5-MeO-DALT
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| Formula | C17H22N2O |
| Molar mass | 270.376g·mol−1 |
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5-MeO-DALTorN,N-diallyl-5-methoxytryptamineis apsychedelictryptaminefirst synthesized byAlexander Shulgin.
Chemistry
[edit]The full name of the chemical isN-allyl-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]prop-2-en-1-amine.It is related to the compounds5-MeO-DPTandDALT.
In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT.[2]
Pharmacology
[edit]5-MeO-DALT binds to5-HT1A,5-HT1D,5-HT1E,5-HT2A,5-HT2B,5-HT2C,5-HT6,α2A,α2B,α2C,H1,κ-opioid,σ1andσ2receptors withKivalues lower than 10μM and also acts as aDATandSERTmonoamine reuptake inhibitor.[3]
| 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 metabolism andcytochrome P450inhibition of 5-MeO-DALT has been described in scientific literature.[4][5]
History
[edit]The first material regarding the synthesis and effects of 5-MeO-DALT was sent fromAlexander Shulginto a research associate named Murple in May 2004, after which it was circulated online. In June 2004 5-MeO-DALT became available from internetresearch chemicalvendors after being synthesized by commercial laboratories in China. In August 2004 the synthesis and effects of 5-MeO-DALT were published byErowid.[6]
Dosage
[edit]Doses ranging from 12–20 mg were tested by Alexander Shulgin's research group.[7]
Therapeutic use
[edit]Numerous anecdotal reports[8]and a small-scale trial[9]indicate the potential of 5-MeO-DALT for the treatment ofcluster headache,one of the most excruciating conditions known to medicine.[10]These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache.[11]
Side effects
[edit]There is no published literature on the toxicity of 5-MeO-DALT.
Legal Status
[edit]China
[edit]As of October 2015 5-MeO-DALT is a controlled substance in China.[12]
Japan
[edit]5-MeO-DALT became a controlled substance inJapanfrom April 2007, by amendment to thePharmaceutical Affairs Law.[13]
United Kingdom
[edit]5-MeO-DALT became a Class A drug in the UK on January 7, 2015 after an update to the tryptamine blanket ban.
Singapore
[edit]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.[14]
Sweden
[edit]Sveriges riksdagadded 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 byMedical Products Agencyin their regulationLVFS 2012:6listed as5-MeO-DALT N-allyl-N-[2-(5-metoxi-1H-indol-3-yl)etyl]-prop-2-en-1-amin.[15]
United States
[edit]5-MeO-DALT is not scheduled at the federal level in theUnited States,[16]but it is likely that it could be considered an analog of5-Meo-DiPT,which is a controlled substance in USA, or an analog of anothertryptamine,in which case purchase, sale, or possession could be prosecuted under theFederal Analog Act.
Florida
[edit]5-MeO-DALT is a Schedule Icontrolled substancein the state ofFloridamaking it illegal to buy, sell, or possess in Florida.[17]
Louisiana
[edit]5-MeO-DALT is a Schedule Icontrolled substancein the state ofLouisianamaking it illegal to buy, sell, or possess in Louisiana.[18]
References
[edit]- ^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).Archivedfrom the original on 2023-08-27.Retrieved2023-08-27.
- ^Chadeayne AR, Pham DN, Golen JA, Manke DR (April 2020)."5-MeO-DALT: the freebase ofN,N-diallyl-5-meth-oxy-tryptamine ".IUCrData.5(Pt 4). International Union of Crystallography (IUCr): x200498.Bibcode:2020IUCrD...500498C.doi:10.1107/s2414314620004988.PMC9462216.PMID36338299.
- ^Cozzi NV, Daley PF (February 2016). "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines".Bioorganic & Medicinal Chemistry Letters.26(3). Elsevier BV: 959–964.doi:10.1016/j.bmcl.2015.12.053.PMID26739781.
- ^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.PMID26297461.S2CID26086597.
- ^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.PMID26599973.S2CID2384720.
- ^Morris H, Smith A (2010-05-02)."The Last Interview With Alexander Shulgin".VICE.
- ^Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs.Archivedfrom the original on 2021-12-13.Retrieved3 September2015– viaYouTube.
- ^Post M (2015)."Cluster Headache Patient Survey: 5-MeO-DALT".Figshare.doi:10.6084/M9.FIGSHARE.1372467.V3.
- ^Post M (2014)."Treatment of Cluster Headache Symptoms using Synthetic Tryptamine N,N-Diallyl-5 Methoxytryptamine".Figshare.doi:10.6084/M9.FIGSHARE.1119697.V1.S2CID73807327.
- ^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.PMC7018790.PMID31997136.
- ^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.PMID26595349.S2CID21948146.
- ^"Quan vu ấn phát 《 phi dược dụng loại ma túy dược phẩm hòa tinh thần dược phẩm liệt quản bạn pháp 》 đích thông tri"(in Chinese). China Food and Drug Administration. 27 September 2015. Archived fromthe originalon 1 October 2015.Retrieved1 October2015.
- ^"Hậu sinh 労 động tỉnh: Bình thành １8 niên độ vô thừa nhận vô hứa khả y dược phẩm đẳng mãi thượng điều tra の kết quả について"(in Japanese).Retrieved24 July2015.
- ^"CNB NEWS RELEASE".Central Narcotics Bureau (CNB). 30 April 2015. Archived fromthe originalon 15 July 2015.Retrieved24 July2015.
- ^Rångemark Åkerman CR (20 April 2012)."Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika"(PDF)(in Swedish).Retrieved3 September2015.
- ^"§1308.11 Schedule I."Archived fromthe originalon 2009-08-27.Retrieved2014-12-17.
- ^"Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL".Florida Statutes.
- ^"Louisiana State Legislature".Retrieved3 September2015.