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 was first synthesized and described by Alexander Shulgin, who disclosed the compound in 2004.[1][3] The drug has been encountered as a novel designer and recreational drug.[3][4]

Use and effects

According to Alexander Shulgin, the dosage of 5-MeO-DALT is 12 to 20Script error: No such module "String".mg orally and its duration is 2 to 4Script error: No such module "String".hours.[1][5] A wider dose range of 12 to 25Script error: No such module "String".mg has also been reported.[6] It is said to onset and peak remarkably quickly via the oral route, with an onset of less than 15Script error: No such module "String".minutes and a peak of 30Script error: No such module "String".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.[7] Case reports of overdose have been published, with effects including loss of consciousness, visual hallucinations, acute delirium, and rhabdomyolysis, among others.[7][8][9] A death related to behavioral intoxication has been reported.[2]

Interactions

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Pharmacology

Pharmacodynamics

5-MeO-DALT activities
Target Affinity (Ki, nM)
5-HT1A 3.26–48 (Ki)
3.4 (EC50Tooltip half-maximal effective concentration)
102% (EmaxTooltip maximal efficacy)
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
nAChTooltip Nicotinic acetylcholine receptor >10,000
I1 ND
σ1 301–398 (rat/guinea pig)
σ2 253 (rat)
TAAR1Tooltip Trace amine-associated receptor 1 ND
MORTooltip μ-Opioid receptor, DORTooltip δ-Opioid receptor >10,000
KORTooltip κ-Opioid receptor 1,132
SERTTooltip Serotonin transporter 499–1,189 (Ki)
>100,000 (IC50Tooltip half-maximal inhibitory concentration) (rat)
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. Refs: [10][11][12][13][14][15][16][17][18]

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

Similarly to other psychedelics, 5-MeO-DALT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[6][14][13] 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][14] 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.[14]

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.[13] In relation to this, multiple targets appear to contribute to the effects of 5-MeO-DALT.[13][4]

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, 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.[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.[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]

Society and culture

Legal status

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]

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 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,[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

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  14. ↑ a b c d e f g Script error: No such module "Citation/CS1".
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  18. ↑ a b c Script error: No such module "Citation/CS1".
  19. ↑ a b c d e Script error: No such module "Citation/CS1".
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  23. ↑ Script error: No such module "citation/CS1".
  24. ↑ Script error: No such module "citation/CS1".
  25. ↑ Script error: No such module "citation/CS1".
  26. ↑ Script error: No such module "citation/CS1".
  27. ↑ Script error: No such module "citation/CS1".
  28. ↑ Script error: No such module "citation/CS1".
  29. ↑ Script error: No such module "citation/CS1".
  30. ↑ Script error: No such module "Citation/CS1".
  31. ↑ Script error: No such module "Citation/CS1".
  32. ↑ Script error: No such module "Citation/CS1".
  33. ↑ Script error: No such module "Citation/CS1".

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External links

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