5-MeO-DALT

Last updated

5-MeO-DALT
5-MeO-DALT.svg
5-MeO-DALT 3D BS.png
Clinical data
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 was first synthesized and described by Alexander Shulgin, who disclosed the compound in 2004. [1] [4] The drug has been encountered as a novel designer and recreational drug. [4] [5]

Contents

Dosage and effects

According to Alexander Shulgin, the dosage 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]

Side effects and 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 3.26–19
5-HT1B 735
5-HT1D 107
5-HT1E 500
5-HT1F ND
5-HT2A 71.7–218 (Ki)
11.3–139.4 (EC50 Tooltip half-maximal effective concentration)
99–114% (Emax Tooltip maximal efficacy)
5-HT2B 59
5-HT2C 456
5-HT3 >10,000
5-HT4 ND
5-HT5A 3,312
5-HT6 153
5-HT7 90
α1Aα1D >10,000
α2A 215
α2B 726
α2C 1,467
β1β3 >10,000
D1D5 >10,000
H1 505
H2 4,250–>10,000
H3 1,712 (guinea pig)
H4 >10,000
M1M5 >10,000
nACh Tooltip Nicotinic acetylcholine receptor>10,000
I1 ND
σ1 301–398 (rat/guinea pig)
σ2 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 receptor1,132
SERT Tooltip Serotonin transporter499–1,189 (Ki)
>100,000 (IC50 Tooltip half-maximal inhibitory concentration) (rat)
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. Refs: [11] [12] [13] [14] [15] [16] [17] [18]

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

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. [19] Conversely, 5-MeO-DALT does not substitute for the entactogen MDMA in such tests. [19] 5-MeO-DALT produces dose-dependent hyperlocomotion in rodents, followed by hypolocomotion at the highest assessed dose. [19] [15] This is in contrast to many other psychedelic tryptamines, which tend to produce only hypolocomotion. [19] 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. [19] 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. [20] [21]

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 and DALT.

In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT. [22]

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]

China

As of October 2015 5-MeO-DALT is a controlled substance in China. [23]

Japan

5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law. [24]

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.

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. [25]

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. [26]

United States

5-MeO-DALT is not scheduled at the federal level in the United States, [27] 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. [28]

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. [29]

Research

Cluster headache

Anecdotal reports [30] and a small-scale trial [31] indicate the potential of 5-MeO-DALT for the treatment of cluster headache, one of the most excruciating conditions known to medicine. [32] These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache. [33]

See also

References

  1. 1 2 3 4 5 6 7 8 9 "#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. 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 7 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 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. doi:10.1021/acs.analchem.9b03104. PMID   31725281.
  18. 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.
  19. 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.
  20. 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.
  21. 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.
  22. 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). International Union of Crystallography (IUCr): x200498. Bibcode:2020IUCrD...500498C. doi: 10.1107/s2414314620004988 . PMC   9462216 . PMID   36338299.
  23. "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.
  24. "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.
  25. "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  26. 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.
  27. "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  28. "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes.
  29. "Louisiana State Legislature" . Retrieved 3 September 2015.
  30. Post M (2015). "Cluster Headache Patient Survey: 5-MeO-DALT". Figshare. doi:10.6084/M9.FIGSHARE.1372467.V3.
  31. 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.
  32. 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.
  33. 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.