Chemistry:5-MeO-DALT

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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][2] It is taken orally.[1]

5-MeO-DALT was first synthesized and described by Alexander Shulgin, who disclosed the compound in 2004.[1][3] It has been encountered as a novel designer and recreational drug.[3][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 time to 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.[2]

Interactions

Pharmacology

Pharmacodynamics

5-MeO-DALT activities
Target Affinity (Ki, nM)
5-HT1A 3.26–48 (Ki)
2.9–3.4 (EC50)
99–102% (Emax)
5-HT1B 551–735
5-HT1D 53–107
5-HT1E 322–500
5-HT1F ND
5-HT2A 48–218 (Ki)
8.4–139.4 (EC50)
91–114% (Emax)
5-HT2B 45–59 (Ki)
18–33 (EC50)
86–90% (Emax)
5-HT2C 456–1,083 (Ki)
75–299a (EC50)
88–99%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 >10,000
I1 ND
σ1 333 (human)
301–398 (rodent)
σ2 340 (human)
253 (rat)
TAAR1 ND
MOR, DOR >10,000
KOR 899–1,132
SERT 499–1,408 (Ki)
>100,000 (IC50) (rat)
930–22,313 (IC50) (human)
>100,000 (EC50) (rat)
NET >10,000 (Ki)
>100,000 (IC50) (rat)
>100,000 (EC50) (rat)
DAT 3,378 (Ki)
>100,000 (IC50) (rat)
>100,000 (EC50) (rat)

The interactions of 5-MeO-DALT with various targets have been reported.[11][12][13][14][15] It binds to a variety of serotonin receptors, as well as a number of other targets.[11][12][13][14][16] The drug is a potent full agonist of the serotonin 5-HT1A and 5-HT2A receptors.[13][17][18][15] It is also an agonist of the serotonin 5-HT2B and 5-HT2C receptors.[17]

Uniquely the substance displayed weak agonist-like activity at the μ-opioid (MOR) and δ-opioid receptors (DOR) along with more significant activity at the κ-opioid receptor (KOR) (∼76% of salvinorin A at 1 μM concentration) with G protein bias over β-arrestin activation.[19]

Similarly to other psychedelics, 5-MeO-DALT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[7][13][12] The drug fully substitutes for the serotonergic psychedelic DOM in rodent drug discrimination tests.[20] Conversely, 5-MeO-DALT does not substitute for the entactogen MDMA in such tests.[20] 5-MeO-DALT produces dose-dependent hyperlocomotion in rodents, followed by hypolocomotion at the highest assessed dose.[20][13] This is in contrast to many other psychedelic tryptamines, which tend to produce only hypolocomotion.[20] 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.[20] It also produces hypothermia.[13]

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.[12] In relation to this, multiple targets appear to contribute to the effects of 5-MeO-DALT.[12][4]

Pharmacokinetics

The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature.[8][21][22][23]

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.[24]

Analogues

Analogues of 5-MeO-DALT include diallyltryptamine (DALT), 4-HO-DALT (daltocin), 4-AcO-DALT (dalcetin), NB-5-MeO-DALT, 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.[3] 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.[3] The drug was encountered as a novel designer drug by at least 2006.[2][3][4][5]

Society and culture

Canada

5-MeO-DALT is not a controlled substance in Canada as of 2025.[25]

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. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 "#56 5-MeO-DALT". https://isomerdesign.com/pihkal/read/tk/56. 
  2. ↑ 2.0 2.1 2.2 "The recreational tryptamine 5-MeO-DALT (N,N-diallyl-5-methoxytryptamine): a brief review". Prog Neuropsychopharmacol Biol Psychiatry 39 (2): 259–262. December 2012. doi:10.1016/j.pnpbp.2012.05.022. PMID 22683457. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 "The Last Interview With Alexander Shulgin". 2010-05-02. https://www.vice.com/en/article/the-last-interview-with-alexander-shulgin-423-v17n5/. 
  4. ↑ 4.0 4.1 4.2 Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. 36. 2018. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. https://bitnest.netfirms.com/external/10.1007/7854_2017_475. "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." 
  5. ↑ 5.0 5.1 "5-MeO-DALT" (in ru). https://aipsin.com/newsubstance/445/. 
  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. ↑ 7.0 7.1 "Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species". Neuropharmacology 167. May 2020. doi:10.1016/j.neuropharm.2019.107933. PMID 31917152. PMC 9191653. http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf. "Table 4 Human potency data for selected hallucinogens. [...]". 
  8. ↑ 8.0 8.1 8.2 "Loss of Consciousness and Visual Hallucinations Related to 5-MeO-DALT Intake, a Case Report Confirmed by Toxicological Analyses". J Anal Toxicol 46 (7). August 2022. doi:10.1093/jat/bkac021. PMID 35365824. 
  9. ↑ "5-MeO-DALT; a novel designer drug on the market causing acute delirium and rhabdomyolysis". Acta Anaesthesiol Scand 60 (9): 1332–1336. October 2016. doi:10.1111/aas.12765. PMID 27453155. 
  10. ↑ "Delirium due to intoxication from the novel synthetic tryptamine 5-MeO-DALT". J Forensic Sci 59 (3): 844–846. May 2014. doi:10.1111/1556-4029.12367. PMID 24329118. 
  11. ↑ 11.0 11.1 Cite error: Invalid <ref> tag; no text was provided for refs named CozziDaley2016
  12. ↑ 12.0 12.1 12.2 12.3 12.4 Cite error: Invalid <ref> tag; no text was provided for refs named KleinCozziDaley2018
  13. ↑ 13.0 13.1 13.2 13.3 13.4 13.5 Cite error: Invalid <ref> tag; no text was provided for refs named PuigsesllosesNadal-GratacósKetsela2024
  14. ↑ 14.0 14.1 Cite error: Invalid <ref> tag; no text was provided for refs named NagaiNonakaKamimura2007
  15. ↑ 15.0 15.1 Cite error: Invalid <ref> tag; no text was provided for refs named KozellEshlemanSwanson2023
  16. ↑ "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. December 2024. doi:10.1021/acschemneuro.4c00513. PMID 39636099. 
  17. ↑ 17.0 17.1 Cite error: Invalid <ref> tag; no text was provided for refs named ArunotayanunDalleyHuang2013
  18. ↑ "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. December 2019. doi:10.1021/acs.analchem.9b03104. PMID 31725281. Bibcode: 2019AnaCh..9115444P. 
  19. ↑ Cite error: Invalid <ref> tag; no text was provided for refs named GlatfelterClarkCavalco2024
  20. ↑ 20.0 20.1 20.2 20.3 20.4 "Locomotor and discriminative stimulus effects of four novel hallucinogens in rodents". Behav Pharmacol 28 (5): 375–385. August 2017. doi:10.1097/FBP.0000000000000309. PMID 28537942. 
  21. ↑ "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". Analytical and Bioanalytical Chemistry (Springer Science and Business Media LLC) 407 (25): 7831–7842. October 2015. doi:10.1007/s00216-015-8955-0. PMID 26297461. https://researchonline.ljmu.ac.uk/id/eprint/3406/1/ABC-01148-2015.R1.pdf. 
  22. ↑ "Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class". Toxicology Letters (Elsevier BV) 241: 82–94. January 2016. doi:10.1016/j.toxlet.2015.11.013. PMID 26599973. https://researchonline.ljmu.ac.uk/id/eprint/2402/1/ToxLett_17.15.49.pdf. 
  23. ↑ "In Vitro Metabolite Identification Studies for the New Psychoactive Substances Furanylfentanyl, TFMPP, and 5-MeO-DALT in Human Liver Microsomes". Current Analytical Chemistry 18 (9): 1003-1016. November 2022. doi:10.2174/1573411018666220603100033. ISSN 1573-4110. 
  24. ↑ "5-MeO-DALT: the freebase of N,N-diallyl-5-meth-oxy-tryptamine". IUCrData (International Union of Crystallography (IUCr)) 5 (Pt 4). April 2020. doi:10.1107/s2414314620004988. PMID 36338299. Bibcode: 2020IUCrD...500498C. 
  25. ↑ "Controlled Drugs and Substances Act". https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html. 
  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. http://www.sfda.gov.cn/WS01/CL0056/130753.html. 
  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). http://www.mhlw.go.jp/houdou/2007/08/h0810-3.html. 
  28. ↑ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. http://www.cnb.gov.sg/Libraries/CNB_Newsroom_Files/CNB_NR_-_30_Apr_2015.sflb.ashx. 
  29. ↑ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (in Swedish). 20 April 2012. https://lakemedelsverket.se/upload/lvfs/LVFS_2012_6.pdf. 
  30. ↑ "§1308.11 Schedule I.". http://www.deadiversion.usdoj.gov/21cfr/cfr/1308/1308_11.htm. 
  31. ↑ "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes. http://leg.state.fl.us/statutes/index.cfm?App_mode=Display_Statute&URL=0800-0899/0893/0893.html. 
  32. ↑ "Louisiana State Legislature". http://legis.la.gov/Legis/Law.aspx?d=98877. 
  33. ↑ "Cluster Headache Patient Survey: 5-MeO-DALT". Figshare. 2015. doi:10.6084/M9.FIGSHARE.1372467.V3. https://figshare.com/articles/journal_contribution/1372467. 
  34. ↑ "Treatment of Cluster Headache Symptoms using Synthetic Tryptamine N,N-Diallyl-5 Methoxytryptamine". Figshare. 2014. doi:10.6084/M9.FIGSHARE.1119697.V1. https://figshare.com/articles/journal_contribution/1119697. 
  35. ↑ "Pharmacotherapy for Cluster Headache". CNS Drugs (Springer Science and Business Media LLC) 34 (2): 171–184. February 2020. doi:10.1007/s40263-019-00696-2. PMID 31997136. 
  36. ↑ "Indoleamine Hallucinogens in Cluster Headache: Results of the Clusterbusters Medication Use Survey". Journal of Psychoactive Drugs (Informa UK Limited) 47 (5): 372–381. 2015-10-20. doi:10.1080/02791072.2015.1107664. PMID 26595349. 



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