4-AcO-DMT

Last updated

4-AcO-DMT
O-Acetylpsilocin chemical structure.png
4-AcO-DMT 3D.png
Clinical data
Other names4-Acetoxy-N,N-dimethyltryptamine; 4-Acetoxy-DMT; 4-AcO-DMT; O-Acetylpsilocin; Acetylpsilocin; Psilocin O-acetate; PSOA; Psilacetin; Psiloacetin; Synthetic shrooms
Routes of
administration 		Oral [1] [2] [3]
Drug class Non-selective serotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Metabolism Deacetylation, others
Metabolites • Psilocin
• Psilocin metabolites
Onset of action 15–40 minutes [3]
Duration of action 3–8 hours [1] [2] [3]
Identifiers
  • 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl acetate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C14H18N2O2
Molar mass 246.310 g·mol−1
3D model (JSmol)
Melting point 172 to 173 °C (342 to 343 °F)
  • CC(=O)Oc2cccc1[nH]cc(CCN(C)C)c12
  • InChI=1S/C14H18N2O2/c1-10(17)18-13-6-4-5-12-14(13)11(9-15-12)7-8-16(2)3/h4-6,9,15H,7-8H2,1-3H3 Yes check.svgY
  • Key:RTLRUOSYLFOFHV-UHFFFAOYSA-N Yes check.svgY
   (verify)

4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT or 4-acetoxy-DMT), also known as O-acetylpsilocin or psilacetin, is a psychedelic drug of the tryptamine family related to psilocybin and psilocin. [4] [5] [6] [7] It is a synthetic derivative of psilocin (4-HO-DMT) in which the hydroxyl group has been acetylated, and is the analogue of psilocybin (4-PO-DMT) in which the phosphate ester has been replaced with an acetate ester. [4] [5] [6] The drug is a prodrug of psilocin and is used orally similarly to psilocybin. [4] [5] [8] [1] [2]

Contents

As a prodrug of psilocin, 4-AcO-DMT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. [4] [9] The hallucinogenic effects of psilocin are thought to be mediated by activation of this receptor, although other receptors also contribute to its effects. [10] [11] [4] 4-AcO-DMT's effects are reported to be similar to those of psilocybin and psilocybin mushrooms. [5] [8] [4] However, it has been said to have reduced side effects such as nausea and body load that can be caused by ingestion of whole psilocybin mushrooms. [5] [8] [4] It is also said to have a faster onset and shorter duration than psilocybin. [8] The drug is not expected to differ from psilocybin or psilocin in terms of safety. [4] 4-AcO-DMT is modestly less potent by weight than psilocybin in animals when they are given at equimolar doses. [5]

4-AcO-DMT was first described in a patent by Albert Hofmann in 1963 and its chemical synthesis was improved by David E. Nichols and colleagues in 1999. [5] [9] [6] It was suggested by Nichols as a more economical and accessible alternative to psilocybin for use in scientific research, as the synthesis of psilocybin is more challenging and as psilocybin is a controlled substance. [5] [9] [6] 4-AcO-DMT was first detected as a designer drug in Europe in 2009. [9] It became increasingly prevalent as a recreational drug in the 2010s and has been the most commonly used novel tryptamine. [5] [8] In the 2020s, 4-AcO-DMT became widely encountered in the form of mushroom edibles in the United States as an alternative to psilocybin. [12] [13] [14] [15] Relatedly, it has sometimes been referred to as "synthetic shrooms". [7] Mushrooms edibles may contain 4-AcO-DMT, Amanita muscaria mushroom constituents, or non-mushroom drugs such as bath salts, and have been linked to poisonings and deaths. [16] [7] [15] [12]

4-AcO-DMT is not scheduled under United States law or any international drug schedules, including the United Nations 1971 Convention on Psychotropic Substances, making it a potentially more accessible alternative to psilocybin for research. [5] It can be imported and possessed for research in the United States if labeled “not for human consumption,” but using it in vivo is illegal and violates the Federal Analogue Act. [4]

Use and effects

In his book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin lists the same dose range of 10 to 20 mg  orally and duration of 3 to 6 hours for psilocin, psilocybin, and 4-AcO-DMT. [1] Another publication gave a 4-AcO-DMT dose range of 10 to 15 mg orally, with a typical dose of 12.5 mg orally, and a duration of about 5 to 8 hours. [2] A further source gave a dose range for the drug of 5 to 30 mg orally, an onset of 15 to 40 minutes, and a duration of 4 to 7 hours. [3] 4-AcO-DMT is a prodrug of psilocin similarly to psilocybin and its effects are reported to be similar or identical to those of psilocybin and psilocybin-containing mushrooms. [5] [8] [3] However, it is said to produce less nausea and body load than psilocybin-containing mushrooms. [5] [8] [4] The drug is also often described as having a faster onset and shorter duration than psilocybin. [8] 4-AcO-DMT is modestly less potent by weight than psilocybin in animals when they are given at equimolar doses. [5]

Specific effects of 4-AcO-DMT have been reported to include psychedelic visuals, closed-eye imagery, synesthesia, insights, disembodiment, euphoria, feelings of bliss and unity, oceanic boundlessness, ego dissolution, sedation, cognitive impairment, and spiritual experiences, among others. [2] [3] Adverse effects have been reported to include psychological side effects such as anxiety, paranoia, and low mood as well as gastrointestinal side effects such as nausea and vomiting. [2]

Side effects

4-AcO-DMT, as a prodrug of psilocin, is not expected to differ from psilocybin or psilocin in terms of safety. [4]

Interactions

Pharmacology

Pharmacodynamics

Psilocin at molecular targets
TargetAffinity (Ki, nM)
5-HT1A 49–567 (Ki)
130–>3,160 (EC50 Tooltip half-maximal effective concentration)
0.7%–96% (Emax Tooltip maximal efficacy)
5-HT1B 31–305
5-HT1D 19–36
5-HT1E 44–52
5-HT1F ND
5-HT2A 6.0–340 (Ki)
2.4–3,836 (EC50)
16–98% (Emax)
5-HT2B 4.6–410 (Ki)
2.4–>20,000 (EC50)
1.4–84% (Emax)
5-HT2C 10–141 (Ki)
9.1–30 (EC50)
86–95% (Emax)
5-HT3 >10,000
5-HT4 ND
5-HT5A 70–84
5-HT6 57–72
5-HT7 3.5–72
α1A–α1B >10,000
α2A 1,379–2,044
α2B 1,271–1,894
α2C 4,404
β1–β2 >10,000
D1 20–>14,000
D2 3,700–>10,000
D3 101–8,900
D4 >10,000
D5 >10,000
H1 1,600–>10,000
H2–H4 >10,000
M1–M5 >10,000
σ1 >10,000
σ2 >10,000
I2 792
TAAR1 1,400 (Ki) (rat)
17,000 (Ki) (mouse)
920–2,700 (EC50) (rodent)
>30,000 (EC50) (human)
SERT Tooltip Serotonin transporter3,650–>10,000 (Ki)
662–3,900 (IC50 Tooltip half-maximal inhibitory concentration)
561 (EC50)
54% (Emax)
NET Tooltip Norepinephrine transporter13,000 (Ki)
14,000 (IC50)
>10,000 (EC50)
DAT Tooltip Dopamine transporter6,000–>30,000 (Ki)
>100,000 (IC50)
>10,000 (EC50)
Notes: The smaller the value, the more avidly psilocin interacts with the site. Sources: [17] [18] [19] [20] [21] [22] [23] [24] [25] [26] [27] [28] [29] [30] [31] [32] [33] [34] [35]

4-AcO-DMT is a prodrug of psilocin (4-HO-DMT). [5] As a prodrug of psilocin, 4-AcO-DMT acts as a non-selective agonist of serotonin receptors, including of the serotonin 5-HT2A receptor. [4] The psychedelic effects of 4-AcO-DMT are mediated specifically by activation of the serotonin 5-HT2A receptor. [4]

Similarly to psilocybin, psilocin, and other serotonergic psychedelics, 4-AcO-DMT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [5] [9] [7] [36] In addition, like psilocybin and other psychedelics, 4-AcO-DMT fully substitutes for the psychedelic DOM in rodent drug discrimination tests. [37] 4-AcO-DMT produces effects such as hypolocomotion and hypothermia in rodents as with psilocin as well. [5]

Pharmacokinetics

There are no clinical studies of the pharmacokinetics of 4-AcO-DMT as of 2024. [5] However, the pharmacokinetics of 4-AcO-DMT have been studied in rodents. [5] The drug was confirmed to act as a prodrug of psilocin similarly to psilocybin (4-PO-DMT). [5] However, given by intraperitoneal injection at equimolar doses, 4-AcO-DMT showed only 70% of the relative bioavailability or total exposure of psilocybin. [5] Hence, 4-AcO-DMT results in modestly lower psilocin levels than psilocybin even when the drugs are given at equivalent doses with adjustment for differences in molecular weight. [5] Along similar lines, the psilocin concentrations with 4-AcO-DMT 15 minutes after administration were 75 to 90% of those of an equimolar dose of psilocybin. [5] The elimination half-life of psilocin was approximately 30 minutes and did not differ between 4-AcO-DMT and psilocybin. [5] Psilocin ester prodrugs like 4-AcO-DMT are cleaved into psilocin by esterase enzymes. [38]

A 2025 in-vitro study examined the stability and metabolism of several psilocin ester prodrugs, including 4-AcO-DMT. [39] The results showed that 4-AcO-DMT was rapidly broken down into psilocin by esterase enzymes, with over 99.9% of the prodrug converted within 5 minutes under conditions mimicking the human body (i.e., in human plasma). [39] These findings support the idea that 4-AcO-DMT is quickly and efficiently converted into psilocin before it enters the bloodstream, and that the prodrug itself likely contributes little to the overall pharmacological effect. [39]

Chemistry

4-AcO-DMT shown in powder form. 4-AcO-DMT 1g.png
4-AcO-DMT shown in powder form.

Synthesis

4-AcO-DMT can be obtained by acetylation of psilocin under alkaline or strongly acidic conditions. It is, therefore, a synthetic compound. 4-AcO-DMT is more resistant than psilocin to oxidation under basic conditions due to its acetoxy group. It is not as difficult as psilocybin to synthesize.[ citation needed ]

Stability

Given enough time in unfavorable conditions, 4-AcO-DMT can sometimes turn into a degraded form which is brown in color and can even progress into a brown/black tar-like substance. Researchers hypothesize this is a polymerization reaction and is said to have no effect on the potency of the substance. Preliminary GCMS analysis of the closely related homologue 4-AcO-DET suggests that this degraded form of 4-AcO-DMT consists mainly of the hydroxy form of the parent molecule. [40]

Analogues

4-AcO-DMT is closely related to psilocin (4-HO-DMT) and psilocybin (4-PO-DMT). [1] It is a lower homologue of 4-AcO-MET, 4-AcO-DET, 4-AcO-MiPT, and 4-AcO-DiPT. [1] Other analogues of 4-AcO-DMT include 4-AcO-DPT, 4-MeO-DMT, and 4-PrO-DMT (O-propionylpsilocin). [1] [41] Other related prodrugs of psilocin besides 4-AcO-DMT, 4-PrO-DMT, and psilocybin include CT-4201, EB-002, RE-109 (4-GO-DMT), and MSP-1014.

History

4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963 by Sandoz via Albert Hofmann and Franz Troxler. [5] [9] [42] [43] The drug's chemical synthesis was improved by David E. Nichols and colleagues in 1999 and it was suggested as a more economical and accessible alternative to psilocybin for use in scientific research. [5] [9] [6] 4-AcO-DMT was first detected as a designer drug in Europe in 2009. [9] It became increasingly prevalent as a recreational drug in the 2010s and has been the most commonly used novel tryptamine. [5] [8] In the 2020s, 4-AcO-DMT became widely encountered in the form of mushroom edibles in the United States as an alternative to psilocybin and psilocybin-containing mushrooms. [12] [13] [14] [15]

Society and culture

International

4-AcO-DMT is not scheduled under any international drug schedules, including the United Nations 1971 Convention on Psychotropic Substances, making it a potentially more accessible alternative to psilocybin for research. [44]

Australia

4-AcO-DMT can be considered an analog of psilocin making it a Schedule 9 prohibited substance in Australia under the Poisons Standard (October 2015). [45] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities. [45]

Czech Republic

4-AcO-DMT is prohibited in Czech Republic except strictly limited research and therapeutical purposes. [46]

Germany

4-AcO-DMT is banned in Germany according to the BtMG since it is an ester of psilocin. [47]

Israel

4-AcO-DMT is technically illegal in Israel as of being a derivative of dimethyltryptamine (DMT).[ citation needed ]

Italy

4-AcO-DMT is illegal in Italy as it is an ester of a prohibited substance.[ citation needed ]

Sweden

The Riksdag added 4-AcO-DMT to Narcotic Drugs Punishments Act under swedish schedule I ("substances, plant materials and fungi which normally do not have medical use" ) as of January 25, 2017, published by Medical Products Agency (MPA) in regulation HSLF-FS 2017:1 listed as "4-acetoxi-N,N-dimetyltryptamin". [48]

United Kingdom

4-AcO-DMT, being an ester of psilocin, is a Class A drug in the United Kingdom under the Misuse of Drugs Act 1971. [49]

United States

In the United States, 4-AcO-DMT can be legally sold and possessed when labeled as “not for human consumption” and intended solely for research purposes. [4] However, its use in humans is prohibited under the Federal Analogue Act, as it is considered a controlled substance analogue of psilocybin. [4] The Controlled Substance Analogue Enforcement Act of 1986 (of which the Federal Analogue Act is part) criminalized the creation of designer drugs. [50] As such, it is illegal in the United States. [51]

4-AcO-DMT is listed (often under 4-Aco-DMT) as a controlled substance at the state level in multiple states in the United States, including in Alabama which has made it a schedule I at the state level on March 18, 2014, along with several other tryptamine analogues. [52]

See also

References

  1. 1 2 3 4 5 6 7 Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252. https://www.erowid.org/library/books_online/tihkal/tihkal18.shtml
  2. 1 2 3 4 5 6 Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG (June 2022). "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology (Berl). 239 (6): 1783–1796. doi:10.1007/s00213-022-06142-4. PMC   9166850 . PMID   35487983.
  3. 1 2 3 4 5 6 "4-AcO-DMT (Ацетилпсилоцин)". АИПСИН (in Russian). Retrieved 1 January 2026.
  4. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 Geiger HA, Wurst MG, Daniels RN (October 2018). "DARK Classics in Chemical Neuroscience: Psilocybin" (PDF). ACS Chem Neurosci. 9 (10): 2438–2447. doi:10.1021/acschemneuro.8b00186. PMID   29956917. A chemically modified psilocin precursor, known as psilacetin (20), O-acetylpsilocin, or 4-acetoxy-N,N-dimethyltryptamine, which replaces the phosphoryloxy group found on psilocybin with an acetoxy group, is also readily available. The substituted acetoxy group is believed to be metabolized in an equivalent manner to the phosphoryloxy group, both producing psilocin during first-pass metabolism.37 This simple modification skirts written laws in the United States when the product is clearly designated "not for human consumption," allowing pseudolegal import and possession for research purposes only; however, if it were to be used in vivo, the user would be in violation of the Federal Analogue Act.38 Although psilacetin has been hypothesized to act as an identical pharmacological substitute for psilocybin, many users report a small, yet significant, difference in the effects of each drug.39 Psilacetin is often described as having a faster onset of action without the anxiety and nausea associated with psilocybin-containing mushroom ingestion (which could be due to avoiding the ingestion of the significant amounts of chitin usually found in these mushrooms) and to have a shorter duration of action with a more peaceful experience throughout, leaving most users with a positive afterglow.37,39
  5. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 Jones NT, Wagner L, Hahn MC, Scarlett CO, Wenthur CJ (2024). "In vivo validation of psilacetin as a prodrug yielding modestly lower peripheral psilocin exposure than psilocybin". Front Psychiatry. 14 1303365. doi: 10.3389/fpsyt.2023.1303365 . PMC   10804612 . PMID   38264637.
  6. 1 2 3 4 5 Nichols D, Fescas S (1999). "Improvements to the Synthesis of Psilocybin and a Facile Method for Preparing the O-Acetyl Prodrug of Psilocin" (PDF). Synthesis. 1999 (6): 935–938. CiteSeerX   10.1.1.690.8071 . doi:10.1055/s-1999-3490. S2CID   32044725. Archived (PDF) from the original on 17 February 2012. Retrieved 17 January 2012.
  7. 1 2 3 4 Wright W (24 June 2024). "4-AcO-DMT Is the Most Accessible (and Mysterious) Drug on the Market Right Now". DoubleBlind Mag. Retrieved 2 February 2025.
  8. 1 2 3 4 5 6 7 8 9 Palamar JJ, Acosta P (January 2020). "A qualitative descriptive analysis of effects of psychedelic phenethylamines and tryptamines". Human Psychopharmacology. 35 (1) e2719. doi:10.1002/hup.2719. PMC   6995261 . PMID   31909513. 4-AcO-DMT (4-acetoxyN,N-dimethyltryptamine, O-acetylpsilocin, or psilacetin) was the most prevalent tryptamine reported with 30.8% of the sample reporting use and two thirds (66.7%) of tryptamine users reporting use. 4-AcO-DMT—often pronounced as "4-akko-DMT"—was reported by most users as producing similar effects as psilocybin mushrooms with less nausea. One participant referred to this compound as "silly pills," which is a play on the name psilocybin. This particular compound was often preferred over natural mushrooms due to the lack of adverse side effects such as nausea, which the natural mushroom tends to produce. Thus, participants often suggested that 4-AcODMT allows one to achieve the same high as psilocybin without adverse physical effects such as nausea and heavy body load. One participant did complain of dry mouth and mentioned that although 4-AcO-DMT feels similar to psilocybin, he said it lacks the "organic" feel produced by psilocybin. [...] Of the most common tryptamines used by this sample, the majority of these compounds were first discovered or first synthesized as early as the 1930s (e.g., 5-MeO-DMT), 1950s (e.g., 4-AcO-DMT), or in the 1970s (e.g., 4-HO-MET and 5-MeO-DIPT). [...] 4-AcO-DMT was the most commonly used tryptamine by participants, and this compound also appears to be among the most prevalent novel tryptamines in recent years (Palamar & Le, 2019; PalmaConesa et al., 2017). [...] 4-AcO-DMT is often described as having a faster onset of action than psilocybin with a high of shorter duration, and as many of our participants noted, use allows them to avoid the nausea commonly associated mushroom ingestion (Geiger et al., 2018). Despite 4-AcO-DMT being among the most prevalent tryptamines, and having been discovered in the 1950s, little academic research has focused on recreational use of this compound.
  9. 1 2 3 4 5 6 7 8 Klein AK, Chatha M, Laskowski LJ, Anderson EI, Brandt SD, Chapman SJ, et al. (April 2021). "Investigation of the Structure-Activity Relationships of Psilocybin Analogues". ACS Pharmacol Transl Sci. 4 (2): 533–542. doi:10.1021/acsptsci.0c00176. PMC   8033608 . PMID   33860183.
  10. ↑ Halberstadt AL (January 2015). "Recent advances in the neuropsychopharmacology of serotonergic hallucinogens". Behav Brain Res. 277: 99–120. doi:10.1016/j.bbr.2014.07.016. PMC   4642895 . PMID   25036425.
  11. ↑ Kwan AC, Olson DE, Preller KH, Roth BL (November 2022). "The neural basis of psychedelic action". Nat Neurosci. 25 (11): 1407–1419. doi:10.1038/s41593-022-01177-4. PMC   9641582 . PMID   36280799.
  12. 1 2 3 Blakinger K, Sheets C (9 August 2024). "Magic mushroom chocolates are having a moment. But do they even contain mushrooms?". Los Angeles Times. Retrieved 1 February 2025.
  13. 1 2 Ovalle D (4 July 2024). "Psychedelic mushroom edibles promise health benefits. Be wary, experts say". Washington Post. Archived from the original on 4 July 2024. Retrieved 1 February 2025.
  14. 1 2 Syal A (18 July 2024). "Mushroom edibles are rising in popularity. It's hard to say what's in them". NBC News. Retrieved 1 February 2025.
  15. 1 2 3 Ducharme J (4 October 2024). "Are Mushroom Edibles Safe and Legal?". TIME. Retrieved 1 February 2025.
  16. ↑ Mole B (5 July 2024). "What we know about microdosing candy illnesses as death investigation underway". Ars Technica. Retrieved 1 February 2025.
  17. ↑ Liu T. "BindingDB BDBM50081701 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol::4-hydroxy-N,N-dimethyltryptamine::CHEMBL65547::N,N-dimethyl-4-hydroxytryptamine::Psilocin::US11427604, Compound (I-45)::US11453689, Compound Psilocin::US11591353, Compound I-45::US11597738, Example 3::US11642336, Compound Psilocin::US20240051978, Compound Psilocin". BindingDB. Retrieved 5 September 2024.
  18. ↑ Liu T. "BindingDB BDBM50171269 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate::4-phosphoryloxy-N,N-dimethyltryptamine::CHEMBL194378::Indocybin::O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine::Psilocybine::US11597738, Example 4::psilocin phosphate ester::psilocybin". BindingDB. Retrieved 5 September 2024.
  19. ↑ "PDSP Database". UNC (in Zulu). Retrieved 2024-09-05.
  20. ↑ "PDSP Database". UNC (in Zulu). Retrieved 2024-09-05.
  21. ↑ Holze F, Singh N, Liechti ME, D'Souza DC (May 2024). "Serotonergic Psychedelics: A Comparative Review of Efficacy, Safety, Pharmacokinetics, and Binding Profile". Biol Psychiatry Cogn Neurosci Neuroimaging. 9 (5): 472–489. doi: 10.1016/j.bpsc.2024.01.007 . PMID   38301886.
  22. ↑ Dodd S, Norman TR, Eyre HA, Stahl SM, Phillips A, Carvalho AF, et al. (August 2023). "Psilocybin in neuropsychiatry: a review of its pharmacology, safety, and efficacy" (PDF). CNS Spectr. 28 (4): 416–426. doi:10.1017/S1092852922000888. PMID   35811423.
  23. ↑ Tylš F, Páleníček T, Horáček J (March 2014). "Psilocybin - summary of knowledge and new perspectives". Eur Neuropsychopharmacol. 24 (3): 342–356. doi:10.1016/j.euroneuro.2013.12.006. PMID   24444771.
  24. ↑ Wojtas A, Gołembiowska K (December 2023). "Molecular and Medical Aspects of Psychedelics". Int J Mol Sci. 25 (1): 241. doi: 10.3390/ijms25010241 . PMC   10778977 . PMID   38203411.
  25. ↑ Rickli A, Moning OD, Hoener MC, Liechti ME (August 2016). "Receptor interaction profiles of novel psychoactive tryptamines compared with classic hallucinogens" (PDF). Eur Neuropsychopharmacol. 26 (8): 1327–1337. doi:10.1016/j.euroneuro.2016.05.001. PMID   27216487.
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  28. ↑ US 11440879,Andrew Carry Kruegel,"Methods of treating mood disorders",published 10 February 2022, assigned to Gilgamesh Pharmaceuticals, Inc.
  29. ↑ Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012). "Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters". The Journal of Pharmacology and Experimental Therapeutics. 341 (1): 251–262. doi:10.1124/jpet.111.188946. PMC   3364510 . PMID   22271821.
  30. ↑ Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.
  31. ↑ Marek GJ, Makai-Bölöni S, Umbricht D, Christian EP, Winters J, Dvorak D, et al. (October 2025). "A novel psychedelic 5-HT2A receptor agonist GM-2505: The pharmacokinetic, safety, and pharmacodynamic profile from a randomized trial healthy volunteer". J Psychopharmacol 2698811251378512. doi:10.1177/02698811251378512. PMID   41099491.
  32. ↑ Wsół A (December 2023). "Cardiovascular safety of psychedelic medicine: current status and future directions". Pharmacol Rep. 75 (6): 1362–1380. doi:10.1007/s43440-023-00539-4. PMC   10661823 . PMID   37874530.
  33. ↑ Chen X, Li J, Yu L, Maule F, Chang L, Gallant JA, et al. (October 2023). "A cane toad (Rhinella marina) N-methyltransferase converts primary indolethylamines to tertiary psychedelic amines". J Biol Chem. 299 (10) 105231. doi:10.1016/j.jbc.2023.105231. PMC   10570959 . PMID   37690691.
  34. ↑ Chen X, Li J, Yu L, Dhananjaya D, Maule F, Cook S, et al. (10 March 2023), Bioproduction platform using a novel cane toad (Rhinella marina) N-methyltransferase for psychedelic-inspired drug discovery (PDF), doi: 10.21203/rs.3.rs-2667175/v1 , retrieved 18 March 2025
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