Chemistry:1P-LSD

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1P-LSD, also known as 1-propionyl-LSD, is a psychedelic drug of the lysergamide family related to LSD. It is an ester derivative of LSD and a homologue of ALD-52 (1A-LSD). The drug originated in 2015 when it appeared as a designer drug sold online.[1] It was first synthesized as a legal LSD alternative by Lizard Labs, a Netherlands based research chemical laboratory.[2][3][4][5][6] It modifies the LSD molecule by adding a propionyl group to the nitrogen atom of LSD's indole group and is a prodrug of LSD.[7][8]

Use and effects

1P-LSD on blotter paper.

The dose range of 1P-LSD is 100 to 200 μg, with a typical dose estimate of 150 μg.[9] Its duration is about 8 to 12 hours for most people.[9] The subjective effects of 1P-LSD are not well-defined in the literature, although they are generally thought to be comparable to those of LSD.[10] In a 2020 study, the qualitative effects of 1P-LSD and LSD were similar when measured using visual analog scales.[11] The properties of 1P-LSD have also been assessed in other studies.[12][9]

Interactions

Pharmacology

Like ALD-52 (1A-LSD), 1P-LSD is believed to act as a prodrug for LSD via hydrolysis of the propionyl group. When 1P-LSD is incubated in human serum or liver cells,[13][14] administered intravenously to rats,[15] or administered either orally or intravenously to human subjects,[11] high levels of LSD and relatively low levels of 1P-LSD are quickly detected, demonstrating that 1P-LSD is rapidly hydrolyzed into LSD in vivo following ingestion. Indeed, following intravenous administration in humans 1P-LSD is detectable in serum for no longer than 4 hours, after which it is completely converted to LSD.[11] These findings are supported by the similar duration and behavioral effects of 1P-LSD and LSD in both animal and human experiments.[13][11]

Chemistry

Properties

The chemical stability of 1P-LSD has been studied.[16][17]

Analogues

Related compounds include 1cP-LSD, 1B-LSD, 1D-LSD, 1V-LSD, ALD-52 (1A-LSD), 1cP-AL-LAD, AL-LAD, ETH-LAD, 1P-ETH-LAD, PRO-LAD, LSM-775, and LSZ, among others.

History

1P-LSD was first described as well as encountered as a novel designer drug in 2015.[18]

Society and culture

As of 2015, 1P-LSD is unscheduled in the United States and Canada, but may be considered illegal if sold or used for human consumption as a structural analog of LSD under the Federal Analogue Act in the US.[13] 1P-LSD is a prohibited or controlled substance in Australia, France,[19] Finland,[20] Denmark,[21] Germany,[22] Estonia,[23] Japan,[24] Latvia,[25] Norway,[26] Romania,[27] Sweden,[28] Switzerland,[29] United Kingdom,[30] Italy,[31] Singapore,[32] the Czech Republic,[33] and Croatia.[34] 1P-LSD has been illegal in Russia since 2017 as an LSD derivative.[35]

See also

  • Substituted lysergamide
  • Lizard Labs
  • 4-AcO-DMT

References

  1. ↑ "Philtre Bulletin Issue 5". WEDINOS. March 2015. http://www.wedinos.org/resources/downloads/Philtre_Issue_5.pdf. 
  2. ↑ "Why Young Brits Are Taking So Much LSD and Ecstasy". Vice. 27 July 2015. https://www.vice.com/en/article/this-is-why-so-many-young-brits-are-taking-so-much-acid-and-ecstasy-892/. 
  3. ↑ "Newer Unregulated Drugs". KFx. April 2015. http://www.kfx.org.uk/resources/NUDlistapr2015.pdf. 
  4. ↑ "A handful of dangerous new legal drugs has public health experts worried". Business Insider UK. 11 August 2015. https://www.businessinsider.com/new-synthetic-drugs-2015-8. 
  5. ↑ "1P-LSD". New Synthetic Drugs Database. http://nsddb.eu/substance/502/. 
  6. ↑ "Self-reported use of novel psychoactive substances among attendees of electronic dance music venues". The American Journal of Drug and Alcohol Abuse 42 (6): 624–632. November 2016. doi:10.1080/00952990.2016.1181179. PMID 27315522. 
  7. ↑ Jose (15 October 2015). "Is 1P-LSD A Prodrug To LSD?". Detect-Kit. https://detect-kit.com/is-1p-lsd-a-prodrug-to-lsd/. 
  8. ↑ "Hydrolysis of amides. Kinetics and mechanism of the basic hydrolysis of N-acylpyrroles, N-acylindoles and N-acylcarbazoles". Journal of Heterocyclic Chemistry 20 (1): 247–248. January–February 1983. doi:10.1002/jhet.5570200154. 
  9. ↑ 9.0 9.1 9.2 "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology (Berl) 239 (6): 1783–1796. June 2022. doi:10.1007/s00213-022-06142-4. PMID 35487983. 
  10. ↑ "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. 32. June 2016. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. OCLC 643052237. 
  11. ↑ 11.0 11.1 11.2 11.3 "Pharmacokinetics and subjective effects of 1P-LSD in humans after oral and intravenous administration". Drug Testing and Analysis 12 (8): 1144–1153. August 2020. doi:10.1002/dta.2821. PMID 32415750. 
  12. ↑ "Genie in a blotter: A comparative study of LSD and LSD analogues' effects and user profile". Hum Psychopharmacol 32 (3). May 2017. doi:10.1002/hup.2599. PMID 28517366. 
  13. ↑ 13.0 13.1 13.2 "Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD)". Drug Testing and Analysis 8 (9): 891–902. September 2016. doi:10.1002/dta.1884. PMID 26456305. 
  14. ↑ "In vitro metabolic fate of nine LSD-based new psychoactive substances and their analytical detectability in different urinary screening procedures". Anal Bioanal Chem 411 (19): 4751–4763. July 2019. doi:10.1007/s00216-018-1558-9. PMID 30617391. 
  15. ↑ "Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD)". Neuropharmacology 172. August 2020. doi:10.1016/j.neuropharm.2019.107856. PMID 31756337. 
  16. ↑ "Validation of an LC-MS/MS method for the quantitative analysis of 1P-LSD and its tentative metabolite LSD in fortified urine and serum samples including stability tests for 1P-LSD under different storage conditions". J Pharm Biomed Anal 174: 270–276. September 2019. doi:10.1016/j.jpba.2019.05.062. PMID 31181490. 
  17. ↑ "Stability studies of ALD-52 and its homologue 1P-LSD". J Forensic Sci 68 (3): 1009–1019. May 2023. doi:10.1111/1556-4029.15224. PMID 36779453. 
  18. ↑ https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2015
  19. ↑ "Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants" (in fr). 20 May 2021. https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554. 
  20. ↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista annetun valtioneuvoston asetuksen liitteen muuttamisesta" (in Finnish). https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2018/840. 
  21. ↑ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015. http://laegemiddelstyrelsen.dk/en/licensing/company-authorisations-and-registrations/euphoriant-substances/lists-of-substances. 
  22. ↑ "Verordnung zur Änderung der Anlage des Neue-psychoaktive-. Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" (in German). https://www.bgbl.de/xaver/bgbl/start.xav#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl119s1083.pdf%27%5D__1563358129436. 
  23. ↑ "Muudatus narkootiliste ja psühhotroopsete ainete I nimekirjas" (in Estonian). Republic of Estonia Agency of Medicines. https://www.sam.ee/en/node/10831. 
  24. ↑ "指定薬物一覧" (in Japanese). Ministry of Health, Labour and Welfare. http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf. 
  25. ↑ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Latvijas Republikas tiesību akti. http://likumi.lv/doc.php?id=121086. 
  26. ↑ "31 Forskrift om narkotika (narkotikaforskriften)" (in Norwegian). Helse- og omsorgsdepartementet. 14 February 2013. https://lovdata.no/dokument/SF/forskrift/2013-02-14-199. 
  27. ↑ "Legea 194/2011 privind combaterea operatiunilor cu produse susceptibile de a avea efecte psihoactive, altele decat cele prevazute de acte normative in vigoare, republicata 2014". http://www.dreptonline.ro/legislatie/legea_194_2011_combaterea_operatiunilor_produse_susceptibile_efecte_psihoactive.php. 
  28. ↑ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" (in Swedish). https://notisum.se/rnp/sls/sfs/20150997.pdf. 
  29. ↑ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat. https://www.admin.ch/opc/de/classified-compilation/20101220/index.html. 
  30. ↑ "Psychoactive Substances Act 2016". https://www.legislation.gov.uk/ukpga/2016/2/contents. 
  31. ↑ "DECRETO 5 ottobre 2021". https://www.gazzettaufficiale.it/eli/id/2021/10/18/21A06118/sg. 
  32. ↑ "Misuse of Drugs Act - Singapore Statutes Online". https://sso.agc.gov.sg/Act/MDA1973. 
  33. ↑ "Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek" (in Czech). Zákony pro lidi. https://www.zakonyprolidi.cz/cs/2013-463. 
  34. ↑ "Popis droga, psihotropnih tvari i biljaka iz kojih se može dobiti droga te tvari koje se mogu uporabiti za izradu droga". https://narodne-novine.nn.hr/clanci/sluzbeni/2019_02_13_259.html. 
  35. ↑ "ИЗМЕНЕНИЯ, КОТОРЫЕ ВНОСЯТСЯ В АКТЫ ПРАВИТЕЛЬСТВА РОССИЙСКОЙ ФЕДЕРАЦИИ В СВЯЗИ С СОВЕРШЕНСТВОВАНИЕМ КОНТРОЛЯ ЗА ОБОРОТОМ НАРКОТИЧЕСКИХ СРЕДСТВ И ПСИХОТРОПНЫХ ВЕЩЕСТВ \ КонсультантПлюс". https://www.consultant.ru/document/cons_doc_LAW_404473/4347f565328bac46bfd843bc52fef25ac88cd925/#dst100135. 

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