5-MeO-DALT
Chemical compound From Wikipedia, the free encyclopedia
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]
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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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| Duration of action | 2–4 hours[1] |
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| Formula | C17H22N2O |
| Molar mass | 270.376 g·mol−1 |
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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
Summarize
Perspective
Pharmacodynamics
| 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]
Pharmacokinetics
The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature.[21][22]
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.
In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT.[23]
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]
Legal status
Summarize
Perspective
China
As of October 2015 5-MeO-DALT is a controlled substance in China.[24]
Japan
5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law.[25]
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.[26]
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.[27]
United States
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.
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.[29]
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.[30]
Research
Cluster headache
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]
See also
References
External links
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