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Deudimethyltryptamine

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Deudimethyltryptamine
Clinical data
Other namesHLP004; HLP-004; CYB004; CYB-004; Deuterated dimethyltryptamine; Deuterated DMT; dDMT; DMT-d10; Decadeutero-DMT
Routes of
administration		Inhalation, intravenous[1][2]
Drug classSerotonergic psychedelic; Serotonin receptor agonist[1][3]
Pharmacokinetic data
Elimination half-life37–40 minutes[4]
Duration of action~40 minutes[4]
Identifiers
  • 1,1,2,2-tetradeuterio-2-(1H-indol-3-yl)-N,N-bis(trideuteriomethyl)ethanamine
CAS Number
PubChem CID
UNII
Chemical and physical data
FormulaC12H16N2
Molar mass188.274 g·mol−1
3D model (JSmol)
  • [2H]C([2H])([2H])N(C([2H])([2H])[2H])C([2H])([2H])C([2H])([2H])C1=CNC2=CC=CC=C21
  • InChI=1S/C12H16N2/c1-14(2)8-7-10-9-13-12-6-4-3-5-11(10)12/h3-6,9,13H,7-8H2,1-2H3/i1D3,2D3,7D2,8D2
  • Key:DMULVCHRPCFFGV-TXNVYZHYSA-N

Deudimethyltryptamine (INNTooltip International Nonproprietary Name; developmental code names HLP004 and CYB004), also known as deuterated dimethyltryptamine (dDMT) or as DMT-d10, is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT) which is under development for the treatment of generalized anxiety disorder, anxiety disorders, and depressive disorders.[1][5][2][3][4][6][7] It is administered by inhalation or intravenous injection.[1][2] The drug is a deuterated isotopologue of DMT with altered pharmacokinetics.[1][5][3][4][8]

Interactions

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Pharmacology

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The pharmacodynamic profile of deudimethyltryptamine, including its interactions with serotonin receptors and its effects in animals, is similar to that of DMT.[3] As with DMT, deudimethyltryptamine is a potent agonist of the serotonin 5-HT2A receptor and produces psychedelic-like effects in animals.[1][9][3] However, deudimethyltryptamine, due to its deuteration, is more resistant to metabolism than DMT and shows a longer elimination half-life (by 2.5- to 2.9-fold) and slower clearance (by 38 to 55%) in animals.[3] The brain to plasma ratio of deudimethyltryptamine was also increased (by 30%) relative to DMT, indicating slightly greater central permeability as well.[3]

The pharmacokinetics and effects of deudimethyltryptamine in humans have been studied and compared with those of DMT.[4][8] Its elimination half-life was 37 to 40 minutes and its duration was approximately 40 minutes.[4] For comparison, the half-life of DMT in humans has been reported to be 9 to 12 minutes (range 5–19 minutes).[10][11] Deudimethyltryptamine produced more robust psychedelic effects than DMT at lower concentrations.[4] Additional details on the pharmacokinetics of deudimethyltryptamine in humans have also been reported.[8]

Chemistry

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Analogues

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Other deuterated drugs related to deudimethyltryptamine or DMT-d10 include the deuterated DMT analogue SPL028 (D2-DMT; α,α-dideutero-DMT), the deuterated psilocin analogue deupsilocin (HLP003; CYB003; d10-psilocin), and the deuterated phenethylamine HLP005 (CYB005).[9][2]

Research

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Deudimethyltryptamine is under development by Helus Pharma (formerly Cybin).[1][5] It is under development for the treatment of generalized anxiety disorder, anxiety disorders, and depressive disorders.[1][5] As of July 2026, deudimethyltryptamine is in phase 2 clinical trials for generalized anxiety disorder and phase 1 trials for anxiety disorders and depressive disorders.[1][5] It was also under development for the treatment of substance-related disorders and other psychiatric disorders, but development for these indications was discontinued.[1]

See also

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References

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  1. 1 2 3 4 5 6 7 8 9 10 "CYB 004". AdisInsight. 14 August 2024. Retrieved 28 October 2024.
  2. 1 2 3 4 Peplow M (June 2024). "Next-generation psychedelics: should new agents skip the trip?". Nature Biotechnology. 42 (6): 827–830. doi:10.1038/s41587-024-02285-1. PMID 38831049. Cybin's pipeline also includes CYB004, a deuterated analog of DMT. When given intravenously, DMT itself is rapidly metabolized and causes an intense trip that lasts less than 20 minutes, which may be too brief to be an effective therapy. In contrast, a single intravenous injection of CYB004 produces a 90-minute trip, and Cybin is about to start recruiting patients to a phase 2 trial of the drug to treat generalized anxiety disorder.
  3. 1 2 3 4 5 6 7 Varty G, Morgan M, Giardino O, Krakowsky J, Mueller T, Canal C, et al. (December 2023). "ACNP 62nd Annual Meeting: Poster Abstracts P1 - P250: P80. Preclinical Characterization of CYB004: A Novel, Deuterated N,N-Dimethyltryptamine (DMT) Analog for the Potential Treatment of Generalized Anxiety Disorder (GAD)". Neuropsychopharmacology. 48 (Suppl 1). Springer Science and Business Media LLC: 63–210 (109–110). doi:10.1038/s41386-023-01755-5. PMC 10729595. PMID 38040809.
  4. 1 2 3 4 5 6 7 Inamdar A, van der Heijden K, Nathan P, Reichelt A, Hegle A, Otto M, et al. (December 2023). "ACNP 62nd Annual Meeting: Poster Abstracts P251 – P500: P425. Early Clinical Development of a Deuterated N,N-Dimethyltryptamine (DMT) Analog for the Treatment of Mental Health Conditions" (PDF). Neuropsychopharmacology. 48 (Suppl 1): 211–354 (310–311). doi:10.1038/s41386-023-01756-4. PMC 10729596. PMID 38040810.
  5. 1 2 3 4 5 "Delving into the Latest Updates on Deuterated dtryptamine with Synapse". Synapse. 27 October 2024. Retrieved 28 October 2024.
  6. ↑ US 2023/0357147, Nivorozhkin A, Palfreyman M, "Deuterated tryptamine derivatives and methods of use", published 8 October 2024, assigned to Cybin IRL Ltd.
  7. ↑ "International Nonproprietary Names for Pharmaceutical Substances (INN)" (PDF). cdn.who.int. p. 36. deudimethyltryptamine 2-(1H-indol-3-yl)-N,N-di[(2H3)methyl](1,1,2,2-2H4)ethan-1-amine serotonin 5-HT2A receptor agonist [...] C12H62H10N2 2742678-60-8 [...]
  8. 1 2 3 4 5 6 "Helus Pharma Corporate Presentation March 2026" (PDF). Helus Pharma. March 2026. Archived from the original on 2026-03-27. Retrieved 2026-03-27.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
  9. 1 2 Cano GH, Dean J, Abreu SP, Rodríguez AH, Abbasi C, Hinson M, et al. (December 2022). "Key Characteristics and Development of Psychoceuticals: A Review". International Journal of Molecular Sciences. 23 (24) 15777. doi:10.3390/ijms232415777. PMC 9779201. PMID 36555419.
  10. ↑ Good M, Joel Z, Benway T, Routledge C, Timmermann C, Erritzoe D, et al. (May 2023). "Pharmacokinetics of N,N-dimethyltryptamine in Humans". European Journal of Drug Metabolism and Pharmacokinetics. 48 (3): 311–327. doi:10.1007/s13318-023-00822-y. PMC 10122081. PMID 37086340.
  11. ↑ van der Heijden KV, Otto ME, Schoones JW, van Esdonk MJ, Borghans LG, van Hasselt JG, et al. (February 2025). "Clinical Pharmacokinetics of N,N-Dimethyltryptamine (DMT): A Systematic Review and Post-hoc Analysis". Clin Pharmacokinet. 64 (2): 215–227. doi:10.1007/s40262-024-01450-8. PMC 11782443. PMID 39838235.
  12. 1 2 3 "HLP004 Helus Pharma Announces Positive Phase 2 Data For Its Novel Serotonergic Agonist in Generalized Anxiety Disorder (GAD)" (PDF). Helus Pharma. March 2026. Archived from the original on 2026-03-06. Retrieved 2026-04-04.{{cite web}}: CS1 maint: bot: original URL status unknown (link)
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