5-MeO-DALT

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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
  • N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine
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 or N,N-

methoxytryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin
.

Chemistry

The full name of the chemical is N-

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

κ-opioid, σ1 and σ2 receptors with Ki 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

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

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. PMID 36338299
    .
  3. PMID 26739781
    .
  4. S2CID 26086597
    .
  5. 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. doi:10.6084/M9.FIGSHARE.1372467.V3
    .
  9. S2CID 73807327
    .
  10. PMID 31997136
    .
  11. 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

Retrieved from "https://en.wikipedia.org/w/index.php?title=5-MeO-DALT&oldid=1211124187"