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;
UNII	2CNT3HAM6G;
CompTox Dashboard (EPA)	DTXSID10937676 ;
Chemical and physical data
Formula	C14H20N2O
Molar mass	232.327 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCN(CCc1cc2c1cc(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 (2017). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. 32: 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. PMID 27272067.
^ Palma-Conesa ÁJ, Ventura M, Galindo L, Fonseca F, Grifell M, Quintana P, Fornís I, Gil C, Farré M, Torrens M (2017). "Something New about Something Old: A 10-Year Follow-Up on Classical and New Psychoactive Tryptamines and Results of Analysis". Journal of Psychoactive Drugs. 49 (4): 297–305. doi:10.1080/02791072.2017.1320732. PMID 28569652. S2CID 45394561.
^ Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020). "Toxicology and Analysis of Psychoactive Tryptamines". International Journal of Molecular Sciences. 21 (23): 9279. doi:10.3390/ijms21239279. PMC 7730282. PMID 33291798.
^ Gessner PK, Godse DD, Krull AH, McMullan JM (March 1968). "Structure-activity relationships among 5-methoxy-n:n-dimethyltryptamine, 4-hydroxy-n:n-dimethyltryptamine (psilocin) and other substituted tryptamines". Life Sciences. 7 (5): 267–77. doi:10.1016/0024-3205(68)90200-2. PMID 5641719.
^ Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry. 22 (4): 428–32. doi:10.1021/jm00190a014. PMID 430481.
^ "EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). New drugs in Europe, 2012.
^ "Forskrift om endring i forskrift om narkotika" [Regulations amending the regulations on drugs]. Lovdata (in Norwegian).

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[pmid27272067-1] Schifano F, Orsolini L, Papanti D, Corkery J (2017). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. 32: 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. PMID 27272067.

[pmid28569652-2] Palma-Conesa ÁJ, Ventura M, Galindo L, Fonseca F, Grifell M, Quintana P, Fornís I, Gil C, Farré M, Torrens M (2017). "Something New about Something Old: A 10-Year Follow-Up on Classical and New Psychoactive Tryptamines and Results of Analysis". Journal of Psychoactive Drugs. 49 (4): 297–305. doi:10.1080/02791072.2017.1320732. PMID 28569652. S2CID 45394561.

[pmid33291798-3] Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA (December 2020). "Toxicology and Analysis of Psychoactive Tryptamines". International Journal of Molecular Sciences. 21 (23): 9279. doi:10.3390/ijms21239279. PMC 7730282. PMID 33291798.

[pmid5641719-4] Gessner PK, Godse DD, Krull AH, McMullan JM (March 1968). "Structure-activity relationships among 5-methoxy-n:n-dimethyltryptamine, 4-hydroxy-n:n-dimethyltryptamine (psilocin) and other substituted tryptamines". Life Sciences. 7 (5): 267–77. doi:10.1016/0024-3205(68)90200-2. PMID 5641719.

[pmid430481-5] Glennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues". Journal of Medicinal Chemistry. 22 (4): 428–32. doi:10.1021/jm00190a014. PMID 430481.

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

[7] "Forskrift om endring i forskrift om narkotika" [Regulations amending the regulations on drugs]. Lovdata (in Norwegian).

[1]

[2]

[3]

[4]

[5]

[6]

[7]

Identifiers

IUPAC name N-Ethyl-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine
CAS Number	16977-53-0^Y
PubChem CID	6619012
ChemSpider	5051184
UNII	2CNT3HAM6G
CompTox Dashboard (EPA)	DTXSID10937676
Chemical and physical data
Formula	C₁₄H₂₀N₂O
Molar mass	232.327 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCN(CCc1cc2c1cc(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

See also

References