5-MeO-DALT

5-MeO-DALT

Legal status
Legal status	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
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)

5-MeO-DALT or N,N-di allyl-5-methoxy tryptamine 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.

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.

The metabolism and cytochrome P450 inhibition of 5-MeO-DALT has been described in scientific literature.

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.

Dosage

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

Therapeutic use

Numerous anecdotal reports and a small-scale trial indicate the potential of 5-MeO-DALT for the treatment of cluster headache, one of the most excruciating conditions known to medicine. These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache.

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.

Japan

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

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.

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.

United States

5-MeO-DALT is not scheduled at the federal level in the United States, 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.

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.

External links

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