5-MeO-DET

5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.

5-MeO-DET
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
Identifiers
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 Y
  • Key:KGDVJQQWCDDEPP-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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.[1][2][3][4][5][6][7]

Effects

Low dosages (0.5–1 mg) are reported to produce a relaxing body high and mild entheogenic effects. Shulgin reports in TiHKAL that higher dosages (1–3 mg) can produce very unpleasant reactions.

See also

References
  1. 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.
  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): 280–9. doi:10.1124/jpet.111.179705. PMC 3126641. PMID 21474568.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
  7. 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.


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