5-MeO-DALT
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Formula | C17H22N2O |
Molar mass | 270.376 g·mol−1 |
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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.[1]
Pharmacology[]
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]
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.[5]
Dosage[]
Doses ranging from 12–20 mg were tested by Alexander Shulgin's research group.[6]
Therapeutic use[]
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]
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.[11]
Japan[]
5-MeO-DALT became a controlled substance in Japan from April 2007, by amendment to the Pharmaceutical Affairs Law.[12]
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.[13]
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.[14]
United States[]
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.
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.[16]
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.[17]
Notes[]
- ^ Chadeayne AR, Pham DN, Golen JA, Manke DR (2020-04-28). "5-MeO-DALT: the freebase of N , N -diallyl-5-methoxytryptamine". IUCrData. 5 (4): x200498. doi:10.1107/S2414314620004988.
- ^ Cozzi NV, Daley PF (February 2016). "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines". Bioorganic & Medicinal Chemistry Letters. 26 (3): 959–964. doi:10.1016/j.bmcl.2015.12.053. PMID 26739781.
- ^ Michely JA, Helfer AG, Brandt SD, Meyer MR, Maurer HH (October 2015). "Metabolism of the new psychoactive substances N,N-diallyltryptamine (DALT) and 5-methoxy-DALT and their detectability in urine by GC-MS, LC-MSn, and LC-HR-MS-MS" (PDF). Analytical and Bioanalytical Chemistry. 407 (25): 7831–42. doi:10.1007/s00216-015-8955-0. PMID 26297461. S2CID 26086597.
- ^ Dinger J, Woods C, Brandt SD, Meyer MR, Maurer HH (January 2016). "Cytochrome P450 inhibition potential of new psychoactive substances of the tryptamine class" (PDF). Toxicology Letters. 241: 82–94. doi:10.1016/j.toxlet.2015.11.013. PMID 26599973.
- ^ Hamilton Morris; Ash Smith (2 May 2010). "The Last Interview With Alexander Shulgin". Vice. Retrieved 3 September 2015.
- ^ "Sasha Shulgin - 5-MeO-DALT, 2C-B-FLY & 5-EtOs". Archived from the original on 2021-12-13. Retrieved 3 September 2015.
- ^ Post M. "Cluster Headache Patient Survey: 5-MeO-DALT". Cite journal requires
|journal=
(help) - ^ Post M. "Treatment of Cluster Headache Symptoms using Synthetic Tryptamine N,N-Diallyl-5 Methoxytryptamine". Cite journal requires
|journal=
(help) - ^ Brandt RB, Doesborg PG, Haan J, Ferrari MD, Fronczek R (February 2020). "Pharmacotherapy for Cluster Headache". CNS Drugs. 34 (2): 171–184. doi:10.1007/s40263-019-00696-2. PMC 7018790. PMID 31997136.
- ^ Schindler EA, Gottschalk CH, Weil MJ, Shapiro RE, Wright DA, Sewell RA (2015-10-20). "Indoleamine Hallucinogens in Cluster Headache: Results of the Clusterbusters Medication Use Survey". Journal of Psychoactive Drugs. 47 (5): 372–81. doi:10.1080/02791072.2015.1107664. PMID 26595349. S2CID 21948146.
- ^ "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. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
- ^ "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.
- ^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
- ^ 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.
- ^ §1308.11 Schedule I.
- ^ Florida Statutes - Chapter 893 - DRUG ABUSE PREVENTION AND CONTROL
- ^ "Louisiana State Legislature". Retrieved 3 September 2015.
External links[]
- Designer drugs
- Entactogens and empathogens
- Entheogens
- Mexamines
- Psychedelic tryptamines
- Allyl compounds