5-MeO-DET

Last updated
5-MeO-DET
5-MeO-DET.svg
5-MeO-DET molecule spacefill.png
Clinical data
Other names5-Methoxy-N,N-diethyltryptamine
Routes of
administration 		Oral, smoking [1]
Drug class Serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Pharmacokinetic data
Onset of action Oral: 20–30 minutes [1]
Smoking: A few minutes [1]
Duration of action Oral: 3–4 hours [1]
Smoking: 1.5 hours [1]
Identifiers
  • N,N-diethyl-2-(5-methoxy-1H-indol-3-yl)ethanamine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C15H22N2O
Molar mass 246.354 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 Yes check.svgY
  • Key:KGDVJQQWCDDEPP-UHFFFAOYSA-N Yes check.svgY
   (verify)

5-MeO-DET, also known as 5-methoxy-N,N-diethyltryptamine is a psychedelic drug of the tryptamine family related to 5-MeO-DMT. [1] It is taken orally but can also be used parenterally. [1]

Contents

The drug produces strong side effects such as lightheadedness, dizziness, and vertigo at low doses that prevent hallucinogenic doses from being tolerated or used. [1] It acts as a serotonin receptor modulator, including as an agonist of the serotonin 5-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), and 4-HO-DPT (deprocin), among others. [1]

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

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin lists 5-MeO-DET's dose as 1 to 3 mg orally and its duration as 3 to 4 hours. [1] The onset was reported to be 20 to 30 minutes. [1] There was also a report of smoking 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 strong side 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 strong lightheadedness, 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 to hypotension or dizziness but perhaps being something to do with the inner 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 for eroticism 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 other 5-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 higher homologues 5-MeO-DMT and 5-MeO-DiPT, respectively, 5-MeO-DET is anticipated to be an active psychedelic at doses of 10 mg or more parenterally 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 homologue 5-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

Pharmacology

Pharmacodynamics

5-MeO-DET inhibits serotonin reuptake with an IC50 Tooltip half-maximal inhibitory concentration value of 2,400 nM and activates the serotonin 5-HT2A receptor with an EC50 Tooltip half-maximal effective concentration value of 8.1 nM. [2] [3] [4] [5] [6] [10] [12] The drug fully substitutes for DOM in rodent drug discrimination tests. [8] It also substitutes for 5-MeO-DMT in rodent drug discrimination tests. [9] In addition, 5-MeO-DET produces the head-twitch response in rodents. [7]

Chemistry

Synthesis

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

Analogues

Analogues of 5-MeO-DET include diethyltryptamine (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, and 4-MeO-DET, among others. [1]

History

5-MeO-DET was first described in the scientific literature by 1968. [10] It was described in greater detail by Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved). [1] The drug was encountered as a novel designer drug in Europe in 2005. [11]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  2. 1 2 Gatch 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. 1 2 Glennon 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. 1 2 Halberstadt 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. 1 2 Lyon 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. 1 2 Blough 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. 1 2 3 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.
  8. 1 2 Glennon 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. 1 2 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. 1 2 3 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 Sci. 7 (5): 267–277. doi:10.1016/0024-3205(68)90200-2. PMID   5641719.
  11. 1 2 https://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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.