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5-MeO-DALT

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5-MeO-DALT
Clinical data
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 checkY
  • Key:HGRHWEAUHXYNNP-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

5-MeO-DALT, also known as N,N-diallyl-5-methoxytryptamine, is a psychedelic drug of the tryptamine family.[1][3] It was first synthesized and described by Alexander Shulgin.

Chemistry

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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 and DALT.

In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT.[4]

Pharmacology

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Pharmacodynamics

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Binding site pKi ± SEM at binding site
5-HT1A 7.70 ± 0.10
5-HT1B 6.13 ± 0.04
5-HT1D 7.00 ± 0.10
5-HT1E 6.30 ± 0.05
5-HT2A 6.66 ± 0.08
5-HT2B 7.23 ± 0.05
5-HT2C 6.34 ± 0.08
5-HT5A 5.48 ± 0.04
5-HT6 6.81 ± 0.03
5-HT7 7.05 ± 0.07
α2A 6.67 ± 0.07
α2B 6.14 ± 0.04
α2C 5.83 ± 0.06
H1 6.30 ± 0.06
H3 5.77 ± 0.04
κOR 5.95 ± 0.07
μOR < 5.00
σ1 6.52 ± 0.06
σ2 6.60 ± 0.05
DAT 5.50 ± 0.20
NET < 5.00
SERT 6.30 ± 0.05

The interactions of 5-MeO-DALT with various targets have been reported.[5][6][7][8]

5-MeO-DALT binds to 5-HT1A, 5-HT1D, 5-HT1E, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT6, α2A, α2B, α2C, H1, κ-opioid, σ1 and σ2 receptors with Ki values lower than 10 μM and also acts as a DAT and SERT monoamine reuptake inhibitor.[5]

5-MeO-DALT produces dose-dependent hyperlocomotion in rodents, followed by hypolocomotion at the highest assessed dose.[9][7] This is in contrast to many other psychedelic tryptamines, which tend to produce only hypolocomotion.[9] 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.[9] It also produces hypothermia.[7] The drug fully substitutes for the serotonergic psychedelic DOM in rodent drug discrimination tests.[9] Conversely, 5-MeO-DALT does not substitute for the entactogen MDMA in such tests.[9] Similarly to other psychedelics, 5-MeO-DALT produces the head-twitch response, a behavioral proxy of psychedelic-like effects, in rodents.[10][7]

Pharmacokinetics

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The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature.[11][12]

History

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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.[13]

Dosage

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Doses ranging from 12–20 mg were tested by Alexander Shulgin's research group.[14] A wider dose range of 12 to 25 mg has also been reported.[10]

Side effects

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There is no published literature on the toxicity of 5-MeO-DALT.

Interactions

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

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As of October 2015 5-MeO-DALT is a controlled substance in China.[15]

Japan

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5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law.[16]

United Kingdom

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5-MeO-DALT became a Class A drug in the UK on January 7, 2015 after an update to the tryptamine blanket ban.

Singapore

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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.[17]

Sweden

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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.[18]

United States

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5-MeO-DALT is not scheduled at the federal level in the United States,[19] 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

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5-MeO-DALT is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[20]

Louisiana

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5-MeO-DALT is a Schedule I controlled substance in the state of Louisiana making it illegal to buy, sell, or possess in Louisiana.[21]

Research

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necdotal reports[22] and a small-scale trial[23] indicate the potential of 5-MeO-DALT for the treatment of cluster headache, one of the most excruciating conditions known to medicine.[24] These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache.[25]

References

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  1. ^ a b c Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  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. ^ 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. PMID 22683457.
  4. ^ Chadeayne AR, Pham DN, Golen JA, Manke DR (April 2020). "5-MeO-DALT: the freebase of N,N-diallyl-5-meth-oxy-tryptamine". IUCrData. 5 (Pt 4). International Union of Crystallography (IUCr): x200498. Bibcode:2020IUCrD...500498C. doi:10.1107/s2414314620004988. PMC 9462216. PMID 36338299.
  5. ^ a b 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.
  6. ^ 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.
  7. ^ a b c d Puigseslloses P, Nadal-Gratacós N, Ketsela G, Weiss N, Berzosa X, Estrada-Tejedor R, Islam MN, Holy M, Niello M, Pubill D, Camarasa J, Escubedo E, Sitte HH, López-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.
  8. ^ Nagai F, Nonaka R, Satoh Hisashi Kamimura K (March 2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". Eur J Pharmacol. 559 (2–3): 132–137. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101.
  9. ^ 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.
  10. ^ 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. Table 4 Human potency data for selected hallucinogens. [...]
  11. ^ 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.
  12. ^ 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.
  13. ^ Morris H, Smith A (2010-05-02). "The Last Interview With Alexander Shulgin". VICE.
  14. ^ Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs. Archived from the original on 2021-12-13. Retrieved 3 September 2015 – via YouTube.
  15. ^ "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
  16. ^ "厚生労働省：平成１8年度無承認無許可医薬品等買上調査の結果について" (in Japanese). Retrieved 24 July 2015.
  17. ^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
  18. ^ Rångemark Åkerman CR (20 April 2012). "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (PDF) (in Swedish). Retrieved 3 September 2015.
  19. ^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
  20. ^ "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes.
  21. ^ "Louisiana State Legislature". Retrieved 3 September 2015.
  22. ^ Post M (2015). "Cluster Headache Patient Survey: 5-MeO-DALT". Figshare. doi:10.6084/M9.FIGSHARE.1372467.V3.
  23. ^ 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.
  24. ^ 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.
  25. ^ Schindler EA, Gottschalk CH, Weil MJ, Shapiro RE, Wright DA, Sewell RA (2015-10-20). "Indoleamine Hallucinogens in Cluster Headache: Results of the Clusterbusters Medication Use Survey". Journal of Psychoactive Drugs. 47 (5). Informa UK Limited: 372–381. doi:10.1080/02791072.2015.1107664. PMID 26595349. S2CID 21948146.
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