en 5-MeO-DALT

5-MeO-DALT
Legal status
Legal status	BR: Class F2 (Prohibited psychotropics); 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 ;
PubChem CID	50878551;
ChemSpider	21106245 ;
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 ; Key:HGRHWEAUHXYNNP-UHFFFAOYSA-N ;
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5-MeO-DALT or N,N-diallyl-5-methoxytryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.

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-HT_1A	7.70 ± 0.10
5-HT_1B	6.13 ± 0.04
5-HT_1D	7.00 ± 0.10
5-HT_1E	6.30 ± 0.05
5-HT_2A	6.66 ± 0.08
5-HT_2B	7.23 ± 0.05
5-HT_2C	6.34 ± 0.08
5-HT_5A	5.48 ± 0.04
5-HT₆	6.81 ± 0.03
5-HT₇	7.05 ± 0.07
α_2A	6.67 ± 0.07
α_2B	6.14 ± 0.04
α_2C	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

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.
^ Morris H, Smith A (2010-05-02). "The Last Interview With Alexander Shulgin". VICE.
^ Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs. Archived from the original on 2021-12-13. Retrieved 3 September 2015 – via YouTube.
^ 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. S2CID 73807327.
^ 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.
^ 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.
^ "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.
^ "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.
^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
^ 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.
^ "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.
^ "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes.
^ "Louisiana State Legislature". Retrieved 3 September 2015.

External links

[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.

[PART_1308_—_SCHEDULES_OF_CONTROLLED_SUBSTANCES_-_1308.11_Schedule_I-16] "§1308.11 Schedule I." Archived from the original on 2009-08-27. Retrieved 2014-12-17.

[Florida_Statutes_-_Chapter_893_-_DRUG_ABUSE_PREVENTION_AND_CONTROL-17] "Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL". Florida Statutes.

[18] "Louisiana State Legislature". Retrieved 3 September 2015.

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5-MeO-DALT