Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and ALD-52: Difference between pages

{{short description|Chemical compound}}

{{more citations needed|date=December 2010}}

{{Infobox drug

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 477235721

| IUPAC_name = (6a''R'',9''R'')-4-Acetyl-''N'',''N''-diethyl-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-''fg'']quinoline-9-carboxamide

| image = ALD-52 image.svg

| width = 120px

| tradename =

| legal_AU = Unscheduled

| legal_BR = F2

| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-07-24 |title=RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |url-status=live |archive-url=https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451 |archive-date=2023-08-27 |access-date=2023-08-27 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-07-25}}</ref>

| legal_CA = Unscheduled

| legal_DE = NpSG

| legal_UK = Class A

| legal_US = Unscheduled, could be persecuted under the [[Federal Analogue Act]].

| legal_status = Unscheduled in the most countries of the world, Illegal in France, Romania, Switzerland, Finland and Singapore<ref>{{cite web|date=20 May 2021|title=Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants|url=https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554|website=www.legifrance.gouv.fr|language=fr}}</ref>

| routes_of_administration = [[wikt:oral|Oral]]

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 3270-02-8

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = R224WJZ8M7

| C=22 | H=27 | N=3 | O=2

| smiles = O=C(n1cc2c3c(C4=C[C@@H](C(=O)N(CC)CC)CN([C@@H]4C2)C)cccc13)C

'''ALD-52''', also known as '''1-[[acetyl]]-LSD''', has [[Structural analog|chemical structural features]] similar to [[lysergic acid diethylamide]] (LSD), a known [[psychedelic drug]].<ref name="Halberstadt_2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, Stratford A, Brandt SD | display-authors = 6 | title = Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD) | journal = Neuropharmacology | volume = 172 | issue = | pages = 107856 | date = August 2020 | pmid = 31756337 | pmc = 9191647 | doi = 10.1016/j.neuropharm.2019.107856 | s2cid = 208155327 }}</ref><ref name=":0">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, Stratford A, Brandt SD | display-authors = 6 | title = Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD) | journal = Neuropharmacology | volume = 172 | pages = 107856 | date = August 2020 | pmid = 31756337 | doi = 10.1016/j.neuropharm.2019.107856 | pmc = 9191647 }}</ref> Similarly, ALD-52 has been reported to produce [[Psychoactive drug|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 use|recreational drug]], and the purported first confirmed detection of the substance on the illicit market occurred in April 2016.<ref name=":0" /><ref>{{Cite web |title=EMCDDA–Europol 2016 Annual Report on the implementation of Council Decision 2005/387/JHA {{!}} www.emcdda.europa.eu |url=https://www.emcdda.europa.eu/publications/implementation-reports/2016_en |access-date=2023-10-16 |website=www.emcdda.europa.eu |language=en}}</ref>

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 [[Psychedelic era|rise in popularity of psychedelics]] in the 1960s, ALD-52 was not widely studied.<ref>{{cite journal |vauthors=Troxler F, Hofmann A |date=1957 |title=Substitutionen am Ringsystem der Lysergsäure I. Substitutionen am Indol-Stickstoff. 43. Mitteilung über Mutterkornalkaloide |trans-title=Substitutions on the ring system of lysergic acid I. Substitutions on the indole nitrogen. 43. Communication on ergot alkaloids |journal=Helvetica Chimica Acta |language=German |volume=40 |issue=6 |pages=1706–1720 |doi=10.1002/hlca.19570400619}}</ref> It is assumed to act as a [[prodrug]] to LSD in humans, but this has yet to be scientifically verified.<ref>{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, Stratford A, Brandt SD | display-authors = 6 | title = Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD) | journal = Neuropharmacology | volume = 172 | pages = 107856 | date = August 2020 | pmid = 31756337 | doi = 10.1016/j.neuropharm.2019.107856 | pmc = 9191647 }}</ref>

== 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&nbsp;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.<ref>{{CiteTiHKAL|name-list-style=vanc}}</ref>

== 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) [[Fever#Pyrogens|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|date=November 2016}}

== History ==

In a [[Reddit AMA]] with the director of the movie ''[[The Sunshine Makers (2015 film)|The Sunshine Makers]]'', [[Tim Scully]] says:

<blockquote>"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."<ref>{{cite web |url=https://www.reddit.com/r/IAmA/comments/5r2wn7/im_filmmaker_cosmo_feilding_mellen_i_made_the/dd4499t/ |title=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! |work=ask me anything |date=30 January 2017 |publisher=reddit |url-status=live |archive-url=https://web.archive.org/web/20170326051052/https://www.reddit.com/r/IAmA/comments/5r2wn7/im_filmmaker_cosmo_feilding_mellen_i_made_the/dd4499t/ |archive-date=2017-03-26}}</ref></blockquote>

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.

== Legal status ==

[[File:ALD-52 animation.gif|thumb|upright|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).<ref>{{cite web |language=da |trans-title=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 |date=June 13, 2018 |url=https://laegemiddelstyrelsen.dk/da/godkendelse/virksomhedstilladelse-og-registrering/euforiserende-stoffer/liste-over-stoffer/~/media/BD3103CB7080427DB7125B0685EF6427.ashx |title=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 |access-date=2019-12-21}}</ref>

=== Finland ===

ALD-52 is labeled a controlled psychoactive substance in Finland as of 2014.<ref>{{cite web|url=https://www.finlex.fi/fi/laki/ajantasa/2014/20141130|title=Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista|language=fi|date=2014|access-date=2022-02-13|archive-date=2020-11-11|archive-url=https://web.archive.org/web/20201111171049/https://www.finlex.fi/fi/laki/ajantasa/2014/20141130|url-status=dead}}</ref>

=== Germany ===

ALD-52 is controlled under the NpSG as of July 18, 2019.<ref>{{cite web |url=https://www.buzer.de/gesetz/12250/v224771-2019-07-18.htm |title=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 |website=www.buzer.de |access-date=2019-12-21}}</ref><ref>{{cite web |url=https://www.gesetze-im-internet.de/npsg/anlage.html |title=Anlage NpSG – Einzelnorm |website=www.gesetze-im-internet.de |access-date=2019-12-21}}</ref> 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.<ref>{{cite web |url=https://www.gesetze-im-internet.de/npsg/__4.html |title=§&nbsp;4 NpSG – Einzelnorm |website=www.gesetze-im-internet.de |access-date=2019-12-21}}</ref>

=== 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.<ref>{{cite web |url=http://likumi.lv/doc.php?id=121086 |title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem |website=LIKUMI.LV |language=lv |access-date=2019-12-21}}</ref>

=== 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 [http://www.dreptonline.ro/legislatie/legea_194_2011_combaterea_operatiunilor_produse_susceptibile_efecte_psihoactive.php 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.<ref>{{cite web |url=https://www.cnb.gov.sg/NewsAndEvents/News/Index/changes-to-misuse-of-drugs-act-(w.e.f.-1-december-2019) |title=Changes to Misuse Of Drugs Act (w.e.f. 1 December 2019) |website=www.cnb.gov.sg |access-date=2019-12-30}}</ref>

=== Switzerland ===

Since March 2018, ALD-52 is illegal in Switzerland and has been put in the [https://www.admin.ch/opc/fr/classified-compilation/20101220/201803010000/812.121.11.pdf 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.<ref name="ACMD tryptamines">{{cite web |url=https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf |title=Update of the Generic Definition for Tryptamines |publisher=UK Home Office |date=10 June 2014 |access-date=10 June 2014 |author=ACMD |page=12 |url-status=live |archive-url=https://web.archive.org/web/20141006123717/https://www.gov.uk/government/uploads/system/uploads/attachment_data/file/318693/UpdateGenericDefinitionTryptamines.pdf |archive-date=6 October 2014}}</ref> The UK Home office accepted this advice and announced a ban of the substance to be enacted on 6 January 2015 as part of [http://www.legislation.gov.uk/uksi/2014/3271/made 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]].<ref>{{cite web |url=https://www.erowid.org/psychoactives/law/analog/analog_info1.shtml |title=Erowid Analog Law Vault: Federal Controlled Substance Analogue Act Summary |website=www.erowid.org |access-date=2019-12-21}}</ref>

== See also ==

* [[Lysergic acid diethylamide]] (LSD)

* [[1cP-LSD]]

* [[1B-LSD]]

* [[1P-LSD]]

* [[1V-LSD]]

* [[1cP-AL-LAD]]

* [[AL-LAD]]

* [[ETH-LAD]]

* [[PRO-LAD]]

* [[LSM-775]]

* [[Lysergic acid 2,4-dimethylazetidide|LSZ]]

* [[O-Acetylpsilocin]] (4-AcO-DMT)

== References ==

{{reflist|2}}

== External links ==

* [http://www.erowid.org/library/books_online/tihkal/tihkal26.shtml Entry #26 from TiHKAL]

* [http://www.everything2.com/?node_id=1116647 everything2]

* [https://web.archive.org/web/20050330023243/http://leda.lycaeum.org/?ID=8772 Lycaeum]

* [http://www.clearwhitelight.org/hatter/ald.htm White Light]

{{Hallucinogens}}

{{Serotonergics}}

{{Ergolines}}

[[Category:Lysergamides]]

[[Category:Euphoriants]]

[[Category:Psychedelic drugs]]

[[Category:Serotonin receptor agonists]]

[[Category:Entheogens]]

[[Category:Designer drugs]]

[[Category:Acetamides]]