ALD-52

Last updated
ALD-52
ALD-52 image.svg
Clinical data
Other names1-Acetyl-N,N-diethyllysergamide, ALD, N-acetyl-LSD, Acetyl lysergic acid diethylamide, d-acetyl lysergic acid diethylamide, d-acetyldiethyllysergamide
Routes of
administration 		Oral
Legal status
Legal status
  • AU:Unscheduled
  • BR: Class F2 (Prohibited psychotropics) [1]
  • CA:Unscheduled
  • DE: NpSG (Industrial and scientific use only)
  • UK: Class A
  • US:Unscheduled, could be persecuted under the Federal Analogue Act.
  • Unscheduled in the most countries of the world, Illegal in France, Romania, Switzerland, Finland and Singapore [2]
Pharmacokinetic data
Metabolism hepatic
Excretion renal
Identifiers
  • (6aR,9R)-4-Acetyl-N,N-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C22H27N3O2
Molar mass 365.477 g·mol−1
3D model (JSmol)
  • O=C(n1cc2c3c(C4=C[C@@H](C(=O)N(CC)CC)CN([C@@H]4C2)C)cccc13)C
  • InChI=1S/C22H27N3O2/c1-5-24(6-2)22(27)16-10-18-17-8-7-9-19-21(17)15(13-25(19)14(3)26)11-20(18)23(4)12-16/h7-10,13,16,20H,5-6,11-12H2,1-4H3/t16-,20-/m1/s1 Yes check.svgY
  • Key:FJOWXGYLIWJFCH-OXQOHEQNSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

ALD-52, also known as 1-acetyl-LSD, has chemical structural features similar to lysergic acid diethylamide (LSD), a known psychedelic drug. [3] [4] Similarly, ALD-52 has been reported to produce psychoactive effects, but its pharmacological effects on humans are poorly understood. Given its psychoactive properties, it has been reported to be consumed as a recreational drug, and the purported first confirmed detection of the substance on the illicit market occurred in April 2016. [4] [5]

Contents

ALD-52 was initially synthesized in 1957 by Albert Hofmann, who is accredited as the first individual to have synthesised LSD, a chemical analogue of ALD-52. Until the rise in popularity of psychedelics in the 1960s, ALD-52 was not widely studied. [6] It is assumed to act as a prodrug to LSD in humans, but this has yet to be scientifically verified. [7]

Effects

In Entry 26 of his compendium TiHKAL , which discussed LSD, chemist Alexander Shulgin touched briefly on the subject of ALD-52. His comments there are vague, second-hand accounts saying doses in the 50–175 μg range have resulted in various conclusions. One account found that there was less visual distortion than with LSD and it seemed to produce less anxiety and tenseness and that it was somewhat less potent. One subject claimed it was more effective in increasing blood pressure, and another could not tell them apart. [8]

Safety

In The Hallucinogens by Hoffer and Osmond (1967), ALD-52 is listed as having a lower (approximately 1/5) intravenous toxicity (in rabbits), a lower (approximately 1/8) pyretogenic effect, an equal psychological effect in humans, and double the "antiserotonin" effect as compared with LSD. Human experiments have not been well documented.[ medical citation needed ]

History

In a Reddit AMA with the director of the movie The Sunshine Makers , Tim Scully says:

"The Orange Sunshine we delivered was LSD 25. ALD 52 was an ill-advised desperate defense strategy that failed miserably... The story of Orange Sunshine is complicated by the fact that The Brotherhood distributed LSD from more than one manufacturer as Orange Sunshine. "Nick and I made the original Orange Sunshine in Windsor. That was the last lab I worked in making LSD. Ron Stark managed several LSD labs in Europe and most of his output was tableted and sold as Orange Sunshine. At least some of the LSD that his labs made was not pure." [9]

Tim Scully has confirmed that the speculation below is incorrect.

The Orange Sunshine variety of LSD that was widely available in California through 1968 and 1969 was produced in the Sonoma County underground chemistry lab of Tim Scully and Nicholas Sand. It was shut down by the police, and Scully was arrested and prosecuted. This resulted in the first drug analogue trial, where Scully claimed that he and his partners did nothing illegal, because they were producing ALD-52, which was not an illicit drug. However, as the prosecution claimed, there were problems with such a rationale—ALD-52 was claimed to readily undergo hydrolysis to LSD, and secondly, the synthesis of ALD-52 required LSD. (The second point was based on the methods available in the scientific literature at the time). Scully was convicted and served time in prison.

ALD-52 ALD-52 animation.gif
ALD-52

Austria

ALD-52 is technically not illegal but it may fall in the NPSG (Neue-Psychoaktive-Substanzen-Gesetz Österreich) as an analogue of LSD.

Denmark

ALD-52 is not listed as an illegal substance in Denmark as of April, 2019, and its chemical class 'lysergamide' is not banned under the Analogue Act (Some LSD analogues are, however, prohibited). [10]

Finland

ALD-52 is labeled a controlled psychoactive substance in Finland as of 2014. [11]

Germany

ALD-52 is controlled under the NpSG as of July 18, 2019. [12] [13] Production and import with the aim to place it on the market, administration to another person and trading is punishable. Possession is illegal but not penalized. [14]

Latvia

ALD-52 is illegal in Latvia. Although it isn't officially scheduled, it is controlled as an LSD structural analog due to an amendment made on June 1, 2015. [15]

Romania

1P-LSD is illegal to produce or sell in Romania. It is not included directly in the list of controlled substances, but it is included in an analogue act. However, it is not, as of yet, classified as illegal to use.

Singapore

ALD-52 is a class A controlled drug, and is illegal to traffic, manufacture, import, export, possess, or consume in Singapore as of December 1, 2019, punishable with a minimum of five years' imprisonment and five strokes of the cane. [16]

Switzerland

Since March 2018, ALD-52 is illegal in Switzerland and has been put in the RS 812.121.11.

United Kingdom

On June 10, 2014, the UK Advisory Council on the Misuse of Drugs (ACMD) recommended that ALD-52 be specifically named in the UK Misuse of Drugs Act as a class A drug despite not identifying it as ever having been sold or any harm associated with its use. [17] The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015 as part of The Misuse of Drugs Act 1971 (Amendment) (No. 2) Order 2014.

United States

ALD-52 is unscheduled in the United States. It may be considered an analogue of LSD, a Schedule I drug under the Controlled Substances Act. As such, the sale for human consumption or the use for illicit non-medical or scientific use could be prosecuted as crimes under the Federal Analogue Act however could be legal for medical and research uses like a research chemical. [18]

See also

Related Research Articles

<span class="mw-page-title-main">LSD</span> Hallucinogenic drug

Lysergic acid diethylamide, commonly known as LSD, and known colloquially as acid or lucy, is a potent psychedelic drug. Effects typically include intensified thoughts, emotions, and sensory perception. At sufficiently high dosages, LSD manifests primarily mental, visual, and auditory hallucinations. Dilated pupils, increased blood pressure, and increased body temperature are typical.

<span class="mw-page-title-main">2C-E</span> Chemical compound

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.

<span class="mw-page-title-main">2,5-Dimethoxy-4-methylamphetamine</span> Chemical compound

2,5-Dimethoxy-4-methylamphetamine is a psychedelic and a substituted amphetamine. It was first synthesized by Alexander Shulgin, and later reported in his book PiHKAL: A Chemical Love Story. DOM is classified as a Schedule I substance in the United States, and is similarly controlled in other parts of the world. Internationally, it is a Schedule I drug under the Convention on Psychotropic Substances. It is generally taken orally.

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

Lysergol is an alkaloid of the ergoline family that occurs as a minor constituent in some species of fungi, and in the morning glory family of plants (Convolvulaceae), including the hallucinogenic seeds of Rivea corymbosa (ololiuhqui), Argyreia nervosa and Ipomoea violacea. Lysergol is not a controlled substance in the USA. Its possession and sale is also legal under the U.S. Federal Analog Act because it does not have a known pharmacological action or a precursor relationship to LSD, which is a controlled substance. However, lysergol is an intermediate in the manufacture of some ergoloid medicines.

<span class="mw-page-title-main">AL-LAD</span> Chemical compound (psychedelic drug)

AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD). It is described by Alexander Shulgin in the book TiHKAL. It is synthesized starting from nor-LSD as a precursor, using allyl bromide as a reactant.

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

ETH-LAD, 6-ethyl-6-nor-lysergic acid diethylamide is an analogue of LSD. Its human psychopharmacology was first described by Alexander Shulgin in the book TiHKAL. ETH-LAD is a psychedelic drug similar to LSD, and is slightly more potent than LSD itself, with an active dose reported at between 20 and 150 micrograms. ETH-LAD has subtly different effects to LSD, described as less demanding. The true tryptamine counterpart of ETH-LAD is MET, a simplified version of this structure.

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

PRO-LAD is an analogue of LSD. It is described by Alexander Shulgin in the book TiHKAL. PRO-LAD is a psychedelic drug similar to LSD, and is around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.

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

BU-LAD, also known as 6-butyl-6-nor-lysergic acid diethylamide, is an analogue of LSD first made by Alexander Shulgin and reported in the book TiHKAL. BU-LAD is a psychedelic drug similar to LSD, but is significantly less potent than LSD, with a dose of 500 micrograms producing only mild effects.

<span class="mw-page-title-main">LSM-775</span> Chemical compound

N-Morpholinyllysergamide (LSM-775) is a derivative of ergine. It is less potent than LSD but is reported to have some LSD-like effects at doses ranging from 75 to 700 micrograms and a shorter duration. There are fewer signs of cardiovascular stimulation and peripheral toxicity with LSM-775 compared to LSD.

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

N,N-Dimethyllysergamide or N,N-dimethyl-D-lysergamide (DAM-57) is a derivative of ergine. There has been a single report of observing N,N-dimethyl-D-lysergamide in the illicit drug market. This compound did induce autonomic disturbances at oral levels of some ten times the dosage required for LSD, presumably in the high hundreds of micrograms. There is some disagreement as to whether there were psychic changes observed.

<span class="mw-page-title-main">Lysergic acid 2,4-dimethylazetidide</span> Chemical compound

Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analog of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.

<span class="mw-page-title-main">Tim Scully</span>

Robert "Tim" Scully is an American computer engineer, best known in the psychedelic underground for his work in the production of LSD from 1966 to 1969, for which he was indicted in 1973 and convicted in 1974. His best known product, dubbed "Orange Sunshine", was considered the standard for quality LSD in 1969. He was featured in the documentary The Sunshine Makers.

<span class="mw-page-title-main">Head-twitch response</span> Head movement in rodants upon 5-HT2A receptor activation

The head-twitch response (HTR) is a rapid side-to-side head movement that occurs in mice and rats after the serotonin 5-HT2A receptor is activated. The prefrontal cortex may be the neuroanatomical locus mediating the HTR. Many serotonergic hallucinogens, including lysergic acid diethylamide (LSD), induce the head-twitch response, and so the HTR is used as a behavioral model of hallucinogen effects. However while there is generally a good correlation between compounds that induce head twitch in mice and compounds that are hallucinogenic in humans, it is unclear whether the head twitch response is primarily caused by 5-HT2A receptors, 5-HT2C receptors or both, though recent evidence shows that the HTR is mediated by the 5-HT2A receptor and modulated by the 5-HT2C receptor. Also, the effect can be non-specific, with head twitch responses also produced by some drugs that do not act through 5-HT2 receptors, such as phencyclidine, yohimbine, atropine and cannabinoid receptor antagonists. As well, compounds such as 5-HTP, fenfluramine, 1-Methylpsilocin, Ergometrine, and 3,4-di-methoxyphenethylamine (DMPEA) can also produce head twitch and do stimulate serotonin receptors, but are not hallucinogenic in humans. This means that while the head twitch response can be a useful indicator as to whether a compound is likely to display hallucinogenic activity in humans, the induction of a head twitch response does not necessarily mean that a compound will be hallucinogenic, and caution should be exercised when interpreting such results.

<span class="mw-page-title-main">25CN-NBOH</span> Chemical compound

25CN-NBOH is a compound indirectly derived from the phenethylamine series of hallucinogens, which was discovered in 2014 at the University of Copenhagen. This compound is notable as one of the most selective agonist ligands for the 5-HT2A receptor yet discovered, with a pKi of 8.88 at the human 5-HT2A receptor and with 100x selectivity for 5-HT2A over 5-HT2C, and 46x selectivity for 5-HT2A over 5-HT2B. A tritiated version of 25CN-NBOH has also been accessed and used for more detailed investigations of the binding to 5-HT2 receptors and autoradiography.

<span class="mw-page-title-main">1P-LSD</span> Chemical compound

1P-LSD is a psychedelic drug of the lysergamide class that is a derivative and functional analogue of LSD and a homologue of ALD-52. It originated in 2015 when it appeared a designer drug sold online. It modifies the LSD molecule by adding a propionyl group to the nitrogen molecule of LSD's indole group.

<span class="mw-page-title-main">1P-ETH-LAD</span> Chemical compound

1P-ETH-LAD is an analog of LSD. 1P-ETH-LAD is a psychedelic drug similar to LSD. Research has shown formation of ETH-LAD from 1P-ETH-LAD incubated in human serum, suggesting that it functions as a prodrug. It is part of the lysergamide chemical class. Like ETH-LAD, this drug has been reported to be significantly more potent than LSD itself, and is reported to largely mimic ETH-LAD's psychedelic effects.

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

ECPLA (N-ethyl-N-cyclopropyllysergamide) is an analog of lysergic acid diethylamide (LSD) developed by Synex Synthetics. In studies in mice, it was found to have approximately 40% the potency of LSD.

<span class="mw-page-title-main">1cP-LSD</span> Chemical compound

1cP-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. In tests on mice it was found to be an active psychedelic with similar potency to 1P-LSD.

<span class="mw-page-title-main">1B-LSD</span> Chemical compound

1B-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. In tests on mice it was found to be an active psychedelic, though with only around 1/7 the potency of LSD itself.

<span class="mw-page-title-main">1V-LSD</span> Chemical compound

1V-LSD, sometimes nicknamed Valerie, is a psychotropic substance and a research chemical with psychedelic effects. 1V-LSD is an artificial derivative of natural lysergic acid, which occurs in ergot alkaloids, as well as being an analogue of LSD. 1V-LSD has been sold online until an amendment to the German NpSG was enforced in 2022 which controls 1P-LSD and now 1cP-LSD, 1V-LSD and several other lysergamides.

References

  1. ↑ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  2. ↑ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants". www.legifrance.gouv.fr (in French). 20 May 2021.
  3. ↑ Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, et al. (August 2020). "Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD)". Neuropharmacology. 172: 107856. doi:10.1016/j.neuropharm.2019.107856. PMC   9191647 . PMID   31756337. S2CID   208155327.
  4. 1 2 Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, et al. (August 2020). "Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD)". Neuropharmacology. 172: 107856. doi:10.1016/j.neuropharm.2019.107856. PMC   9191647 . PMID   31756337.
  5. ↑ "EMCDDA–Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA | www.emcdda.europa.eu". www.emcdda.europa.eu. Retrieved 2023-10-16.
  6. ↑ Troxler F, Hofmann A (1957). "Substitutionen am Ringsystem der Lysergsäure I. Substitutionen am Indol-Stickstoff. 43. Mitteilung über Mutterkornalkaloide" [Substitutions on the ring system of lysergic acid I. Substitutions on the indole nitrogen. 43. Communication on ergot alkaloids]. Helvetica Chimica Acta (in German). 40 (6): 1706–1720. doi:10.1002/hlca.19570400619.
  7. ↑ Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, et al. (August 2020). "Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD)". Neuropharmacology. 172: 107856. doi:10.1016/j.neuropharm.2019.107856. PMC   9191647 . PMID   31756337.
  8. ↑ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN   0-9630096-9-9. OCLC   38503252.
  9. ↑ "I'm filmmaker Cosmo Feilding Mellen. I made The Sunshine Makers, a documentary about Tim Scully, who was jailed for trying to turn on the world using LSD. Expand your mind... Ask us anything!". ask me anything. reddit. 30 January 2017. Archived from the original on 2017-03-26.
  10. ↑ "Samlet liste over euforiserende stoffer opført på bilag 1 til bekendtgørelsen om euforiserende stoffer nr. 557 af 31. maj 2011 og stoffer reguleret herefter via ændringsbekendtgørelser" [Comprehensive list of euphoric substances listed in Appendix 1 to the Executive Order on Euphoric Substances No 557 of 31 May 2011 and substances regulated thereafter via amendments] (in Danish). June 13, 2018. Retrieved 2019-12-21.
  11. ↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" (in Finnish). 2014. Archived from the original on 2020-11-11. Retrieved 2022-02-13.
  12. ↑ "Änderungen NpSG vom 18 July 2019 durch Artikel 1 der Verordnung zur Änderung der Anlage des Neue-psychoaktive-Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes". www.buzer.de. Retrieved 2019-12-21.
  13. ↑ "Anlage NpSG – Einzelnorm". www.gesetze-im-internet.de. Retrieved 2019-12-21.
  14. ↑ "§ 4 NpSG – Einzelnorm". www.gesetze-im-internet.de. Retrieved 2019-12-21.
  15. ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem". LIKUMI.LV (in Latvian). Retrieved 2019-12-21.
  16. ↑ "Changes to Misuse Of Drugs Act (w.e.f. 1 December 2019)". www.cnb.gov.sg. Retrieved 2019-12-30.
  17. ↑ ACMD (10 June 2014). "Update of the Generic Definition for Tryptamines" (PDF). UK Home Office. p. 12. Archived (PDF) from the original on 6 October 2014. Retrieved 10 June 2014.
  18. ↑ "Erowid Analog Law Vault: Federal Controlled Substance Analogue Act Summary". www.erowid.org. Retrieved 2019-12-21.
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