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 [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
Duration of action 3–4 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]

Contents

Use and effects

Low dosages (0.5–1 mg) are reported to produce a relaxing body high and mild entheogenic effects. [1] Shulgin reports in TiHKAL that higher dosages (1–3 mg) can produce very unpleasant reactions. [1] One user referred to it as a "torture psychedelic". [1] The prominent adverse effects of 5-MeO-DET even at low doses prevent it from being taken at fully hallucinogenic doses. [1] Its duration is said to be 3 to 4 hours. [1]

Interactions

Pharmacology

5-MeO-DET inhibits serotonin reuptake with an IC50 value of 2.4 μM and activates 5-HT2A receptors with an EC50 value of 8.11 nM. [2] [3] [4] [5] [6] [7] [8] The drug fully substitutes for DOM in rodent drug discrimination tests. [9] It also substitutes for 5-MeO-DMT in rodent drug discrimination tests. [10]

See also

References

  1. 1 2 3 4 5 6 7 8 Shulgin, Alexander; Shulgin, Ann (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  2. ↑ 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.
  3. ↑ 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): 280–9. doi:10.1124/jpet.111.179705. PMC   3126641 . PMID   21474568.
  4. ↑ 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.
  5. ↑ Halberstadt AL, Geyer MA (September 2011). "Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens". Neuropharmacology. 61 (3): 364–81. doi:10.1016/j.neuropharm.2011.01.017. PMC   3110631 . PMID   21256140.
  6. ↑ 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.
  7. ↑ 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): 291–7. doi:10.1016/0014-2999(88)90432-3. PMID   3350047.
  8. ↑ 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): 4135–44. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.
  9. ↑ 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.
  10. ↑ 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.
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