1P-LSD

Last updated
1P-LSD
1P-LSD Structural Formulae V.1.svg
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
  • (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
Formula C23H29N3O2
Molar mass 379.504 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 (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]

Contents

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

1P-LSD on blotter paper 1P-LSD.jpg
1P-LSD on blotter paper

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.

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]

See also

Related Research Articles

<span class="mw-page-title-main">LSD</span> Hallucinogenic drug

Lysergic acid diethylamide, commonly known as LSD, is a potent psychedelic drug that intensifies thoughts, emotions, and sensory perception. Often referred to as acid or lucy, LSD can cause mystical, spiritual, or religious experiences. At higher doses, it primarily induces visual and auditory hallucinations. LSD is not considered addictive, because it does not produce compulsive drug-seeking behavior. Using LSD can lead to adverse psychological reactions, such as anxiety, paranoia, and delusions. Additionally, it may trigger "flashbacks," also known as hallucinogen persisting perception disorder (HPPD), where individuals experience persistent visual distortions after use.

<span class="mw-page-title-main">Lysergic acid</span> Precursor for a range of ergoline alkaloids produced by the ergot fungus

Lysergic acid, also known as D-lysergic acid and (+)-lysergic acid, is a precursor for a wide range of ergoline alkaloids that are produced by the ergot fungus and found in the seeds of Argyreia nervosa, and Ipomoea species.

<span class="mw-page-title-main">Substituted lysergamide</span> Class of chemical compounds

Amides of lysergic acid are collectively known as lysergamides or ergoamides, and include a number of compounds with potent agonist and/or antagonist activity at various serotonin and dopamine receptors. Lysergamides contain an embedded tryptamine structure, and as a result can produce similar, often psychedelic, effects to those of the true tryptamines.

<span class="mw-page-title-main">ALD-52</span> Chemical compound

ALD-52, also known as 1-acetyl-LSD, has chemical structural features similar to lysergic acid diethylamide (LSD), a known psychedelic drug. Similarly, ALD-52 has been reported to produce psychoactive effects, but its pharmacological effects on humans are poorly understood. Given its psychoactive properties, it has been reported to be consumed as a recreational drug, and the purported first confirmed detection of the substance on the illicit market occurred in April 2016.

<span class="mw-page-title-main">Lysergic acid hydroxyethylamide</span> Chemical compound

ᴅ-Lysergic acid α-hydroxyethylamide, also known as ᴅ-lysergic acid methyl carbinolamide, is an ergoamide and an ergoline. It is perhaps the main constituent of the parasitic fungus, Claviceps paspali; and found in trace amounts in Claviceps Purpurea. C. paspali and C. purpurea are ergot-spreading fungi. Periglandula, Clavicipitacepus fungi, are permanently symbiotically connected to an estimated 450 species of Convolvulaceae and thus generate LAH in some of them. The most well-known ones are Ipomoea tricolor, Turbina corymbosa (coaxihuitl), and Argyreia nervosa.

<span class="mw-page-title-main">AL-LAD</span> Chemical compound (psychedelic drug)

AL-LAD, also known as 6-allyl-6-nor-LSD, is a psychedelic drug and an analog of lysergic acid diethylamide (LSD). It is described by Alexander Shulgin in the book TiHKAL. It is synthesized starting from nor-LSD as a precursor, using allyl bromide as a reactant.

<span class="mw-page-title-main">ETH-LAD</span> Chemical compound

ETH-LAD, 6-ethyl-6-nor-lysergic acid diethylamide is an analogue of LSD. Its human psychopharmacology was first described by Alexander Shulgin in the book TiHKAL. ETH-LAD is a psychedelic drug similar to LSD, and is slightly more potent than LSD itself, with an active dose reported at between 20 and 150 micrograms. ETH-LAD has subtly different effects to LSD, described as less demanding.

<span class="mw-page-title-main">PRO-LAD</span> Chemical compound

PRO-LAD is an analogue of LSD. It is described by Alexander Shulgin in the book TiHKAL. PRO-LAD is a psychedelic drug similar to LSD, and is around as potent as LSD itself with an active dose reported at between 100 and 200 micrograms.

<span class="mw-page-title-main">LSM-775</span> Chemical compound

N-Morpholinyllysergamide, also known as lysergic acid morpholide, is a derivative of ergine (lysergamide). It is less potent than lysergic acid diethylamide (LSD) but is reported to have some LSD-like effects at doses ranging from 75 to 700 micrograms and a shorter duration. LSM-775 may only produce weak or threshold psychedelic effects in humans.

<span class="mw-page-title-main">Lysergic acid 2,4-dimethylazetidide</span> Chemical compound

Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) is an analog of LSD developed by the team led by David E. Nichols at Purdue University. It was developed as a rigid analog of LSD with the diethylamide group constrained into an azetidine ring in order to map the binding site at the 5-HT2A receptor. There are three possible stereoisomers around the azetidine ring, with the (S,S)-(+) isomer being the most active, slightly more potent than LSD itself in drug discrimination tests using trained rats.

<span class="mw-page-title-main">1P-ETH-LAD</span> Chemical compound

1P-ETH-LAD is an analog of LSD. 1P-ETH-LAD is a psychedelic drug similar to LSD. Research has shown formation of ETH-LAD from 1P-ETH-LAD incubated in human serum, suggesting that it functions as a prodrug. It is part of the lysergamide chemical class. Like ETH-LAD, this drug has been reported to be significantly more potent than LSD itself, and is reported to largely mimic ETH-LAD's psychedelic effects.

<span class="mw-page-title-main">ECPLA</span> Chemical compound

ECPLA (N-ethyl-N-cyclopropyllysergamide) is an analog of lysergic acid diethylamide (LSD) developed by Synex Synthetics. In studies in mice, it was found to have approximately 40% the potency of LSD.

<span class="mw-page-title-main">1cP-LSD</span> Chemical compound

1cP-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. It was first synthesized as a legal-LSD alternative by Lizard Labs, a Netherlands based research chemical laboratory. In tests on mice it was found to be an active psychedelic with similar potency to 1P-LSD.

<span class="mw-page-title-main">1B-LSD</span> Chemical compound

1B-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. In tests on mice it was found to be an active psychedelic, though with only around 1/7 the potency of LSD itself.

<span class="mw-page-title-main">1V-LSD</span> Chemical compound

1V-LSD, sometimes nicknamed Valerie, is a psychotropic substance and a research chemical with psychedelic effects. 1V-LSD is an artificial derivative of natural lysergic acid, which occurs in ergot alkaloids, as well as being an analogue of LSD. 1V-LSD has been sold online until an amendment to the German NpSG was enforced in 2022 which controls 1P-LSD and now 1cP-LSD, 1V-LSD and several other lysergamides.

<span class="mw-page-title-main">1cP-AL-LAD</span> Chemical compound

1cP-AL-LAD is an analog of lysergic acid diethylamide (LSD) which has psychedelic effects and is thought to act as a prodrug for AL-LAD. It has been sold as a designer drug, first identified in France in June 2021.

<span class="mw-page-title-main">1P-AL-LAD</span> Chemical compound

1P-AL-LAD is a derivative of lysergic acid diethylamide (LSD) which has psychedelic effects and has been sold as a designer drug. It is believed to act as a prodrug for AL-LAD and produces a head-twitch response in animal studies.

<span class="mw-page-title-main">1T-LSD</span> Chemical compound

1T-LSD is an acylated derivative of lysergic acid diethylamide (LSD), which has been sold as a designer drug. It was first identified in Japan in 2023 on blotter paper misrepresented as containing 1D-LSD, but which on analysis was determined to contain 1T-LSD instead. It was also detected in Germany around the same time.

<span class="mw-page-title-main">1S-LSD</span> Chemical compound, Novel psychoactive substance analog, LSD prodrug

1S-LSD is a psychotropic substance and research chemical belonging to the lysergamide class. It is the trimethylsilyl derivative of 1P-LSD and functions as a prodrug and functional analogue of LSD. 1S-LSD was developed in response to legal restrictions on similar compounds, such as 1D-LSD, which were banned in Germany under the NpSG law in June 2024.

<span class="mw-page-title-main">Descarboxylysergic acid</span> Pharmaceutical compound

Descarboxylysergic acid, or 8-descarboxylysergic acid, also known as 9,10-didehydro-6-methylergoline or as 6-methyl-9-ergolene, is a drug of the ergoline family related to lysergic acid and lysergamides like lysergic acid diethylamide (LSD). It is the analogue of lysergic acid in which the carboxyl group at the C8 position of the molecule has been removed. Descarboxylysergic acid was synthesized in an attempt to help elucidate the minimum structural requirements for biological activity of ergoline and lysergamide drugs like LSD.

References

  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.
  10. 1 2 3 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.
  12. 1 2 3 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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