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1P-LSD

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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
Pharmacokinetic data
Bioavailability~100%[1]
MetabolismHydrolysis[1]
MetabolitesLSD[1]
Eliminationhalf-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
PubChemCID
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 as1-propionyl-LSD, is apsychedelic drug of thelysergamide family related toLSD. It is anesterderivative of LSD and ahomologue ofALD-52 (1A-LSD). The drug originated in 2015 when it appeared as adesigner drug sold online.[3] It was first synthesized as a legal LSD alternative byLizard Labs, a Netherlands basedresearch chemical laboratory.[4][5][6][7][8] It modifies the LSD molecule by adding apropionyl group to the nitrogen atom of LSD'sindole group and is aprodrug of LSD.[9][10]

Use and effects

[edit]
See also:LSD § Uses, andLSD § 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.[2] Itsduration 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 ofLSD.[11] In a 2020 study, the qualitative effects of 1P-LSD and LSD were similar when measured usingvisual analog scales.[1] The properties of 1P-LSD have also been assessed in other studies.[12][2]

Interactions

[edit]
See also:Psychedelic drug § Interactions, andTrip killer § Serotonergic psychedelic antidotes

Pharmacology

[edit]

LikeALD-52 (1A-LSD), 1P-LSD is believed to act as aprodrug for LSD viahydrolysis of thepropionyl 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 LSDin 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

[edit]

Synthesis

[edit]

Thechemical synthesis of 1P-LSD has been described in a patent from 2024.[16]

Properties

[edit]

Thechemical stability of 1P-LSD has been studied.[17][18]

Analogues

[edit]

Related compounds include1cP-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, andLSZ, among others.

History

[edit]

1P-LSD was first described as well as encountered as a noveldesigner drug in 2015.[19]

Society and culture

[edit]

Legal status

[edit]

As of 2015, 1P-LSD is unscheduled in theUnited States andCanada, but may be considered illegal if sold or used for human consumption as a structural analog of LSD under theFederal Analogue Act in the US.[13] 1P-LSD is a prohibited or controlled substance in Australia, France,[20] Finland,[21] Denmark,[22] Germany,[23] Estonia,[24] Japan,[25] Latvia,[26] Norway,[27] Romania,[28] Sweden,[29] Switzerland,[30] United Kingdom,[31] Italy,[32] Singapore,[33] the Czech Republic,[34] and Croatia.[35] 1P-LSD has been illegal in Russia since 2017 as an LSD derivative.[36]

See also

[edit]

References

[edit]
  1. ^abcdefghijGrumann 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. ^abcdMallaroni 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. Retrieved28 July 2015.
  4. ^Daly M (27 July 2015)."Why Young Brits Are Taking So Much LSD and Ecstasy". Vice. Retrieved11 August 2015.
  5. ^"Newer Unregulated Drugs"(PDF). KFx. April 2015. Retrieved13 August 2015.
  6. ^Speiser M (11 August 2015)."A handful of dangerous new legal drugs has public health experts worried".Business Insider UK. Retrieved13 August 2015.
  7. ^"1P-LSD". New Synthetic Drugs Database. Archived fromthe original on 2016-07-03. Retrieved2016-01-29.
  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 fromthe original on 2015-10-15. Retrieved15 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. ^abcBrandt 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. ^WO 2024/028495, Stratford A, Williamson JP, "Prodrugs of Substituted Ergolines", published 8 February 2024, assigned to Synex Holdings BV 
  17. ^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.
  18. ^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.
  19. ^https://isomerdesign.com/bitnest/external/EMCDDA/New-Drugs-In-Europe-2015
  20. ^"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.
  21. ^"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).
  22. ^"Lists of euphoriant substances". The Danish Medicines Agency. September 2015.
  23. ^"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).
  24. ^"Muudatus narkootiliste ja psühhotroopsete ainete I nimekirjas" (in Estonian). Republic of Estonia Agency of Medicines. Archived fromthe original on 2019-04-25. Retrieved2019-02-04.
  25. ^"指定薬物一覧"(PDF) (in Japanese). Ministry of Health, Labour and Welfare.
  26. ^"Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Latvijas Republikas tiesību akti.
  27. ^"31 Forskrift om narkotika (narkotikaforskriften)" (in Norwegian). Helse- og omsorgsdepartementet. 14 February 2013.
  28. ^"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. Retrieved2020-07-24.
  29. ^"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).
  30. ^"Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
  31. ^"Psychoactive Substances Act 2016".legislation.gov.uk. Retrieved28 November 2023.
  32. ^"DECRETO 5 ottobre 2021".
  33. ^"Misuse of Drugs Act - Singapore Statutes Online".sso.agc.gov.sg.
  34. ^"Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek" (in Czech). Zákony pro lidi.
  35. ^"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. Retrieved2023-01-02.
  36. ^"ИЗМЕНЕНИЯ, КОТОРЫЕ ВНОСЯТСЯ В АКТЫ ПРАВИТЕЛЬСТВА РОССИЙСКОЙ ФЕДЕРАЦИИ В СВЯЗИ С СОВЕРШЕНСТВОВАНИЕМ КОНТРОЛЯ ЗА ОБОРОТОМ НАРКОТИЧЕСКИХ СРЕДСТВ И ПСИХОТРОПНЫХ ВЕЩЕСТВ \ КонсультантПлюс".www.consultant.ru. Retrieved2023-02-07.

External links

[edit]
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