5-MeO-DET

5-MeO-DET
Legal status
Legal status	DE: NpSG (Industrial and scientific use only); UK: Class A;
Identifiers
CAS Number	2454-70-8 ;
PubChem CID	417608;
ChemSpider	369669 ;
UNII	LM6R54JKYE;
ChEMBL	ChEMBL342986 ;
CompTox Dashboard (EPA)	DTXSID30329130 ;
Chemical and physical data
Formula	C15H22N2O
Molar mass	246.354 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:KGDVJQQWCDDEPP-UHFFFAOYSA-N ;
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5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.

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5-MeO-DET inhibits serotonin reuptake with an IC₅₀ value of 2.4 μM and activates 5-HT_2A receptors with an EC₅₀ value of 8.11 nM.^[1]^[2]^[3]^[4]^[5]^[6]^[7]

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.

[1]
Schulze-Alexandru M, Kovar KA, Vedani A (December 1999). "Quasi-atomistic Receptor Surrogates for the 5-HT_2A 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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[1] [1]
Schulze-Alexandru M, Kovar KA, Vedani A (December 1999). "Quasi-atomistic Receptor Surrogates for the 5-HT_2A 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] [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] [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] [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] [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] [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] [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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5-MeO-DET

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Pharmacology

Effects

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