: Medical Consequences Associated with Their Intake. Curr Top Behav Neurosci. 2017;32:351-380. doi:10.1007/7854_2016_15 PMID 27272067
^ Palma-Conesa AJ, Ventura M, Galindo L, Fonseca F, Grifell M, Quintana P, Fornís I, Gil C, Farré M, Torrens M. Something New about Something Old: A 10-Year Follow-Up on Classical and New Psychoactive Tryptamines and Results of Analysis. Journal of Psychoactive Drugs 2017; 49(4): 297-305. doi:10.1080/02791072.2017.1320732
^ Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA. Toxicology and Analysis of Psychoactive Tryptamines. International Journal of Molecular Sciences. 2020; 21(23):9279. doi:10.3390/ijms21239279
^ Gessner PK, Godse DD, Krull AH, McMullan JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7(5): 267–277. doi:10.1016/0024-3205(68)90200-2
^ Glennon RA, Gessner PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. doi:10.1021/jm00190a014
^ EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012
^ Forskrift om endring i forskrift om narkotika

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[1] Schifano F, Orsolini L, Papanti D, Corkery J. NPS: Medical Consequences Associated with Their Intake. Curr Top Behav Neurosci. 2017;32:351-380. doi:10.1007/7854_2016_15 PMID 27272067

[2] Palma-Conesa AJ, Ventura M, Galindo L, Fonseca F, Grifell M, Quintana P, Fornís I, Gil C, Farré M, Torrens M. Something New about Something Old: A 10-Year Follow-Up on Classical and New Psychoactive Tryptamines and Results of Analysis. Journal of Psychoactive Drugs 2017; 49(4): 297-305. doi:10.1080/02791072.2017.1320732

[3] Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA. Toxicology and Analysis of Psychoactive Tryptamines. International Journal of Molecular Sciences. 2020; 21(23):9279. doi:10.3390/ijms21239279

[4] Gessner PK, Godse DD, Krull AH, McMullan JM. Structure-activity relationships among 5-methoxy-N:N-dimethyltryptamine, 4-hydroxy-N:N-dimethyltryptamine (psilocin) and other substituted tryptamines. Life Sci., 1 Mar 1968, 7(5): 267–277. doi:10.1016/0024-3205(68)90200-2

[5] Glennon RA, Gessner PK. Serotonin receptor binding affinities of tryptamine analogues. J. Med. Chem., 1 Jan 1979, 22 (4), pp 428–432. doi:10.1021/jm00190a014

[6] EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA (New drugs in Europe, 2012

[7] Forskrift om endring i forskrift om narkotika

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See also

References