4-AcO-DMT

Last updated

4-AcO-DMT
O-Acetylpsilocin chemical structure.png
O-Acetylpsilocin.png
Clinical data
Other names4-Acetoxy-N,N-dimethyltryptamine; 4-Acetoxy-DMT; 4-AcO-DMT; O-Acetylpsilocin; Psilacetin; Psiloacetin; Synthetic shrooms
Routes of
administration 		Oral, intravenous, intranasal, rectal
Drug class Serotonergic psychedelic; Hallucinogen; Serotonin receptor agonist
ATC code
  • None
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • BR: Class F2 (Prohibited psychotropics)
  • CA:Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US:Unscheduled
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. [1] [2] [3] [4] 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. [1] [2] [3] The drug is a prodrug of psilocin and is orally active similarly to psilocybin. [1] [2] [5]

Contents

As a prodrug of psilocin, 4-AcO-DMT acts as a non-selective serotonin receptor agonist, including of the serotonin 5-HT2A receptor. [1] [6] The hallucinogenic effects of psilocin are thought to be mediated by activation of this receptor, although other receptors also contribute to its effects. [7] [8] [1] 4-AcO-DMT's effects are reported to be similar to those of psilocybin and psilocybin mushrooms. [2] [5] [1] 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. [2] [5] [1] It is also said to have a faster onset and shorter duration than psilocybin. [5] The drug is not expected to differ from psilocybin or psilocin in terms of safety. [4] [1] 4-AcO-DMT is slightly less potent by weight than psilocybin, due to their differences in molecular weight and/or metabolism. [2]

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. [2] [6] [3] [4] 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. [2] [6] [3] [4] 4-AcO-DMT was first detected as a designer drug in Europe in 2009. [6] It became increasingly prevalent as a recreational drug in the 2010s and has been the most commonly used novel tryptamine. [2] [5] In the 2020s, 4-AcO-DMT became widely encountered in the form of mushroom edibles ("legal shrooms") in the United States as a legal alternative to psilocybin. [9] [10] [11] [12] Relatedly, it has sometimes been referred to as "synthetic shrooms". [4] 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. [13] [4] [12] [9]

4-AcO-DMT is not an explicitly controlled substance anywhere in the world as of 2023. [2] [1] However, it may technically be a controlled substance under laws throughout the world like the United States's Federal Analogue Act due to its close structural similarity to psilocybin and psilocin. [1] [4] Hence, sale and use of 4-AcO-DMT as a recreational drug exists in a legal gray area. [4] [1]

Effects

Claims of subjective differences in effects between the acetylated and non-acetylated forms of psilocin vary: some users report that 4-AcO-DMT lasts slightly longer, whilst others report that it lasts for a considerably shorter time. [14] [ better source needed ] Many users report less body load and nausea compared with psilocin. [5] Some users find that the visual effects produced by 4-AcO-DMT more closely resemble those produced by DMT than those produced by psilocin or psilocybin. Despite the preceding reports however, there have been no controlled clinical studies to distinguish the subjective effects of psilacetin, psilocin, and psilocybin.

Pharmacology

In the body, 4-AcO-DMT is deacetylated to psilocin by deacetylases/acetyltransferases during first pass metabolism and during subsequent passes through the liver (evident as psilacetin is also active via parenteral routes of ingestion). [2] [ additional citation(s) needed ]

Similarly to psilocybin, psilocin, and other psychedelics, 4-AcO-DMT produces the head-twitch response, a behavioral proxy of psychedelic effects, in rodents. [2] [6] [4] [15] In addition, similarly to psilocybin and other psychedelics, 4-AcO-DMT fully substitutes for DOM in rodent drug discrimination tests. [16] The drug also produces effects such as hypolocomotion and hypothermia in rodents similarly to psilocin. [2]

Chemistry

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

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.

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 homolog 4-AcO-DET suggests that this degraded form of 4-AcO-DMT consists mainly of the hydroxy form of the parent molecule. [17]

4-AcO-DMT is a lower homolog of 4-AcO-MET, 4-AcO-DET, 4-AcO-MiPT and 4-AcO-DiPT. Other analogues include 4-AcO-DPT, 4-MeO-DMT, and 4-PrO-DMT.

History

4-AcO-DMT and several other esters of psilocin were patented on January 16, 1963, by Sandoz Ltd via Albert Hofmann and Franz Troxler. [18] [19] Despite this, psilacetin remains a psychedelic compound with a limited history of use. It is theorized to be a prodrug of psilocin, as is psilocybin, which occurs naturally in many species of psychedelic mushrooms. This is because the aromatic acetyl moiety on the 4th position of the indole ring system is subject to deacetylation in acidic conditions such as those found in the stomach. [20] Psilacetin is O-acetylated psilocin, whereas psilocybin is O-phosphorylated.

Society and culture

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). [21] 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. [21]

United States

4-AcO-DMT is ambiguously legal for use as a lab reagent or research chemical; however, it is an acetate ester of psilocin, meaning it would be considered akin to a Schedule I Controlled Substance under the Federal Analogue Act if sold for human consumption.

4-AcO-DMT is listed (often under 4-Aco-DMT) as a controlled substance at the state level in multiple states in the USA, including Alabama which has made it a schedule I at the state level on March 18th, 2014, along with several other tryptamine analogs. [22]

United Kingdom

4-AcO-DMT, being an ester of psilocin, is a Class A drug in the UK under the Misuse of Drugs Act 1971. [23]

Czech Republic

4-AcO-DMT is prohibited in Czech republic except strictly limited research and therapeutical purposes. [24]

Italy

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

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". [25]

Israel

4-AcO-DMT is technically illegal in Israel as of being a derivative of DMT.

Germany

4-AcO-DMT is banned according to the BtMG since it's an ester of psilocin. [26]

Related Research Articles

<span class="mw-page-title-main">Psilocybin</span> Chemical compound found in some species of mushrooms

Psilocybin, also known as 4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT), and formerly sold under the brand name Indocybin, is a naturally occurring psychedelic prodrug compound produced by more than 200 species of fungi. Psilocybin is itself biologically inactive but is quickly converted by the body to psilocin, which has mind-altering effects similar, in some aspects, to those of other classical psychedelics. Effects include euphoria, hallucinations, changes in perception, a distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

<span class="mw-page-title-main">Psilocybin mushroom</span> Mushrooms containing psychoactive indole alkaloids

Psilocybin mushrooms, commonly known as magic mushrooms,shrooms, or broadly as hallucinogenic mushrooms, are a polyphyletic informal group of fungi that contain psilocybin, which turns into psilocin upon ingestion. The most potent species are members of genus Psilocybe, such as P. azurescens, P. semilanceata, and P. cyanescens, but psilocybin has also been isolated from approximately a dozen other genera, including Panaeolus, Inocybe, Pluteus, Gymnopilus, and Pholiotina.

<span class="mw-page-title-main">5-MeO-AMT</span> Chemical compound

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.

<span class="mw-page-title-main">Psilocin</span> Chemical compound

Psilocin, also known as 4-hydroxy-N,N-dimethyltryptamine (4-OH-DMT), is a substituted tryptamine alkaloid and a serotonergic psychedelic. It is present in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocybin, as well as 4-AcO-DMT (psilacetin), are prodrugs of psilocin.

<span class="mw-page-title-main">Bufotenin</span> Psychedelic drug found in toads, mushrooms and plants

Bufotenin, also known as dimethylserotonin or as 5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT), is a serotonergic psychedelic of the tryptamine family. It is a derivative of the psychedelic dimethyltryptamine (DMT) and of the neurotransmitter serotonin. The compound is an alkaloid found in some species of mushrooms, plants, and toads. It is also found naturally in the human body in small amounts. Bufotenin, for instance derived from the trees Anadenanthera colubrina and Anadenanthera peregrina, appears to have a long history of entheogenic use in South America.

<span class="mw-page-title-main">Diethyltryptamine</span> Chemical compound

DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET. However, despite its structural similarity to DMT, its activity is induced by an oral dose of around 50–100 mg, without the aid of MAO inhibitors, and the effects last for about 2–4 hours.

<span class="mw-page-title-main">4-HO-DET</span> Chemical compound

4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin, ethocybin, and 4-HO-DIPT.

<span class="mw-page-title-main">Baeocystin</span> Chemical compound

Baeocystin, also known as norpsilocybin or 4-phosphoryloxy-N-methyltryptamine (4-PO-NMT), is a zwitterionic alkaloid and analogue of psilocybin. It is found as a minor compound in most psilocybin mushrooms together with psilocybin, norbaeocystin, aeruginascin, and psilocin. Baeocystin is the N-demethylated derivative of psilocybin and the 4-phosphorylated derivative of 4-HO-NMT (4-hydroxy-N-methyltryptamine). The structures at right illustrate baeocystin in its zwitterionic form.

<span class="mw-page-title-main">4-HO-MiPT</span> Chemical compound

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.

<span class="mw-page-title-main">Ethocybin</span> Chemical compound

Ethocybin is a homologue of the mushroom alkaloid psilocybin, and a semi-synthetic psychedelic alkaloid of the tryptamine family. Effects of ethocybin are comparable to those of a shorter LSD or psilocybin trip, although intensity and duration vary depending on dosage, individual physiology, and set and setting.

<span class="mw-page-title-main">Substituted tryptamine</span> Class of indoles

Substituted tryptamines, or simply tryptamines, also known as serotonin analogues (i.e., 5-hydroxytryptamine 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.

<span class="mw-page-title-main">4-AcO-MET</span> Chemical compound

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.

<span class="mw-page-title-main">4-PrO-DMT</span> Chemical compound

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. A number of related derivatives have been synthesized as prodrugs of psilocin for medical applications.

<i>O</i>-Acetylbufotenine Psychedelic tryptamine

O-Acetylbufotenine, or bufotenine O-acetate, also known as 5-acetoxy-N,N-dimethyltryptamine (5-AcO-DMT) or O-acetyl-N,N-dimethylserotonin, is a synthetic tryptamine derivative and putative serotonergic psychedelic. It is the O-acetylated analogue of the naturally occurring peripherally selective serotonergic tryptamine bufotenine and is thought to act as a centrally penetrant prodrug of bufotenine.

<span class="mw-page-title-main">4-HO-TMT</span> Serotonergic compound

4-HO-TMT, or 4-OH-TMT, also known as 4-hydroxy-N,N,N-trimethyltryptammonium or as dephosphorylated aeruginascin, is a substituted tryptamine derivative and the active form of aeruginascin (4-PO-TMT), analogously to how psilocin (4-HO-DMT) is the active form of psilocybin (4-PO-DMT). 4-HO-TMT is closely related to bufotenidine, the N-trimethyl analogue of serotonin.

<i>O</i>-Pivalylbufotenine Tryptamine serotonergic psychedelic

O-Pivalylbufotenine, or bufotenine O-pivalate, also known as 5-pivaloxy-N,N-dimethyltryptamine or O-pivalyl-N,N-dimethylserotonin, is a synthetic tryptamine derivative and putative serotonergic psychedelic. It is the O-pivalyl analogue of the naturally occurring but peripherally selective serotonergic tryptamine bufotenine and is thought to act as a centrally penetrant prodrug of bufotenine.

<span class="mw-page-title-main">4-Hydroxytryptamine</span> Serotonin receptor agonist

4-Hydroxytryptamine, also known as N,N-didesmethylpsilocin, is a naturally occurring tryptamine alkaloid. It is closely related chemically to the neurotransmitter serotonin, the psychedelic psilocin, and is the active form of the tryptamine alkaloid norbaeocystin.

Diamond Shruumz, also sometimes referred to as Diamond Shrooms, is a brand of mushroom edibles sold by Prophet Premium Blends, a company located in Santa Ana, California in the United States. It includes chocolate bar, gummy, and candy cone products. The products are marketed with words such as "magic", "nootropic", and "microdosing". They do not include a full list of ingredients, but are listed as containing a proprietary "mushroom blend". Diamond Shruumz products are sold both online and in some retail stores such as vape shops in the United States.

A mushroom edible, also sometimes known as "legal shrooms", is a food item that may contain hallucinogens associated with those in psychoactive mushrooms, such as psilocybin mushrooms or Amanita muscaria mushrooms. They include chocolate bars and gummies, among others.

References

  1. 1 2 3 4 5 6 7 8 9 10 11 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
  2. 1 2 3 4 5 6 7 8 9 10 11 12 13 Jones NT, Wagner L, Hahn MC, Scarlett CO, Wenthur CJ (2023). "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.
  3. 1 2 3 4 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.
  4. 1 2 3 4 5 6 7 8 9 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.
  5. 1 2 3 4 5 6 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.
  6. 1 2 3 4 5 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. PMID   33860183.
  7. ↑ 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.
  8. ↑ 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.
  9. 1 2 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.
  10. ↑ Ovalle D (4 July 2024). "Psychedelic mushroom edibles promise health benefits. Be wary, experts say". Washington Post. Archived from the original on 3 July 2024. Retrieved 1 February 2025.
  11. ↑ 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.
  12. 1 2 Ducharme J (4 October 2024). "Are Mushroom Edibles Safe and Legal?". TIME. Retrieved 1 February 2025.
  13. ↑ Mole B (5 July 2024). "What we know about microdosing candy illnesses as death investigation underway". Ars Technica. Retrieved 1 February 2025.
  14. ↑ "4-AcO-DMT (also 4-acetoxy-N,N-dimethyltryptamine) : Erowid Exp: Main Index". www.erowid.org. Archived from the original on 2010-07-28.
  15. ↑ Halberstadt AL, Geyer MA (2018). "Effect of Hallucinogens on Unconditioned Behavior". Curr Top Behav Neurosci. 36: 159–199. doi:10.1007/7854_2016_466. PMC   5787039 . PMID   28224459.
  16. ↑ Gatch MB, Hoch A, Carbonaro TM (April 2021). "Discriminative Stimulus Effects of Substituted Tryptamines in Rats". ACS Pharmacol Transl Sci. 4 (2): 467–471. doi:10.1021/acsptsci.0c00173. PMID   33860176.
  17. ↑ "Erowid 4-Acetoxy-DET Vaults : 4-Acetoxy-DET / Ethacetin Degradation". erowid.org. 4 July 2003. Retrieved 10 September 2023.
  18. ↑ USpatent 3075992,Hofmann A, Troxler F,"Esters of indoles", assigned to Sandoz Ltd.
  19. ↑ US 3075992
  20. ↑ Staněk J, Černá MJ (January 1963). "Acidic deacetylation of sugar acetates". Tetrahedron Letters. 4 (1): 35–7. doi:10.1016/S0040-4039(01)90572-6.
  21. 1 2 "Poisons Standard October 2015". Federal Register of Legislation. Australian Government. 30 September 2015. Archived from the original on 2016-01-19. Retrieved 2016-01-06.
  22. ↑ "Controlled Substances List" (PDF). Alabama State Board of Health. 22 February 2024. p. 50. Archived from the original (PDF) on 8 August 2024. Retrieved 18 August 2024.
  23. ↑ Misuse of Drugs Act 1971 (Schedule 2 Part I). 1971.
  24. ↑ "Government regulation of the list of the addictive substances". Federal Register of Legislation. Czech Government.
  25. ↑ "Föreskrifter om ändring i Läkemedelsverkets föreskrifter (LVFS 2011:10) om förteckningar över narkotika" [Regulations on changes in the Swedish Medicines Agency's regulations (LVFS 2011:10) on lists of narcotics](PDF) (in Swedish). Archived (PDF) from the original on 2017-10-31. Retrieved 2017-04-21.
  26. ↑ "Anlage I BtMG". Einzelnorm (in German). Retrieved 2024-11-21.
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