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5-MeO-DET

From Wikipedia, the free encyclopedia
Psychedelic drug
Pharmaceutical compound
5-MeO-DET
Skeletal formula
Space-filling model of 5-MeO-DET
Clinical data
Other names5-Methoxy-N,N-diethyltryptamine
Routes of
administration
Oral,smoking[1]
Drug classSerotonin receptor agonist;Serotonin5-HT2A receptoragonist;Serotonergic psychedelic;Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Onset of actionOral: 20–30 minutes[1]
Smoking: A few minutes[1]
Duration of actionOral: 3–4 hours[1]
Smoking: 1.5 hours[1]
Identifiers
  • N,N-diethyl-2-(5-methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
  • CCN(CC)CCc1c[nH]c2ccc(OC)cc12
  • InChI=1S/C15H22N2O/c1-4-17(5-2)9-8-12-11-16-15-7-6-13(18-3)10-14(12)15/h6-7,10-11,16H,4-5,8-9H2,1-3H3 checkY
  • Key:KGDVJQQWCDDEPP-UHFFFAOYSA-N checkY
  (verify)

5-MeO-DET, also known as5-methoxy-N,N-diethyltryptamine is apsychedelic drug of thetryptamine family related to5-MeO-DMT.[1] It is takenorally but can also be usedparenterally.[1]

The drug produces strongside effects such aslightheadedness,dizziness, andvertigo at low doses that preventhallucinogenic doses from beingtolerated or used.[1] It acts as aserotonin receptor modulator, including as anagonist of theserotonin5-HT2A receptor.[2][3][4][5][6][7] 5-MeO-DET produces psychedelic-like effects in animals.[8][9][7]Analogues of 5-MeO-DET include 5-MeO-DMT,5-MeO-DPT,dipropyltryptamine (DPT), and4-HO-DPT (deprocin), among others.[1]

5-MeO-DET was first described in the literature by 1968.[10] It was further described byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a noveldesigner drug in 2005.[11]

Use and effects

[edit]

In his bookTiHKAL (Tryptamines I Have Known and Loved),Alexander Shulgin lists 5-MeO-DET's dose as 1 to 3 mgorally and itsduration as 3 to 4 hours.[1] Theonset was reported to be 20 to 30 minutes.[1] There was also a report ofsmoking at a dose of 10 mg, with an onset of a few minutes and a duration of 1.5 hours, but this dose resulted in strongside effects that resulted in the user describing it as a "torture psychedelic".[1]

The effects of 5-MeO-DET at oral doses have been reported to include stronglightheadedness,dizziness,vertigo, spaciness, body heaviness, fragility, need to lay down and stay that way,intoxication,drunkenness,uncomfortableness,negative mood,depression,tinnitus,sexual enhancement, wanting the drug to wear off as soon as possible, and unwillingness to take the drug again.[1] Although there was an awareness of another interesting dimension beyond the side effects, there was a sense of the lightheadedness blocking everything else.[1] This side effect was described as not being due tohypotension or dizziness but perhaps being something to do with theinner ear (e.g., vertigo).[1] According to one report, if the lightheadedness or dizziness could be removed, 5-MeO-DET would be one of the best drugs foreroticism imaginable.[1] In the high-dose smoked report, the effects included dizziness,intense heartbeat,trembling,anxiety,restlessness,cold sweating,paleness,abdominal cramps,feeling sick, some "visions", inability to concentrate on the visionary effects due to side effects, and feeling very glad when the drug wore off.[1] As mentioned previously, the user described 5-MeO-DET as a "torture psychedelic" with this route and dose.[1]

According to Shulgin, 5-MeO-DET possesses an unexpected new property of lightheadedness, vertigo, and intoxication suggestive of "neurotoxicity" that emerges at very low doses and that has not been observed with other5-methoxytryptamines.[1] These side effects have effectively precluded exploration of and ability to tolerate higher doses of the drug.[1] Per Shulgin, based on extrapolation from its lower and higherhomologues5-MeO-DMT and5-MeO-DiPT, respectively, 5-MeO-DET is anticipated to be an active psychedelic at doses of 10 mg or moreparenterally and probably orally, but these doses cannot be achieved due to its strong side effects.[1] This resulted in Shulgin stating that 5-MeO-DET was "one of the most provocative temptresses I have ever encountered" among the tryptamines and that it was a case of "having a protégé that you absolutely know will be a success if allowed to come to fulfillment, and yet you know that uncontrolled circumstances will prevent that fulfillment".[1] He has said that these side effects may be unique to 5-MeO-DET and also pondered whether the same action that causes them could simultaneously be responsible for the "terrific erotic enhancement" the drug produces.[1]

5-MeO-DET's higher homologue5-MeO-DPT was also tested by Shulgin in hopes that the vertigo-related side effects could be removed.[1] His experience with this drug was mixed, with it being better-tolerated and allowing for higher doses than 5-MeO-DET, but side effects nonetheless still outweighing desired effects.[1] Shulgin explored and hypothesized about other possible 5-methoxytryptamines as well.[1]

Interactions

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

Pharmacology

[edit]

Pharmacodynamics

[edit]

5-MeO-DETinhibits serotonin reuptake with anIC50Tooltip half-maximal inhibitory concentration value of 2,400 nM and activates theserotonin5-HT2A receptor with anEC50Tooltip half-maximal effective concentration value of 8.1 nM.[2][3][4][5][6][10][12] The drug fully substitutes forDOM in rodentdrug discrimination tests.[8] It also substitutes for5-MeO-DMT in rodent drug discrimination tests.[9] In addition, 5-MeO-DET produces thehead-twitch response in rodents.[7]

Chemistry

[edit]

Synthesis

[edit]

Thechemical synthesis of 5-MeO-DET has been described.[1]

Analogues

[edit]

Analogues of 5-MeO-DET includediethyltryptamine (DET),4-HO-DET (ethocin),ethocybin (4-PO-DET),5-HO-DET,5-MeO-DMT,5-MeO-DPT,5-MeO-DiPT,5-MeO-DALT,5-MeO-MET,5-MeO-MPT,5-MeO-MiPT,5-MeO-pyr-T, and4-MeO-DET, among others.[1]

History

[edit]

5-MeO-DET was first described in thescientific literature by 1968.[10] It was described in greater detail byAlexander Shulgin in his 1997 bookTiHKAL (Tryptamines I Have Known and Loved).[1] The drug was encountered as a noveldesigner drug inEurope in 2005.[11]

See also

[edit]

References

[edit]
  1. ^abcdefghijklmnopqrstuvwxyzaaabacadShulgin, Alexander;Shulgin, Ann (September 1997).TiHKAL: The Continuation.Berkeley, California:Transform Press.ISBN 0-9630096-9-9.OCLC 38503252.
  2. ^abGatch MB, Forster MJ, Janowsky A, Eshleman AJ (July 2011)."Abuse liability profile of three substituted tryptamines".The Journal of Pharmacology and Experimental Therapeutics.338 (1):280–289.doi:10.1124/jpet.111.179705.PMC 3126641.PMID 21474568.
  3. ^abGlennon RA, Gessner PK (April 1979). "Serotonin receptor binding affinities of tryptamine analogues".Journal of Medicinal Chemistry.22 (4):428–432.doi:10.1021/jm00190a014.PMID 430481.
  4. ^abHalberstadt AL, Geyer MA (September 2011)."Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens".Neuropharmacology.61 (3):364–381.doi:10.1016/j.neuropharm.2011.01.017.PMC 3110631.PMID 21256140.
  5. ^abLyon RA, Titeler M, Seggel MR, Glennon RA (January 1988). "Indolealkylamine analogs share 5-HT2 binding characteristics with phenylalkylamine hallucinogens".European Journal of Pharmacology.145 (3):291–297.doi:10.1016/0014-2999(88)90432-3.PMID 3350047.
  6. ^abBlough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014)."Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes".Psychopharmacology.231 (21):4135–4144.doi:10.1007/s00213-014-3557-7.PMC 4194234.PMID 24800892.
  7. ^abcPuigseslloses 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.
  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. ^abGlennon 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. ^abcGessner 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 Sci.7 (5):267–277.doi:10.1016/0024-3205(68)90200-2.PMID 5641719.
  11. ^abhttps://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2005
  12. ^Schulze-Alexandru M, Kovar KA, Vedani A (December 1999). "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances".Quantitative Structure-Activity Relationships.18 (6):548–560.CiteSeerX 10.1.1.669.1877.doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B.

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