5-MeO-DALT

Chemical compound From Wikipedia, the free encyclopedia

5-MeO-DALT

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

Quick Facts Legal status, Identifiers ...
5-MeO-DALT
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Legal status
Legal status
  • BR: Class F2 (Prohibited psychotropics)[1]
  • 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
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 Y
  • Key:HGRHWEAUHXYNNP-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)
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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-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 10μM and also acts as a DAT and SERT monoamine reuptake inhibitor.[3]

More information Binding site, pKi ± SEM at binding site ...
Binding site pKi ± SEM at binding site
5-HT1A7.70 ± 0.10
5-HT1B6.13 ± 0.04
5-HT1D7.00 ± 0.10
5-HT1E6.30 ± 0.05
5-HT2A6.66 ± 0.08
5-HT2B7.23 ± 0.05
5-HT2C6.34 ± 0.08
5-HT5A5.48 ± 0.04
5-HT66.81 ± 0.03
5-HT77.05 ± 0.07
α2A6.67 ± 0.07
α2B6.14 ± 0.04
α2C5.83 ± 0.06
H16.30 ± 0.06
H35.77 ± 0.04
κOR5.95 ± 0.07
μOR< 5.00
σ16.52 ± 0.06
σ26.60 ± 0.05
DAT5.50 ± 0.20
NET< 5.00
SERT6.30 ± 0.05
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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.

Interactions

Summarize
Perspective

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

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