5-MeO-DALT

Last updated

5-MeO-DALT
5-MeO-DALT.svg
5-MeO-DALT 3D BS.png
Clinical data
Trade names Foxtrot
Other namesN,N-Diallyl-5-methoxytryptamine; 5-Methoxy-N,N-diallyltryptamine; 5-Methoxy-DALT; Foxtrot
Routes of
administration 		Oral [1]
Drug class Serotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics) [2]
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • UN:Unscheduled.
  • In general unscheduled and not approved for human consumption, Illegal in China, Japan, Singapore, Sweden, Florida and Louisiana
Pharmacokinetic data
Duration of action 2–4 hours [1]
Identifiers
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C17H22N2O
Molar mass 270.376 g·mol−1
3D model (JSmol)
  • C=CCN(CCC1=CNC2=C1C=C(OC)C=C2)CC=C
  • InChI=1S/C17H22N2O/c1-4-9-19(10-5-2)11-8-14-13-18-17-7-6-15(20-3)12-16(14)17/h4-7,12-13,18H,1-2,8-11H2,3H3 Yes check.svgY
  • Key:HGRHWEAUHXYNNP-UHFFFAOYSA-N Yes check.svgY
   (verify)

5-MeO-DALT, also known as N,N-diallyl-5-methoxytryptamine or as foxtrot, is a psychedelic drug of the tryptamine and 5-methoxytryptamine families. [1] [3] It is taken orally. [1]

Contents

5-MeO-DALT was first synthesized and described by Alexander Shulgin, who disclosed the compound in 2004. [1] [4] It has been encountered as a novel designer and recreational drug. [4] [5]

Use and effects

According to Alexander Shulgin in a follow-up entry to his book TiHKAL (Tryptamines I Have Known and Loved), the dose of 5-MeO-DALT is 12 to 20 mg orally and its duration is 2 to 4 hours. [1] [6] A wider dose range of 12 to 25 mg has also been reported. [7] It is said to onset and peak remarkably quickly via the oral route, with an onset of less than 15 minutes and a peak of 30 minutes. [1] The effects of 5-MeO-DALT were reported by Shulgin to include positive emotional changes, lightheadedness, increased appreciation of music and sex, and closed-eye visuals. [1] There was said to be a lack of open-eye visuals and it was said to be relatively light in psychedelic character. [1]

Overdose

There is little published literature on the toxicity of 5-MeO-DALT. [8] Case reports of overdose have been published, with effects including loss of consciousness, visual hallucinations, acute delirium, and rhabdomyolysis, among others. [8] [9] [10] A death related to behavioral intoxication has been reported. [3]

Interactions

Pharmacology

Pharmacodynamics

5-MeO-DALT activities
Target Affinity (Ki, nM)
5-HT1A 3.26–48 (Ki)
3.4 (EC50 Tooltip half-maximal effective concentration)
102% (Emax Tooltip maximal efficacy)
5-HT1B 551–735
5-HT1D 53–107
5-HT1E 322–500
5-HT1F ND
5-HT2A 48–218 (Ki)
11.3–139.4 (EC50)
97a–114% (Emax)
5-HT2B 45–59
5-HT2C 456–1,083 (Ki)
299a (EC50)
99%a (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 3,312
5-HT6 87–153
5-HT7 87–90
α1A–α1D >10,000
α2A 215–228
α2B 726–956
α2C 1,467–641
β1–β3 >10,000
D1–D2 >10,000
D3 699
D4–D5 >10,000
H1 505–1,373
H2 4,250–>10,000
H3 2,820 (human)
1,712 (guinea pig)
H4 >10,000
M1–M5 >10,000
nACh Tooltip Nicotinic acetylcholine receptor>10,000
I1 ND
σ1 333 (human)
301–398 (rodent)
σ2 340 (human)
253 (rat)
TAAR1 Tooltip Trace amine-associated receptor 1ND
MOR Tooltip μ-Opioid receptor, DOR Tooltip δ-Opioid receptor>10,000
KOR Tooltip κ-Opioid receptor899–1,132
SERT Tooltip Serotonin transporter499–1,408 (Ki)
>100,000 (IC50 Tooltip half-maximal inhibitory concentration) (rat)
930–22,313 (IC50) (human)
>100,000 (EC50) (rat)
NET Tooltip Norepinephrine transporter>10,000 (Ki)
>100,000 (IC50) (rat)
>100,000 (EC50) (rat)
DAT Tooltip Dopamine transporter3,378 (Ki)
>100,000 (IC50) (rat)
>100,000 (EC50) (rat)
Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified. Footnotes:a = Stimulation of IP1 Tooltip inositol phosphate formation. Refs: [11] [12] [13] [14] [15] [16] [17] [18] [19] [20]

The interactions of 5-MeO-DALT with various targets have been reported. [13] [14] [15] [19] [17] It binds to a variety of serotonin receptors, as well as a number of other targets. [13] [14] [15] [19] [21] The drug is a potent full agonist of the serotonin 5-HT1A and 5-HT2A receptors. [15] [16] [18] [17] It is also an agonist of the serotonin 5-HT2B and 5-HT2C receptors. [16]

Similarly to other psychedelics, 5-MeO-DALT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents. [7] [15] [14] The drug fully substitutes for the serotonergic psychedelic DOM in rodent drug discrimination tests. [22] Conversely, 5-MeO-DALT does not substitute for the entactogen MDMA in such tests. [22] 5-MeO-DALT produces dose-dependent hyperlocomotion in rodents, followed by hypolocomotion at the highest assessed dose. [22] [15] This is in contrast to many other psychedelic tryptamines, which tend to produce only hypolocomotion. [22] 5-MeO-DMT and 5-MeO-AMT are locomotor depressants, whereas 5-MeO-DET and 5-MeO-MiPT are mixed locomotor stimulants/depressants similarly to 5-MeO-DALT. [22] It also produces hypothermia. [15]

The head-twitch response induced by 5-MeO-DALT in rodents was found to be positively related to its serotonin 5-HT2A receptor affinity and negatively related to its serotonin 5-HT1A receptor affinity. [14] In relation to this, multiple targets appear to contribute to the effects of 5-MeO-DALT. [14] [5]

Pharmacokinetics

The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature. [23] [24]

Chemistry

The full name of the chemical is N-allyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl] prop-2-en-1- amine. It is related to the compounds 5-MeO-DPT, DALT, 4-HO-DALT, and 4-AcO-DALT.

Synthesis

The chemical synthesis of 5-MeO-DALT has been described. [1]

Crystal structure

In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT. [25]

Analogues

Analogues of 5-MeO-DALT include diallyltryptamine (DALT), 4-HO-DALT (daltocin), 4-AcO-DALT (dalcetin), 5-MeO-DMT, 5-MeO-DET, 5-MeO-DPT, 5-MeO-DiPT, 5-MeO-MALT, 5-MeO-MiPT, and 5-MeO-iPALT (ASR-3001), among others.

History

The first material regarding the synthesis and effects of 5-MeO-DALT was sent from Alexander Shulgin to a research associate named Murple in May 2004, after which it was circulated online. In June 2004 5-MeO-DALT became available from internet research chemical vendors after being synthesized by commercial laboratories in China. In August 2004 the synthesis and effects of 5-MeO-DALT were published by Erowid. [4] Shulgin has stated that 5-MeO-DALT had not previously existed in the scientific literature. [1] 5-MeO-DALT was not included in the original published version of TiHKAL , but an entry for the compound was subsequently written and released in 2004. [4]

Society and culture

China

As of October 2015 5-MeO-DALT is a controlled substance in China. [26]

Japan

5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law. [27]

Singapore

5-MeO-DALT is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015. [28]

Sweden

Sveriges riksdag added 5-MeO-DALT to schedule I ("substances, plant materials and fungi which normally do not have medical use") as narcotics in Sweden as of May 1, 2012, published by Medical Products Agency in their regulation LVFS 2012:6 listed as 5-MeO-DALT N-allyl-N-[2-(5-metoxi-1H-indol-3-yl)etyl]-prop-2-en-1-amin. [29]

United Kingdom

5-MeO-DALT became a Class A drug in the UK on January 7, 2015 after an update to the tryptamine blanket ban.

United States

5-MeO-DALT is not scheduled at the federal level in the United States, [30] but it is likely that it could be considered an analog of 5-Meo-DiPT, which is a controlled substance in USA, or an analog of another tryptamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

Florida

5-MeO-DALT is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida. [31]

Louisiana

5-MeO-DALT is a Schedule I controlled substance in the state of Louisiana making it illegal to buy, sell, or possess in Louisiana. [32]

Research

Cluster headache

Anecdotal reports [33] and a small-scale trial [34] indicate the potential of 5-MeO-DALT for the treatment of cluster headache, one of the most excruciating conditions known to medicine. [35] These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache. [36]

See also

References

  1. 1 2 3 4 5 6 7 8 9 10 11 "#56 5-MeO-DALT". Isomer Design. Retrieved 28 March 2025.
  2. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. 1 2 Corkery JM, Durkin E, Elliott S, Schifano F, Ghodse AH (December 2012). "The recreational tryptamine 5-MeO-DALT (N,N-diallyl-5-methoxytryptamine): a brief review". Prog Neuropsychopharmacol Biol Psychiatry. 39 (2): 259–262. doi:10.1016/j.pnpbp.2012.05.022. hdl: 2299/12763 . PMID   22683457.
  4. 1 2 3 4 Morris H, Smith A (2010-05-02). "The Last Interview With Alexander Shulgin". VICE.
  5. 1 2 Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN   978-3-662-55878-2. PMID   28401524. The N,N-disubstituted compound 5-methoxy-N,N-diallyltryptamine (5-MeO-DALT 18) has recently appeared as a new "legal high" on the illicit market (Corkery et al. 2012; Strano Rossi et al. 2014). Results from broad-based receptor screening led Cozzi and Daley (2016) to conclude that multiple serotonin receptors, as well as several non-serotonergic sites are important for the psychoactive effects of 18 and other N,N-diallyltryptamines.
  6. ↑ Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs. Archived from the original on 2021-12-13. Retrieved 3 September 2015– via YouTube.
  7. 1 2 Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD (May 2020). "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species" (PDF). Neuropharmacology. 167 107933. doi:10.1016/j.neuropharm.2019.107933. PMC   9191653 . PMID   31917152. Table 4 Human potency data for selected hallucinogens. [...]
  8. 1 2 Dufayet L, Langrand J, Alvarez JC, Islam Larabi A (August 2022). "Loss of Consciousness and Visual Hallucinations Related to 5-MeO-DALT Intake, a Case Report Confirmed by Toxicological Analyses". J Anal Toxicol. 46 (7) e186–e190. doi:10.1093/jat/bkac021. PMID   35365824.
  9. ↑ Kalasho A, Vibe Nielsen S (October 2016). "5-MeO-DALT; a novel designer drug on the market causing acute delirium and rhabdomyolysis". Acta Anaesthesiol Scand. 60 (9): 1332–1336. doi:10.1111/aas.12765. PMID   27453155.
  10. ↑ Jovel A, Felthous A, Bhattacharyya A (May 2014). "Delirium due to intoxication from the novel synthetic tryptamine 5-MeO-DALT". J Forensic Sci. 59 (3): 844–846. doi:10.1111/1556-4029.12367. PMID   24329118.
  11. ↑ "Kᵢ Database". PDSP. 28 March 2025. Retrieved 28 March 2025.
  12. ↑ Liu T. "BindingDB BDBM50435344 CHEMBL2391541". BindingDB. Retrieved 28 March 2025.
  13. 1 2 3 Cozzi NV, Daley PF (February 2016). "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines" (PDF). Bioorganic & Medicinal Chemistry Letters. 26 (3): 959–964. doi:10.1016/j.bmcl.2015.12.053. PMID   26739781.
  14. 1 2 3 4 5 6 Klein LM, Cozzi NV, Daley PF, Brandt SD, Halberstadt AL (November 2018). "Receptor binding profiles and behavioral pharmacology of ring-substituted N,N-diallyltryptamine analogs" (PDF). Neuropharmacology. 142: 231–239. doi:10.1016/j.neuropharm.2018.02.028. PMC   6230509 . PMID   29499272.
  15. 1 2 3 4 5 6 7 Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-Arnau R (August 2024). "Structure-activity relationships of serotonergic 5-MeO-DMT derivatives: insights into psychoactive and thermoregulatory properties". Mol Psychiatry. 29 (8): 2346–2358. doi:10.1038/s41380-024-02506-8. PMC   11412900 . PMID   38486047.
  16. 1 2 3 Arunotayanun W, Dalley JW, Huang XP, Setola V, Treble R, Iversen L, Roth BL, Gibbons S (June 2013). "An analysis of the synthetic tryptamines AMT and 5-MeO-DALT: emerging 'Novel Psychoactive Drugs'" . Bioorg Med Chem Lett. 23 (11): 3411–3415. doi:10.1016/j.bmcl.2013.03.066. PMID   23602445.
  17. 1 2 3 Kozell LB, Eshleman AJ, Swanson TL, Bloom SH, Wolfrum KM, Schmachtenberg JL, Olson RJ, Janowsky A, Abbas AI (April 2023). "Pharmacologic Activity of Substituted Tryptamines at 5-Hydroxytryptamine (5-HT)2A Receptor (5-HT2AR), 5-HT2CR, 5-HT1AR, and Serotonin Transporter". J Pharmacol Exp Ther. 385 (1): 62–75. doi:10.1124/jpet.122.001454. PMC   10029822 . PMID   36669875.
  18. 1 2 Pottie E, Cannaert A, Van Uytfanghe K, Stove CP (December 2019). "Setup of a Serotonin 2A Receptor (5-HT2AR) Bioassay: Demonstration of Its Applicability To Functionally Characterize Hallucinogenic New Psychoactive Substances and an Explanation Why 5-HT2AR Bioassays Are Not Suited for Universal Activity-Based Screening of Biofluids for New Psychoactive Substances". Anal Chem. 91 (24): 15444–15452. Bibcode:2019AnaCh..9115444P. doi:10.1021/acs.analchem.9b03104. PMID   31725281.
  19. 1 2 3 Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain" . Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID   17223101.
  20. ↑ Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID   39636099.
  21. ↑ Glatfelter GC, Clark AA, Cavalco NG, Landavazo A, Partilla JS, Naeem M (December 2024). "Serotonin 1A Receptors Modulate Serotonin 2A Receptor-Mediated Behavioral Effects of 5-Methoxy-N,N-dimethyltryptamine Analogs in Mice". ACS Chem Neurosci. 15 (24): 4458–4477. doi:10.1021/acschemneuro.4c00513. PMID   39636099.
  22. 1 2 3 4 5 Gatch MB, Dolan SB, Forster MJ (August 2017). "Locomotor and discriminative stimulus effects of four novel hallucinogens in rodents". Behav Pharmacol. 28 (5): 375–385. doi:10.1097/FBP.0000000000000309. PMC   5498282 . PMID   28537942.
  23. ↑ Michely JA, Helfer AG, Brandt SD, Meyer MR, Maurer HH (October 2015). "Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MSn, and LC-HR-MS-MS" (PDF). Analytical and Bioanalytical Chemistry. 407 (25). Springer Science and Business Media LLC: 7831–7842. doi:10.1007/s00216-015-8955-0. PMID   26297461. S2CID   26086597.
  24. ↑ Dinger J, Woods C, Brandt SD, Meyer MR, Maurer HH (January 2016). "Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class" (PDF). Toxicology Letters. 241. Elsevier BV: 82–94. doi:10.1016/j.toxlet.2015.11.013. PMID   26599973. S2CID   2384720.
  25. ↑ Chadeayne AR, Pham DN, Golen JA, Manke DR (April 2020). "5-MeO-DALT: the freebase of N,N-diallyl-5-meth-oxy-tryptamine". IUCrData. 5 (Pt 4) x200498. International Union of Crystallography (IUCr). Bibcode:2020IUCrD...500498C. doi: 10.1107/s2414314620004988 . PMC   9462216 . PMID   36338299.
  26. ↑ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  27. ↑ "厚生労働省：平成１8年度無承認無許可医薬品等買上調査の結果について" (in Japanese). Retrieved 24 July 2015.
  28. ↑ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  29. ↑ Rångemark Åkerman CR (20 April 2012). "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (PDF) (in Swedish). Retrieved 3 September 2015.
  30. ↑ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  31. ↑ "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes.
  32. ↑ "Louisiana State Legislature" . Retrieved 3 September 2015.
  33. ↑ Post M (2015). "Cluster Headache Patient Survey: 5-MeO-DALT". Figshare. doi:10.6084/M9.FIGSHARE.1372467.V3.
  34. ↑ Post M (2014). "Treatment of Cluster Headache Symptoms using Synthetic Tryptamine N,N-Diallyl-5 Methoxytryptamine". Figshare. doi:10.6084/M9.FIGSHARE.1119697.V1. S2CID   73807327.
  35. ↑ Brandt RB, Doesborg PG, Haan J, Ferrari MD, Fronczek R (February 2020). "Pharmacotherapy for Cluster Headache". CNS Drugs. 34 (2). Springer Science and Business Media LLC: 171–184. doi:10.1007/s40263-019-00696-2. PMC   7018790 . PMID   31997136.
  36. ↑ Schindler EA, Gottschalk CH, Weil MJ, Shapiro RE, Wright DA, Sewell RA (2015-10-20). "Indoleamine Hallucinogens in Cluster Headache: Results of the Clusterbusters Medication Use Survey". Journal of Psychoactive Drugs. 47 (5). Informa UK Limited: 372–381. doi:10.1080/02791072.2015.1107664. PMID   26595349. S2CID   21948146.
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