5-MeO-DALT

5-MeO-DALT or N,N-diallyl-5-methoxytryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.

5-MeO-DALT

Legal status
Legal status	BR: Class F2 (Prohibited psychotropics)[1] DE: NpSG (Industrial and scientific use only) UK: Class A Illegal in China, Japan, Singapore, Sweden, Florida and Louisiana
Identifiers
IUPAC name N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine
CAS Number	928822-98-4 Y
PubChem CID	50878551
ChemSpider	21106245 Y
UNII	V25VK0QTAA
KEGG	C22723
ChEMBL	ChEMBL2391541
CompTox Dashboard (EPA)	DTXSID30239169
Chemical and physical data
Formula	C17H22N2O
Molar mass	270.376 g·mol−1
3D model (JSmol)	Interactive image
SMILES C=CCN(CCC1=CNC2=C1C=C(OC)C=C2)CC=C
InChI 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
NY (what is this?)  (verify)

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 and DALT.

In April 2020, Chadeayne et al. solved the crystal structure of the freebase form of 5-MeO-DALT.^[2]

Pharmacology

5-MeO-DALT binds to 5-HT_1A, 5-HT_1D, 5-HT_1E, 5-HT_2A, 5-HT_2B, 5-HT_2C, 5-HT₆, α_2A, α_2B, α_2C, H₁, κ-opioid, σ₁ and σ₂ receptors with K_i values lower than 10μM and also acts as a DAT and SERT monoamine 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 and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature.^[4][5]

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.^[6]

Dosage

Doses ranging from 12–20 mg were tested by Alexander Shulgin's research group.^[7]

Therapeutic use

Numerous anecdotal reports^[8] and a small-scale trial^[9] indicate the potential of 5-MeO-DALT for the treatment of cluster 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

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

Legal Status

China

As of October 2015 5-MeO-DALT is a controlled substance in China.^[12]

Japan

5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law.^[13]

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.^[14]

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.^[15]

United States

5-MeO-DALT is not scheduled at the federal level in the United States,^[16] 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.^[17]

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.^[18]

References

1. 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.
2. 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.
3. 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. PMID 26739781.
4. 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.
5. 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.
6. Morris H, Smith A (2010-05-02). "The Last Interview With Alexander Shulgin". VICE.
7. Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs. Archived from the original on 2021-12-13. Retrieved 3 September 2015 – via YouTube.
8. Post M (2015). "Cluster Headache Patient Survey: 5-MeO-DALT". Figshare. doi:10.6084/M9.FIGSHARE.1372467.V3.
9. 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.
10. 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.
11. 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.
12. "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.
13. "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.
14. "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
15. 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.
16. "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
17. "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes.
18. "Louisiana State Legislature". Retrieved 3 September 2015.

External links

• Erowid 5-MeO-DALT vault
• 5-MeO-DALT Thread at UKChemicalResearch