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| Formula | C17H22N2O |
| Molar mass | 270.376 g·mol−1 |
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5-MeO-DALT or N,N-diallyl-5-methoxytryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.
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]
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]
| 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]
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]
Doses ranging from 12–20 mg were tested by Alexander Shulgin's research group. [7]
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]
There is no published literature on the toxicity of 5-MeO-DALT.
As of October 2015 5-MeO-DALT is a controlled substance in China. [12]
5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law. [13]
5-MeO-DALT became a Class A drug in the UK on January 7, 2015 after an update to the tryptamine blanket ban.
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]
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]
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.
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]
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]
α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine family. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.
2C-E is a psychedelic phenethylamine of the 2C family. It was first synthesized by Alexander Shulgin and documented in his book PiHKAL. Like the other substances in its family, it produces sensory and cognitive effects in its physical reactions with living organisms.
2C-T-2 is a psychedelic and entactogenic phenethylamine of the 2C family. It was first synthesized in 1981 by Alexander Shulgin, and rated by him as one of the "magical half-dozen" most important psychedelic phenethylamine compounds. The drug has structural and pharmacodynamic properties similar to those of 2C-T-7.
5-MeO-DMT (5-methoxy-N,N-dimethyltryptamine), also known as O-methylbufotenin or mebufotenin, is a naturally occurring psychedelic of the tryptamine family. It is found in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad. It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include five-methoxy, the power, bufo, and toad venom.
5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).
5-MeO-αMT, or 5-methoxy-α-methyltryptamine, also known as α,O-dimethylserotonin (Alpha-O), is a serotonergic psychedelic of the tryptamine family. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT.
4-Hydroxy-N,N-diisopropyltryptamine is a synthetic psychedelic drug. It is a higher homologue of psilocin, 4-HO-DET, and is a positional isomer of 4-HO-DPT and has a tryptamine molecular sub-structure.
Diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural.
5-MeO-MiPT is a psychedelic and hallucinogen of the tryptamine family. It used by some as an entheogen. It has structural and pharmacodynamic properties similar to the drugs 5-MeO-DiPT, DiPT, and MiPT. It is commonly used as a "substitute" for 5-MeO-DiPT because of the very similar structure and effects.
5-MeO-DET or 5-methoxy-N,N-diethyltryptamine is a hallucinogenic tryptamine.
Butylone, also known as β-keto-N-methylbenzodioxolylbutanamine (βk-MBDB), is an entactogen, psychedelic, and stimulant psychoactive drug of the phenethylamine, amphetamine, phenylisobutylamine, and cathinone families. It is the β-keto analogue of MBDB and the substituted methylenedioxyphenethylamine analogue of buphedrone.
4-HO-MiPT is a synthetic substituted aromatic compound and a lesser-known psychedelic tryptamine. It is thought to be a serotonergic psychedelic, similar to magic mushrooms, LSD and mescaline. Its molecular structure and pharmacological effects somewhat resemble those of the tryptamine psilocin, which is the primary psychoactive chemical in magic mushrooms.
5-MeO-DPT, also known as 5-methoxy-N,N-dipropyltryptamine, is a psychedelic and entheogenic designer drug of the tryptamine family related to dipropyltryptamine (DPT) and 5-MeO-DMT.
N-Methyltryptamine (NMT), also known as monomethyltryptamine, is a chemical compound of the tryptamine family and a naturally occurring compound found in the human body and certain plants.
5-Methoxytryptamine, also known as serotonin methyl ether or O-methylserotonin and as mexamine, is a tryptamine derivative closely related to the neurotransmitters serotonin and melatonin. It has been shown to occur naturally in the body in low levels, especially in the pineal gland. It is formed via O-methylation of serotonin or N-deacetylation of melatonin.
4-HO-MET is a lesser-known psychedelic drug. It is a structural and functional analog of psilocin as well as the 4-hydroxyl analog of methylethyltryptamine (MET). 4-HO-MET was first synthesized by Alexander Shulgin. In his book TiHKAL, the dosage is listed as 10-20 mg. 4-HO-MET produces psilocin-like distortion of color, sound, and form. Very little data exists about the pharmacological properties, metabolism, and toxicity of 4-HO-MET. There have been no reports of deaths from 4-HO-MET, even though there exist anecdotal reports of the ingestion of up to 150 mg, more than an order of magnitude above the effective dose.
α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a tryptamine derivative closely related to the neurotransmitter serotonin (5-HT). It acts as a non-selective serotonin receptor agonist and has been used extensively in scientific research to study the function of the serotonin system.
N,N-Diallyltryptamine (DALT) is a tryptamine derivative which has been identified as a new psychoactive substance. It has been used as an intermediate in the preparation of radiolabeled diethyltryptamine.
4-acetoxy-MET (4-acetoxy-N-methyl-N-ethyltryptamine), also known as 4-AcO-MET or metacetin, is a hallucinogenic tryptamine. It is the acetate ester of 4-HO-MET, and a homologue of 4-AcO-DMT. It is a novel compound with very little history of human use. It is sometimes sold as a research chemical by online retailers.
MALT is a lesser-known drug from the tryptamine family. It is a novel compound with very little history of human use. It is closely related to methylpropyltryptamine (MPT), as well as N-methyltryptamine. It has been sold online as a designer drug. Very little information on the pharmacology or toxicity of MALT is available.
