 | |
 | |
| Legal status | |
|---|---|
| Legal status | |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| UNII | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C17H22N2O |
| Molar mass | 270.376 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) (verify) | |
5-MeO-DALT or N,N-di allyl-5-methoxy tryptamine 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. [1]
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. [2]
| 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. [3] [4]
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. [5]
Doses ranging from 12–20 mg were tested by Alexander Shulgin's research group. [6]
Numerous anecdotal reports [7] and a small-scale trial [8] indicate the potential of 5-MeO-DALT for the treatment of cluster headache, one of the most excruciating conditions known to medicine. [9] These observations are consistent with evidence of efficacy of other chemically-related indoleamines in the treatment of cluster headache. [10]
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. [11]
5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law. [12]
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. [13]
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. [14]
5-MeO-DALT is not scheduled at the federal level in the United States, [15] 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. [16]
5-MeO-DALT is a Schedule I controlled substance in the state of Louisiana making it illegal to buy, sell, or possess in Louisiana. [17]
α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.
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) or O-methyl-bufotenin is a psychedelic of the tryptamine class. It is found in a wide variety of plant species, and also is secreted by the glands of at least one toad species, the Colorado River toad. Like its close relatives DMT and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include Five-methoxy, The power, and Toad venom.
5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).
5-MeO-aMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in ethanol.
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 hallucinogenic drug, 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 chemical class. 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, is a psychedelic and entheogenic designer drug.
N-Methyltryptamine (NMT) is a member of the substituted tryptamine chemical class and a natural product which is biosynthesized in the human body from tryptamine by certain N-methyltransferase enzymes, such as indolethylamine N-methyltransferase. It is a common component in human urine. NMT is an alkaloid derived from L-tryptophan that has been found in the bark, shoots and leaves of several plant genera, including Virola, Acacia, Mimosa, and Desmanthus—often together with the related compounds N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT).
5-Methoxy-2,N,N-trimethyltryptamine is a psychoactive drug of the tryptamine chemical class which acts as a psychedelic. It was first synthesized by Alexander Shulgin and reported in his book TiHKAL. 5-MeO-TMT is claimed to show psychoactive effects at a dosage of 75–150 mg orally, but these are relatively mild compared to those of other similar compounds. This suggests that while the methyl group on the 2-position of the molecule has impaired the binding of metabolic enzymes like monoamine oxidase (MAO), it is also interfering with binding to and/or activation of the serotonin 5-HT2A receptor, the target responsible for mediating the hallucinogenic effects of such compounds.
5-MeO-pyr-T (5-methoxy-N,N-tetramethylenetryptamine) is a lesser-known psychedelic drug. It is the 5-methoxy analog of pyr-T. 5-MeO-pyr-T was first synthesized by Hunt & Brimblecombe, who credited S. Mitzal for characterization of chemical properties. Later human tests were reported by Alexander Shulgin, in his book TiHKAL. An oral dosage of 0.5 to 2 mg, and an inhaled dosage of 2–3 mg are reported. 5-MeO-pyr-T causes varying reactions, such as amnesia, tinnitus, vomiting, and a 5-MeO-DMT-like rushing sensation. At the highest dosage reported in TiHKAL, the subject describes awakening from an apparent fugue state during which they were wandering the streets, with complete amnesia upon awakening.
6-MeO-THH, or 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline derivative and a structural isomer of tetrahydroharmine (7-MeO-THH). 6-MeO-THH is mentioned in Alexander Shulgin's book TiHKAL, stating that 6-MeO-THH is very similar to the other carbolines. Limited testing suggests that it possesses mild psychoactive effects at 1.5 mg/kg and is said to be about one-third as potent as 6-methoxyharmalan. It has been isolated from certain plants of the Virola family.
Dimemebfe (5-MeO-BFE) is a recreational drug and research chemical. It acts as an agonist for the 5-HT1A and 5-HT2 family of serotonin receptors. It is related in structure to the psychedelic tryptamine derivative 5-MeO-DMT, but with the indole nitrogen replaced by oxygen, making dimemebfe a benzofuran derivative. It is several times less potent as a serotonin agonist than 5-MeO-DMT and with relatively more activity at 5-HT1A, but still shows strongest effects at the 5-HT2 family of receptors.
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.
Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.
4-Propionoxy-N,N-dimethyltryptamine is a synthetic psychedelic drug from the tryptamine family with psychedelic effects, and is believed to act as a prodrug for psilocin. It produces a head-twitch response in mice. It has been sold online as a designer drug since May 2019. It was first identified as a new psychoactive substance in Sweden, in July 2019.
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.
