1P-LSD

1P-LSD or 1-propionyl-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 has been sold online as a designer drug since 2015.[1][2][3][4][5][6] It modifies the LSD molecule by adding a propionyl group to the nitrogen molecule of LSD's indole.[7][8]

1P-LSD
Legal status
Legal status
  • DE: NpSG (Industrial and scientific use only)
  • UK: Under Psychoactive Substances Act
  • Illegal in Czech Republic, Denmark, Estonia, France, Japan, Latvia, Lithuania, Norway, Romania, Singapore, Sweden, Switzerland
Identifiers
IUPAC name
  • (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
Chemical and physical data
FormulaC23H29N3O2
Molar mass379.504 g·mol−1
3D model (JSmol)
SMILES
  • CCN(CC)C(=O)[C@H]1CN(C)[C@@H]2Cc3cn(C(=O)CC)c4cccc(C2=C1)c34
InChI
  • 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

Pharmacology

Since LSD is detected when 1P-LSD is incubated in human serum,[9] 1P-LSD acts, at least in part, as a prodrug for LSD.[10]

Effects
1P-LSD on blotter paper

The effects profile of 1P-LSD is not well defined in the scientific literature. It is generally thought to be comparable to that of LSD.[11] A study in 2020 found that intravenous administration of 1P-LSD has a somewhat shorter duration than LSD in humans. 1P-LSD is present for a very short time (4 hours) prior to being completed metabolized to LSD. The 2020 study found that it is not possible to reliably distinguish between the oral uptake of LSD and 1P-LSD until unique metabolites are detected by sensitive analytical methods. Qualitative effects were similar when comparing intravenous and oral delivery between the two drugs. The slow onset after intravenous application for 1P-LSD appears to be due to the slowed passage of LSD into the central nervous system compared to other serotonergic hallucinogens. Some users in the study reported an absence of "bad drug effects", but this is likely due to the setting than as a characteristic of 1P-LSD.[12]

As of 2015, 1P-LSD is not regulated under the United States Controlled Substances Act and is classified as a research chemical not intended for human consumption.[9] 1P-LSD is a controlled substance in France,[13] Finland,[14] Denmark,[15] Germany,[16] Estonia,[17] Japan,[18] Latvia,[19] Norway,[20] Romania,[21] Sweden,[22] Switzerland,[23] United Kingdom, Italy, Singapore[24] and the Czech Republic (banned in 2018).[25]

See also

References
  1. "Philtre Bulletin Issue 5" (PDF). WEDINOS. March 2015. Retrieved 28 July 2015.
  2. Daly, Max (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. Brandt, Simon D.; Kavanagh, Pierce V.; Westphal, Folker; Stratford, Alexander; Elliott, Simon P.; Hoang, Khoa; Wallach, Jason; Halberstadt, Adam L. (September 2016). "Return of the lysergamides. Part I: Analytical and behavioral characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD)". Drug Test Anal. 8 (9): 891–902. doi:10.1002/dta.1884. PMC 4829483. PMID 26456305.
  10. Grumann, Christina; Henkel, Kerstin; Brandt, Simon D.; Stratford, Alexander; Passie, Torsten; Auwärter, Volker (May 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. ISSN 1942-7611. PMID 32415750.
  11. 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.
  12. Grumann, Christina; Henkel, Kerstin; Brandt, Simon D.; Stratford, Alexander; Passie, Torsten; Auwarter, Volker (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. S2CID 218657712. Retrieved 16 June 2022.
  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.
  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. "Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.
  25. "Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek" (in Czech). Zákony pro lidi.
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