5-MeO-DALT

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5-MeO-DALT
5-MeO-DALT.svg
Systematic (IUPAC) name
N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine
Legal status
Legal status
  • UK: Class A
  • Illegal in China, Japan, Singapore, Sweden, Florida and Louisiana
Identifiers
CAS Number 928822-98-4 N
PubChem CID 50878551
ChemSpider 21106245 YesY
Chemical data
Formula C17H22N2O
Molar mass 270.375 g/mol
 NYesY (what is this?)  (verify)

5-MeO-DALT or N,N-di allyl-5-methoxy tryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.

Chemistry[edit]

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.

Pharmacology[edit]

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.[1]

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.[2][3]

History[edit]

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.[4]

Dosage[edit]

Doses ranging from 12–20 mg were tested by Alexander Shulgin's research group.[5]

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.[6]

Japan[edit]

5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law.[7]

United Kingdom[edit]

5-MeO-DALT became a Class A drug in the UK on January 7th 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.[8]

Sweden[edit]

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.[9]

United States[edit]

5-MeO-DALT is not scheduled at the federal level in the United States,[10] but it is likely that it could be considered an analog of 5-Meo-DiPT or another tryptamine, in which case purchase, sale, or possession could be prosecuted under the Federal Analog Act.

Florida[edit]

5-MeO-DALT is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida.[11]

Louisiana[edit]

5-MeO-DALT is a Schedule I controlled substance in the state of Louisiana making it illegal to buy, sell, or possess in Louisiana.[12]

Notes[edit]

  1. ^ Nicholas V. Cozzi; Paul F. Daley (December 2015). "Receptor binding profiles and quantitative structure-affinity relationships of some 5–substituted-n,n-diallyltryptamines". Bioorganic & Medicinal Chemistry Letters. doi:10.1016/j.bmcl.2015.12.053. 
  2. ^ Julian A. Michely; Andreas G. Helfer; Simon D. Brandt; Markus R. Meyer; Hans H. Maurer (August 2015). "Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC–MS, LC–MS n , and LC–HR–MS–MS". Analytical and Bioanalytical Chemistry. 407: 7831–42. doi:10.1007/s00216-015-8955-0. PMID 26297461. 
  3. ^ Julia Dinger; Campbell Woods; Simon D. Brandt; Markus R. Meyer; Hans H. Maurer (January 2016). "Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class". Toxicology Letters. 241: 82–94. doi:10.1016/j.toxlet.2015.11.013. PMID 26599973. 
  4. ^ Hamilton Morris; Ash Smith (2 May 2010). "The Last Interview With Alexander Shulgin". Vice. Retrieved 3 September 2015. 
  5. ^ "Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs". Retrieved 3 September 2015. 
  6. ^ "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. Retrieved 1 October 2015. 
  7. ^ "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. 
  8. ^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Retrieved 24 July 2015. 
  9. ^ Generaldirektör Christina Rångemark Åkerman (20 April 2012). "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" (PDF) (in Swedish). Retrieved 3 September 2015. 
  10. ^ §1308.11 Schedule I.
  11. ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
  12. ^ "Louisiana State Legislature". Retrieved 3 September 2015. 

External links[edit]