1P-LSD
{{Short description|Chemical compound}}
{{Infobox drug
| IUPAC_name = (6aR,9R)-N,N-Diethyl-7-methyl-4-propanoyl-6,6a,8,9-tetrahydroindolo[4,3-fg]quinoline-9-carboxamide
| image = 1P-LSD_Structural_Formulae_V.1.svg
| tradename =
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU = S8
| legal_BR = F2
| legal_CA = Unscheduled.
| legal_DE = NpSG
| legal_UK = PSA
| legal_status = In general Unscheduled, unless that was sold for human consumption, could be sold for medical and research purposes.
| legal_US = Unscheduled (may be considered illegal if sold for human consumption as an analog of LSD under the federal analogue act)
| legal_UN = Unscheduled
| routes_of_administration =
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 2349358-81-0
| ATC_prefix =
| ATC_suffix =
| PubChem = 119025985
| ChemSpiderID = 52085129
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 23R2G2G79C
| synonyms = 1-Propanoyl-LSD; 1-Propionyl-LSD
| C=23 | H=29 | N=3 |O=2
| SMILES = CCN(CC)C(=O)[C@H]1CN(C)[C@@H]2Cc3cn(C(=O)CC)c4cccc(C2=C1)c34
| StdInChI = 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
| StdInChIKey = JSMQOVGXBIDBIE-OXQOHEQNSA-N
}}
1P-LSD, also known as 1-propanoyl-lysergic acid diethylamide (1-propionyl-LSD), 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.{{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}} It was first synthesized as a legal-LSD alternative by Lizard Labs, a Netherlands based research chemical laboratory.{{Cite web |date=2024-09-12 |title=1P-LSD 100mcg Blotters {{!}} Chemical Collective |url=https://chemical-collective.com/product/1p-lsd-100mcg-blotters/ |access-date=2024-09-13 |website=chemical-collective.com |language=en-US}}{{cite web | url=https://www.vice.com/en/article/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 }}{{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}}{{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}}{{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 }}{{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 }} It modifies the LSD molecule by adding a propionyl group to the nitrogen atom of LSD's indole group.{{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}}{{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}}
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, administered intravenously to rats,{{cite journal |display-authors=6 |vauthors=Halberstadt AL, Chatha M, Klein AK, McCorvy JD, Meyer MR, Wagmann L, Stratford A, Brandt SD |date=August 2020 |title=Pharmacological and biotransformation studies of 1-acyl-substituted derivatives of d-lysergic acid diethylamide (LSD) |journal=Neuropharmacology |volume=172 |pages=107856 |doi=10.1016/j.neuropharm.2019.107856 |pmc=9191647 |pmid=31756337}} or administered either orally or intravenously to human subjects,{{cite journal |vauthors=Grumann C, Henkel K, Brandt SD, Stratford A, Passie T, Auwärter V |date=August 2020 |title=Pharmacokinetics and subjective effects of 1P-LSD in humans after oral and intravenous administration |journal=Drug Testing and Analysis |volume=12 |issue=8 |pages=1144–1153 |doi=10.1002/dta.2821 |pmid=32415750 |doi-access=free}} 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. These findings are supported by the similar duration and behavioral effects of 1P-LSD and LSD in both animal and human experiments.
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.{{cite book | vauthors = Schifano F, Orsolini L, Papanti D, Corkery J | title = Neuropharmacology of New Psychoactive Substances (NPS) | chapter = NPS: Medical Consequences Associated with Their Intake | series = Current Topics in Behavioral Neurosciences| volume = 32 | pages = 351–380 | date = June 2016 | pmid = 27272067 | doi = 10.1007/7854_2016_15 | isbn = 978-3-319-52442-9 | doi-access = free | oclc = 643052237 }} In a 2020 study, the qualitative effects of 1P-LSD and LSD were similar when measured using visual analog scales.
Interactions
{{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
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.{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, Wallach J, Halberstadt AL | display-authors = 6 | title = Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD) | journal = Drug Testing and Analysis | volume = 8 | issue = 9 | pages = 891–902 | date = September 2016 | pmid = 26456305 | pmc = 4829483 | doi = 10.1002/dta.1884 }} 1P-LSD is a prohibited or controlled substance in Australia, France,{{cite web|date=20 May 2021|title=Arrêté du 20 mai 2021 modifiant l'arrêté du 22 février 1990 fixant la liste des substances classées comme stupéfiants|url=https://www.legifrance.gouv.fr/jorf/id/JORFTEXT000043523554|website=www.legifrance.gouv.fr|language=fr}} Finland,{{cite web |title=Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista annetun valtioneuvoston asetuksen liitteen muuttamisesta |trans-title=Government decree amending the annex to the government decree on psychoactive substances prohibited on the consumer market |language=Finnish |url=https://www.finlex.fi/fi/lainsaadanto/saadoskokoelma/2018/840}} Denmark,{{cite web | url=http://laegemiddelstyrelsen.dk/en/licensing/company-authorisations-and-registrations/euphoriant-substances/lists-of-substances | title=Lists of euphoriant substances | publisher=The Danish Medicines Agency | date=September 2015}} Germany,{{cite web |title=Verordnung zur Änderung der Anlage des Neue-psychoaktive-. Stoffe-Gesetzes und von Anlagen des Betäubungsmittelgesetzes |trans-title=Regulation amending the Annex to the New Psychoactive Substances Act and Appendices to the Narcotics Act |language=German |url=https://www.bgbl.de/xaver/bgbl/start.xav#__bgbl__%2F%2F*%5B%40attr_id%3D%27bgbl119s1083.pdf%27%5D__1563358129436}} Estonia,{{cite web | url=https://www.sam.ee/en/node/10831 | title=Muudatus narkootiliste ja psühhotroopsete ainete I nimekirjas | publisher=Republic of Estonia Agency of Medicines | language=Estonian | access-date=2019-02-04 | archive-date=2019-04-25 | archive-url=https://web.archive.org/web/20190425061119/https://www.sam.ee/en/node/10831 | url-status=dead }} Japan,{{cite web | url=http://www.mhlw.go.jp/seisakunitsuite/bunya/kenkou_iryou/iyakuhin/yakubuturanyou/dl/meisho.pdf | title=指定薬物一覧 | publisher=Ministry of Health, Labour and Welfare | language=Japanese}} Latvia,{{cite web | url=http://likumi.lv/doc.php?id=121086 | title=Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem | publisher=Latvijas Republikas tiesību akti | language=Latvian}} Norway,{{cite web | url=https://lovdata.no/dokument/SF/forskrift/2013-02-14-199 | title=31 Forskrift om narkotika (narkotikaforskriften) | publisher=Helse- og omsorgsdepartementet | language=Norwegian | date= 14 February 2013}} Romania,{{Cite web|title=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|url=http://www.dreptonline.ro/legislatie/legea_194_2011_combaterea_operatiunilor_produse_susceptibile_efecte_psihoactive.php|access-date=2020-07-24|website=www.dreptonline.ro}} Sweden,{{cite web |title=Förordning om ändring i förordningen (1999:58) om förbud mot vissa hälsofarliga varor |trans-title=Ordinance (1999: 58) on the prohibition of certain dangerous goods |language=Swedish |url=https://notisum.se/rnp/sls/sfs/20150997.pdf }} Switzerland,{{cite web | url=https://www.admin.ch/opc/de/classified-compilation/20101220/index.html | title=Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien | publisher=Der Bundesrat | language=German}} United Kingdom,{{Cite web |title=Psychoactive Substances Act 2016 |url=https://www.legislation.gov.uk/ukpga/2016/2/contents |access-date=28 November 2023 |website=legislation.gov.uk}} Italy,{{cite web|url=https://www.gazzettaufficiale.it/eli/id/2021/10/18/21A06118/sg|title= DECRETO 5 ottobre 2021 }} Singapore,{{cite web|title=Misuse of Drugs Act - Singapore Statutes Online|url=https://sso.agc.gov.sg/Act/MDA1973|website=sso.agc.gov.sg}} the Czech Republic,{{cite web | url=https://www.zakonyprolidi.cz/cs/2013-463 | title=Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek | publisher=Zákony pro lidi | language=Czech}} and Croatia.{{Cite web |title=Popis droga, psihotropnih tvari i biljaka iz kojih se može dobiti droga te tvari koje se mogu uporabiti za izradu droga |url=https://narodne-novine.nn.hr/clanci/sluzbeni/2019_02_13_259.html |access-date=2023-01-02 |website=narodne-novine.nn.hr}} 1P-LSD has been illegal in Russia since 2017 as an LSD derivative.{{Cite web |title=ИЗМЕНЕНИЯ, КОТОРЫЕ ВНОСЯТСЯ В АКТЫ ПРАВИТЕЛЬСТВА РОССИЙСКОЙ ФЕДЕРАЦИИ В СВЯЗИ С СОВЕРШЕНСТВОВАНИЕМ КОНТРОЛЯ ЗА ОБОРОТОМ НАРКОТИЧЕСКИХ СРЕДСТВ И ПСИХОТРОПНЫХ ВЕЩЕСТВ \ КонсультантПлюс |url=https://www.consultant.ru/document/cons_doc_LAW_404473/4347f565328bac46bfd843bc52fef25ac88cd925/#dst100135 |access-date=2023-02-07 |website=www.consultant.ru}}
See also
References
{{Reflist|30em}}
External links
- [https://isomerdesign.com/pihkal/explore/5916 1P-LSD - Isomer Design]
- [https://psychonautwiki.org/wiki/1P-LSD 1P-LSD - PsychonautWiki]
- [https://tripsitter.com/1p-lsd/ 1P-LSD: Is “Legal Acid” Legit? Is it Safe? - Tripsitter]
- [https://psychedelicreview.com/compound/1p-lsd/ 1P-LSD - Psychedelic Science Review]
{{Psychedelics}}
{{Serotonin receptor modulators}}
{{Ergolines}}