# 5-MeO-DALT

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.

## 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-HT$_6$, α$_{2A}$, α$_{2B}$, α$_{2C}$, H$_1$, κ-opioid, σ$_1$ and σ$_2$ receptors with K$_i$ values lower than 10μM and also acts as a DAT and SERT monoamine reuptake inhibitor.
| 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-HT$_6$ | 6.81 ± 0.03 |
| 5-HT$_7$ | 7.05 ± 0.07 |
| α$_{2A}$ | 6.67 ± 0.07 |
| α$_{2B}$ | 6.14 ± 0.04 |
| α$_{2C}$ | 5.83 ± 0.06 |
| H$_1$ | 6.30 ± 0.06 |
| H$_3$ | 5.77 ± 0.04 |
| κOR | 5.95 ± 0.07 |
| μOR | < 5.00 |
| σ$_1$ | 6.52 ± 0.06 |
| σ$_2$ | 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.

## 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.