1-Acetyl-5-MeO-DMT

vanc 6 1-Acetyl-5-MeO-DMT.svg skin-invert-image 225px Serotonergic psychedelic; Hallucinogen None 39998-63-5 85809049 129443806 5266842 "Methyl amide 5-MeO-DMT"; 1-Acetyl-5-methoxy-N,N-dimethyltryptamine; 1A-5-MeO-DMT; 1-Ac-5-MeO-DMT; "Example 2-16" 1-[3-[2-(dimethylamino)ethyl]-5-methoxyindol-1-yl]ethanone 15 20 2 2 CC(=O)N1C=C(C2=C1C=CC(=C2)OC)CCN(C)C 1S/C15H20N2O2/c1-11(18)17-10-12(7-8-16(2)3)14-9-13(19-4)5-6-15(14)17/h5-6,9-10H,7-8H2,1-4H3 FALARLKUFDIOTH-UHFFFAOYSA-N 1-Acetyl-5-MeO-DMT, also known as "methyl amide 5-MeO-DMT" or as 1-acetyl-5-methoxy-N,N-dimethyltryptamine, is a psychedelic drug of the tryptamine and 5-methoxytryptamine families related to 5-MeO-DMT. Kargbo RB April 2023 Orally Active Forms of DMT, 5-MeO-DMT, and Long-Acting MDMA for the Treatment of Neuropsychiatric Disorders ACS Medicinal Chemistry Letters 14 4 367–368 10.1021/acsmedchemlett.3c00077 10108390 37077395 Parent DMT and 5-MeO−DMT suffer from inherent pharmacokinetic limitations: DMT has an ultrashort half-life (t1/2 = 8−13 min in mice) and is orally inactive without MAOI coadministration, while 5-MeO−DMT also requires MAOI to achieve meaningful oral exposure. To overcome these barriers, Terran Biosciences has developed proprietary prodrugs designed for single oral dosing that bypass first-pass metabolism and subsequently potentially improve CNS delivery after bioconversion (WO2023283364A2).50 Preclinical data demonstrate the success of this approach: oral administration of a DMT prodrug (compound Exp. 2−17, 10 mg/kg) in rats achieved a t1/2 of 1.24 h [10.3 h] for DMT, whereas parent DMT given orally is essentially inactive without MAOI coadministration. Similarly, a 5-MeO−DMT prodrug (Exp. 2− 19, 10 mg/kg) yielded a Cmax of 106 ng/mL, and a t1/2 of 2.02 h for 5-MeO−DMT.50 Zhang T, Lin C, Wang X 25 May 2026 Overcoming Pharmacokinetic and Peripheral Safety Challenges in Psychedelic Therapies: The Promise of Advanced Drug Delivery Systems ACS Pharmacology & Translational Science acsptsci.6c00146 10.1021/acsptsci.6c00146 2575-9108 N,n-dimethyltryptamine and related psychedlics and uses thereof Google Patents 7 July 2022 https://patents.google.com/patent/WO2023283364 29 May 2026 It is the 1-acetyl derivative of 5-MeO-DMT. The drug is a prodrug of 5-MeO-DMT with modified pharmacokinetic properties compared to 5-MeO-DMT in rodents. It is assumed to be cleaved into 5-MeO-DMT by amidase enzymes. Various analogues of 1-acetyl-5-MeO-DMT that are likewise 5-MeO-DMT or dimethyltryptamine (DMT) prodrugs have also been described and have shown widely varying pharmacokinetic parameters, for instance half-life. Palfreyman MG, Varty GB, Stang E, Boltaev U, Avery K, Nivorozhkin A Modification of natural tryptamines for the treatment of neuropsychiatric diseases Journal of Psychopharmacology 39 12 1338–1350 December 2025 41045211 10.1177/02698811251368362 In addition to psilocin, DMT and 5-MeO-DMT have been made into prodrugs despite lacking the 4-hydroxyl group attach- ment point. In one approach, the -1H position of the indole moi- ety has been successfully utilized in formation of DMT/5-MeO-DMT prodrugs including carbamate, aminal/hemi- aminal, phosphoramidate, amide, and urea prodrugs (e.g., see Ala-1H DMT and Ala-1H 5-MeO-DMT in Table 2 (Alexander et al., 2024)). [...] Table 2. Psilocybin and other tryptamine prodrugs. [...] 1-Acetyl-5-MeO-DMT was first described in the literature in a patent by Terran Biosciences in 2023. It has been one of the major prodrug compounds highlighted from the patent. See also Substituted tryptamine 1-Benzoyl-DMT (1-Bz-DMT) NBoc-DMT (N′-tert-butoxycarbonyl-DMT) N-Phosphonooxymethyl-DMT (N-POM-DMT) ALD-52 (1-acetyl-LSD; 1A-LSD) References Category:5-HT2A agonists Category:5-Methoxytryptamines Category:Acetyl compounds Category:Designer prodrugs Category:N,N-Dialkyltryptamines Category:Dimethylamino compounds Category:Psychedelic tryptamines Category:Serotonin receptor agonists