5-MeO-DALT

5-MeO-DALT
Clinical data
Trade namesFoxtrot
Other namesN,N-Diallyl-5-methoxytryptamine; 5-Methoxy-N,N-diallyltryptamine; 5-Methoxy-DALT; Foxtrot
Routes of
administration		Oral[1]
Drug classSerotonin receptor agonist; Serotonergic psychedelic; Hallucinogen
Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics)[2]
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • UN: Unscheduled.
  • In general unscheduled and not approved for human consumption, Illegal in China, Japan, Singapore, Sweden, Florida and Louisiana
Pharmacokinetic data
Duration of action2–4 hours[1]
Identifiers
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H22N2O
Molar mass270.376 g·mol−1
3D model (JSmol)
  • C=CCN(CCC1=CNC2=C1C=C(OC)C=C2)CC=C
  • InChI=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 Y
  • Key:HGRHWEAUHXYNNP-UHFFFAOYSA-N Y
  (verify)

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

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

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

See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

Pharmacodynamics

5-MeO-DALT activities
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
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
nAChTooltip Nicotinic acetylcholine receptor >10,000
I1 ND
σ1 333 (human)
301–398 (rodent)
σ2 340 (human)
253 (rat)
TAAR1Tooltip Trace amine-associated receptor 1 ND
MORTooltip μ-Opioid receptor, DORTooltip δ-Opioid receptor >10,000
KORTooltip κ-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 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.[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

The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature.[9][24][25][26]

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.[27]

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.[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

Canada

5-MeO-DALT is not a controlled substance in Canada as of 2025.[28]

China

As of October 2015 5-MeO-DALT is a controlled substance in China.[29]

Japan

5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law.[30]

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.[31]

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.[32]

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,[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

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

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

Cluster headache

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

References

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  2. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, 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). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. ^ 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.
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  5. ^ 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.
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  24. ^ Michely JA, Helfer AG, Brandt SD, Meyer MR, Maurer HH (October 2015). "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" (PDF). Analytical and Bioanalytical Chemistry. 407 (25). Springer Science and Business Media LLC: 7831–7842. doi:10.1007/s00216-015-8955-0. PMID 26297461. S2CID 26086597.
  25. ^ Dinger J, Woods C, Brandt SD, Meyer MR, Maurer HH (January 2016). "Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class" (PDF). Toxicology Letters. 241. Elsevier BV: 82–94. doi:10.1016/j.toxlet.2015.11.013. PMID 26599973. S2CID 2384720.
  26. ^ Zheng T, Wu L, Wu G, Chen Y, Zhou S (November 2022). "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. doi:10.2174/1573411018666220603100033. ISSN 1573-4110.
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  33. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  34. ^ "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes.
  35. ^ "Louisiana State Legislature". Retrieved 3 September 2015.
  36. ^ Post M (2015). "Cluster Headache Patient Survey: 5-MeO-DALT". Figshare. doi:10.6084/M9.FIGSHARE.1372467.V3.
  37. ^ Post M (2014). "Treatment of Cluster Headache Symptoms using Synthetic Tryptamine N,N-Diallyl-5 Methoxytryptamine". Figshare. doi:10.6084/M9.FIGSHARE.1119697.V1. S2CID 73807327.
  38. ^ Brandt RB, Doesborg PG, Haan J, Ferrari MD, Fronczek R (February 2020). "Pharmacotherapy for Cluster Headache". CNS Drugs. 34 (2). Springer Science and Business Media LLC: 171–184. doi:10.1007/s40263-019-00696-2. PMC 7018790. PMID 31997136.
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