5-MeO-MET explained

Image Class:skin-invert-image
Width:225px
Image Class2:bg-transparent
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Class:Serotonin receptor modulator
Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Onset:Unknown
Duration Of Action:Unknown
Cas Number:16977-53-0
Unii:2CNT3HAM6G
Chemspiderid:5051184
Pubchem:6619012
Synonyms:5-OMe-MET; 5-Methoxy-N-methyl-N-ethyltryptamine
C:14
H:20
N:2
O:1
Iupac Name:N-ethyl-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine
Smiles:CCN(CCc1c[nH]c2c1cc(OC)cc2)C
Stdinchi: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
Stdinchikey:AVECDEWGCOLCPZ-UHFFFAOYSA-N

5-MeO-MET, also known as 5-methoxy-N-methyl-N-ethyltryptamine, is a serotonin receptor modulator, putative serotonergic psychedelic, and relatively rare designer drug of the tryptamine family related to psychedelic drugs like methylethyltryptamine (MET) and 5-MeO-DMT.[1] [2] [3] [4] [5]

Use and effects

5-MeO-MET was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved). Relatedly, its properties, such as dose and duration, and its effects were not described.

Pharmacology

Pharmacodynamics

Early studies found 5-MeO-MET to be more potent in animal behavioral tests than 5-MeO-DMT. Subsequent studies confirmed that 5-MeO-MET interacts with serotonin receptors similarly to other psychedelic tryptamines.[6] A more modern study found that 5-MeO-MET is a potent serotonin 5-HT1A receptor ligand and serotonin 5-HT2A receptor agonist and produces the head-twitch response, a behavioral proxy of psychedelics, in rodents.[7] Its activities were of similar potency as 5-MeO-DMT.

Chemistry

Analogues

Analogues of 5-MeO-MET include methylethyltryptamine (MET), 4-HO-MET (metocin), 4-AcO-MET (metacetin), 4-PrO-MET, 5-HO-MET, bretisilocin (5-fluoro-MET), 7F-5-MeO-MET, 5-MeO-DMT, 5-MeO-DET, 5-MeO-MPT, 5-MeO-EPT, 5-MeO-MALT, and 5-MeO-MiPT, among others.

History

5-MeO-MET was first synthesized and limitedly studied in the 1960s.[8] [9] The drug was first identified on the illicit market in June 2012 in Sweden.[10] It was made illegal in Norway in 2013.[11]

Society and culture

Legal status

Canada

5-MeO-MET is not a controlled substance in Canada as of 2025.[12]

Sweden

5-MeO-MET is a controlled substance in Sweden.[13]

United States

5-MeO-MET is not an explicitly controlled substance in the United States. However, it could be considered a controlled substance under the Federal Analogue Act if intended for human consumption.

See also

External links

Notes and References

  1. Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R . Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties . Mol Psychiatry . 29 . 8 . 2346–2358 . August 2024 . 38486047 . 11412900 . 10.1038/s41380-024-02506-8 .
  2. Book: Brimblecombe RW, Pinder RM . Indolealkylamines and Related Compounds . 98–144 . Hallucinogenic Agents . 1975 . Wright-Scientechnica . Bristol . 978-0-85608-011-1 . 2176880 . OL4850660M . Compounds of interest which have not been tested in man include 5-methoxy-N-ethyl-N-methyltryptamine, which is more potent than the N,N-dimethyl analogue in behavioural tests in rodents (Gessner and others, 1968), [...].
  3. Book: Schifano F, Orsolini L, Papanti D, Corkery J . Neuropharmacology of New Psychoactive Substances (NPS) . NPS: Medical Consequences Associated with Their Intake . Current Topics in Behavioral Neurosciences. 32 . 351–380 . 2017 . 27272067 . 10.1007/7854_2016_15 . 978-3-319-52442-9 . free .
  4. Palma-Conesa ÁJ, 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 . 49 . 4 . 297–305 . 2017 . 28569652 . 10.1080/02791072.2017.1320732 . 45394561 .
  5. Malaca S, Lo Faro AF, Tamborra A, Pichini S, Busardò FP, Huestis MA . Toxicology and Analysis of Psychoactive Tryptamines . International Journal of Molecular Sciences . 21 . 23 . December 2020 . 9279 . 33291798 . 7730282 . 10.3390/ijms21239279 . free .
  6. Klein MT, Dukat M, Glennon RA, Teitler M . Toward selective drug development for the human 5-hydroxytryptamine 1E receptor: a comparison of 5-hydroxytryptamine 1E and 1F receptor structure-affinity relationships . J Pharmacol Exp Ther . 337 . 3 . 860–867 . June 2011 . 21422162 . 3101003 . 10.1124/jpet.111.179606 .
  7. Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M . December 2024 . Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice . ACS Chem Neurosci . 15 . 24 . 4458–4477 . 10.1021/acschemneuro.4c00513 . 39636099.
  8. 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 Sciences . 7 . 5 . 267–77 . March 1968 . 5641719 . 10.1016/0024-3205(68)90200-2 .
  9. Glennon RA, Gessner PK . Serotonin receptor binding affinities of tryptamine analogues . Journal of Medicinal Chemistry . 22 . 4 . 428–32 . April 1979 . 430481 . 10.1021/jm00190a014 .
  10. Web site: EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA . New drugs in Europe, 2012 .
  11. Web site: Forskrift om endring i forskrift om narkotika . Regulations amending the regulations on drugs . Norwegian . Lovdata .
  12. Web site: Controlled Drugs and Substances Act . Department of Justice Canada . 19 January 2026.
  13. Web site: 5-MeO-MET . АИПСИН . ru . 7 January 2026.

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