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(Redirected from Simplified/partial ergoline)

The ergoline ring system numbered and labeled.

The chemical structure of LSD, the most well-known lysergamide.

Partial or simplified ergolines and lysergamides are analogues of ergolines and lysergamides like the psychedelic drug LSD in which one or more atoms or bonds, for instance within the ergoline ring system, have been removed.^[1]^[2]^[3]^[4] Additional substitutions may also be added, for instance on the A ring of the ergoline nucleus.^[1]^[2]^[3] It is notable that the ergoline ring system contains embedded tryptamine and phenethylamine moieties within its structure, and so some partial ergolines are simple tryptamines, cyclized tryptamines, simple phenethylamines, and/or cyclized phenethylamines.

In terms of pharmacology, partial lysergamides include serotonin and dopamine receptor agonists. Some, like NDTDI (9-nor-LSD), DEMPDHPCA (dides-B,C-LSD), DEIMDHPCA (4-nor-LSD), and LPH-5 ((S)-2C-TFM-3PIP), are serotonin 5-HT_2A receptor agonists and have psychedelic-like and/or psychoplastogenic effects. Some, like 8-OH-DPAT, LY-178210 (LY-228729; 4,α-methylene-5-carboxamido-DPT), Bay R 1531 (LY-197206; 4,α-methylene-5-MeO-DPT), and LY-293284 (4,α-methylene-5-acetyl-DPT), are selective serotonin 5-HT_1A receptor agonists. Others, like ropinirole, rotigotine, nolomirole, and RU-28251 (4,α-methylene-DPT), are dopamine D₂-like receptor agonists. Though limitedly studied, partial ergolines have generally shown markedly reduced potency in terms of hallucinogen-like effects compared to LSD.^[5]

Examples of partial lysergamides that are simple tryptamines include N-DEAOP-NMT (9,10-dinor-LSD) and 5-MeO-N-DEAOP-NMT and examples that are simple phenethylamines include N-DEAOP-NMPEA and 25D-NM-NDEAOP. An example of a cyclized tryptamine-like compound is DEIMDHPCA, while examples of cyclized phenethylamines include DEMPDHPCA, DEMPDHPCA-2C-D, and LPH-5. Some, like 8-OH-DPAT and rotigotine, are 2-aminotetralins. Others, like NDTDI and LY-178210, are tricyclic compounds that contain both tryptamine and phenethylamine components. Tochergamine is a simplified analogue of ergometrine that was studied as an oxytocic agent but was abandoned.

Structures within the ergoline ring system

👁 The tryptamine moiety.

The tryptamine moiety.
👁 The phenethylamine moiety.

The phenethylamine moiety.

List of simplified or partial lysergamides

[edit]

Structure	Name	Chemical name	CAS #
👁 Image	Descarboxylysergic acid (DCLA; 9,10-didehydro-6-methylergoline)	(6aR)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline	51867-17-5
👁 Image	NDTDI (9-desmethine-LSD; 9-nor-LSD; 8,10-seco-LSD)	N,N-diethyl-3-(methyl(1,3,4,5-tetrahydrobenzo[cd]indol-4-yl)amino)propanamide	?
👁 Image	RU-28251 (4,α-methylene-DPT)^[6]^[7]	N,N-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine	?
👁 Image	Bay R 1531 (LY-197206; 4,α-methylene-5-MeO-DPT)	1,3,4,5-tetrahydro-6-methoxy-N,N-dipropyl-benz[cd]indol-4-amine	98770-54-8
👁 Image	LY-293284 (4,α-methylene-5-acetyl-DPT)	(4R)-6-acetyl-4-(di-n-propylamino)-1,3,4,5-tetrahydrobenz[c,d]indole	141318-62-9
👁 Image	LY-178210 (LY-228729; 4,α-methylene-5-carboxamido-DPT)	4-(dipropylamino)-1,3,4,5-tetrahydrobenzo[cd]indole-6-carboxamide	114943-19-0
👁 Image	LY-301317 ((R)-4,α-methylene-5-(1,3-oxazol-5-yl)-DPT)	(4R)-6-(1,3-oxazol-5-yl)-N,N-dipropyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine	?
👁 Image	RU-28306 (4,α-methylene-DMT)	N,N-dimethyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine	73625-11-3
👁 Image	6-MeO-RU-28306 (4,α-methylene-5-MeO-DMT)^[8]^[9]	6-methoxy-N,N-dimethyl-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine	?
👁 Image	RU-27849 (4,α-methylene-T)	1,3,4,5-tetrahydrobenzo[cd]indol-4-amine	77963-70-3
👁 Image	FHATHBIN (4,α-methylene-5-HT; 6-HO-RU-27849)	6-hydroxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine	?
👁 Image	6-MeO-RU-27849 (4,α-methylene-5-MT)^[10]^[11]^[12]	6-methoxy-1,3,4,5-tetrahydrobenzo[cd]indol-4-amine	?
👁 Image	N-DEAOP-NMT (desvinyl-LSD; 9,10-dinor-LSD)	N-(3-diethylamino-3-oxopropyl)-N-methyltryptamine
👁 Image	N-DEAOP-NET (desvinyl-ETH-LAD; 9,10-dinor-ETH-LAD)	N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-tryptamine
👁 Image	N-DEAOP-5-MeO-NMT	N-(3-diethylamino-3-oxopropyl)-N-methyl-5-methoxytryptamine
👁 Image	N-DEAOP-5-MeO-NET	N-(3-diethylamino-3-oxopropyl)-N-ethyl-5-methoxytryptamine
👁 Image	10,11-Seco-LSD^[13]	9,10-didehydro-N,N-diethyl-6-methyl-10,11-secoergoline-8β-carboxamide	2640392-96-5
👁 Image	CT-5252	methyl-12-bromo-8,9-didehydro-2,3β-dihydro-6-methyl-10,11-secoergoline-8-carboxylate
👁 Image	10,11-Secoergoline (α,N-tetramethylene-T)	3-(piperidin-2-ylmethyl)-1H-indole	5275-05-8
👁 Image	FAEFHI	4-(2-aminoethyl)-1H-indol-5-ol
👁 Image	4-API	4-(2-aminopropyl)indole	21005-59-4
👁 Image	DMAI (4-DMAEI; BD-214)	4-(N,N-dimethylaminoethyl)indole	84401-01-4
👁 Image	DEAI (4-DEAEI; BD-271)	4-(N,N-diethylaminoethyl)indole	?
👁 Image	DPAI (4-DPAEI; 2-desoxo-2-ene-ropinirole; BD-179)	4-(N,N-dipropylaminoethyl)indole	76149-15-0
👁 Image	Ropinirole (SK&F-101468)	4-[2-(dipropylamino)ethyl]-1,3-dihydro-2H-indol-2-one	91374-21-9
👁 Image	7-Hydroxyropinirole (SK&F-89124)	4-[2-(dipropylamino)ethyl]-7-hydroxy-1,3-dihydroindol-2-one	81654-62-8
👁 Image	DEIMDHPCA (4-desmethylene-LSD; 4-nor-LSD; 3,5-seco-LSD)	(3R)-N,N-diethyl-5-(1H-indol-4-yl)-1-methyl-3,6-dihydro-2H-pyridine-3-carboxamide	2640392-28-3
👁 Image	RU-27251 (3,5-secoergoline)^[14]	4-piperidin-3-yl-1H-indole	16176-75-3
👁 Image	WXVL_BT0793LQ2118^[15]^[16]	6-fluoro-4-(1-methyl-1,2,5,6-tetrahydropyridin-3-yl)-1H-indole	?
👁 Image	Diaza-2C-DFLY	8-(aminoethyl)-1,5-dihydropyrrolo[2,3-f]indole
👁 Image	DEMPDHPCA (dides-B,C-LSD; 1-deaza-2,3,4-trinor-LSD)^[17]^[13]	N,N-diethyl-1-methyl-5-phenyl-3,6-dihydro-2H-pyridine-3-carboxamide
👁 Image	DEMPDHPCA-PMA^[17]	N,N-diethyl-1-methyl-3-(4-methoxyphenyl)-1,2,5,6-tetrahydropyridine-5-carboxamide
👁 Image	DEMPDHPCA-M (DEMPDHPCA-mescaline)^[17]	N,N-diethyl-1-methyl-3-(3,4,5-trimethoxyphenyl)-1,2,5,6-tetrahydropyridine-5-carboxamide
👁 Image	DEMPDHPCA-NAP^[17]	N,N-diethyl-1-methyl-3-(1-naphthyl)-1,2,5,6-tetrahydropyridine-5-carboxamide
👁 Image	DEMPDHPCA-2C-D^[2]	1-methyl-3-(1-oxo-1-diethylaminomethyl)-5-(2,5-dimethoxy-4-methylphenyl)-3,6-dihydro-2H-pyridine
👁 Image	"Compound XXIII"^[3]^[18]^[19]	?	?
👁 Image	2C-B-3PIP	3-(4-bromo-2,5-dimethoxyphenyl)piperidine	?
👁 Image	LPH-5 ((S)-2C-TFM-3PIP)	(S)-3-(2,5-Dimethoxy-4-(trifluoromethyl)phenyl)piperidine	2641630-97-7
👁 Image	"Compound 163" or "VIII"^[17]^[20]^[21]	N,N-diethyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo(f)quinoline-2-carboxamide
👁 Image	Debenzergoline (propyldebenzergoline)	trans-(±)-2,3,4,4a,5,7,9,9a-octahydro-1-propyl-1H-pyrrolo[3,4-g]quinoline
👁 Image	N-DEAOP-PEA (PEA-NDEPA)	N-diethylaminocarbonylethylphenethylamine
👁 Image	N-DEAOP-NMPEA (PEA-NM-NDEPA; 1-deaza-2,3,4,9-tetranor-LSD)^[22]	N-diethylaminocarbonylethyl-N-methylphenethylamine
👁 Image	3,4-DMPEA-NDEPA	N-diethylaminocarbonylethyl-3,4-dimethoxyphenethylamine
👁 Image	M-NDEPA (mescaline-NDEPA)^[23]	N-diethylaminocarbonylethyl-3,4,5-trimethoxyamphetamine	?
👁 Image	DOM-NDEPA^[24]	N-diethylaminocarbonylethyl-2,5-dimethoxy-4-methylamphetamine	?
👁 Image	DOB-NDEPA^[25]	N-diethylaminocarbonylethyl-2,5-dimethoxy-4-bromoamphetamine	260810-30-8
👁 Image	DOI-NDEPA^[25]	N-diethylaminocarbonylethyl-2,5-dimethoxy-4-iodoamphetamine	260810-31-9
👁 Image	DOTFM-NDEPA^[25]	N-diethylaminocarbonylethyl-2,5-dimethoxy-4-trifluoromethylamphetamine	260810-29-5
👁 Image	TMA-2-NDEPA^[26]	N-diethylaminocarbonylethyl-2,4,5-trimethoxyphenethylamine
👁 Image	25D-NM-NDEAOP (25D-NM-NDEPA)	N-methyl-N-(3-diethylamino-3-oxopropyl)-2,5-dimethoxy-4-methylphenethylamine
👁 Image	2-Aminotetralin (2-AT)	1,2,3,4-tetrahydronaphthalen-2-amine	2954-50-9
👁 Image	CHF-1024	5,6-dihydroxy-N-methyl-2-aminotetralin	39478-89-2
👁 Image	Nolomirole (CHF-1035)	5,6-diisobutyryloxy-N-methyl-2-aminotetralin	90060-42-7
👁 Image	5-OH-DPAT	5-hydroxy-N,N-dipropyl-2-aminotetralin	68593-96-4
👁 Image	7-OH-DPAT	7-hydroxy-N,N-dipropyl-2-aminotetralin	74938-11-7
👁 Image	8-OH-DPAT	8-hydroxy-N,N-dipropyl-2-aminotetralin	78950-78-4
👁 Image	UH-301	(S)-5-fluoro-8-hydroxy-N,N-dipropyl-2-aminotetralin	127126-22-1
👁 Image	UH-232	(1S,2R)-5-methoxy-1-methyl-N,N-propyl-2-aminotetralin	95999-12-5
👁 Image	Rotigotine	6-[propyl(2-thiophen-2-ylethyl)amino]-5,6,7,8-tetrahydronaphthalen-1-ol	99755-59-6
👁 Image	THPC	N,N-diethyl-1-methyl-3,6-dihydro-2H-pyridine-5-carboxamide	26070-52-0
👁 Image	Nikethamide	N,N-diethyl-3-pyridinecarboxamide	59-26-7

Structural comparisons

[edit]

👁 LSD (left) and N-DEAOP-NMPEA (right) structures.

LSD (left) and N-DEAOP-NMPEA (right) structures.
👁 LSD (left) and N-DEAOP-NMT (right) structures.

LSD (left) and N-DEAOP-NMT (right) structures.
👁 25D-NM-NDEAOP (left), DOM-NDEPA (middle), and LSD (right) structures.

25D-NM-NDEAOP (left), DOM-NDEPA (middle), and LSD (right) structures.
👁 DEMPDHPCA (left) and LSD (right) structures.

DEMPDHPCA (left) and LSD (right) structures.
👁 LSD (left) and DEIMDHPCA (right) structures.

LSD (left) and DEIMDHPCA (right) structures.
👁 LSD (left) and 10,11-seco-LSD (right) structures.

LSD (left) and 10,11-seco-LSD (right) structures.
👁 LSD (left), NDTDI (middle), and N-DEAOP-NMT (right) structures.

LSD (left), NDTDI (middle), and N-DEAOP-NMT (right) structures.

Related compounds

[edit]

Structure	Name	Chemical name	CAS #
👁 Image	Chanoclavine (chanoclavine-I)	[9(9a)E]-9-methyl-9,9a-didehydro-7,8-seco-9a-homoergolin-8-ol	2390-99-0
👁 Image	Chanoclavine II	(2E)-2-methyl-3-[(4R,5S)-4-(methylamino)-1,3,4,5-tetrahydrobenzo[cd]indol-5-yl]prop-2-en-1-ol	1466-08-6
👁 Image	Paliclavine	(9R)-6,8-dimethyl-7,8-didehydro-6,7-secoergolin-9-ol	52052-66-1
👁 Image	DLX-0002700 (see DLX-2270)^[27]^[28]	6-fluoro-N,5-dimethyl-1-azatricyclo[6.3.1.0^4,12]dodeca-2,4(12),5,7-tetraen-10-amine	?
👁 Image	Compound 21 ^[29]^[30]	(10S)-3-bromo-N,N-dimethyl-1-azatricyclo[6.3.1.0^4,12]dodeca-2,4,6,8(12)-tetraen-10-amine	3091662-68-6
👁 Image	2C-B-5-hemiFLY-α6 (BNAP)	8-bromo-6-methoxy-2a,3,4,5-tetrahydro-2H-naphtho[1,8-bc]furan-4-amine	?
👁 Image	DOB-5-hemiFLY (bromo-semi-fly; B-SF; 5-MeO-7-Br-4-APDB)	1-(7-bromo-5-methoxy-2,3-dihydro-1-benzofuran-4-yl)propan-2-amine	178557-10-3
👁 Image	2C-B-morpholine	2-(4-bromo-2,5-dimethoxyphenyl)morpholine	807631-07-8
👁 Image	Naxagolide	(4aR,10bR)-4-propyl-2,3,4a,5,6,10b-hexahydrobenzo[h][1,4]benzoxazin-9-ol	88058-88-2
👁 Image	S32504	(4aR,10bR)-4-propyl-2,3,4a,5,6,10b-hexahydrobenzo[h][1,4]benzoxazine-9-carboxamide	?
👁 Image	Pardoprunox	7-(4-methylpiperazin-1-yl)-3H-1,3-benzoxazol-2-one	269718-84-5
👁 Image	Bifeprunox	7-[4-(biphenyl-3-ylmethyl)piperazin-1-yl]-1,3-benzoxazol-2(3H)-one	350992-10-8
👁 Image	Quinpirole	(4aR,8aR)-5-propyl-1,4,4a,6,7,8,8a,9-octahydropyrazolo[5,4-g]quinoline	80373-22-4
👁 Image	Quinelorane	(5aR,9aR)-6-propyl-5a,7,8,9,9a,10-hexahydro-5H-pyrido[2,3-g]quinazolin-2-amine	97466-90-5
👁 Image	Quinagolide	N,N-diethyl-N-[(3S,4aS,10aR)-6-hydroxy-1-propyl-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolin-3-yl]sulfamide	87056-78-8
👁 Image	25B-NAcPip	N-(piperidin-1-ylcarbonylmethyl)-4-bromo-2,5-dimethoxyphenethylamine
👁 Image	25B-NBOMe	N-(2-methoxybenzyl)-4-bromo-2,5-dimethoxyphenethylamine	1026511-90-9
👁 Image	"Compound 37"^[31]^[2]^[32]	N-(2-diethylamino-2-oxoethyl)-N-methyl-2-amino-1,2,3,4,4a,8a-hexahydronaphthalene
👁 Image	Tochergamine	N,N-diethyl-2-(1,2,3,4-tetrahydronaphthalen-1-ylamino)acetamide

References

[edit]

^ ^a ^b Shulgin AT (1976). "Psychotomimetic Agents". In Gordon M (ed.). Psychopharmacological Agents: Use, Misuse and Abuse. Medicinal Chemistry: A Series of Monographs. Vol. 4. Academic Press. pp. 59–146. doi:10.1016/b978-0-12-290559-9.50011-9. ISBN 978-0-12-290559-9. The largest number of structural analogs of LSD that have been prepared involve the opening of one or more of the rings of the parent lysergic acid system. The compounds with the piperidine ring (ring D) opened [see (I)] are encountered as natural products in the several Convolvulaceae discussed in Section II,B on ololiuqui. The opening of ring C (by cleavage of the 10-11 bond to the indole "4 position") results in a series of N-α-disubstituted tryptamines. Additionally, analogs are known with the indolic nitrogen replaced with sulfur (benzothiophenes) and with an aliphatic chain (tetralins). A recent review covers this chemistry (Campaigne and Knapp, 1971), but there is apparently no human psychopharmacology as yet known.
^ ^a ^b ^c ^d Nichols DE (May 1973). Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid (Thesis). University of Iowa. p. 23. OCLC 1194694085. Archived from the original on 2025-04-06. Retrieved 2025-06-01.
^ ^a ^b ^c Campaigne E, Knapp DR (June 1971). "Structural analogs of lysergic acid". J Pharm Sci. 60 (6): 809–814. doi:10.1002/jps.2600600602. PMID 4942861.
^ Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320.
^ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144 (128). ISBN 978-0-85608-011-1. OCLC 2176880. OL 4850660M. Archived from the original on 2025-05-27. Retrieved 2025-06-02. Various attempts to simplify the LSD structure by breaking it down into molecular fragments have, with the exception of the tryptamines, generally led to profoundly deleterious effects on the hallucinogenic activity (Campaigne and Knapp, 1971).
^ Euvrard, Catherine; Ferland, Louise; Fortin, Michel; Oberlander, Claude; Labrie, Fernand; Boissier, Jacques R. (1981). "Dopaminergic activity of some simplified ergoline derivatives". Drug Development Research. 1 (2): 151–161. doi:10.1002/ddr.430010208. ISSN 0272-4391.
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^ ^a ^b WO 2021076572, David E. Olson; Lee Dunlap & Florence Wagner et al., "Ergoline-like compounds for promoting neural plasticity", published 22 April 2021, assigned to Delix Therapeutics, Inc. and The Regents of the University of California
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^ Lyu J, Kapolka N, Gumpper R, Alon A, Wang L, Jain MK, Barros-Álvarez X, Sakamoto K, Kim Y, DiBerto J, Kim K, Tummino TA, Huang S, Irwin JJ, Tarkhanova OO, Moroz Y, Skiniotis G, Kruse AC, Shoichet BK, Roth BL (March 2024). "AlphaFold2 structures template ligand discovery". bioRxiv 10.1101/2023.12.20.572662.
^ ^a ^b ^c ^d ^e Mangner TJ (1978). Potential Psychotomimetic Antagonists. N,n -diethyl-1-methyl-3-aryl-1, 2, 5, 6-tetrahydropyridine-5-carboxamides (Ph.D. thesis). University of Michigan. doi:10.7302/11268. Archived from the original on 30 March 2025. Table 1. Human psychotomimetic potencies of LSD analogs. [...]
^ Plieninger, Hans (1953). "Die Synthese von Modellsubstanzen für die Lysergsäure I. Mitteilung". Chemische Berichte. 86 (1): 25–31. doi:10.1002/cber.19530860106. ISSN 0009-2940. Retrieved 2 June 2025. Die Synthese der 1.6-Dimethyl-5-[4-methoxy-phenyl]-pyridin- carbonsäure-(3), ihres Tetrahydro- und Hexahydro-Derivates, sowie einer Reihe anderer uterusaktivor Amine Wird beschrieben. [...] Da die Verbindungen V und VI auf den Kaninchenuterus in situ auch nur eine verhaltnismäßig schwache Wirkung ausüben, wurde versucht, der LysergsäureeKonstitution näherzukommen. Bekanntlich tritt bei den hydrierten Mutterkornalkaloiden die Uteruswirkung zugunsten der sympaticolytischen Wirkung zurück. In der Annahme, daß die Uteruswirksomkeit auch bei unseren Modellsubstanzen durch die Doppelbindung in 3.4-Stellung gesteigert wird, haben wir die Verbindung XIV und XV nach dem folgenden Formelschema synthetisiert. Vorher hotten wir vergeblich versucht, die Pyridine Verbindung X bzw. ihr Methosulfat partiell zu hydrieren. [...] Die Einwirkung von p-Methoxy-phenyl-magnesiumbromid¹¹) auf einen Überschuß an Ketoester führt zu dem nicht kristallisierenden tert. Alkohol XIV, wobei die größere. Reaktionsfähigkeit der Ketogruppe gegenüber der Estergruppe ausgenützt wird. Durch Wasserabspaltung mittels Thionylchlorids in Pyridin¹²) erhält man in mäßiger Ausbeute ein schön kristallisiertes Oxalat der Formel XV bzw. XVI. Eine Entscheidung, in welcher Richtung die Wasserabspaltung erfolgt ist, steht vorläufig noch aus. Die Verbindung zeigte sich in ihrer pharmakologischen Wirkung den gesättigten Derivaten V und VI deutlich überlegen.
^ "COc1ccc(cc1)C2=CC(CN(C)C2C)C(O)=O". MolView. Retrieved 2 June 2025.
^ Horii Z, Kurihara T, Yamamoto S, Ninomiya I (November 1967). "Studies on ergot alkaloids and related compounds. XIV. Synthesis of N-alkyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinoline-2-carboxamides and stereochemistry of diethyl 4-methyl-1-oxo-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline-2,2-dicarboxylate". Chem Pharm Bull (Tokyo). 15 (11): 1641–1650. doi:10.1248/cpb.15.1641. PMID 5583819. Our previous report1) introduced the synthesis of a potent oxytocic ethyl 4-methyl-2,3,4,4a,5,6-hexahydrobenzo[f]quinoline-2-carboxylate (VII). Recently, Ohta and his coworkers also prepared V] by a convenient method starting from the Mannich product (II). However, they did not deal with the stereochemistry of the compounds involved. In the course of work searching for compounds with potent activity related to lysergic acid, we now wish to describe two routes of preparations of diethyl-, n-butyl- and 2-hydroxyisopropylamide derivatives of VI, which can be regarded as LSD25 analogs lacking only a pyrrole ring, and also discuss the stereochemistry of this series of compounds. [...] Of these amide derivatives, the diethylamide (VIII) was also prepared by an alternative route as follows. [...] Experimental. [...] N,N-Diethyl-4-methyl-2,3,4,4a,5,6-hexahydrobenzo(f)quinoline-2-carboxamide (VIII)—[...]
^ "1829 - PiHKAL·info". Isomer Design. 26 February 2025. Retrieved 24 March 2025.
^ Norris PE, Blicke FF (December 1952). "Potential ergot substitutes: esters and amides of beta-amino acids". J Am Pharm Assoc. 41 (12): 637–639. doi:10.1002/jps.3030411204. PMID 13022416. Six esters and amides of derivatives of β-alanine which are related to lysergic acid have been prepared and tested for oxytocic activity. None of these products possess a significant oxytocic activity. [...] The purpose of this investigation was to synthesize amides and also esters of compounds (II–V) which represent fragments of the lysergic acid molecule in the hope that some of these products might possess oxytocic activity. Various modified fragments of the lysergic acid molecule have been synthesized previously; it was claimed that some of the compounds are active oxytocics (1—7). [...] Pharmacologic data indicated that none of the esters or amides of compounds II—V which were prepared possess a significant oxytocic action when compared to the clinically used oxytocics. However, the diethylamide of N-methyl-N-[β′-(3-indolyl)-ethyl]-β-alanine (IIIc) appeared to have an oxytocic activity approximately ten times stronger than that of the diethylamide of N-methyl-N-(β′-phenethyl)-β-alanine (IIc).
^ "PiHKAL·info - M-NDEPA". Isomer Design. 28 February 2025. Retrieved 24 March 2025.
^ "PiHKAL·info". DOM-NDEPA. 28 February 2025. Retrieved 24 March 2025.
^ ^a ^b ^c Schulze-Alexandru, Meike; Kovar, Karl-Artur; Vedani, Angelo (1999). "Quasi-atomistic Receptor Surrogates for the 5-HT2A Receptor: A 3D-QSAR Study on Hallucinogenic Substances" (PDF). Quantitative Structure-Activity Relationships. 18 (6): 548–560. doi:10.1002/(SICI)1521-3838(199912)18:6<548::AID-QSAR548>3.0.CO;2-B. ISSN 0931-8771. Retrieved 1 April 2025. Table 3. New phenylalkylamine and tryptamine congeners. Cf. also Figure 5. [...] Figure 5. Molecular structures of the new 5-HT2A congeneric ligands. Cf. also Table 3. [...] Table 4. Predicted binding affinities of new compounds, index by substance classes. [...]
^ "TMA-2-NDEPA". Isomer Design. 28 February 2025. Retrieved 24 March 2025.
^ "6-fluoro-N,5-dimethyl-1-azatricyclo[6.3.1.04,12]dodeca-2,4(12),5,7-tetraen-10-amine". PubChem. Retrieved 2 April 2026.
^ "Mixed serotonin receptor binders for treatment of psychotic disorders". Google Patents. 20 December 2024. Retrieved 2 April 2026.
^ Sabnis RW. Novel Mixed Serotonin Receptor Binder Compounds as 5‑HT2C Agonists for Treating Psychotic Disorders. ACS Med Chem Lett. 2025 Jul 29;16(8):1505-1506. doi:10.1021/acsmedchemlett.5c00427 PMID 40832520
^ https://pubchem.ncbi.nlm.nih.gov/compound/176415137
^ Marini-Bettolo, G. B., Chiavarelli, S., & Bovet, D. (1951). Synthetic Sympatholytic Substances of the Ergotamine Series. I. Nitrogen-Substituted Derivatives of the dl-1, 2, 3, 4-Tetrahydro-2-Naphthylamine-Containing Amino and Amido Functional Groups. Gazz. Chim. Ital, 80, 281–298. https://scholar.google.com/scholar?cluster=2759784031777399013
^ "PiHKAL·info". search. 26 February 2025. Retrieved 24 March 2025.

External links

[edit]

Psychedelics

Tryptamines

No ring subs.	CE-T DALT DBT DET (T-9) DiPT DMT DMT-d4 (D₄DMT) DPT EiPT EPT HLP004 (CYB004; deuDMT) iPALT (ALiPT) MALT McPT MET MiPT MPT N-POM-DMT NMT PALT PiPT SPL028 (D₂-DMT) Tryptamine (T)
4-Hydroxytryptamines	1-Methylpsilocin (CMY, CMY-16) 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) HLP003 (CYB003; deupsilocin) Psilocin (4-HO-DMT; CX-59) Psilomethoxin (5-MeO-4-HO-DMT) 4-Phosphoryloxytryptamines: 5-Methoxypsilocybin (5-MeO-4-PO-DMT) 5-Methylpsilocybin (5-Me-4-PO-DMT) 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	1-Acetyl-5-MeO-DMT 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-DMT-d4 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.	1-Benzoyl-DMT 2-Methyltryptamine 2,N,N-TMT (2-methyl-DMT) 4,N,N-TMT (4-methyl-DMT) 4-MeS-DMT 5-Bromo-DMT 5-Chloro-DMT 5-Fluoro-DMT 5-MeS-DMT 5-Nitro-T (Nitro-I) 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) 6-TFMO-DMT Bretisilocin (GM-2505; 5-fluoro-MET) HBL20016 (5-MeS-6-F-DMT) 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, Pharm-136) 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) Unknown psychedelic activity: β-Carbolines (e.g., 1-ethyl-6-hydroxytryptoline, 1-(2,4,5-trimethoxyphenyl)-6-chlorotryptoline)
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 Unknown psychedelic activity: Quinolinylethylamines (e.g., mefloquine)

Phenethylamines

Scalines	2-Bromomescaline 4-D (4-trideuteromescaline) Allylescaline (AL) Alpha-D (α-D; α,α-dideuteromescaline) Alpha,Beta-D (α,β-D; α,β-dideuteromescaline) Beta-D (β-D; β,β-dideuteromescaline) Cyclopropylmescaline (CPM) Difluoroescaline (DFE) Difluoromescaline (DFM) N,N-Diformylmescaline Escaline (E) Fluoroescaline (FE) Fluoroproscaline (FP) N-Formylmescaline Isobuscaline (IB) Isoproscaline (IP) Mescaline (M; 3,4,5-TMPEA) Metadifluoromescaline (MDFM) Metaescaline (ME) Methallylescaline (MAL) N-Methylmescaline (M-M) Proscaline (P) 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) Desoxyscalines: 4-Desoxymescaline (desoxy, desoxymescaline) Others: Jimscaline Tomscaline
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 2C-T-36 (2C-T-TFM; CYB210010; CYB2108) CYB2108D (deuterated 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, 2CT-5-EtO, 2CT2-2-EtO, 2CT7-2-EtO, ASR-2001 (2CB-5-PrO))
3C-x	3C-AL 3C-BZ 3C-DFE 3C-E 3C-FP 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-DragonFLY 2C-E-FLY 2C-EF-FLY 2C-I-FLY 2CBFly-NBOMe Bromo-DragonFLY DOB-FLY DOH-FLY TFMFly Hemi/semi-FLY drugs: 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 25x-NBF: 25B-NBF 25C-NBF 25I-NBF 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) BMB-202 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: HLP005 (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) 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 Unknown psychedelic activity: Aporphines and noraporphines (e.g., glaucine, 11-methoxyasimilobine, 2-hydroxy-11-(2-methylallyl)oxynoraporphine)

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)
2-LSP
LSP (3-LSP)
LSZ (LA-SS-Az)
Lysergic acid pyrrolinide (LPN)
Methylergometrine (methylergonovine, methylergobasine)
MiPLA
TRALA-12 (didehydro-LSD; DDH-LSD)

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)

Bioisosteres: JRT (isotryptamine-LSD)

Others

9-Oxaergolines (e.g., RU-29717)
γ-Carbolines (e.g., tiflucarbine)
Arylpiperazines (e.g., 2C-B-PP, 2-NP, mCPP, MK-212, ORG-12962, pCPP, pFPP, quipazine, TFMPP, VCU-1012)
Dihydrobenzoxazines (e.g., efavirenz)
Phenoxyethylamines (e.g., CT-4719, ORG-37684)
Pyridopyrroloquinoxalines (e.g., IHCH-7113)
Quinazolinylethylamines (e.g., RH-34)

Natural sources

Phenethylamines: Pachycereus pringlei (saguesa, elephant cactus, cardon)
Peyote (Lophophora williamsii; peyotl)
Echinopsis cacti (e.g., San Pedro, Peruvian torch)

Serotonin receptor modulators

5-HT₁

5-HT_1A

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) F-17464 Flesinoxan Flibanserin Flumexadol GR-46611 Hypidone Lesopitron LY-293284 LY-301317 LY-315712 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 AZD-3676 Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) Flopropione Lecozotan LY-206130 LY-297996 ((–)-LY206130) LY-426965 Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-272183 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-HT_1B

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) GR-46611 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 AZD-3676 Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol) Elzasonan Ergolines (e.g., metergoline) F-12682 F-14258 GR-127935 LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 SB-272183 SB-616234 Trelanserin Yohimbine
Negative allosteric modulators: 5-HT-moduline
Miscellaneous: HG1 (5-HT-moduline antagonist)
Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)

5-HT_1D

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-12682 F-14258 GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin SB-272183 Yohimbine Ziprasidone
Negative allosteric modulators: 5-HT-moduline
Unknown/unsorted: Acetryptine Ergolines (e.g., lisuride, lysergol, pergolide)

5-HT_1E

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-HT_1F

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
Unknown/unsorted: LY-53857 LY-86057

5-HT₂

5-HT_2A

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, BMB-202) 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 Aporphines and noraporphines (e.g., (S)-glaucine, 11-methoxyasimilobine, 2-hydroxy-11-(2-methylallyl)oxynoraporphine) BMB-201 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, VCU-1012) 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) Barettin Butanserin Chlorprothixene Cinanserin CSP-2503 Deramciclane DLX-2270 Dotarizine DSP-6745 Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Fananserin FCE-24379 Flibanserin Glemanserin Irindalone KB-128 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 R-96544 R-102444 Rauwolscine Ritanserin Roluperidone S-14671 SpAMDA 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-HT_2B

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: 1-Methylmedmain 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) KB-128 Ketanserin LY-393558 mCPP Medmain Metadoxine Metitepine (methiothepin) Minaprine MW073 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-HT_2C

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 Aporphines and noraporphines (e.g., MQ02-439, (S)-glaucine, nornuciferine, asimilobine, 11-chloroasimilobine, 11-methoxyasimilobine) ATHX-105 Bexicaserin BMB-101 BMB-105 BMB-201 Centhaquine CP-809101 Dimemebfe DLX-2270 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 KB-128 Lorcaserin Lumocaserin LY03020 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, CPI-CG-8) 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 DSP-6745 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 Itasetron 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: 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-HT_5A

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 DSP-6745 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

Dopamine receptor modulators

D₁-like

Agonists	Benzazepines: 6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines: Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride Dihydrexidine derivatives: A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine Phenethylamines: BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dipropyldopamine (DPDA) Dopamine Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Lu AE04621 Melevodopa L-Phenylalanine L-Tyrosine XP21279 Others: A-68930 Apomorphine Isocorypalmine Lu AF28996 Nuciferine PF-2334 PF-06412562 PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine RU-29717 SKF-89,145 SKF-89,615 SKF-89,626 Stepholidine Tavapadon Tetrahydropalmatine
PAMs	Tetrahydroisoquinolines: DETQ DPTQ Glovadalen Mevidalen Others: ASP-4345
Antagonists	Typical antipsychotics: Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol Atypical antipsychotics: Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Ziprasidone Zotepine Others: A-69024 Berupipam Ecopipam EEDQ Lu AF35700 (d8-zicronapine) Metitepine (methiothepin) Odapipam Perlapine SCH-23390 SDZ-PSD-958 Zicronapine

D₂-like

Agonists

Phenethylamines: Deoxyepinephrine (N-methyldopamine, epinine)
Dipropyldopamine (DPDA)
Dopamine
Dopexamine
Etilevodopa
Ibopamine
L-DOPA (levodopa)
Lu AE04621
L-Phenylalanine
RU-24213
L-Tyrosine
Melevodopa
XP21279

Atypical antipsychotics: Alentemol (U-66444B)
Aripiprazole (+sertraline)
Aripiprazole lauroxil
Bifeprunox
Brexpiprazole
Brilaroxazine
Cariprazine
F-15063
Lumateperone
Norclozapine

Antagonists

Typical antipsychotics: Acepromazine
Acetophenazine
Azaperone
Benperidol
Bromperidol
Butaclamol
Butaperazine
Chloracizine
Chlorproethazine
Chlorpromazine
Chlorprothixene
Ciclindole
Clopenthixol
Clothixamide
Clopimozide
Droperidol
Fluacizine
Fluanisone
Flucindole
Fluotracen
Flupentixol (flupenthixol) (+melitracen)
Fluphenazine
Fluprothixene
Fluspirilene
Haloperidol
Homopipramol
Lenperone
Levomepromazine (methotrimeprazine)
Levosulpiride
Loxapine
Mesoridazine
Moperone
Naranol
Nemonapride
Penfluridol
Perathiepin
Perazine
Pericyazine (periciazine)
Perphenazine (+amitriptyline)
Piflutixol (pifluthixol)
Pimozide
Pipamperone
Preclamol
Prochlorperazine
Promazine
Prothipendyl
Spiperone (spiroperidol)
Sulforidazine
Sulpiride
Sultopride
Teflutixol
Thiopropazate
Thioproperazine
Thioridazine
Thiothixene
Timiperone
Trifluoperazine (+tranylcypromine)
Triflupromazine
Trifluperidol
Zetidoline
Zuclopenthixol

Antiemetics/gastroprokinetics/sedatives: Aceprometazine
AS-8112
Alimemazine
Alizapride
Benzquinamide
Bromopride
Clebopride
Deudomperidone
Domperidone
Eticlopride
Hydroxyzine
Itopride
Metoclopramide
Metopimazine
Promethazine
Thiethylperazine
Trazpiroben
Trimethobenzamide

See also: Receptor/signaling modulators
Adrenergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

v t e Ergolines
Ergolines (incl. lysergines)	13-Fluorolysergol Acetergamine BAM-2101 BAM-2201 Brazergoline Bromerguride (2-bromolisuride) Cianergoline Delergotrile Descarboxylysergic acid Dihydrolysergic acid Disulergine Dosergoside Ergolene Ergoline Etisulergine FCE-22716 LEK-8829 Lergotrile Lisuride LY-158A (6-ethylpergolide) LY-53857 LY-86057 LY-108742 LY-116467 (LY-062; 6-methylpergolide) LY-193525 LY-197541 LY-215840 LY-225297 LY-254239 Lysergene Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mesulergine Metergoline Nicergoline Pergolide Pibocin A Pibocin B Proterguride Romergoline SDZ 208-911 SDZ 208-912 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 LEK-1814 LEK-8804 (N-(2-propynyl)lysergamide) LEK-8822 LEK-8827 LEK-8841 Lumi-LSD LY-215,840 Lysergic acid 2-heptylamide Lysergic acid 2-hexylamide 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) NIBR2130 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) 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 2-pentylamide (2-LSP) Lysergic acid 3-pentylamide (LSP, 3-LSP) Methylergometrine (methylergonovine, methylergobasine; Methergine) Methylisopropyllysergamide (MiPLA) Methylpropyllysergamide (LAMPA, LMP-55) 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 TRALA-12 (didehydro-LSD; DDH-LSD) Unsorted lysergamides: 1-Dimethylaminomethyl-LSD 2-Br-14-Me-LSD 12-Hydroxy-LSD 12-Methoxy-LSD 13-Fluoro-LSD 13-Hydroxy-LSD 14-Hydroxy-LSD 14-Methoxy-LSD 14-Methyl-LSD CE-LAD Dihydroergometrine (dihydroergonovine, dihydroergobasine) Ergovalide FLUORETH-LAD FP-LAD Lysergic acid azepane (LA-Azepane) Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine) LEK-8842 (TRALA-01) LA-Cispip (LA-cis-2,6-DiMePip) LA-Cispyr (LA-cis-2,5-DiMePyr) Lysergic acid α-methylbenzylamide Lysergic acid amylamide Lysergic acid butylamide Lysergic acid ethyl-2-butylamide Lysergic acid ethyl-2-hydroxyethylamide (LEO) Lysergic acid ethyl-2-methoxyethylamide (LA-MeO) Lysergic acid methyl-2-butylamide Lysergic acid piperidide (LA-Pip, LSD-Pip) Lysergic acid pyrrolinide (LPN) Lysergic acid tert-butylamide (LAtB) Lysergyl-L-valyl methyl ester 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 LY-301317 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	9-Oxaergolines: 6-Ethyl-9-oxaergoline (EOE) 9-Oxaergoline RU-29717 (N-propyl-9-oxaergoline) Voxergolide (RU-41656) Others: A-86929 Adrogolide Centpyraquin (IHCH-7162) CY-208,243 FCE-24379 IHCH-7179 JRT (isotryptamine-LSD) Naxagolide Quinagolide Quinelorane Quinpirole S32504 SDZ SER-082
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

v t e Chemical classes of psychoactive drugs
Stimulants	Amphetamine-type/dopamine releasing agents: Alkylamines Cycloalkylaminopropanes Arylpiperazines Benzylpiperazines Phenylpiperazines Phenethylamines Aminorexes/phenyloxazolamines Amphetamines/α-methylphenethylamines Cathinones/β-ketoamphetamines β-Hydroxyamphetamines/cathinols Naphthylaminopropanes Phentermines Phenylisobutylamines/α-ethylphenethylamines α-Propylphenethylamines Phenylmorpholines/phenmetrazines Thiopropamines/thienylaminopropanes Cocaine-type/typical dopamine reuptake inhibitors: Phenethylamines Phenidates/benzylpiperidines Phenylethylpyrrolidines Pyrrolidinophenones Phenyltropanes/cocaine analogues Modafinil-type/atypical dopamine reuptake inhibitors: Modafinil analogues Phenylpiracetams Caffeine-type/adenosine receptor antagonists: Xanthines/methylxanthines Nicotine-type/nicotinic acetylcholine receptor agonists: Nicotine analogues
Depressants	GABA_A receptor positive allosteric modulators: Alcohols/ethanol analogues Barbiturates Benzodiazepines Pyrrolobenzodiazepines Thienobenzodiazepines Thienodiazepines Thienotriazolodiazepines Triazolobenzodiazepines Carbamates Ethers Neuroactive steroids Nonbenzodiazepines β-Carbolines Cyclopyrrolones Imidazopyridines Pyrazolopyrimidines Phenols Piperidinediones Quinazolinones GABA_A receptor agonists: Isoxazoles GHB receptor agonists: 1,4-Butanediols α₂δ subunit-containing voltage-gated calcium channel blockers: Gabapentinoids Opioids/μ-opioid receptor agonists: Benzimidazoles Nitazenes Fentanyl analogues/phenylpiperidines Mitragyna alkaloids Morphinans/phenanthrenes Opiates/opium alkaloids Utopioids Antihistamines/H₁ receptor antagonists: Benzimidazoles Diarylmethanes Ethylenediamines Tricyclics Dibenzocycloheptenes
Hallucinogens	Serotonergic psychedelics/serotonin 5-HT_2A receptor agonists: Arylpiperazines Phenylpiperazines Quinolinylpiperazines Cyclized phenethylamines 3-Benzazepines Cyclized tryptamines Azepinoindoles Ibogalogs Iboga alkaloids β-Carbolines Harmala alkaloids Ergolines Lysergamides Simplified/partial lysergamides Phenethylamines (methoxyphenethylamines) 2Cs 25-NB/NBOMes 2C-Os 2C-Ts HOT-x TWEETIOs Amphetamines/α-methylphenethylamines 3Cs 3C-Desoxyscalines Dimethoxyamphetamines/DMAs DOx Alephs Ethylenedioxyamphetamines/EDxx Methylenedioxyamphetamines/MDxx Trimethoxyamphetamines/TMAs BOx Desoxyscalines FLYs/benzofurans Phenylisobutylamines/α-ethylphenethylamines 4Cs Scalines Thioscalines Ψ-PEAs Tryptamines α-Alkyltryptamines α-Alkyl-β-ketotryptamines 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Miscellaneous Dissociatives/NMDA receptor antagonists: Adamantanes Arylcyclohexylamines Diarylethylamines Morphinans κ-Opioid receptor agonists: Benzomorphans Salvinorins GABA_A receptor agonists: Isoxazoles Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes Tropanes Others: Cyclized tryptamines Azepinoindoles Iboga alkaloids (Phyto)cannabinoids
Entactogens	Serotonin releasing agents: Phenethylamines 2-Aminoindanes 2-Aminotetralins Amphetamines Benzofuranylaminopropanes Benzothiophenylaminopropanes Ethylenedioxyamphetamines/EDxx Indanylaminopropanes Indolylaminopropanes Methylenedioxyamphetamines/MDxx Tetralinylaminopropanes Tryptamines α-Alkyltryptamines Miscellaneous
Psychiatric drugs	Anxiolytics: Azapirones Benzodiazepines Pyrrolobenzodiazepines Thienobenzodiazepines Thienodiazepines Thienotriazolodiazepines Triazolobenzodiazepines Antidepressants: Tricyclic antidepressants Dibenzazepines Dibenzocycloheptenes Dibenzothiepins Dibenzoxazepines Dibenzoxepins Tetracyclic antidepressants Antipsychotics/dopamine D₂ receptor antagonists or partial agonists: Benzamides Benzimidazoles Benzisothiazoles Benzisoxazoles Butyrophenones Diphenylbutylpiperidines Phenylpiperazines Tricyclics Dibenzazepines Dibenzodiazepines Dibenzothiazepines Dibenzothiepins Dibenzoxazepines Phenothiazines Thienobenzodiazepines Mood stabilizers/anticonvulsants: Gabapentinoids Tricyclics Dibenzazepines Valproates
Others	Nootropics: Racetams Phenylpiracetams Miscellaneous: 3-Benzazepines Adamantanes Catecholamines Tetrahydroisoquinolines Yohimbans

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Category:

Partial ergolines

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URL: https://en.wikipedia.org/wiki/Simplified/partial_ergoline

⇱ Partial lysergamide - Wikipedia

List of simplified or partial lysergamides

Structural comparisons

Related compounds

See also

References

External links