en 1P-LSD

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
	IUPAC name (6aR,9R)-N,N-Diethyl-7-methyl-4-propanoyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide;
CAS Number	2349358-81-0 ;
PubChem CID	119025985;
ChemSpider	52085129;
UNII	23R2G2G79C;
CompTox Dashboard (EPA)	DTXSID701016895 ;
Chemical and physical data
Formula	C23H29N3O2
Molar mass	379.504 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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] It was first synthesized as a legal-LSD alternative by Lizard Labs, a Netherlands based research chemical laboratory.^[2]^[3]^[4]^[5]^[6]^[7] It modifies the LSD molecule by adding a propionyl group to the nitrogen atom of LSD's indole group.^[8]^[9]

Pharmacology

Like ALD-52, 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,^[10] administered intravenously to rats,^[11] or administered either orally or intravenously to human subjects,^[12] 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.^[12] These findings are supported by the similar duration and behavioral effects of 1P-LSD and LSD in both animal and human experiments.^[10]^[12]

Effects

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.^[13] In a 2020 study, the qualitative effects of 1P-LSD and LSD were similar when measured using visual analog scales.

Legal status

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.^[10] 1P-LSD is a prohibited or controlled substance in Australia, France,^[14] Finland,^[15] Denmark,^[16] Germany,^[17] Estonia,^[18] Japan,^[19] Latvia,^[20] Norway,^[21] Romania,^[22] Sweden,^[23] Switzerland,^[24] United Kingdom,^[25] Italy,^[26] Singapore,^[27] the Czech Republic,^[28] and Croatia.^[29] 1P-LSD has been illegal in Russia since 2017 as an LSD derivative.^[30]

References

^ "Philtre Bulletin Issue 5" (PDF). WEDINOS. March 2015. Retrieved 28 July 2015.
^ "1P-LSD 100mcg Blotters | Chemical Collective". chemical-collective.com. 2024-09-12. Retrieved 2024-09-13.
^ Daly M (27 July 2015). "Why Young Brits Are Taking So Much LSD and Ecstasy". Vice. Retrieved 11 August 2015.
^ "Newer Unregulated Drugs" (PDF). KFx. April 2015. Retrieved 13 August 2015.
^ Speiser M (11 August 2015). "A handful of dangerous new legal drugs has public health experts worried". Business Insider UK. Retrieved 13 August 2015.
^ "1P-LSD". New Synthetic Drugs Database. Archived from the original on 2016-07-03. Retrieved 2016-01-29.
^ 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.
^ 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.
^ 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.
^ ^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.
^ 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.
^ ^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.
^ 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.
^ "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.
^ "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).
^ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015.
^ "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).
^ "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.
^ "指定薬物一覧" (PDF) (in Japanese). Ministry of Health, Labour and Welfare.
^ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Latvijas Republikas tiesību akti.
^ "31 Forskrift om narkotika (narkotikaforskriften)" (in Norwegian). Helse- og omsorgsdepartementet. 14 February 2013.
^ "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.
^ "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).
^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
^ "Psychoactive Substances Act 2016". legislation.gov.uk. Retrieved 28 November 2023.
^ "DECRETO 5 ottobre 2021".
^ "Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.
^ "Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek" (in Czech). Zákony pro lidi.
^ "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.
^ "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.

[1] "Philtre Bulletin Issue 5" (PDF). WEDINOS. March 2015. Retrieved 28 July 2015.

[2] "1P-LSD 100mcg Blotters | Chemical Collective". chemical-collective.com. 2024-09-12. Retrieved 2024-09-13.

[3] Daly M (27 July 2015). "Why Young Brits Are Taking So Much LSD and Ecstasy". Vice. Retrieved 11 August 2015.

[4] "Newer Unregulated Drugs" (PDF). KFx. April 2015. Retrieved 13 August 2015.

[5] Speiser M (11 August 2015). "A handful of dangerous new legal drugs has public health experts worried". Business Insider UK. Retrieved 13 August 2015.

[6] "1P-LSD". New Synthetic Drugs Database. Archived from the original on 2016-07-03. Retrieved 2016-01-29.

[7] 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.

[8] 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.

[9] 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.

[Brandt_S-10] 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.

[11] 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.

[:0-12] 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.

[13] 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.

[14] "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.

[15] "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).

[16] "Lists of euphoriant substances". The Danish Medicines Agency. September 2015.

[17] "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).

[18] "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.

[19] "指定薬物一覧" (PDF) (in Japanese). Ministry of Health, Labour and Welfare.

[20] "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Latvijas Republikas tiesību akti.

[21] "31 Forskrift om narkotika (narkotikaforskriften)" (in Norwegian). Helse- og omsorgsdepartementet. 14 February 2013.

[22] "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.

[23] "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).

[24] "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.

[25] "Psychoactive Substances Act 2016". legislation.gov.uk. Retrieved 28 November 2023.

[26] "DECRETO 5 ottobre 2021".

[27] "Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.

[28] "Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek" (in Czech). Zákony pro lidi.

[29] "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.

[30] "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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1P-LSD

Pharmacology

Effects

Legal status

See also

References

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