5-MeO-DET

5-MeO-DET
Skeletal formula
Space-filling model of 5-MeO-DET
Clinical data
Other names5-Methoxy-N,N-diethyltryptamine
Routes of
administration		Oral[1]
Drug classSerotonin 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 action3–4 hours[1]
Identifiers
IUPAC name
  • 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
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
SMILES
  • CCN(CC)CCc1c[nH]c2ccc(OC)cc12
InChI
  • 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 as 5-methoxy-N,N-diethyltryptamine is a psychedelic drug of the tryptamine family related to 5-MeO-DMT.[1] It is taken orally.[1]

Use and effects

Low doses (0.5–1 mg) are reported to produce a relaxing body high and mild entheogenic effects.[1] Shulgin reports in TiHKAL (Tryptamines I Have Known and Loved) that higher doses (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

Pharmacodynamics

5-MeO-DET inhibits serotonin reuptake with an IC50Tooltip half-maximal inhibitory concentration value of 2,400 nM and activates the serotonin 5-HT2A receptor with an EC50Tooltip half-maximal effective concentration value of 8.1 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 9 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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