5-MeO-MET

  1. Home
  2. Wiki
5-MeO-MET
Clinical data
Other names5-OMe-MET; 5-Methoxy-N-methyl-N-ethyltryptamine
Drug classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
Pharmacokinetic data
Onset of actionUnknown[1]
Duration of actionUnknown[1]
Identifiers
  • N-ethyl-2-(5-methoxy-1H-indol-3-yl)-N-methylethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H20N2O
Molar mass232.327 g·mol−1
3D model (JSmol)
  • CCN(CCc1c[nH]c2c1cc(OC)cc2)C
  • 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, 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.[2][3][4][5][6]

Use and effects

[edit]

5-MeO-MET was not included nor mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved).[1] Relatedly, its properties, such as dose and duration, and its effects were not described.[1]

Interactions

[edit]
See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]

Pharmacodynamics

[edit]

Early studies found 5-MeO-MET to be more potent in animal behavioral tests than 5-MeO-DMT.[3][7] Subsequent studies confirmed that 5-MeO-MET interacts with serotonin receptors similarly to other psychedelic tryptamines.[8][9] 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.[2][10] Its activities were of similar potency as 5-MeO-DMT.[2]

Chemistry

[edit]

Analogues

[edit]

Analogues of 5-MeO-MET include methylethyltryptamine (MET), 4-HO-MET (metocin), 4-AcO-MET (metacetin), 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

[edit]

5-MeO-MET was first synthesized and limitedly studied in the 1960s.[3][7][8] The drug was first identified on the illicit market in June 2012 in Sweden.[11] It was made illegal in Norway in 2013.[12]

See also

[edit]

References

[edit]
  1. ^ a b c d Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  2. ^ a b c 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 (August 2024). "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC 11412900. PMID 38486047.
  3. ^ a b c Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. 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), [...]
  4. ^ Schifano F, Orsolini L, Papanti D, Corkery J (2017). "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. PMID 27272067.
  5. ^ 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.
  6. ^ 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.
  7. ^ a b 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.
  8. ^ a b 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.
  9. ^ Klein MT, Dukat M, Glennon RA, Teitler M (June 2011). "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. doi:10.1124/jpet.111.179606. PMC 3101003. PMID 21422162.
  10. ^ 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. doi:10.1021/acschemneuro.4c00513. PMID 39636099.
  11. ^ "EMCDDA–Europol 2012 Annual Report on the implementation of Council Decision 2005/387/JHA" (PDF). New drugs in Europe, 2012.
  12. ^ "Forskrift om endring i forskrift om narkotika" [Regulations amending the regulations on drugs]. Lovdata (in Norwegian).
[edit]