5-MeO-DALT
| Clinical data | |
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| Trade names | Foxtrot |
| Other names | N,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 |
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| Pharmacokinetic data | |
| Duration of action | 2-4 hours[1] |
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| Chemical and physical data | |
| Formula | C17H22N2O |
| Molar mass | 270.376 g*mol-1 |
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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][3] It is taken orally.[1]
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][6]
Use and effects
[edit]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][7] A wider dose range of 12 to 25 mg has also been reported.[8] 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
[edit]There is little published literature on the toxicity of 5-MeO-DALT.[9] Case reports of overdose have been published, with effects including loss of consciousness, visual hallucinations, acute delirium, and rhabdomyolysis, among others.[9][10][11] A death related to behavioral intoxication has been reported.[3]
Interactions
[edit]Pharmacology
[edit]Pharmacodynamics
[edit]| Target | Affinity (Ki, nM) |
|---|---|
| 5-HT1A | 3.26-48 (Ki) 2.9-3.4 (EC50Tooltip half-maximal effective concentration) 99-102% (EmaxTooltip maximal efficacy) |
| 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 |
| a1A-a1D | >10,000 |
| a2A | 215-228 |
| a2B | 726-956 |
| a2C | 1,467-641 |
| b1-b3 | >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 |
| nAChTooltip Nicotinic acetylcholine receptor | >10,000 |
| I1 | ND |
| s1 | 333 (human) 301-398 (rodent) |
| s2 | 340 (human) 253 (rat) |
| TAAR1Tooltip Trace amine-associated receptor 1 | ND |
| MORTooltip m-Opioid receptor, DORTooltip d-Opioid receptor | >10,000 |
| KORTooltip k-Opioid receptor | 899-1,132 |
| SERTTooltip Serotonin transporter | 499-1,408 (Ki) >100,000 (IC50Tooltip half-maximal inhibitory concentration) (rat) 930-22,313 (IC50) (human) >100,000 (EC50) (rat) |
| NETTooltip Norepinephrine transporter | >10,000 (Ki) >100,000 (IC50) (rat) >100,000 (EC50) (rat) |
| DATTooltip Dopamine transporter | 3,378 (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 IP1Tooltip inositol phosphate formation. Refs: [12][13][14][15][16][17][18][19][20][21] | |
The interactions of 5-MeO-DALT with various targets have been reported.[14][15][16][20][18] It binds to a variety of serotonin receptors, as well as a number of other targets.[14][15][16][20][22] The drug is a potent full agonist of the serotonin 5-HT1A and 5-HT2A receptors.[16][17][19][18] 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 m-opioid (MOR) and d-opioid receptors (DOR) along with more significant activity at the k-opioid receptor (KOR) (~76% of salvinorin A at 1 mM concentration) with G protein bias over b-arrestin activation.[21]
Similarly to other psychedelics, 5-MeO-DALT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[8][16][15] The drug fully substitutes for the serotonergic psychedelic DOM in rodent drug discrimination tests.[23] Conversely, 5-MeO-DALT does not substitute for the entactogen MDMA in such tests.[23] 5-MeO-DALT produces dose-dependent hyperlocomotion in rodents, followed by hypolocomotion at the highest assessed dose.[23][16] This is in contrast to many other psychedelic tryptamines, which tend to produce only hypolocomotion.[23] 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.[23] It also produces hypothermia.[16]
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.[15] In relation to this, multiple targets appear to contribute to the effects of 5-MeO-DALT.[15][5]
Pharmacokinetics
[edit]The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature.[9][24][25][26]
Chemistry
[edit]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
[edit]The chemical synthesis of 5-MeO-DALT has been described.[1]
Crystal structure
[edit]In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT.[27]
Analogues
[edit]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
[edit]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] The drug was encountered as a novel designer drug by at least 2006.[3][4][5][6]
Society and culture
[edit]Legal status
[edit]Canada
[edit]5-MeO-DALT is not a controlled substance in Canada as of 2025.[28]
China
[edit]As of October 2015 5-MeO-DALT is a controlled substance in China.[29]
Japan
[edit]5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law.[30]
Singapore
[edit]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.[31]
Sweden
[edit]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.[32]
United Kingdom
[edit]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
[edit]5-MeO-DALT is not scheduled at the federal level in the United States,[33] 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
[edit]5-MeO-DALT is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[34]
Louisiana
[edit]5-MeO-DALT is a Schedule I controlled substance in the state of Louisiana making it illegal to buy, sell, or possess in Louisiana.[35]
Research
[edit]Cluster headache
[edit]Anecdotal reports[36] and a small-scale trial[37] indicate the potential of 5-MeO-DALT for the treatment of cluster headache, one of the most excruciating conditions known to medicine.[38] These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache.[39]
See also
[edit]References
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- ^ Anvisa (2023-07-24). "RDC No 804 - Listas de Substancias Entorpecentes, Psicotropicas, 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). Diario Oficial da Uniao (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
- ^ a b c 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.
- ^ a b c d e Morris H, Smith A (2010-05-02). "The Last Interview With Alexander Shulgin". VICE.
- ^ a b c 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.
- ^ a b "5-MeO-DALT". AIPSIN (in Russian). Retrieved 2 January 2026.
- ^ Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs. Archived from the original on 2021-12-13. Retrieved 3 September 2015 - via YouTube.
- ^ a b 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.
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- ^ a b c 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.
- ^ a b c d e f 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.
- ^ a b c d e f g Puigseslloses P, Nadal-Gratacos N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, Lopez-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.
- ^ a b c 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.
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- ^ a b c d e 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.
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