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6-MeO-DMT

From Wikipedia, the free encyclopedia
Non-hallucinogenic 5-HT2A agonist

Pharmaceutical compound
6-MeO-DMT
Clinical data
Other names6-Methoxy-N,N-dimethyltryptamine; 6-Methoxy-DMT; 6-Methoxy-N,N-DMT; 6-OMe-DMT
Drug classSerotonin receptor agonist; Non-hallucinogenicserotonin5-HT2A receptoragonist
Identifiers
  • 2-(6-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
CAS Number
PubChemCID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC13H18N2O
Molar mass218.300 g·mol−1
3D model (JSmol)
  • CN(C)CCC1=CNC2=C1C=CC(=C2)OC
  • InChI=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
  • Key:AWOWBKXVYZRYSP-UHFFFAOYSA-N

6-MeO-DMT, or6-methoxy-N,N-dimethyltryptamine, also known as6-OMe-DMT, is aserotonergic drug of thetryptamine family.[1][2][3] It is the 6-methoxyderivative of theserotonergic psychedelicN,N-dimethyltryptamine (DMT) and is apositional isomer of the psychedelic5-MeO-DMT.[3][4]

Use and effects

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6-MeO-DMT was only briefly mentioned inAlexander Shulgin's bookTiHKAL (Tryptamines I Have Known and Loved) and its properties and effects were not described.[5]

Pharmacology

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Pharmacodynamics

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Similarly toanalogues like DMT and 5-MeO-DMT, 6-MeO-DMT acts as aserotonin5-HT2A receptoragonist as well as anon-selective agonist of many otherserotonin receptors.[1][2][6][3] However, in contrast to these agents, but similarly to certain other serotonin 5-HT2A receptor agonists like6-fluoro-DET,2-bromo-LSD,lisuride,25N-N1-Nap, andtabernanthalog, 6-MeO-DMT does not produce thehead-twitch response (HTR) or other psychedelic-like effects in animals and hence appears to be non-hallucinogenic.[1][2][7][6] Similarly, 6-MeO-DMT failed to substitute forDOM in rodentdrug discrimination tests.[8] On the other hand, it did substitute for the atypical psychedelic 5-MeO-DMT in rodent drug discrimination tests, with about 4-fold lowerpotency than 5-MeO-DMT.[9] 6-MeO-DMT has yet to be tested in humans.[10][2]

In addition to its apparent lack of hallucinogenicity, 6-MeO-DMT shows dramatically reducedpotency as an agonist of all of the serotonin receptors compared to 5-MeO-DMT.[6] Itsaffinity for the serotonin 5-HT2A receptor was 12- to 43-fold lower than that of 5-MeO-DMT and was 6-fold lower than that of DMT and its affinity for the serotonin5-HT1A receptor was 110-fold lower relative to 5-MeO-DMT.[3][1][11]

Chemistry

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Analogues

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Analogues of 6-MeO-DMT includedimethyltryptamine (DMT),6-methoxytryptamine (6-MT or 6-MeO-T),6-hydroxy-DMT (6-HO-DMT),6-fluoro-DMT,4-MeO-DMT,5-MeO-DMT, and7-MeO-DMT, among others. Some further analogues include theisotryptamines5-MeO-isoDMT,6-MeO-isoDMT, andzalsupindole ((R)-5-MeO-α-Me-isoDMT).

History

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6-MeO-DMT was first described in thescientific literature by 1968.[12][13][14] It was specifically assessed in astructure–activity relationship (SAR)animal study of serotonergic tryptamines.[12][13] The drug's lack of hallucinogen-like effects in animals was first described by at least 1983.[8]

See also

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References

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  1. ^abcdDuan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants".Chemical Reviews.124 (1):124–163.doi:10.1021/acs.chemrev.3c00375.PMID 38033123.Nevertheless, substitutions at positions 6 or 7 were reported to reduce or even abolish the binding ability to 5-HT2 receptors. For example, 6-OMe-DMT (35, Ki = 7300 nM) and 7-OMe-DMT (36, Ki = 5400 nM) exhibited reduced affinity compared to that of DMT (Ki = 1200 nM) at [3H]-ketanserin-labeled 5-HT2Rs.124
  2. ^abcdWallach J, Cao AB, Calkins MM, Heim AJ, Lanham JK, Bonniwell EM, et al. (December 2023)."Identification of 5-HT2A receptor signaling pathways associated with psychedelic potential".Nature Communications.14 (1): 8221.Bibcode:2023NatCo..14.8221W.doi:10.1038/s41467-023-44016-1.PMC 10724237.PMID 38102107.
  3. ^abcdGlennon RA, Dukat M, Grella B, Hong S, Costantino L, Teitler M, et al. (August 2000). "Binding of beta-carbolines and related agents at serotonin (5-HT(2) and 5-HT(1A)), dopamine (D(2)) and benzodiazepine receptors".Drug Alcohol Depend.60 (2):121–132.doi:10.1016/s0376-8716(99)00148-9.hdl:11380/17721.PMID 10940539.
  4. ^"2-(6-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine".PubChem. U.S. National Library of Medicine. Retrieved26 October 2024.
  5. ^Shulgin A,Shulgin A (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252.
  6. ^abcCameron LP, Tombari RJ, Lu J, Pell AJ, Hurley ZQ, Ehinger Y, et al. (January 2021)."A non-hallucinogenic psychedelic analogue with therapeutic potential".Nature.589 (7842):474–479.Bibcode:2021Natur.589..474C.doi:10.1038/s41586-020-3008-z.PMC 7874389.PMID 33299186.Extended Data Fig. 5: Pharmacological profiles of ibogalogs and related compounds. [...]
  7. ^Dunlap LE, Azinfar A, Ly C, Cameron LP, Viswanathan J, Tombari RJ, et al. (February 2020)."Identification of PsychoplastogenicN,N-Dimethylaminoisotryptamine (isoDMT) Analogues through Structure-Activity Relationship Studies".Journal of Medicinal Chemistry.63 (3):1142–1155.doi:10.1021/acs.jmedchem.9b01404.PMC 7075704.PMID 31977208.
  8. ^abGlennon RA, Young R, Jacyno JM, Slusher M, Rosecrans JA (January 1983). "DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines".Eur J Pharmacol.86 (3–4):453–459.doi:10.1016/0014-2999(83)90196-6.PMID 6572591.
  9. ^Glennon RA, Young R, Rosecrans JA, Kallman MJ (1980). "Hallucinogenic agents as discriminative stimuli: a correlation with serotonin receptor affinities".Psychopharmacology (Berl).68 (2):155–158.doi:10.1007/BF00432133.PMID 6776558.
  10. ^Glennon RA, Dukat M (June 2024)."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.doi:10.1021/acsptsci.4c00157.PMC 11184610.PMID 38898956.
  11. ^Lyon RA, Titeler M, Seggel MR, Glennon RA (January 1988)."Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens".Eur J Pharmacol.145 (3):291–297.doi:10.1016/0014-2999(88)90432-3.PMID 3350047. Archived fromthe original on 2024-04-21.
  12. ^abSwonger AK, Rech RH (1978). "Hallucinogens".Psychopharmacology of Aversively Motivated Behavior. Boston, MA: Springer US. pp. 345–383.doi:10.1007/978-1-4684-2394-5_6.ISBN 978-1-4684-2396-9.
  13. ^abGessner 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):267–277.doi:10.1016/0024-3205(68)90200-2.PMID 5641719.
  14. ^Ahlborg U, Holmstedt B, Lindgren JE (1968). "Fate and metabolism of some hallucinogenic indolealkylamines".Pharmacology, Behavior, and Clinical Aspects, Proceedings of a Symposium held at the College of Physicians and Surgeons, Columbia University, New York. Advances in Pharmacology. Vol. 6. pp. 213–229.doi:10.1016/s1054-3589(08)60320-8.ISBN 978-0-12-032906-9.PMID 5658325.

External links

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5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
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