Explore 4-Acetoxy-N,N-dimethyltryptamine | PiHKAL · info

Exploring 4-Acetoxy-N,N-dimethyltryptamine. To explore a different substance…

Names

4-AcO-DMT
4-Acetoxy-N,N-dimethyltryptamine
PSOA
Psilacetin

IUPAC name

3-[2-(Dimethylamino)ethyl]-1H-indol-4-yl acetate

ID 5370 · Formula C₁₄H₁₈N₂O₂ · Molecular weight 246.305

Tags Tryptamine

InChI InChI=1S/C14H18N2O2/c1-10(17)18-13-6-4-5-12-14(13)11(9-15-12)7-8-16(2)3/h4-6,9,15H,7-8H2,1-3H3

InChI Key RTLRUOSYLFOFHV-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES CN(CCc1c[nH]c2c1c(ccc2)OC(=O)C)C

ChemSpider 21106357
PubChem 15429212
Wikidata Q3491364
Erowid 4-Acetoxy-DMT
Wikipedia O-Acetylpsilocin
Blotter 4-AcO-DMT
PsychonautWiki 4-AcO-DMT
Trout’s Notes 4-Acetoxy-DMT. In Some Simple Tryptamines, 2nd ed., p. 64
Project Response 4-AcO-DMT (1667-16)
bluelight.org The Big & Dandy 4-AcO-DMT Thread Part 5
bluelight.org The Big & Dandy 4-AcO-DMT Thread Part 4
bluelight.org The Big & Dandy 4-AcO-DMT Thread Part 3
bluelight.org The Big & Dandy 4-AcO-DMT Thread Part 2
bluelight.org The Big & Dandy 4-AcO-DMT Thread Part 1
swgdrug.org 4-AcO-DMT
aipsin.com 4-AcO-DMT (Acetylpsilocin) (Iss. 17, May 2021: X-109)

TiHKAL #19 5-HO-DMT

Nichols, DE; Frescas, SP. Improvements to the synthesis of psilocybin and a facile method for preparing the O-acetyl prodrug of psilocin. Synthesis, 1 Jun 1999, 1999, 935–938. 1.5 MB. https://doi.org/10.1055/s-1999-3490 #2 NMR

Chadeayne, AR; Golen, JA; Manke, DR. The crystal structure of 4-AcO-DMT fumarate. Psychedelic Sci. Rev., 25 Mar 2019, 13. 1.5 MB. #4-AcO-DMT other

Meyers-Riggs, B. 4-Hydroxy tryptamines. countyourculture, countyourculture: rational exploration of the underground, 7 Jul 2012.

Chapman, SJ. PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra. BLOTTER, 1 Mar 2018, 3 (1). 1.2 MB. https://doi.org/10.16889/isomerdesign-5

Chapman, SJ. PeakAL: Protons I Have Known and Loved, Too — Another Fifty Shades of Grey-Market Spectra. Supplementary Data. BLOTTER, 1 Mar 2018, 3 (1). 5.7 MB. https://doi.org/10.16889/isomerdesign-5-supp

EMCDDA. New drugs in Europe, 2009, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2010. 321 kB. #13

Geiger, HA; Wurst, MG; Daniels, RN. DARK classics in chemical neuroscience: Psilocybin. ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2438–2447. 580 kB. https://doi.org/10.1021/acschemneuro.8b00186 #20

Sexton, JD; Nichols, CD; Hendricks, PS. Population survey data informing the therapeutic potential of classic and novel phenethylamine, tryptamine, and lysergamide psychedelics. Front. Psychiatry, 11 Feb 2020, 10 (896). 529 kB. https://doi.org/10.3389/fpsyt.2019.00896 #4-AcO-DMT

Elliott, SP; Holdbrook, T; Brandt, SD. Prodrugs of new psychoactive substances (NPS): A new challenge. J. Forensic Sci., 13 Jan 2020, 65 (3), 913-920. 815 kB. https://doi.org/10.1111/1556-4029.14268 #4-AcO-DMT MS,UV

Chadeayne, AR; Golen, JA; Manke, DR. Bis(4-acetoxy-N,N-dimethyltryptammonium) fumarate: A new crystalline form of psilacetin, an alternative to psilocybin as a psilocin prodrug. Acta Crystallogr. E, 1 Jun 2019, 75 (6), 900–902. 597 kB. https://doi.org/10.1107/S2056989019007370 #Psilacetin other

Palamar, JJ; Acosta, P. A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines. Hum. Psychopharmacol. Clin. Exp., 1 Jan 2020, 35 (1), e2719. 764 kB. https://doi.org/10.1002/hup.2719 #4-AcO-DMT

Chadeayne, AR; Pham, DNK; Reid, BG; Golen, JA; Manke, DR. Active metabolite of aeruginascin (4-hydroxy-N,N,N-trimethyltryptamine): Synthesis, structure, and serotonergic binding affinity. ACS Omega, 14 Jul 2020, 5 (27), 16940–16943. 2.8 MB. https://doi.org/10.1021/acsomega.0c02208 #psilacetin NMR,other

Klein, AK; Chatha, M; Laskowski, LJ; Anderson, EI; Brandt, SD; Chapman, SJ; McCorvy, JD; Halberstadt, AL. Investigation of the structure–activity relationships of psilocybin analogues. ACS Pharmacol. Transl. Sci., 9 Apr 2021, 4 (2), 533-542. 1.9 MB. https://doi.org/10.1021/acsptsci.0c00176 #4-AcO-DMT

Glatfelter, GC; Pottie, E; Partilla, JS; Sherwood, AM; Kaylo, K; Pham, DNK; Naeem, M; Sammeta, VR; DeBoer, S; Golen, JA; Hulley, EB; Stove, CP; Chadeayne, AR; Manke, DR; Baumann, MH. Structure–activity relationships for psilocybin, baeocystin, aeruginascin, and related analogues to produce pharmacological effects in mice. ACS Pharmacol. Transl. Sci., 11 Nov 2022, 5 (11), 1181–1196. 4.8 MB. https://doi.org/10.1021/acsptsci.2c00177 #Psilacetin MS,NMR,other

5-AcO-DMT · 5-Acetoxy-N,N-dimethyltryptamine

4-HO-mor-T · 4-Hydroxy-mor-tryptamine

N-Methoxyoxoethyl-N-methyltryptamine · N-Methoxyoxoethyl-NMT

5-Isobutanoyloxy-T · 5-Isobutanoyloxytryptamine

Hypahorine · α-Carboxy-N,N,N-trimethyltryptamine⁺ · α-Carboxy-TMT+

DM-235 · Sunifiram

Nefiracetam

Dioxino[2,3-e]-N,N-dimethyltryptamine · Dioxino[2,3-e]-DMT

4-HO-N-oxetanyl-NMT · 4-Hydroxy-N-oxetanyl-N-methyltryptamine

4-AcO-AET · 4-Acetoxy-α-ethyltryptamine

Propyltryptophan · α-Carboxy-N-propyltryptamine · α-Carboxy-NPT

2C-CN-3PIP

7 Dec 2019 · · Isomer Design