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1-Acetyl-5-MeO-DMT

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1-Acetyl-5-MeO-DMT
Clinical data
Other names"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]
Drug classSerotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • 1-[3-[2-(dimethylamino)ethyl]-5-methoxyindol-1-yl]ethanone
CAS Number
PubChem CID
ChemSpider
ChEMBL
Chemical and physical data
FormulaC15H20N2O2
Molar mass260.337 g·mol−1
3D model (JSmol)
  • CC(=O)N1C=C(C2=C1C=CC(=C2)OC)CCN(C)C
  • InChI=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
  • Key: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.[2][3][1] It is the 1-acetyl derivative of 5-MeO-DMT.[2][1] The drug is a prodrug of 5-MeO-DMT with modified pharmacokinetic properties compared to 5-MeO-DMT in rodents.[2][3][1] It is assumed to be cleaved into 5-MeO-DMT by amidase enzymes.[1] 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.[2][3][1][4] 1-Acetyl-5-MeO-DMT was first described in the literature in a patent by Terran Biosciences in 2023.[2][3][1] It has been one of the major prodrug compounds highlighted from the patent.[2][1]

See also

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References

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  1. 1 2 3 4 5 6 7 8 "N,n-dimethyltryptamine and related psychedlics and uses thereof". Google Patents. 7 July 2022. Retrieved 29 May 2026.
  2. 1 2 3 4 5 6 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. doi:10.1021/acsmedchemlett.3c00077. PMC 10108390. PMID 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
  3. 1 2 3 4 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. doi:10.1021/acsptsci.6c00146. ISSN 2575-9108.
  4. ↑ Palfreyman MG, Varty GB, Stang E, Boltaev U, Avery K, Nivorozhkin A (December 2025). "Modification of natural tryptamines for the treatment of neuropsychiatric diseases". Journal of Psychopharmacology. 39 (12): 1338–1350. doi:10.1177/02698811251368362. PMID 41045211. 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. [...]
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