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1P-LSD

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1P-LSD
Clinical data
Other names1-Propanoyl-lysergic acid diethylamide; 1-Propanoyl-LSD; 1-Propionyl-LSD
Routes of
administration		Oral[1]
Drug classSerotonin receptor agonist; Serotonin 5-HT2A receptor agonist; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
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.
Pharmacokinetic data
Bioavailability~100%[1]
MetabolismHydrolysis[1]
MetabolitesLSD[1]
Elimination half-lifeInitial: ~0.2 hours[1]
Duration of action8–12 hours[2][1]
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, 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.[3] It was first synthesized as a legal LSD alternative by Lizard Labs, a Netherlands based research chemical laboratory.[4][5][6][7][8] 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.[9][10]

Use and effects

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1P-LSD on blotter paper.

The dose range of 1P-LSD is 100 to 200 μg, with a typical dose estimate of 150 μg.[2] Its duration is about 8 to 12 hours for most people.[2] 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.[11] In a 2020 study, the qualitative effects of 1P-LSD and LSD were similar when measured using visual analog scales.[1] The properties of 1P-LSD have also been assessed in other studies.[12][2]

Interactions

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See also: Psychedelic drug § Interactions, and Trip killer § Serotonergic psychedelic antidotes

Pharmacology

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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,[1] 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.[1] These findings are supported by the similar duration and behavioral effects of 1P-LSD and LSD in both animal and human experiments.[13][1]

Chemistry

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Properties

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

Analogues

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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

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

Society and culture

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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

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References

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  1. ^ a b c d e f g h i j 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.
  2. ^ a b c d Mallaroni P, Mason NL, Vinckenbosch FR, Ramaekers JG (June 2022). "The use patterns of novel psychedelics: experiential fingerprints of substituted phenethylamines, tryptamines and lysergamides". Psychopharmacology (Berl). 239 (6): 1783–1796. doi:10.1007/s00213-022-06142-4. PMC 9166850. PMID 35487983.
  3. ^ "Philtre Bulletin Issue 5" (PDF). WEDINOS. March 2015. Retrieved 28 July 2015.
  4. ^ Daly M (27 July 2015). "Why Young Brits Are Taking So Much LSD and Ecstasy". Vice. Retrieved 11 August 2015.
  5. ^ "Newer Unregulated Drugs" (PDF). KFx. April 2015. Retrieved 13 August 2015.
  6. ^ Speiser M (11 August 2015). "A handful of dangerous new legal drugs has public health experts worried". Business Insider UK. Retrieved 13 August 2015.
  7. ^ "1P-LSD". New Synthetic Drugs Database. Archived from the original on 2016-07-03. Retrieved 2016-01-29.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ Schifano F, Orsolini L, Papanti D, Corkery J (June 2016). "NPS: Medical Consequences Associated with Their Intake". Neuropharmacology of New Psychoactive Substances (NPS). Current Topics in Behavioral Neurosciences. Vol. 32. pp. 351–380. doi:10.1007/7854_2016_15. ISBN 978-3-319-52442-9. OCLC 643052237. PMID 27272067.
  12. ^ Coney LD, Maier LJ, Ferris JA, Winstock AR, Barratt MJ (May 2017). "Genie in a blotter: A comparative study of LSD and LSD analogues' effects and user profile". Hum Psychopharmacol. 32 (3). doi:10.1002/hup.2599. PMID 28517366.
  13. ^ 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.
  14. ^ Wagmann L, Richter LH, Kehl T, Wack F, Bergstrand MP, Brandt SD, Stratford A, Maurer HH, Meyer MR (July 2019). "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. doi:10.1007/s00216-018-1558-9. PMID 30617391.
  15. ^ 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.
  16. ^ Grumann C, Henkel K, Stratford A, Hermanns-Clausen M, Passie T, Brandt SD, Auwärter V (September 2019). "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. doi:10.1016/j.jpba.2019.05.062. PMID 31181490.
  17. ^ Zhang SH, Tang AS, Chin RS, Goh JY, Ong MC, Lim WJ, Yap AT, So CW (May 2023). "Stability studies of ALD-52 and its homologue 1P-LSD". J Forensic Sci. 68 (3): 1009–1019. 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". www.legifrance.gouv.fr (in French). 20 May 2021.
  20. ^ "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).
  21. ^ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015.
  22. ^ "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).
  23. ^ "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.
  24. ^ "指定薬物一覧" (PDF) (in Japanese). Ministry of Health, Labour and Welfare.
  25. ^ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Latvijas Republikas tiesību akti.
  26. ^ "31 Forskrift om narkotika (narkotikaforskriften)" (in Norwegian). Helse- og omsorgsdepartementet. 14 February 2013.
  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". www.dreptonline.ro. Retrieved 2020-07-24.
  28. ^ "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).
  29. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
  30. ^ "Psychoactive Substances Act 2016". legislation.gov.uk. Retrieved 28 November 2023.
  31. ^ "DECRETO 5 ottobre 2021".
  32. ^ "Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.
  33. ^ "Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek" (in Czech). Zákony pro lidi.
  34. ^ "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.
  35. ^ "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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