4-MeO-DET

4-MeO-DET
Clinical data
Other names4-OMe-DET; 4-Methoxy-N,N-diethyltryptamine; 4-Methoxy-DET
Routes of
administration		Oral, smoking[1]
ATC code
  • None
Pharmacokinetic data
Onset of actionUnknown[1]
Duration of actionUnknown[1]
Identifiers
  • N,N-diethyl-2-(4-methoxy-1H-indol-3-yl)ethanamine
PubChem CID
ChemSpider
Chemical and physical data
FormulaC15H22N2O
Molar mass246.354 g·mol−1
3D model (JSmol)
  • CCN(CC)CCC1=CNC2=C1C(=CC=C2)OC
  • InChI=1S/C15H22N2O/c1-4-17(5-2)10-9-12-11-16-13-7-6-8-14(18-3)15(12)13/h6-8,11,16H,4-5,9-10H2,1-3H3
  • Key:HIVMOHVUFLVCMM-UHFFFAOYSA-N

4-MeO-DET, also known as 4-methoxy-N,N-diethyltryptamine, is a chemical compound of the tryptamine and 4-methoxytryptamine families related to psilocin (4-HO-DMT).[1] It is the 4-methoxy derivative of diethyltryptamine (DET), the O-methyl ether 4-HO-DET (ethocin), and a positional isomer of 5-MeO-DET.[1]

Use and effects

According to Alexander Shulgin in his 1997 book TiHKAL (Tryptamines I Have Known and Loved), 4-MeO-DET is completely inactive at doses of up to 30 mg orally or smoked.[1][2] Hence, its dose range is unknown but greater than 30 mg and its duration is unknown.[1] Higher doses were not assessed.[1][2]

Chemistry

Analogues

Analogues of 4-MeO-DET include diethyltryptamine (DET), 4-methoxytryptamine (4-MT or 4-MeO-T), 4-HO-DET (ethocin), 4-AcO-DET (ethacetin), 5-MeO-DET, 4-MeO-DMT, 4-MeO-DiPT, and 4-MeO-MiPT, among others.[1] 4-MeO-MiPT is known to be active, producing erotic-enhancing effects but little in the way of visuals, whereas 4-MeO-DMT and 4-MeO-DiPT have been found to be active in preclinical research but have not been tested in humans.[1][3][4][5]

History

Aside from 4-MeO-DET's description in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved), 4-MeO-DET does not appear to have been otherwise described in the literature.[1]

See also

References

  1. ^ a b c d e f g h i j k Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252. "The 4-methyl ether of psilocin, 4-MeO-DMT, is especially appealing, in that it is a simple homologue of psilocin and it is quite stable. But the methyl group as an ether link lacks the lability of the phosphate or acetate esters, and it cannot be easily hydrolyzed off to form psilocin. The immediate homologue is 4-MeO-DET which is completely without action either orally or by smoking at dosages up to 30 mgs. The two remaining DMT isomers are with the methoxy at the 6-position (to give 6-MeO-DMT originally thought to be a minor alkaloid in B. caapi) and at the 7-position (to give 7-MeO-DMT which was observed as a minor impurity in the preparation of 7-MeO-MIPT)."
  2. ^ a b "PiHKAL info" (PDF).
  3. ^ Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, et al. (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". The Journal of Pharmacology and Experimental Therapeutics. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC 10029822. PMID 36669875.
  4. ^ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. In contrast to the pronounced enhancement of hallucinogenic activity associated with methylation of the 5-hydroxyl group of bufotenin, 4-methoxy-N,N-dimethyltryptamine (4.26) is less potent than psilocybin. The respective ED50 values (µmoles/kg., i.p.) for disrupting size-discrimination performance in monkeys and swimming ability in rodents are 18·9 and 2·9 (Uyeno, 1969) and 20·1 and 8·7 (Uyeno, 1971). Perhaps these results reflect the differing lipid solubilities of the compounds, because bufotenin, 5-MeO-DMT, psilocin, and compound 4.26 have respective chloroform-water partition coefficients of 0·06, 3·30, 5·52, and 2·28 (Gessner and others, 1968). Clearly, little advantage in physico-chemical characteristics is gained by methylation of the 4-hydroxy group of psilocin compared to the 5-hydroxy group of bufotenin.
  5. ^ Nichols DE, Glennon RA (1984). "Medicinal Chemistry and Structure-Activity Relationships of Hallucinogens". In Jacobs BL (ed.). Hallucinogens: Neurochemical, Behavioral, and Clinical Perspectives. New York: Raven Press. pp. 95–142. ISBN 978-0-89004-990-7. OCLC 10324237.
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