1P-LSD - Wikipedia

Chemical compound Pharmaceutical compound 1P-LSD

Clinical data
Other names	1-Propanoyl-lysergic acid diethylamide; 1-Propanoyl-LSD; 1-Propionyl-LSD
Routes ofadministration	Oral[1]
Drug class	Serotonin 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]
Metabolism	Hydrolysis[1]
Metabolites	LSD[1]
Elimination half-life	Initial: ~0.2 hours[1]
Duration of action	8–12 hours[2][1]
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 Y
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, 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

[edit] See also: LSD § Uses, and LSD § Effects

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

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

Pharmacology

[edit]

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

[edit]

Synthesis

[edit]

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

Properties

[edit]

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

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.[19][20][21]

Society and culture

[edit]

Legal status

[edit]

1P-LSD is unscheduled in the United States[22] and Canada, but may be considered illegal if sold or used for human consumption as an analogue of LSD under the Federal Analogue Act in the United States.[13] 1P-LSD is a prohibited or controlled substance in Australia, France,[23] Finland,[24] Denmark,[25] Germany,[26] Estonia,[27] Japan,[28] Latvia,[29] Norway,[30] Romania,[31] Sweden,[32] Switzerland,[33] United Kingdom,[34] Italy,[35] Singapore,[36] the Czech Republic,[37] and Croatia.[38] 1P-LSD has been illegal in Russia since 2017 as an LSD derivative.[39]

See also

[edit]

• Substituted lysergamide
• Lizard Labs
• 4-AcO-DMT

References

[edit]

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. ^ 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. ^ "N-Пропионил-ЛСД (1P-LSD)". АИПСИН (in Russian). Retrieved 2 January 2026.
21. ^ "N-Пропионил-ЛСД". АИПСИН (in Russian). Retrieved 2 January 2026.
22. ^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF), United States: U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
23. ^ "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.
24. ^ "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).
25. ^ "Lists of euphoriant substances". The Danish Medicines Agency. September 2015.
26. ^ "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).
27. ^ "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.
28. ^ "指定薬物一覧" (PDF) (in Japanese). Ministry of Health, Labour and Welfare.
29. ^ "Noteikumi par Latvijā kontrolējamajām narkotiskajām vielām, psihotropajām vielām un prekursoriem" (in Latvian). Latvijas Republikas tiesību akti.
30. ^ "31 Forskrift om narkotika (narkotikaforskriften)" (in Norwegian). Helse- og omsorgsdepartementet. 14 February 2013.
31. ^ "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.
32. ^ "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).
33. ^ "Verordnung des EDI über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien" (in German). Der Bundesrat.
34. ^ "Psychoactive Substances Act 2016". legislation.gov.uk. Retrieved 28 November 2023.
35. ^ "DECRETO 5 ottobre 2021".
36. ^ "Misuse of Drugs Act - Singapore Statutes Online". sso.agc.gov.sg.
37. ^ "Nařízení vlády č. 463/2013 Sb. Nařízení vlády o seznamech návykových látek" (in Czech). Zákony pro lidi.
38. ^ "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.
39. ^ "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.

External links

[edit]

• 1P-LSD - Isomer Design
• 1P-LSD - PsychonautWiki
• 1P-LSD: Is “Legal Acid” Legit? Is it Safe? - Tripsitter
• 1P-LSD - Lysergamide Psychedelics - TripSitter
• 1P-LSD - Psychedelic Science Review

v t e Psychedelics
Tryptamines	No ring subs. CYB004 (deuDMT) DALT DBT DET (T-9) DiPT DMT DPT EiPT EPT iPALT (ALiPT) MALT McPT MET MiPT MPT NMT PALT PiPT SPL028 (D2-DMT) Tryptamine (T) 4-Hydroxytryptamines 4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-McPT 4-HO-MET (metocin) 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-NALT 4-HO-NBnT 4-HO-NET 4-HO-NiPT 4-HO-NPT 4-HO-TMT 4-HO-5-MeO-DMT 4-HO-T (4-HT) 4-MeO-DMT CYB003 (deupsilocin) Psilocin (4-HO-DMT; CX-59) 4-Phosphoryloxytryptamines: Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Ethocybin (4-PO-DET; CEY-19) Norbaeocystin (4-PO-T) Psilocybin (4-PO-DMT; CY-39) 4-Acyloxytryptamines: 4-AcO-DALT (daltacetin) 4-AcO-DET (ethacetin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin) 4-AcO-DPT (depracetin) 4-AcO-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-GO-DMT (RE-109) 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET Luvesilocin (4-GO-DiPT; RE-104, FT-104) 5-Hydroxytryptamines 5-HO-MET Bufotenin (5-HO-DMT) Serotonin (5-HT; 5-HO-T) 5-Acyloxytryptamines: O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT) 5-Methoxytryptamines 4-HO-5-MeO-DMT 5-MeO-2,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (mebufotenin) 5-MeO-DPT 5-MeO-EiPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NiPT 5-MeO-NMT 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MeO-T (5-MT) ASR-3001 (5-MeO-iPALT) NB-5-MeO-DALT NB-5-MeO-MiPT Other ring subs. 2,N,N-TMT (2-methyl-DMT) 4,N,N-TMT (4-methyl-DMT) 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-PhO-T (OVT2) 5-N,N-TMT (5-methyl-DMT) 7,N,N-TMT (7-methyl-DMT) 5-MeO-2,N,N-TMT 6-Fluoro-DMT 6-Hydroxy-DET (6-HO-DET) Bretisilocin (GM-2505; 5-fluoro-MET) NBoc-DMT (NB-DMT) α-Alkyltryptamines 4-HO-AMT 4-Methyl-AMT 5-Fluoro-AMT 6-Fluoro-AMT AMT (Indopan) α-Methylserotonin (5-HO-αMT) α,N,N-TMT (α-Me-DMT; Alpha-N) N-Hydroxy-AMT 5-Methoxy-α-alkyltryptamines: 5-MeO-AET 5-MeO-AMT (α,O-DMS; Alpha-O) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT) Others N-DEAOP-Ts (e.g., N-DEAOP-NET, N-DEAOP-NMT, 5-MeO-N-DEAOP-NMT, 5-MeO-N-DEAOP-NET) Structure undisclosed: CT-4201 EB-002 (EB-373) MSP-1014 MYCO-004 Cyclized Ergolines/lysergamides (e.g., LSD) Ibogalogs (e.g., ibogainalog, tabernanthalog) O-Methylnordehydrobufotenine Partial ergolines (e.g., NDTDI, RU-28306, CT-5252) Piperidinylethylindoles (e.g., pip-T) Pyrrolidinylethylindoles (e.g., pyr-T, 5-MeO-pyr-T) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5-MeO-MPMI, MSP-2020) Tetrahydropyridinylindoles (e.g., RU-28253 (5-MeO-THPI), NEtPhOH-THPI) Bioisosteres Benzofurans (e.g., 5-MeO-DiBF (1-oxa-5-MeO-DiPT), dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT), mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT)) Benzothiophenes (e.g., 3-APBT (1-thia-AMT)) Indazolethylamines (e.g., AL-38022A, O-methyl-AL-34662) Indenylethylamines (e.g., C-DMT) Isotryptamines (e.g., 6-MeO-isoDMT, Ro60-0175) MYCO-005 Quinolinylethylamines (e.g., mefloquine)
Phenethylamines	Scalines 2-Bromomescaline 4-D (4-trideuteromescaline) 4-Desoxymescaline (desoxy) Allylescaline (AL) Beta-D (β-D; β-dideuteromescaline) Cyclopropylmescaline (CPM) Difluoroescaline (DFE) Difluoromescaline (DFM) N,N-Diformylmescaline Escaline (E) Fluoroescaline (FE) Fluoroproscaline (FP) N-Formylmescaline Isobuscaline (IB) Isoproscaline (IP) Jimscaline Mescaline (M; 3,4,5-TMPEA) Metadifluoromescaline (MDFM) Metaescaline (ME) Methallylescaline (MAL) N-Methylmescaline (M-M) Proscaline (P) Tomscaline Trichocereine (N,N-dimethylmescaline; MM-M) Trifluoroescaline (TFE) Trifluoromescaline (TFM) Thioscalines: 3-Thioasymbescaline (3-TASB) 3-Thioescaline (3-TE) 3-Thiomescaline (3-TM) 3-Thiometaescaline (3-TME) 4-Thioasymbescaline (4-TASB) 4-Thioescaline (4-TE) 4-Thiomescaline (4-TM) 5-Thioasymbescaline (5-TASB) Thiobuscaline (TB; 4-TB) Thioproscaline (TP; 4-TP) 2C-x 2C-B 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-H 2C-I 2C-iBu 2C-iP 2C-N 2C-P 2C-Se 2C-Se-TFM 2C-tBu 2C-TFE 2C-TFM 2C-YN 2C-V 2C-T-x: 2C-T 2C-T-2 2C-T-3 (2C-T-20) 2C-T-4 2C-T-7 2C-T-8 2C-T-9 2C-T-13 2C-T-15 2C-T-16 2C-T-17 2C-T-19 2C-T-21 2C-T-21.5 2C-T-22 2C-T-25 2C-T-27 2C-T-28 2C-T-30 CYB210010 (2C-T-TFM, 2C-T-36) 2C-O-x: 2C-O (2,4,5-TMPEA; TMPEA-2) 2C-O-4 2C-O-22 Others: 2C-B-AN 2C-DB 2C-G-x (e.g., 2C-G-3, 2C-G-5) β-Keto-2C-B (βk-2C-B) β-Keto-2C-I (βk-2C-I) β-Methyl-2C-B (BMB) BOx (e.g., BOB, BOD, BOHB) HOT-x (e.g., HOT-2, HOT-7, HOT-17) N-Ethyl-2C-B TWEETIOs (e.g., 2CB-2-EtO, 2CD-2-EtO, 2CD-5-EtO, 2CE-5-EtO, 2CE-5iPrO, 2CT2-2-EtO, ASR-2001 (2CB-5-PrO)) 3C-x 3C-AL 3C-BZ 3C-DFE 3C-E 3C-MAL 3C-P TMA (3C-M) DOx DOAM DOB DOBU DOC DOEF DOET DOH (2,5-DMA) DOI DOIB DOIP DOM DON DOPR DOTFM DOYN Aleph-x (DOT-x): Aleph (DOT) Aleph-2 Aleph-4 Aleph-6 Aleph-7 TMA-2 and derivatives (Mxx): MALM MEM MDFEM MFEM MIPM MMALM MPM MTFEM TMA-2 Others: DODB DODC DOM-NBOMe DOTMA Ganeshas (G-x) (e.g., Ganesha (G, G-0), G-3, G-5) MME (TMA2-5-EtO) N-Hydroxy-DOM 4C-x 4C-B 4C-D (Ariadne) 4C-I 4C-P (4C-Pr) 4C-T-2 4C-TFM Ψ-PEA 2,4,6-TMPEA-NBOMe Ψ-2C-DFMO (ψ-2C-O-35) Ψ-2C-T-4 Ψ-DODFMO Ψ-DOM TMA-6 (Ψ-TMA-2) MDxx 5-Methyl-MDA 6-Methyl-MDA DMMDA DMMDA-2 EIDA EMDA-2 IDA Lophophine (MMDPEA) Lys-MDA MDA (tenamfetamine) MDHMA (FLEA; MDMOH) MDMA (midomafetamine; ecstasy) MDOH MMDA MMDA-2 MMDA-3a MMDA-3b MMDMA N-t-BOC-MDMA (R)-MDMA FLY 2C-B-FLY 2C-B-BUTTERFLY 2C-B-DragonFLY 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY DOH-FLY TFMFly Hemi/semi-FLY drugs: 2CB-5-hemiFLY DOH-5-hemiFLY (semi-fly; SF) DOB-5-hemiFLY (bromo-semi-fly; B-SF) 25x-NB (NBOMes) 25x-NBOMe: 25B-NBOMe 25C-NBOMe 25CN-NBOMe 25D-NBOMe 25E-NBOMe 25F-NBOMe 25G-NBOMe 25H-NBOMe 25I-NBOMe 25iP-NBOMe 25N-NBOMe 25O-NBOMe 25P-NBOMe 25T-NBOMe 25T2-NBOMe 25T4-NBOMe 25T7-NBOMe 25TFM-NBOMe 25x-NBOH: 25B-NBOH 25C-NBOH 25CN-NBOH 25E-NBOH 25I-NBOH Others: 2,4,6-TMPEA-NBOMe 25B-NB (N-benzyl-2C-B) 2C-B-AN 2C2-NBOMe 2CBCB-NBOMe 2CBFly-NBOMe DOM-NBOMe NBOMe-escaline NBOMe-mescaline TGF-8027 Others 25B-NAcPip 2-DM-DOM 4-HA 5-DM-DOM Benzofurans (e.g., 5-APB, 5-APDB, 6-APB, 6-APDB, F, F-2, F-22) Benzothiophenes (e.g., 5-APBT, 6-APBT) CT-5172 DMAs (e.g., 2,4-DMA, 3,4-DMA) Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs (e.g., 25D-NM-NDEAOP, DOB-NDEPA, DOI-NDEPA, DOM-NDEPA, DOTFM-NDEPA, M-NDEPA, TMA-2-NDEPA) PMA (4-MA) Thio-2Cs (e.g., 2C-5-TOET) Thio-DOx (e.g., 2-TOM, 5-TOET, 5-TOM, TOMSO) TMAs (e.g., TMA-3, TMA-4, TMA-5) ZDCM-04 (DOC-fenethylline) Structure undisclosed: CYB005 Cyclized 1-Aminomethylindanes (e.g., 2CB-Ind, jimscaline) 2-Aminoindanes (e.g., DOM-AI) 3-Benzazepines (e.g., lorcaserin) 3-Phenylpiperidines (e.g., LPH-5, LPH-48) Benzocyclobutenes (e.g., 2CBCB-NBOMe, TCB-2, tomscaline) Benzoxepins (e.g., BBOX, IBOX, TFMBOX) DMBMPP (juncosamine) Ergolines/lysergamides (e.g., LSD) Glaucine Partial ergolines (e.g., NDTDI, DEIMDHPCA, DEMPDHPCA, DEMTMPDHPCA, DEMNDHPCA) Phenylcyclopropylamines (e.g., DMCPA, TMT) Phenyloxazolamines (aminorexes) (e.g., 2C-B-aminorex) Pyridopyrroloquinoxalines (e.g., IHCH-7113) Z3517967757 ZC-B
Lysergamides	No substitutions: Ergine (LSA, LA-111) Isoergine (iso-LSA, iso-LA) Amide-substituted lysergamides: DAL DAM (DAM-57) DiPLA DPL EcPLA EiPLA EPLA (LEP; LEP-57) Ergometrine (ergonovine, ergobasine) ETFELA iPLA LA-3Cl-SB (Cl-LSB) LAE (LAE-32) LAM LAMPA LAP LME (LME-54) LMP (LMP-55) LPD (LPD-824) LSB LSD (LSD-25, METH-LAD; lysergide) LSD-Pip LSDP (DPL) LSH (LAH) LSM (LSM-775) LSP LSZ (LA-SS-Az) Lysergic acid pyrrolinide (LPN) Methylergometrine (methylergonovine, methylergobasine) MiPLA 6-Alkyllysergamides: BU-LAD CE-LAD (CHLORETH-LAD) CPM-LAD CYP-LAD (TRALA-22) ETH-LAD FLUORETH-LAD (FE-LAD) FP-LAD IP-LAD NBOMe-LAD PARGY-LAD PRO-LAD 1-Alkyllysergamides (prodrugs): Methysergide (1-methylmethylergonovine; UML-491) MLA-74 (1-methyl-LAE) MLD-41 (1-methyl-LSD) MPD-75 (1-methyl-LPD) OML-632 (1-hydroxymethyl-LSD) 1-Acyllysergamides (prodrugs): 1-Formyl-LSD 1B-LSD 1BP-LSD 1Bz-LSD 1cP-AL-LAD 1cP-LSD 1cP-MiPLA 1D-AL-LAD 1D-LSD 1DD-LSD 1F-LSD 1Fe-LSD 1H-LSD 1P-AL-LAD 1P-ETH-LAD 1P-LSD 1P-MiPLA 1S-LSD 1SB-LSD (1BS-LSD) 1T-AL-LAD 1T-LSD 1V-LSD ALA-10 (1-acetyl-LAE; 1A-LAE) ALD-52 (1-acetyl-LSD; 1A-LSD) Others: 2,3-Dihydro-LSD 12-Hydroxy-LSD 12-Methoxy-LSD Bioisosteres: JRT (isoindole-LSD)
Others	Arylpiperazines (e.g., 2C-B-PP, 2-NP, mCPP, MK-212, ORG-12962, pCPP, pFPP, quipazine, TFMPP) Dihydrobenzoxazines (e.g., efavirenz) Phenoxyethylamines (e.g., CT-4719, ORG-37684) Pyridopyrroloquinoxalines (e.g., IHCH-7113) Quinazolinylethylamines (e.g., RH-34) Structure undisclosed: BMB-202 EGX-A EGX-B HBL20016 Lucid-PSYCH (Lucid-201) MSP-4018 MSP-4019 MSP-4020
Natural sources	Tryptamines: Acacia spp. (e.g., Acacia acuminata, Acacia confusa) Ayahuasca and vinho de Jurema (e.g., Psychotria viridis (chacruna), Dipolopterys cabrerana (chaliponga, chacruna), Mimosa tenuiflora (Mimosa hostilis; jurema)) Brosimum (e.g., Brosimum acutifolium (takini)) Hallucinogenic snuffs (e.g., Anadenanthera peregrina (yopo, jopo, cohoba, parica, ebene), Anadenanthera colubrina (vilca, cebil)) Incilius alvarius (Bufo alvarius; Colorado River toad, Sonoran Desert toad; bufo) Psilocybin-containing mushrooms (magic mushrooms, shrooms) (e.g., Psilocybe cubensis, Psilocybe mexicana (teonanacatl)) Phenethylamines: Pachycereus pringlei (saguesa, elephant cactus, cardon) Peyote (Lophophora williamsii; peyotl) Echinopsis cacti (e.g., San Pedro, Peruvian torch) Lysergamides: Achnatherum robustum (sleepy grass) Epichloë spp. Ergot (Claviceps) (e.g., Claviceps purpurea, Claviceps paspali) Morning glory (Convolvulaceae) seeds (e.g., Ipomoea tricolor (tlitliltzin, badoh negro; Ipomoea violacea), Ipomoea corymbosa (coaxihuitl, ololiúqui; Rivea Corymbosa, Turbina Corymbosa), Argyreia nervosa (Hawaiian baby woodrose; HBWR)) Periglandula spp. (e.g., Periglandula ipomoeae, Periglandula clandestina)
See also: Hallucinogens Entactogens Tryptamines Phenethylamines Ergolines and lysergamides Serotonin receptor modulators List of psychedelic drugs

v t e Serotonin receptor modulators
5-HT1	5-HT1A Agonists: 4-F-5-MeO-pyr-T 5-MeO-pip-T 5-MeO-pyr-T 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine) Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone) Azapirones (e.g., buspirone, eptapirone (F-11440), gepirone, perospirone, tandospirone) Bay R 1531 Befiradol (NLX-112; F-13640) BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide) F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 (NLX-101) Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP Naluzotan NBUMP NLX-204 NLX-266 Osemozotan (MKC-242) Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin) TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine Positive allosteric modulators: Oleamide Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) AV965 Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) FCE-24379 Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine Unknown/unsorted: Acetryptine Carvedilol Ergolines (e.g., ergometrine (ergonovine)) 5-HT1B Agonists: Alniditan Anpirtoline AZ10419369 Benzofurans (e.g., 5-MAPB, 6-MAPB, BK-5-MAPB, BK-6-MAPB) Benzothiophenes (e.g., 5-MAPBT, 6-MAPBT, BK-5-MAPBT) CGS-12066 (CGS-12066A, CGS-12066B) CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) mCPP Methylenedioxyphenethylamines (e.g., MDMA, methylone) PGI-7043 PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g., avitriptan, donitriptan, eletriptan, IS-159, sumatriptan, zolmitriptan) TFMPP Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT) Vortioxetine Antagonists: AOP-208 (LB-208) AR-A000002 Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol) Elzasonan Ergolines (e.g., metergoline) F-14258 GR-127935 Isamoltane LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 SB-616234 Trelanserin Yohimbine Negative allosteric modulators: 5-HT-moduline Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride) 5-HT1D Agonists: Alniditan CGS-12066 (CGS-12066A, CGS-12066B) CP-122288 CP-135807 CP-286601 Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide) GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, IS-159, naratriptan, rizatriptan, sumatriptan, zolmitriptan) Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT) Antagonists: BRL-15572 Elzasonan Ergolines (e.g., metergoline) F-14258 GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin Yohimbine Ziprasidone Negative allosteric modulators: 5-HT-moduline Unknown/unsorted: Acetryptine Ergolines (e.g., lisuride, lysergol, pergolide) 5-HT1E Agonists: BRL-54443 Ergolines (e.g., methysergide) Serotonin (5-HT) Triptans (e.g., eletriptan) Tryptamines (e.g., tryptamine) Antagonists: Metitepine (methiothepin) Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine) 5-HT1F Agonists: BRL-54443 CP-122288 Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide) Lasmiditan LY-334370 LY-344864 Serotonin (5-HT) Triptans (e.g., eletriptan, naratriptan, sumatriptan) Tryptamines (e.g., 5-MT) Antagonists: Metitepine (methiothepin) Mianserin
5-HT2	5-HT2A Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe) 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) AL-34662 AL-37350A Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g., DOB, DOC, DOI, DOM) Efavirenz Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergometrine (ergonovine), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide) Flumexadol IHCH-7113 Jimscaline Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP) Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Positive allosteric modulators: AB0124 CTW0404 CTW0419 JPC0323 (R)-Glaucine Oleamide Antagonists: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine) AMDA Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine) Butanserin Chlorprothixene Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Landipirdine LY03017 LY-393558 mCPP Medifoxamine Metitepine (methiothepin) Metrenperone MIN-117 (WF-516) MT-1207 Naftidrofuryl Nantenine Nelotanserin NH130 Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Seganserin Serotonin antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone) Temanogrel Teniloxazine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TGBA01AD Trelanserin Tricyclic antidepressants (e.g., amitriptyline) Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine) Volinanserin Xylamidine Yohimbine Unknown/unsorted: Ergolines (e.g., dihydroergotamine, nicergoline) 5-HT2B Agonists: 4-Methylaminorex Aminorex Amphetamines (e.g., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine) BW-723C86 DOx (e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) Piperazines (e.g., TFMPP) PNU-22394 Ro60-0175 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, 5-MT, α-Me-5-HT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Antagonists: Agomelatine Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N-desalkylquetiapine (norquetiapine), N-desmethylclozapine (norclozapine), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone) Cyproheptadine EGIS-7625 Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine) Ketanserin LY-393558 mCPP Metadoxine Metitepine (methiothepin) Pirenperone Pizotifen Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine) Trazodone Typical antipsychotics (e.g., chlorpromazine) TIK-301 Yohimbine Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine)) 5-HT2C Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) A-372159 AL-38022A Alstonine ATHX-105 Centhaquine CP-809101 Dimemebfe DOx (e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide) Flumexadol Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) MK-212 ORG-12962 ORG-37684 Oxaflozane PHA-57378 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP) PNU-22394 PNU-181731 PRX-00933 (BVT-933; GW-876167) Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Vabicaserin VR-1065 WAY-629 WAY-161503 YM-348 Positive allosteric modulators: CTW0415 CYD-1-79 JPC0323 Oleamide PNU-69176E VA012 VA240 Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine) Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fluoxetine FR260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) LY03017 Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SB-247853 SDZ SER-082 Seganserin Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TIK-301 Tramadol Trazodone Tricyclic antidepressants (e.g., amitriptyline, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine) Xylamidine Unknown/unsorted: Efavirenz Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))
5-HT3–7	5-HT3 Agonists: Alcohols (e.g., butanol, ethanol (alcohol), trichloroethanol) m-CPBG Phenylbiguanide Piperazines (e.g., BZP, mCPP, quipazine) RS-56812 Serotonin (5-HT) SR-57227 SR-57227A Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ)) Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane) YM-31636 Positive allosteric modulators: 5-Aminoindole 5-Chloroindole 5-Hydroxyindole Catechol Chloroform meta-Chlorophenylbiguanide (mCPBG) Colchicine Ethanol (alcohol) Halothane Indole Isoflurane TMPPAA Antagonists: Alosetron Anpirtoline Arazasetron AS-8112 Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine) Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine) Thujone Tropanserin Tropisetron Typical antipsychotics (e.g., loxapine) Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon) Vortioxetine Zacopride Zatosetron Negative allosteric modulators: Bupropion Colchicine Hydroxybupropion Unknown/unsorted: LY-53857 Piperazines (e.g., naphthylpiperazine) 5-HT4 Agonists: 5-MT BIMU8 Capeserod Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Minesapride Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) Tegaserod Usmarapride Velusetrag Zacopride Antagonists: GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070 5-HT5A Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD) Serotonin (5-HT) Tryptamines (e.g., 5-CT) UCSF648 Valerenic acid Antagonists: Asenapine Latrepirdine (dimebolin) Metitepine (methiothepin) Ritanserin SB-699551 Unknown/unsorted: Ergolines (e.g., metergoline, methysergide) Piperazines (e.g., naphthylpiperazine) 5-HT6 Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide) Hypidone Serotonin (5-HT) Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, ST-1936, tryptamine) WAY-181187 WAY-208466 Antagonists: ABT-354 Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone) AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Landipirdine Latrepirdine (dimebolin) Masupirdine Metitepine (methiothepin) MS-245 PRX-07034 PZKKN-94 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g., amoxapine, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine) Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide) Piperazines (e.g., naphthylpiperazine) 5-HT7 Agonists: 8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g., LSD) LP-12 LP-44 LP-211 RU-24969 Sarizotan Serotonin (5-HT) Triptans (e.g., frovatriptan) Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT) Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine) Butaclamol DR-4485 EGIS-12233 Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine) Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide) Vortioxetine Negative allosteric modulators: Oleamide Unknown/unsorted: Ergolines (e.g., lisuride, pergolide) Piperazines (e.g., naphthylpiperazine)
See also: Receptor/signaling modulators Adrenergics Dopaminergics Melatonergics Monoamine reuptake inhibitors and releasing agents Monoamine metabolism modulators Monoamine neurotoxins

v t e Ergolines
Ergolines(incl. lysergines)	13-Fluorolysergol Acetergamine Brazergoline Bromerguride (2-bromolisuride) Cianergoline Delergotrile Descarboxylysergic acid Dihydrolysergic acid Disulergine Dosergoside Ergolene Ergoline Etisulergine Lergotrile Lisuride LY-53857 LY-86057 LY-108742 Lysergene Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mesulergine Metergoline Nicergoline Pergolide Pibocin B Proterguride Romergoline Sergolexole Terguride Tiomergine
Clavines(6,8-dimethylergolines)	6,8-Dimethylergoline (clavine) 9-Deacetoxyfumigaclavine C Agroclavine Costaclavin Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Penniclavine Setoclavine Partial ergolines and related: Chanoclavine Chanoclavine II Cycloclavine Paliclavine
Lysergamides(lysergic acid amides)	Non-hallucinogenic lysergamides: 1P-BOL-148 2-Bromo-LSD (bromolysergide; BOL-148) 2-Iodo-LSD 2-Oxo-LSD (2-keto-LSD) 2-Oxo-3-hydroxy-LSD 9,10-Dihydro-LSD Amesergide AWD 52-39 Cabergoline D13H (possibly XC101-D13H) Ergometrinine Iso-LSD (d-iso-LSD) l-Iso-LSD l-LSD Lumi-LSD LY-215,840 Lysergic acid cyclobutylamide (LAcB) Lysergic acid cyclopentylamide (cepentil; LCyP) Lysergic acid dibutylamide (LBB-66) MBL-61 (MOB-61; 1-methyl-2-bromo-LSD) MIL (1-methyl-2-iodo-LSD) PHENETHY-LAD SPT-348 Psychedelic lysergamides: 1B-LSD 1BP-LSD 1Bz-LSD 1cP-AL-LAD 1cP-LSD 1cP-MiPLA 1D-AL-LAD 1D-LSD 1DD-LSD 1F-LSD 1Fe-LSD 1H-LSD 1P-AL-LAD 1P-ETH-LAD 1P-LSD 1P-MiPLA 1S-LSD 1SB-LSD (1BS-LSD) 1T-AL-LAD 1T-LSD 1V-LSD 2,3-Dihydro-LSD AL-LAD ALA-10 (1-acetyl-LAE) ALD-52 (1-acetyl-LSD) BU-LAD CPM-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) Diisopropyllysergamide (DiPLA) Dipropyllysergamide (DPL) Ergine (lysergic acid amide; LSA; LA-111; lysergamide) Ergometrine (ergonovine, ergobasine) ETH-LAD Ethylcyclopropyllysergamide (EcPLA) Ethylisopropyllysergamide (EiPLA) Ethylpropyllysergamide (EPLA; LEP-57) Ethyltrifluoroethyllysergamide (ETFELA) IP-LAD Isoergine (isolysergic acid amide; iso-LSA; iso-LA; isolysergamide) Isopropyllysergamide (iPLA; LAiP) Methylpropyllysergamide (LAMPA, LMP-55) Lysergic acid diethylamide (LSD; d-LSD; lysergide) Lysergic acid ethylamide (LAE-32, LAE) Lysergic acid hydroxyethylamide (LSH, LAH) Lysergic acid methylamide (LAM) Lysergic acid methylethylamide (LME-54) Lysergic acid morpholide (LSM-775) Lysergic acid propylamide (LAP) Lysergic acid pyrrolidide (LPD-824) Lysergic acid 2-butylamide (LSB) Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine) Lysergic acid 3-pentylamide (LSP) Methylergometrine (methylergonovine, methylergobasine; Methergine) Methylisopropyllysergamide (MiPLA) Methysergide (1-methylmethylergonovine; UML-491) MLA-74 (1-methyl-LAE) MLD-41 (1-methyl-LSD) MPD-75 (1-methyllysergic acid pyrrolidide) NBOMe-LAD OML-632 (1-hydroxymethyl-LSD) PARGY-LAD PRO-LAD Unsorted lysergamides: 1-Dimethylaminomethyl-LSD 12-Hydroxy-LSD 12-Methoxy-LSD 13-Fluoro-LSD 13-Hydroxy-LSD 14-Hydroxy-LSD 14-Methoxy-LSD CE-LAD Dihydroergometrine (dihydroergonovine, dihydroergobasine) FLUORETH-LAD FP-LAD Lysergic acid azepane (LA-Azepane) Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine) Lysergic acid amylamide Lysergic acid butylamide Lysergic acid ethyl-2-hydroxyethylamide (LEO) Lysergic acid ethyl-2-methoxyethylamide (LA-MeO) Lysergic acid piperidide (LA-Pip, LSD-Pip) Lysergic acid pyrrolinide (LPN) Lysergic acid tert-butylamide (LAtB) MAL-LAD Propisergide (1-methylergonovine)
Ergopeptines(peptide ergolines)	Bromocriptine Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergosine Dihydroergotamine Epicriptine Ergocornine Ergocristine Ergocryptine Ergoloid (dihydroergotoxine; Hydergine) Ergonine Ergosine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Mergocriptine Metergotamine
Partial ergolines	2-Aminotetralins (e.g., 8-OH-DPAT, rotigotine) 3,4-DMPEA-NDEPA 5-MeO-N-DEAOP-NET 5-MeO-N-DEAOP-NMT 10,11-Secoergoline (α,N-Pip-T) 10,11-Seco-LSD 25B-NAcPip 25D-NM-NDEAOP (25D-NM-NDEPA) 2C-B-3PIP Bay R 1531 (LY-197206) CT-5252 Diaza-2C-DFLY Debenzergoline DEIMDHPCA (3,5-seco-LSD) DEMPDHPCA DEMPDHPCA-2C-D DEMPDHPCA-mescaline DEMPDHPCA-NAP DEMPDHPCA-PMA DOB-NDEPA DOI-NDEPA DOM-NDEPA DOTFM-NDEPA DPAI (4-DPAEI; 2-desoxo-2-ene-ropinirole) FAEFHI FHATHBIN 7-Hydroxyropinirole (SK&F-89124) LPH-5 ((S)-2C-TFM-3PIP) LY-178210 LY-293284 M-NDEPA 6-MeO-RU-28306 N-DEAOP-NMPEA (PEA-NM-NDEPA) N-DEAOP-NMT NDTDI (8,10-seco-LSD) Phenethylamines Ropinirole RU-27251 RU-27849 RU-28251 RU-28306 TMA-2-NDEPA Tryptamines WXVL_BT0793LQ2118 Related: Nikethamide THPC Tochergamine
Related compounds	A-86929 Adrogolide Centpyraquin (IHCH-7162) CY-208,243 IHCH-7179 JRT (isoindole-LSD) Naxagolide Quinagolide Quinelorane Quinpirole S32504 SDZ SER-082 Voxergolide
Natural sources	Fungi: Clavicipitaceae Claviceps spp. (ergot) Claviceps paspali Claviceps purpurea Epichloë spp. Periglandula spp. Periglandula clandestina Periglandula ipomoeae Periglandula turbinae Plants (infected/symbiotic with the above fungi): Achnatherum robustum (sleepy grass) Convolvulaceae (morning glory) Argyreia nervosa (Hawaiian baby woodrose) Ipomoea asarifolia (ginger-leaf morning-glory) Ipomoea corymbosa (coaxihuitl, ololiúqui) Ipomoea tricolor (tlitliltzin, badoh negro)
See also: Tryptamines Phenethylamines Psychedelics List of lysergamides