1-Benzoyl-DMT

vanc 6 1-Benzoyl-DMT.svg skin-invert-image 200px Serotonergic psychedelic; Hallucinogen None 481661-45-4 166467678 "DMT benzamide"; "Dimethyltryptamine benzamide"; 1-Benzoyl-N,N-dimethyltryptamine; 1Bz-DMT; "Example 2-17" [3-[2-(dimethylamino)ethyl]indol-1-yl]-phenylmethanone 19 20 2 1 CN(C)CCC1=CN(C2=CC=CC=C21)C(=O)C3=CC=CC=C3 1S/C19H20N2O/c1-20(2)13-12-16-14-21(18-11-7-6-10-17(16)18)19(22)15-8-4-3-5-9-15/h3-11,14H,12-13H2,1-2H3 JWUSHQNZPBFVEL-UHFFFAOYSA-N 1-Benzoyl-DMT, also known as "DMT benzamide" or as 1-benzoyl-N,N-dimethyltryptamine, is a psychedelic drug of the tryptamine family related to dimethyltryptamine (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-benzoyl derivative of DMT. The drug is a prodrug of DMT with modified pharmacokinetic properties compared to DMT in rodents. It is assumed to be cleaved into DMT by amidase enzymes. Various analogues of 1-benzoyl-DMT that are likewise DMT or 5-MeO-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-Benzoyl-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 NBoc-DMT (N′-tert-butoxycarbonyl-DMT) 1-Acetyl-5-MeO-DMT (1A-5-MeO-DMT) N-Phosphonooxymethyl-DMT (N-POM-DMT) 1Bz-LSD (1-benzoyl-LSD) References Category:5-HT2A agonists Category:Designer prodrugs Category:N,N-Dialkyltryptamines Category:Dimethylamino compounds Category:Phenyl compounds Category:Psychedelic tryptamines Category:Serotonin receptor agonists