"},"class":{"wt":"[[Serotonin receptor agonist]]; [[Serotonergic psychedelic]]; [[Hallucinogen]]\n\n"},"legal_BR":{"wt":"F2"},"legal_BR_comment":{"wt":"{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}"},"legal_UK":{"wt":"Class A"},"legal_DE":{"wt":"NpSG"},"legal_UN":{"wt":"Unscheduled."},"legal_status":{"wt":"In general unscheduled and not approved for human consumption, Illegal in China, Japan, Singapore, Sweden, Florida and Louisiana\n\n"},"bioavailability":{"wt":""},"protein_bound":{"wt":""},"metabolism":{"wt":""},"onset":{"wt":""},"elimination_half-life":{"wt":""},"duration_of_action":{"wt":"2–4 hours"},"excretion":{"wt":""},"CAS_number_Ref":{"wt":"{{cascite|correct|CAS}}"},"CAS_number":{"wt":"928822-98-4"},"UNII_Ref":{"wt":"{{fdacite|correct|FDA}}"},"UNII":{"wt":"V25VK0QTAA"},"PubChem":{"wt":"50878551"},"KEGG":{"wt":"C22723"},"ChemSpiderID_Ref":{"wt":"{{chemspidercite|correct|chemspider}}"},"ChemSpiderID":{"wt":"21106245"},"ChEMBL":{"wt":"2391541"},"synonyms":{"wt":"''N'',''N''-Diallyl-5-methoxytryptamine; 5-Methoxy-''N'',''N''-diallyltryptamine; 5-Methoxy-DALT; Foxtrot\n\n"},"C":{"wt":"17"},"H":{"wt":"22"},"N":{"wt":"2"},"O":{"wt":"1"},"SMILES":{"wt":"C=CCN(CCC1=CNC2=C1C=C(OC)C=C2)CC=C"},"StdInChI_Ref":{"wt":"{{stdinchicite|correct|chemspider}}"},"StdInChI":{"wt":"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"},"StdInChIKey_Ref":{"wt":"{{stdinchicite|correct|chemspider}}"},"StdInChIKey":{"wt":"HGRHWEAUHXYNNP-UHFFFAOYSA-N"}},"i":0}}]}" id="mwBg">Pharmaceutical compound
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Clinical data | |
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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 |
3D model (JSmol) | |
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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 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]
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]
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]
Target | Affinity (Ki, nM) |
---|---|
5-HT1A | 3.26–48 (Ki) 3.4 (EC50 ) 102% (Emax ) |
5-HT1B | 735 |
5-HT1D | 107 |
5-HT1E | 500 |
5-HT1F | ND |
5-HT2A | 71.7–218 (Ki) 11.3–139.4 (EC50) 97–114% (Emax) |
5-HT2B | 59 |
5-HT2C | 456–573 (Ki) 299 (EC50) 99% (Emax) |
5-HT3 | >10,000 |
5-HT4 | ND |
5-HT5A | 3,312 |
5-HT6 | 153 |
5-HT7 | 90 |
α1A–α1D | >10,000 |
α2A | 215 |
α2B | 726 |
α2C | 1,467 |
β1–β3 | >10,000 |
D1–D5 | >10,000 |
H1 | 505 |
H2 | 4,250–>10,000 |
H3 | 1,712 (guinea pig) |
H4 | >10,000 |
M1–M5 | >10,000 |
nACh | >10,000 |
I1 | ND |
σ1 | 301–398 (rat/guinea pig) |
σ2 | 253 (rat) |
TAAR1 | ND |
MOR , DOR | >10,000 |
KOR | 1,132 |
SERT | 499–1,189 (Ki) >100,000 (IC50 ) (rat) 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) |
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] [19] |
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] 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. [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] [15] 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. [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]
The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature. [21] [22]
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.
In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT. [23]
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]
As of October 2015 5-MeO-DALT is a controlled substance in China. [24]
5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law. [25]
5-MeO-DALT became a Class A drug in the UK on January 7, 2015 after an update to the tryptamine blanket ban.
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. [26]
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. [27]
5-MeO-DALT is not scheduled at the federal level in the United States, [28] 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.
5-MeO-DALT is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida. [29]
5-MeO-DALT is a Schedule I controlled substance in the state of Louisiana making it illegal to buy, sell, or possess in Louisiana. [30]
Anecdotal reports [31] and a small-scale trial [32] indicate the potential of 5-MeO-DALT for the treatment of cluster headache, one of the most excruciating conditions known to medicine. [33] These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache. [34]
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.
Table 4 Human potency data for selected hallucinogens. [...]