6-MeO-DMT explained

Width:200px
Class:Serotonin receptor agonist
Non-hallucinogenic serotonin 5-HT2A receptor agonist
Cas Number:2426-88-2
Pubchem:12017579
Chemspiderid:23118889
Chembl:281408
Synonyms:6-Methoxy-N,N-dimethyltryptamine; 6-Methoxy-DMT; 6-Methoxy-N,N-DMT; 6-OMe-DMT
Iupac Name:2-(6-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
C:13
H:18
N:2
O:1
Smiles:CN(C)CCC1=CNC2=C1C=CC(=C2)OC
Stdinchi:1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-8-11(16-3)4-5-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
Stdinchikey:AWOWBKXVYZRYSP-UHFFFAOYSA-N

6-MeO-DMT, or 6-methoxy-N,N-dimethyltryptamine, also known as 6-OMe-DMT, is a serotonergic drug of the tryptamine family.[1] [2] It is the 6-methoxy derivative of the serotonergic psychedelic N,N-dimethyltryptamine (DMT) and is a positional isomer of the serotonergic psychedelic 5-MeO-DMT.[3]

Similarly to analogues like DMT and 5-MeO-DMT, 6-MeO-DMT acts as a serotonin 5-HT2A receptor agonist as well as a non-selective agonist of many other serotonin receptors. However, in contrast to these agents, but similarly to certain other serotonin 5-HT2A receptor agonists like 6-fluoro-DET, 2-bromo-LSD, lisuride, 25N-N1-Nap, and tabernanthalog, 6-MeO-DMT does not produce the head-twitch response (HTR) or other psychedelic-like effects in animals and hence appears to be non-hallucinogenic.[4] [5] This is thought to be due to biased agonism of the serotonin 5-HT2A receptor; more specifically, weak activation of the Gq pathway with an efficacy for this pathway of less than 70%. However, the non-hallucinogenic nature of 6-MeO-DMT has yet to be confirmed in humans.[6] In addition to its apparent lack of hallucinogenicity, 6-MeO-DMT shows dramatically reduced potency as an agonist of all of the serotonin receptors compared to 5-MeO-DMT.

6-MeO-DMT was first described in the scientific literature by 1968.[7] [8] [9] It was specifically assessed in a structure–activity relationship (SAR) animal study of serotonergic tryptamines. The drug's lack of hallucinogen-like effects in animals, as determined by the HTR, was first described by at least 2020.

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Notes and References

  1. Duan W, Cao D, Wang S, Cheng J . Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants . Chemical Reviews . 124 . 1 . 124–163 . January 2024 . 38033123 . 10.1021/acs.chemrev.3c00375 .
  2. Wallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, Hennessey JJ, Bock HA, Anderson EI, Sherwood AM, Morris H, de Klein R, Klein AK, Cuccurazzu B, Gamrat J, Fannana T, Zauhar R, Halberstadt AL, McCorvy JD . Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential . Nature Communications . 14 . 1 . 8221 . December 2023 . 38102107 . 10724237 . 10.1038/s41467-023-44016-1 . 2023NatCo..14.8221W .
  3. Web site: 2-(6-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine . PubChem . U.S. National Library of Medicine . 26 October 2024.
  4. Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, Myers-Turnbull D, Taylor JC, Grodzki AC, Lein PJ, Kokel D, Olson DE . Identification of Psychoplastogenic N,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies . Journal of Medicinal Chemistry . 63 . 3 . 1142–1155 . February 2020 . 31977208 . 7075704 . 10.1021/acs.jmedchem.9b01404 .
  5. Cameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, Vargas MV, McCarroll MN, Taylor JC, Myers-Turnbull D, Liu T, Yaghoobi B, Laskowski LJ, Anderson EI, Zhang G, Viswanathan J, Brown BM, Tjia M, Dunlap LE, Rabow ZT, Fiehn O, Wulff H, McCorvy JD, Lein PJ, Kokel D, Ron D, Peters J, Zuo Y, Olson DE . A non-hallucinogenic psychedelic analogue with therapeutic potential . Nature . 589 . 7842 . 474–479 . January 2021 . 33299186 . 7874389 . 10.1038/s41586-020-3008-z . 2021Natur.589..474C . Extended Data Fig. 5: Pharmacological profiles of ibogalogs and related compounds. [...] .
  6. Glennon RA, Dukat M . 1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane (DOI): From an Obscure to Pivotal Member of the DOX Family of Serotonergic Psychedelic Agents - A Review . ACS Pharmacology & Translational Science . 7 . 6 . 1722–1745 . June 2024 . 38898956 . 10.1021/acsptsci.4c00157 . 11184610 . May 8, 2025 .
  7. Book: Swonger AK, Rech RH . Psychopharmacology of Aversively Motivated Behavior . Hallucinogens . Springer US . Boston, MA . 1978 . 978-1-4684-2396-9 . 10.1007/978-1-4684-2394-5_6 . 345–383.
  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 . 267–277 . March 1968 . 5641719 . 10.1016/0024-3205(68)90200-2 .
  9. Book: Ahlborg U, Holmstedt B, Lindgren JE . Pharmacology, Behavior, and Clinical Aspects, Proceedings of a Symposium held at the College of Physicians and Surgeons, Columbia University, New York . Fate and metabolism of some hallucinogenic indolealkylamines . Advances in Pharmacology . 6 . Pt B . 213–229 . 1968 . 5658325 . 10.1016/s1054-3589(08)60320-8 . 978-0-12-032906-9 .

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