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'''1P-LSD''' ('''1-propanoyl-lysergic acid diethylamide''') is a [[psychedelic drug]] of the [[Lysergamides|lysergamide]] class that is a [[derivative (chemistry)|derivative]] and [[Functional analog (chemistry)|functional analogue]] of [[Lysergic acid diethylamide|LSD]] and a [[Homologous series|homologue]] of [[ALD-52]]. It originated in 2015 when it appeared a [[designer drug]] sold online.<ref>{{cite web | url=http://www.wedinos.org/resources/downloads/Philtre_Issue_5.pdf | title=Philtre Bulletin Issue 5 | publisher=WEDINOS | date=March 2015 | access-date=28 July 2015}}</ref><ref>{{cite web | url=https://www.vice.com/read/this-is-why-so-many-young-brits-are-taking-so-much-acid-and-ecstasy-892 | title=Why Young Brits Are Taking So Much LSD and Ecstasy | publisher=Vice | date=27 July 2015 | access-date=11 August 2015 | vauthors = Daly M }}</ref><ref>{{cite web | url=http://www.kfx.org.uk/resources/NUDlistapr2015.pdf | title=Newer Unregulated Drugs | publisher=KFx | date=April 2015 | access-date=13 August 2015}}</ref><ref>{{cite web | url=https://www.businessinsider.com/new-synthetic-drugs-2015-8 | title=A handful of dangerous new legal drugs has public health experts worried| work=Business Insider UK | vauthors = Speiser M | date=11 August 2015 | access-date=13 August 2015}}</ref><ref>{{cite web | url=http://nsddb.eu/substance/502/ | title=1P-LSD | publisher=New Synthetic Drugs Database | access-date=2016-01-29 | archive-url=https://web.archive.org/web/20160703170103/http://nsddb.eu/substance/502/ | archive-date=2016-07-03 | url-status=dead }}</ref><ref>{{cite journal | vauthors = Palamar JJ, Acosta P, Sherman S, Ompad DC, Cleland CM | title = Self-reported use of novel psychoactive substances among attendees of electronic dance music venues | journal = The American Journal of Drug and Alcohol Abuse | volume = 42 | issue = 6 | pages = 624–632 | date = November 2016 | pmid = 27315522 | pmc = 5093056 | doi = 10.1080/00952990.2016.1181179 }}</ref> It modifies the LSD molecule by adding a [[Propionic acid|propionyl group]] to the nitrogen molecule of LSD's [[Indole ring|indole]] group.<ref>{{cite web |author=Jose |date=15 October 2015 |title=Is 1P-LSD A Prodrug To LSD? |url=https://detect-kit.com/is-1p-lsd-a-prodrug-to-lsd/ |url-status=dead |archive-url=https://web.archive.org/web/20151015162637/http://detect-kit.com/is-1p-lsd-a-prodrug-to-lsd/ |archive-date=2015-10-15 |access-date=15 October 2015 |publisher=Detect-Kit}}</ref><ref>{{cite journal |vauthors=Linda P, Stener A, Cipiciani A, Savelli G |date=January–February 1983 |title=Hydrolysis of amides. Kinetics and mechanism of the basic hydrolysis of N-acylpyrroles, N-acylindoles and N-acylcarbazoles |journal=Journal of Heterocyclic Chemistry |volume=20 |issue=1 |pages=247–248 |doi=10.1002/jhet.5570200154}}</ref>
'''1P-LSD''' ('''1-propanoyl-lysergic acid diethylamide''') is a [[psychedelic drug]] of the [[Lysergamides|lysergamide]] class that is a [[derivative (chemistry)|derivative]] and [[Functional analog (chemistry)|functional analogue]] of [[Lysergic acid diethylamide|LSD]] and a [[Homologous series|homologue]] of [[ALD-52]]. It originated in 2015 when it appeared a [[designer drug]] sold online.<ref>{{cite web | url=http://www.wedinos.org/resources/downloads/Philtre_Issue_5.pdf | title=Philtre Bulletin Issue 5 | publisher=WEDINOS | date=March 2015 | access-date=28 July 2015}}</ref><ref>{{cite web | url=https://www.vice.com/read/this-is-why-so-many-young-brits-are-taking-so-much-acid-and-ecstasy-892 | title=Why Young Brits Are Taking So Much LSD and Ecstasy | publisher=Vice | date=27 July 2015 | access-date=11 August 2015 | vauthors = Daly M }}</ref><ref>{{cite web | url=http://www.kfx.org.uk/resources/NUDlistapr2015.pdf | title=Newer Unregulated Drugs | publisher=KFx | date=April 2015 | access-date=13 August 2015}}</ref><ref>{{cite web | url=https://www.businessinsider.com/new-synthetic-drugs-2015-8 | title=A handful of dangerous new legal drugs has public health experts worried| work=Business Insider UK | vauthors = Speiser M | date=11 August 2015 | access-date=13 August 2015}}</ref><ref>{{cite web | url=http://nsddb.eu/substance/502/ | title=1P-LSD | publisher=New Synthetic Drugs Database | access-date=2016-01-29 | archive-url=https://web.archive.org/web/20160703170103/http://nsddb.eu/substance/502/ | archive-date=2016-07-03 | url-status=dead }}</ref><ref>{{cite journal | vauthors = Palamar JJ, Acosta P, Sherman S, Ompad DC, Cleland CM | title = Self-reported use of novel psychoactive substances among attendees of electronic dance music venues | journal = The American Journal of Drug and Alcohol Abuse | volume = 42 | issue = 6 | pages = 624–632 | date = November 2016 | pmid = 27315522 | pmc = 5093056 | doi = 10.1080/00952990.2016.1181179 }}</ref> It modifies the LSD molecule by adding a [[Propionic acid|propionyl group]] to the nitrogen atom of LSD's [[Indole ring|indole]] group.<ref>{{cite web |author=Jose |date=15 October 2015 |title=Is 1P-LSD A Prodrug To LSD? |url=https://detect-kit.com/is-1p-lsd-a-prodrug-to-lsd/ |url-status=dead |archive-url=https://web.archive.org/web/20151015162637/http://detect-kit.com/is-1p-lsd-a-prodrug-to-lsd/ |archive-date=2015-10-15 |access-date=15 October 2015 |publisher=Detect-Kit}}</ref><ref>{{cite journal |vauthors=Linda P, Stener A, Cipiciani A, Savelli G |date=January–February 1983 |title=Hydrolysis of amides. Kinetics and mechanism of the basic hydrolysis of N-acylpyrroles, N-acylindoles and N-acylcarbazoles |journal=Journal of Heterocyclic Chemistry |volume=20 |issue=1 |pages=247–248 |doi=10.1002/jhet.5570200154}}</ref>


== Pharmacology ==
== Pharmacology ==

Revision as of 14:01, 25 August 2024

1P-LSD
Legal status
Legal status
  • AU: S8 (Controlled drug)
  • BR: Class F2 (Prohibited psychotropics)
  • CA: Unscheduled.
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
  • US: Unscheduled (may be considered illegal if sold for human consumption as an analog of LSD under the federal analogue act)
  • UN: Unscheduled
  • In general Unscheduled, unless that was sold for human consumption, could be sold for medical and research purposes.
Identifiers
  • (6aR,9R)-N,N-Diethyl-7-methyl-4-propanoyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H29N3O2
Molar mass379.504 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@H]1CN(C)[C@@H]2Cc3cn(C(=O)CC)c4cccc(C2=C1)c34
  • InChI=1S/C23H29N3O2/c1-5-21(27)26-14-15-12-20-18(17-9-8-10-19(26)22(15)17)11-16(13-24(20)4)23(28)25(6-2)7-3/h8-11,14,16,20H,5-7,12-13H2,1-4H3/t16-,20-/m1/s1
  • Key:JSMQOVGXBIDBIE-OXQOHEQNSA-N

1P-LSD (1-propanoyl-lysergic acid diethylamide) 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.[1][2][3][4][5][6] It modifies the LSD molecule by adding a propionyl group to the nitrogen atom of LSD's indole group.[7][8]

Pharmacology

Like ALD-52, 1P-LSD is believed to act as prodrug for LSD via hydrolysis of the propionyl group. When 1P-LSD is incubated in human serum,[9] administered intravenously to rats,[10] 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.[9][11]

Effects

1P-LSD on blotter paper

The subjective effects of 1P-LSD are not well defined in the scientific literature, although they are generally thought to be comparable to that of LSD.[12] In a 2020 study, the qualitative effects of 1P-LSD and LSD were similar when measured using visual analog scales.

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.[9] 1P-LSD is a prohibited or controlled substance in Australia, France,[13] Finland,[14] Denmark,[15] Germany,[16] Estonia,[17] Japan,[18] Latvia,[19] Norway,[20] Romania,[21] Sweden,[22] Switzerland,[23] United Kingdom,[24] Italy,[citation needed] Singapore,[25] the Czech Republic,[26] and Croatia.[27] 1P-LSD has been illegal in Russia since 2017 as an LSD derivative.[28]

See also

References

  1. ^ "Philtre Bulletin Issue 5" (PDF). WEDINOS. March 2015. Retrieved 28 July 2015.
  2. ^ Daly M (27 July 2015). "Why Young Brits Are Taking So Much LSD and Ecstasy". Vice. Retrieved 11 August 2015.
  3. ^ "Newer Unregulated Drugs" (PDF). KFx. April 2015. Retrieved 13 August 2015.
  4. ^ Speiser M (11 August 2015). "A handful of dangerous new legal drugs has public health experts worried". Business Insider UK. Retrieved 13 August 2015.
  5. ^ "1P-LSD". New Synthetic Drugs Database. Archived from the original on 2016-07-03. Retrieved 2016-01-29.
  6. ^ Palamar JJ, Acosta P, Sherman S, Ompad DC, Cleland CM (November 2016). "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. doi:10.1080/00952990.2016.1181179. PMC 5093056. PMID 27315522.
  7. ^ Jose (15 October 2015). "Is 1P-LSD A Prodrug To LSD?". Detect-Kit. Archived from the original on 2015-10-15. Retrieved 15 October 2015.
  8. ^ Linda P, Stener A, Cipiciani A, Savelli G (January–February 1983). "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. doi:10.1002/jhet.5570200154.
  9. ^ a b c Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, et al. (September 2016). "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. doi:10.1002/dta.1884. PMC 4829483. PMID 26456305.
  10. ^ 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.
  11. ^ a b c Grumann C, Henkel K, Brandt SD, Stratford A, Passie T, Auwärter V (August 2020). "Pharmacokinetics and subjective effects of 1P-LSD in humans after oral and intravenous administration". Drug Testing and Analysis. 12 (8): 1144–1153. doi:10.1002/dta.2821. PMID 32415750.
  12. ^ Schifano F, Orsolini L, Papanti D, Corkery J (June 2016). "NPS: Medical Consequences Associated with Their Intake". Current Topics in Behavioral Neurosciences. 32: 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. OCLC 643052237. PMID 27272067.
  13. ^ "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.
  14. ^ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista annetun valtioneuvoston asetuksen liitteen muuttamisesta" [Government decree amending the annex to the government decree on psychoactive substances prohibited on the consumer market] (in Finnish).
  15. ^ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015.
  16. ^ "Verordnung zur Änderung der Anlage des Neue-psychoaktive-. Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes" [Regulation amending the Annex to the New Psychoactive Substances Act and Appendices to the Narcotics Act] (in German).
  17. ^ "Muudatus narkootiliste ja psühhotroopsete ainete I nimekirjas" (in Estonian). Republic of Estonia Agency of Medicines. Archived from the original on 2019-04-25. Retrieved 2019-02-04.
  18. ^ "指定薬物一覧" (PDF) (in Japanese). Ministry of Health, Labour and Welfare.
  19. ^ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Latvijas Republikas tiesību akti.
  20. ^ "31 Forskrift om narkotika (narkotikaforskriften)" (in Norwegian). Helse- og omsorgsdepartementet. 14 February 2013.
  21. ^ "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". www.dreptonline.ro. Retrieved 2020-07-24.
  22. ^ "Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor" [Ordinance (1999: 58) on the prohibition of certain dangerous goods] (PDF) (in Swedish).
  23. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
  24. ^ "Psychoactive Substances Act 2016". legislation.gov.uk. Retrieved 28 November 2023.
  25. ^ "Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.
  26. ^ "Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek" (in Czech). Zákony pro lidi.
  27. ^ "Popis droga, psihotropnih tvari i biljaka iz kojih se može dobiti droga te tvari koje se mogu uporabiti za izradu droga". narodne-novine.nn.hr. Retrieved 2023-01-02.
  28. ^ "ИЗМЕНЕНИЯ, КОТОРЫЕ ВНОСЯТСЯ В АКТЫ ПРАВИТЕЛЬСТВА РОССИЙСКОЙ ФЕДЕРАЦИИ В СВЯЗИ С СОВЕРШЕНСТВОВАНИЕМ КОНТРОЛЯ ЗА ОБОРОТОМ НАРКОТИЧЕСКИХ СРЕДСТВ И ПСИХОТРОПНЫХ ВЕЩЕСТВ \ КонсультантПлюс". www.consultant.ru. Retrieved 2023-02-07.
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