Psychedelic drug
Pharmaceutical compound
Psilocin Clinical data Other names Psilocine; Psilocyn; Psilotsin; 4-Hydroxy-N ,N -dimethyltryptamine; 4-Hydroxy-DMT; 4-Hydroxy-N ,N -DMT; 4-HO-DMT; 4-OH-DMT; PSOH; PAL-153; PAL153; CX-59; CX59 Routes of Oral ,intravenous [ 1] [ 2] Drug class Serotonergic psychedelic ;Hallucinogen ;Serotonin receptor agonist ;Serotonin 5-HT2A receptor agonist [ 3] ATC code Legal status Legal status Pharmacokinetic dataBioavailability Oral psilocybin : 52.7 ± 20.4% (as psilocin)[ 3] [ 1] Metabolism Liver , othertissues :[ 6] [ 3] [ 1] [ 7] Demethylation anddeamination (MAO Tooltip monoamine oxidase )Oxidation (ALDH Tooltip aldehyde dehydrogenase )Glucuronidation (UGTs )Metabolites • Psilocin-O -glucuronide[ 3] [ 1] [ 3] [ 1] [ 3] [ 1] [ 3] [ 1] Onset of action 15–40 minutes[ 2] Eliminationhalf-life Oral psilocybin: 2.3–3 hours (as psilocin)[ 3] [ 1] [ 5] IV Tooltip Intravenous injection psilocybin: 1.2 hours (as psilocin)[ 1] [ 5] Duration of action 3–6 hours[ 2] Excretion Urine (mainly as psilocin-O -glucuronide, 2–4% unchanged)[ 3] [ 1] [ 5] Identifiers CAS Number PubChem CID IUPHAR/BPS ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA) ECHA InfoCard 100.007.543 Chemical and physical data Formula C 12 H 16 N 2 O Molar mass −1 3D model (JSmol ) Melting point 173 to 176 °C (343 to 349 °F) InChI=1S/C12H16N2O/c1-14(2)7-6-9-8-13-10-4-3-5-11(15)12(9)10/h3-5,8,13,15H,6-7H2,1-2H3
Y Key:SPCIYGNTAMCTRO-UHFFFAOYSA-N
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Psilocin , also known as4-hydroxy-N ,N -dimethyltryptamine (4-HO-DMT ), is apsychedelic drug andfungal alkaloid of thetryptamine and4-hydroxytryptamine families.[ 8] [ 9] [ 2] phosphate ester psilocybin , it is found in most species ofpsilocybin-containing mushrooms , such asPsilocybe cubensis Psilocybe mexicana hallucinogenic effects, although concentrations of psilocin are variably lower than those of psilocybin.[ 5] [ 9] [ 10] orally and its effects includeperceptual changes andvisual effects,emotional changes,ego dissolution ,time dilation , andmystical experiences , among others.[ 2] [ 11] [ 12] synthetic acyl esters such as4-AcO-DMT (psilacetin;O -acetylpsilocin) and4-PrO-DMT (O -propionylpsilocin), areprodrugs of psilocin and have similar properties and effects.[ 8] [ 13] [ 2]
Psilocin acts as anon-selective serotonin receptor agonist , including of theserotonin 5-HT2A receptor among others.[ 14] hallucinogenic effects specifically via activation of the serotonin 5-HT2A receptor.[ 15] [ 16] [ 17] serotonin receptors , such as the serotonin5-HT1A and5-HT2C receptors , may also contribute to its effects.[ 18] [ 19] [ 20] analogues of psilocin includedimethyltryptamine (DMT), itspositional isomer bufotenin (5-HO-DMT), its higherhomologue 4-HO-MET (metocin), and others.[ 2]
Psilocin and psilocybin were discovered via isolation from psilocybin-containing mushrooms byAlbert Hofmann in 1958.[ 8] [ 21] [ 22] Western re-discovery of psilocybin-containing mushrooms byRobert Gordon Wasson andValentina Pavlovna Wasson inMexico in 1955.[ 21] [ 22] entheogen as well asrecreational psychedelic drug.[ 21] [ 8] [ 23] controlled substances in theUnited States and internationally under theUnited Nations in 1971.[ 24] [ 25] active form of psilocybin, has became of interest for potential use inmedicine to treatpsychiatric disorders such asdepression .[ 21] [ 23] [ 26] Australia in 2023[ 27] [ 28] late-stage clinical trials in the United States and other countries.[ 29] [ 30] [ 31]
Driedpsilocybin mushrooms . (Notice the characteristic blue bruising by the stems of the mushrooms.) Psilocin is usedrecreationally ,spirituality orshamanically , andmedically . It is most commonly used in the form of itsprodrugs such aspsilocybin and4-AcO-DMT (psilacetin). However, psilocin may also be used itself, either in the form ofpsilocybin-containing mushrooms (which variably contain psilocin up to similar amounts as psilocybin) or insynthetic form.[ 2]
Psilocin is usually usedorally , but may also be takenintravenously . In terms ofdose , it is slightly morepotent than psilocybin, about 1.4-fold so (i.e., 1.4 mg psilocybin equals about 1.0 mg psilocin).[ 5] [ 32] [ 33] ester prodrug moiety , which results in itsmolecular weight being about 40% lower than that of psilocybin (204 g/mol and 284 g/mol, respectively).[ 32] [ 34] [ 33] mg orally.[ 15] [ 35] [ 16] [ 2]
In his bookTiHKAL Tryptamines I Have Known and Loved ),Alexander Shulgin described the properties and effects of psilocin, either as psilocin itself, as aprodrug likepsilocybin or4-AcO-DMT , or asPsilocybe cubensis [ 2] mg orally and theduration as 3 to 6 hours.[ 2] onset , in the case of psilocin specifically, was 15 to 40 minutes.[ 2] perceptual and related effects included brightened colors, increasedvisual contrast ,closed-eye visuals such as patterns, textures, and colors,open-eye visuals such as colors,distortions , and movement,pareidolia , increased appreciation of scenery, perceiving beauty, and enhancedimagination .[ 2] intoxicated ,high , and/orstimulated , feelings ofpeacefulness and serenity,emotional amplification,mood swings , feelings ofneuroticism andintroversion , feelings ofdespair ,apathy , andunpleasantness ,anxiety ,confusion ,distractibility , impairment, and feeling heavy andtired .[ 2] Side effects includedchills ,nausea ,vomiting , andmotion sickness , but nohangover .[ 2]
In other reports, the effects observed after ingestion of psilocin can include but are not limited totachycardia ,dilated pupils ,restlessness orarousal ,euphoria ,open andclosed eye visuals (common at medium to high doses),synesthesia (e.g. hearing colors and seeing sounds), increasedbody temperature ,headache ,sweating andchills , andnausea .[ 1]
There has been no directlethality associated with psilocin.[ 36] [ 37] withdrawal syndrome when chronic use of this drug is ceased.[ 36] [ 38] cross tolerance among psilocin,mescaline ,lysergic acid diethylamide (LSD), and other psychedelics due todownregulation of these receptors.[ 8] [ 15] [ 17] [ 19]
Psilocin at molecular targetsTarget Affinity (Ki , nM) 5-HT1A 49–567 (Ki )EC50 Tooltip half-maximal effective concentration )Emax Tooltip maximal efficacy ) 5-HT1B 31–305 5-HT1D 19–36 5-HT1E 44–52 5-HT1F ND 5-HT2A 6.0–340 (Ki )EC50 ) Emax ) 5-HT2B 4.6–410 (Ki )EC50 ) Emax ) 5-HT2C 10–141 (Ki )EC50 ) Emax ) 5-HT3 >10,000 5-HT4 ND 5-HT5A 70–84 5-HT6 57–72 5-HT7 3.5–72 α1A –α1B >10,000 α2A 1,379–2,044 α2B 1,271–1,894 α2C 4,404 β1 –β2 >10,000 D1 20–>14,000 D2 3,700–>10,000 D3 101–8,900 D4 >10,000 D5 >10,000 H1 1,600–>10,000 H2 –H4 >10,000 M1 –M5 >10,000 σ1 >10,000 σ2 >10,000 I2 792 TAAR1 1,400 (Ki ) (rat)i ) (mouse)EC50 ) (rodent) EC50 ) (human) SERT Tooltip Serotonin transporter 3,650–>10,000 (Ki )IC50 Tooltip half-maximal inhibitory concentration )EC50 ) Emax ) NET Tooltip Norepinephrine transporter 13,000 (Ki )IC50 ) EC50 ) DAT Tooltip Dopamine transporter 6,000–>30,000 (Ki )IC50 ) EC50 ) Notes: The smaller the value, the more avidly psilocin interacts with the site.Sources: [ 39] [ 40] [ 41] [ 42] [ 43] [ 44] [ 5] [ 45] [ 46] [ 47] [ 48] [ 49] [ 50] [ 51] [ 52] [ 53] [ 54] [ 55] [ 56]
Psilocin is thepharmacologically active agent in the body after ingestion ofpsilocybin or some species of psychedelic mushrooms. Psilocybin is rapidlydephosphorylated in the body to psilocin which acts as aserotonin 5-HT2A ,5-HT2C and5-HT1A receptor agonist orpartial agonist . Psilocin exhibitsfunctional selectivity in that it activatesphospholipase A2 instead of activatingphospholipase C as theendogenous ligand serotonin does. Psilocin isstructurally similar to serotonin (5-hydroxytryptamine),[ 36] hydroxyl group being on the 4-position rather than the 5 and thedimethyl groups on thenitrogen . Its effects are thought to come from its agonist activity at 5-HT2A receptors in theprefrontal cortex . Psilocin's psychedelic effects are directly correlated with the drug'soccupancy at thesereceptor sites .[ 57] dopamine receptors only affects thenoradrenergic system at very high doses.[ 58]
Psilocin has been reported to act as a highlypotent positive allosteric modulator of thetropomyosin receptor kinase B (TrkB), one of thereceptors ofbrain-derived neurotrophic factor (BDNF).[ 59] [ 60] [ 61] [ 14]
Thecryo-EM structures of the serotonin 5-HT2A receptor with psilocin, as well as with various other psychedelics and serotonin 5-HT2A receptor agonists, have been solved and published byBryan L. Roth and colleagues.[ 62] [ 63]
Psilocin'selimination half-life ranges from 1 to 3 hours depending onroute of administration ofpsilocybin .[ 5]
Psilocin, also known as 4-hydroxy-N ,N -dimethyltryptamine (4-HO-DMT), is atryptamine derivative .[ 2] structurally related to theneurotransmitter serotonin (which is 5-hydroxytryptamine, also known as 5-HT or 5-HO-T), as well as to thenaturally occurring psychedelicsdimethyltryptamine (N ,N -dimethyltryptamine; DMT) andbufotenin (5-hydroxy-N ,N -DMT; 5-HO-DMT).Psilocybin is psilocin'sO -phosphate ester (4-phosphoryloxy-N ,N -DMT; 4-PO-DMT).[ 2]
Thechemical synthesis of psilocin has been described.[ 2] dephosphorylation ofpsilocybin under stronglyacidic or underalkaline conditions (hydrolysis ). A synthetic route uses the Speeter–Anthony tryptamine synthesis procedure. First, 4-hydroxyindole isFriedel-Crafts -acylated with oxalyl chloride in position 3. The compound is further reacted withdimethylamine , yielding the indole-3-yl-glyoxamide. Finally, this 4-hydroxyindole-3-N ,N -dimethylglyoxamide is reduced by lithium aluminum hydride yielding psilocin.[ 64]
Psilocin is relatively unstable in solution due to itsphenolic hydroxy (-OH) group.[citation needed In the presence ofoxygen , it readily forms bluish and dark black degradation products.[ 65] Fe3+ ions .[citation needed
Analogues of psilocin (4-HO-DMT) includedimethyltryptamine (DMT),4-hydroxytryptamine (4-HT or 4-HO-T),norpsilocin (4-HO-NMT),4-HO-TMT ,4-HO-MET (metocin),4-HO-DET (ethocin),4-HO-MPT (meprocin),4-HO-DPT (deprocin),4-HO-MiPT (miprocin),4-HO-DiPT (diprocin),4-MeO-DMT , and5-MeO-DMT , among others.[ 2] [ 66] [ 67] [ 68]
A number ofester prodrugs of psilocin are known, such aspsilocybin (4-PO-DMT),4-AcO-DMT , and4-PrO-DMT .[ 8] [ 13] [ 2] O -phosphate ester of psilocin, while 4-AcO-DMT is theO -acetyl ester and 4-PrO-DMT is theO -propionyl ester.[ 8] [ 13] [ 2] 4-GO-DMT (4-HO-DMTO -glutarate; RE109), which is related toluvesilocin (4-GO-DiPT; RE104).[ 69] [ 70] norbaeocystin (4-PO-T),baeocystin (4-PO-NMT),aeruginascin (4-PO-TMT), andethocybin (4-PO-DET), among others.[ 2] [ 9] [ 71]
Bufotenin (5-HO-DMT) and6-HO-DMT arepositional isomers of psilocin.[ 72] [ 66] [ 67] [ 68]
1-Methylpsilocin is aserotonin 5-HT2C receptor -preferringagonist .[ 73] 4-Fluoro-DMT is known.[ 73] 1-isopropyl-6-fluoropsilocin (O-4310).[ 74] [ 75]
Sulfur analogues of psilocin are known with abenzothienyl replacement[ 76] 4-SH-DMT .[ 77]
Psilocin and itsphosphorylated cousin,psilocybin , were first isolated and named in 1958 by Swiss chemistAlbert Hofmann .[ 8] [ 21] hallucinogenic mushroom Psilocybe mexicana [ 8] [ 21] [ 78]
Society and culture [ edit ] Psilocin is aSchedule I drug under theConvention on Psychotropic Substances .[ 79]
Psilocin is considered a Schedule 9 prohibited substance in Australia under thePoisons Standard (October 2015).[ 80] [ 80]
Psilocin and psilocybin are banned in Russia, due to their status as narcotic drugs, with a criminal penalty for possession of more than 50 mg.[ 81]
Psilocin is a Schedule Icontrolled substance in theUnited States since 1971.[ 24]
Psilocin is being evaluated under the developmental code name PLZ-1015 for the treatment ofpervasive developmental disorders likeautism in children.[ 31] prodrug psilocybin is also being studied for treatment ofdepression and a variety of otherconditions .[ 26] [ 30]
^a b c d e f g h i j k Lowe H, Toyang N, Steele B, Valentine H, Grant J, Ali A, Ngwa W, Gordon L (May 2021)."The Therapeutic Potential of Psilocybin" .Molecules .26 (10): 2948.doi :10.3390/molecules26102948 PMC 8156539 PMID 34063505 .S2CID 235227972 . ^a b c d e f g h i j k l m n o p q r s t u v Shulgin, Alexander ;Shulgin, Ann (September 1997).TiHKAL: The Continuation Berkeley, California :Transform Press .ISBN 0-9630096-9-9 OCLC 38503252 .https://www.erowid.org/library/books_online/tihkal/tihkal18.shtml ^a b c d e f g h i Dodd S, Norman TR, Eyre HA, Stahl SM, Phillips A, Carvalho AF, Berk M (July 2022)."Psilocybin in neuropsychiatry: a review of its pharmacology, safety, and efficacy" .CNS Spectr .28 (4):416– 426.doi :10.1017/S1092852922000888 PMID 35811423 . ^ Anvisa (2023-07-24)."RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).Diário Oficial da União (published 2023-07-25).Archived from the original on 2023-08-27. Retrieved2023-08-27 .^a b c d e f g Tylš F, Páleníček T, Horáček J (March 2014)."Psilocybin - summary of knowledge and new perspectives" .Eur Neuropsychopharmacol .24 (3):342– 356.doi :10.1016/j.euroneuro.2013.12.006 .PMID 24444771 . ^ MacCallum CA, Lo LA, Pistawka CA, Deol JK (2022)."Therapeutic use of psilocybin: Practical considerations for dosing and administration" .Frontiers in Psychiatry .13 1040217.doi :10.3389/fpsyt.2022.1040217 PMC 9751063 PMID 36532184 . ^ Coppola M, Bevione F, Mondola R (February 2022)."Psilocybin for Treating Psychiatric Disorders: A Psychonaut Legend or a Promising Therapeutic Perspective?" .Journal of Xenobiotics .12 (1):41– 52.doi :10.3390/jox12010004 PMC 8883979 PMID 35225956 . ^a b c d e f g h i Geiger HA, Wurst MG, Daniels RN (October 2018)."DARK Classics in Chemical Neuroscience: Psilocybin" (PDF) .ACS Chem Neurosci .9 (10):2438– 2447.doi :10.1021/acschemneuro.8b00186 .PMID 29956917 . ^a b c Pepe M, Hesami M, de la Cerda KA, Perreault ML, Hsiang T, Jones AM (December 2023). "A journey with psychedelic mushrooms: From historical relevance to biology, cultivation, medicinal uses, biotechnology, and beyond".Biotechnol Adv .69 : 108247.doi :10.1016/j.biotechadv.2023.108247 .PMID 37659744 . {{cite journal }}: CS1 maint: article number as page number (link )^ Gotvaldová K, Borovička J, Hájková K, Cihlářová P, Rockefeller A, Kuchař M (November 2022)."Extensive Collection of Psychotropic Mushrooms with Determination of Their Tryptamine Alkaloids" .International Journal of Molecular Sciences .23 (22) 14068.doi :10.3390/ijms232214068 PMC 9693126 PMID 36430546 . ^ Al-Imam A, Lora R, Motyka MA, Marletta E, Vezzaro M, Moczko J, Younus M, Michalak M (May 2025). "Opinion Mining of Erowid's Experience Reports on LSD and Psilocybin-Containing Mushrooms".Drug Saf .48 (5):559– 575.doi :10.1007/s40264-025-01530-z .PMID 40032797 . ^ James E, Robertshaw TL, Hoskins M, Sessa B (September 2020). "Psilocybin occasioned mystical-type experiences".Hum Psychopharmacol .35 (5): e2742.doi :10.1002/hup.2742 .PMID 32573835 . {{cite journal }}: CS1 maint: article number as page number (link )^a b c Glatfelter GC, Naeem M, Pham DN, Golen JA, Chadeayne AR, Manke DR, Baumann MH (April 2023)."Receptor Binding Profiles for Tryptamine Psychedelics and Effects of 4-Propionoxy-N,N-dimethyltryptamine in Mice" .ACS Pharmacol Transl Sci .6 (4):567– 577.doi :10.1021/acsptsci.2c00222 .PMC 10111620 PMID 37082754 . ^a b Jain MK, Gumpper RH, Slocum ST, Schmitz GP, Madsen JS, Tummino TA, Suomivuori CM, Huang XP, Shub L, DiBerto JF, Kim K, DeLeon C, Krumm BE, Fay JF, Keiser M, Hauser AS, Dror RO, Shoichet B, Gloriam DE, Nichols DE, Roth BL (July 2025)."The polypharmacology of psychedelics reveals multiple targets for potential therapeutics" (PDF) .Neuron .113 (19): 3129–3142.e9.doi :10.1016/j.neuron.2025.06.012 .PMID 40683247 .Recent studies have suggested that psychedelics such as LSD directly interact with TrkB with high affinity, promoting BDNF-mediated neuroplasticity and antidepressant-like effects via allosteric potentiation of BDNF signaling in active synapses.8 To investigate this, we screened LSD across 450 human kinases, including TrkB, but found no significant interactions between LSD and any tested human kinases. Further experiments in transfected cells revealed no effect of LSD or psilocin on BDNF-mediated activation of a TrkB reporter. We note that similar negative preliminary results, which have not yet been published in a peer-reviewed journal, were recently reported by Boltaev et al.63 ^a b c Nichols DE (February 2004). "Hallucinogens".Pharmacol Ther .101 (2):131– 181.doi :10.1016/j.pharmthera.2003.11.002 .PMID 14761703 . ^a b Nichols DE (April 2016)."Psychedelics" .Pharmacol Rev .68 (2):264– 355.doi :10.1124/pr.115.011478 .PMC 4813425 PMID 26841800 . ^a b Halberstadt AL (January 2015)."Recent advances in the neuropsychopharmacology of serotonergic hallucinogens" .Behav Brain Res .277 :99– 120.doi :10.1016/j.bbr.2014.07.016 .PMC 4642895 PMID 25036425 . ^ Cameron LP, Benetatos J, Lewis V, Bonniwell EM, Jaster AM, Moliner R, Castrén E, McCorvy JD, Palner M, Aguilar-Valles A (November 2023)."Beyond the 5-HT2A Receptor: Classic and Nonclassic Targets in Psychedelic Drug Action" .J Neurosci .43 (45):7472– 7482.doi :10.1523/JNEUROSCI.1384-23.2023 .PMC 10634557 PMID 37940583 . ^a b Halberstadt AL, Geyer MA (September 2011)."Multiple receptors contribute to the behavioral effects of indoleamine hallucinogens" .Neuropharmacology .61 (3):364– 381.doi :10.1016/j.neuropharm.2011.01.017 .PMC 3110631 PMID 21256140 . ^ Erkizia-Santamaría I, Alles-Pascual R, Horrillo I, Meana JJ, Ortega JE (October 2022). "Serotonin 5-HT2A, 5-HT2c and 5-HT1A receptor involvement in the acute effects of psilocybin in mice. In vitro pharmacological profile and modulation of thermoregulation and head-twich response".Biomed Pharmacother .154 : 113612.doi :10.1016/j.biopha.2022.113612 .PMID 36049313 . {{cite journal }}: CS1 maint: article number as page number (link )^a b c d e f Nichols DE (October 2020). "Psilocybin: from ancient magic to modern medicine".J Antibiot (Tokyo) .73 (10):679– 686.doi :10.1038/s41429-020-0311-8 .PMID 32398764 . ^a b Fradet M, Kelly CM, Donnelly AJ, Suppes T (December 2024). "Psilocybin and hallucinogenic mushrooms".CNS Spectr .29 (6):611– 632.doi :10.1017/S1092852924002487 .PMID 39789676 . ^a b Scala M, Fabbri C, Fusar-Poli P, Di Lorenzo G, Ferrara M, Amerio A, Fusar-Poli L, Pichiecchio A, Asteggiano C, Menchetti M, De Ronchi D, Fanelli G, Serretti A (December 2024). "The revival of psilocybin between scientific excitement, evidence of efficacy, and real-world challenges".CNS Spectr .29 (6):570– 584.doi :10.1017/S1092852924002268 .PMID 39655426 . ^a b https://www.govinfo.gov/content/pkg/STATUTE-84/pdf/STATUTE-84-Pg1236.pdf ^ https://www.incb.org/documents/Psychotropics/conventions/convention_1971_en.pdf ^a b Madden K, Flood B, Young Shing D, Ade-Conde M, Kashir I, Mark M, MacKillop J, Bhandari M, Adili A (October 2024)."Psilocybin for clinical indications: A scoping review" .J Psychopharmacol .38 (10):839– 845.doi :10.1177/02698811241269751 .PMC 11481402 PMID 39135496 . ^ Nutt DJ, Hunt P, Schlag AK, Fitzgerald P (December 2024)."The Australia story: Current status and future challenges for the clinical applications of psychedelics" .British Journal of Pharmacology bph.17398.doi :10.1111/bph.17398 PMID 39701143 . ^ Donley CN, Dixon Ritchie G, Dixon Ritchie O (2023)."From prohibited to prescribed: The rescheduling of MDMA and psilocybin in Australia" .Drug Science, Policy and Law .9 20503245231198472.doi :10.1177/20503245231198472 ISSN 2050-3245 . ^ Melani A, Bonaso M, Biso L, Zucchini B, Conversano C, Scarselli M (January 2025)."Uncovering Psychedelics: From Neural Circuits to Therapeutic Applications" .Pharmaceuticals (Basel) .18 (1): 130.doi :10.3390/ph18010130 PMC 11769142 PMID 39861191 . ^a b Najib J (October 2024). "The role of psilocybin in depressive disorders".Curr Med Res Opin .40 (10):1793– 1808.doi :10.1080/03007995.2024.2396536 .PMID 39177339 . ^a b "Psilocybin - COMPASS Pathways" .AdisInsight . 15 May 2024. Retrieved5 September 2024 .^a b Albert Hofmann (1968)."Psychotomimetic Agents" . In Burger A (ed.).Drugs Affecting the Central Nervous System 169– 235.OCLC 245452885 .OL 13539506M .Psilocin is approximately 1.4 times as potent as psilocybin. This ratio is the same as that of the molecular weights of the two drugs. ^a b Wolbach AB, Miner EJ, Isbell H (1962). "Comparison of psilocin with psilocybin, mescaline and LSD-25".Psychopharmacologia .3 (3):219– 223.doi :10.1007/BF00412109 .PMID 14007905 .Psilocin is approximately 1.4 times as potent as psilocybin. This ratio is the same as that of the molecular weights of the two drugs. ^ Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds".Hallucinogenic Agents 98– 144.ISBN 978-0-85608-011-1 OCLC 2176880 .OL 4850660M .Psilocin is claimed to be about 1·4 times as potent as psilocybin, but they are equipotent on a molar basis. ^ Fantegrossi WE, Murnane KS, Reissig CJ (January 2008)."The behavioral pharmacology of hallucinogens" (PDF) .Biochem Pharmacol .75 (1):17– 33.doi :10.1016/j.bcp.2007.07.018 .PMC 2247373 PMID 17977517 . ^a b c Diaz J (1996).How Drugs Influence Behavior: A Neurobehavioral Approach . Englewood Cliffs: Prentice Hall.ISBN 978-0-02-328764-0 ^ Garcia-Romeu A, Kersgaard B, Addy PH (August 2016)."Clinical applications of hallucinogens: A review" .Experimental and Clinical Psychopharmacology .24 (4):229– 68.doi :10.1037/pha0000084 .PMC 5001686 PMID 27454674 . ^ Assessing Drug Risks: A Scientific Framework . European Monitoring Centre for Drugs and Drug Addiction. Luxembourg: EMCDDA. 2016.^ Liu T."BindingDB BDBM50081701 3-[2-(dimethylamino)ethyl]-1H-indol-4-ol::4-hydroxy-N,N-dimethyltryptamine::CHEMBL65547::N,N-dimethyl-4-hydroxytryptamine::Psilocin::US11427604, Compound (I-45)::US11453689, Compound Psilocin::US11591353, Compound I-45::US11597738, Example 3::US11642336, Compound Psilocin::US20240051978, Compound Psilocin" .BindingDB . Retrieved5 September 2024 . ^ Liu T."BindingDB BDBM50171269 3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate::4-phosphoryloxy-N,N-dimethyltryptamine::CHEMBL194378::Indocybin::O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine::Psilocybine::US11597738, Example 4::psilocin phosphate ester::psilocybin" .BindingDB . Retrieved5 September 2024 . ^ "PDSP Database" .UNC (in Zulu). Retrieved2024-09-05 .^ "PDSP Database" .UNC (in Zulu). 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(June 2019)."Psychedelic effects of psilocybin correlate with serotonin 2A receptor occupancy and plasma psilocin levels" .Neuropsychopharmacology .44 (7):1328– 1334.doi :10.1038/s41386-019-0324-9 .PMC 6785028 PMID 30685771 . ^ Jerome L (March–April 2007)."Psilocybin Investigator's Brochure" (PDF) . 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University of North Carolina at Chapel Hill Department of Pharmacology Research Retreat September 16th, 2022 – William and Ida Friday Center. ^ Kargbo RB, Sherwood A, Walker A, Cozzi NV, Dagger RE, Sable J, et al. (July 2020)."Direct Phosphorylation of Psilocin Enables Optimized cGMP Kilogram-Scale Manufacture of Psilocybin" .ACS Omega .5 (27):16959– 16966.doi :10.1021/acsomega.0c02387 .PMC 7364850 PMID 32685866 .S2CID 220599227 . ^ Lenz C, Wick J, Braga D, García-Altares M, Lackner G, Hertweck C, et al. (January 2020)."Injury-Triggered Blueing Reactions of Psilocybe "Magic" Mushrooms" .Angewandte Chemie .59 (4):1450– 1454.Bibcode :2020ACIE...59.1450L .doi :10.1002/anie.201910175 .PMC 7004109 PMID 31725937 . ^a b Gumpper RH, Nichols DE (October 2024). 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Tryptamines
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others Cyclized Ergolines /lysergamides (e.g.,LSD )β-Carbolines andHarmala alkaloidsharmine ,harmaline ,6-methoxyharmalan )Iboga alkaloids18-MAC ,18-MC ,coronaridine ,ibogaine ,ibogamine ,ME-18-MC ,noribogaine ,tabernanthine ,voacangine )Ibogalogs (e.g.,ibogainalog )O -MethylnordehydrobufoteninePartial 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 )Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI) ,NEtPhOH-THPI )Bioisosteres Benzofurans (e.g.,5-MeO-DiBF ,dimemebfe (5-MeO-BFE) ,mebfap )Benzothiophenes (e.g.,3-APBT )Indazolethylamines (e.g.,AL-38022A ,O -methyl-AL-34662Indenylethylamines (e.g.,C-DMT )Isotryptamines (e.g.,6-MeO-isoDMT ,Ro60-0175 )MYCO-005 Quinolinylethylamines (e.g.,mefloquine )
Phenethylamines
Scalines 2C-x 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 BOB ,BOD ,BOH-2C-B )HOT-x HOT-2 ,HOT-7 ,HOT-17 )N -Ethyl-2C-BTWEETIOs 2CD-2-ETO ,2CD-5-ETO ,2CE-5-ETO ,2CE-5iPrO ,2CT2-5-ETO ,ASR-2001 (2CB-5PrO) )3C-x DOx 4C-x Ψ-PEA MDxx FLY 25x-NB (NBOMes) Others 2-TOET 2-TOM 25B-NAcPip 4-HA 5-TOET 5-TOM 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 25D-NM-NDEAOP ,DOB-NDEPA ,DOI-NDEPA ,DOM-NDEPA ,DOTFM-NDEPA ,M-NDEPA ,TMA-2-NDEPA )PMA (4-MA) TMAs TMA-3 ,TMA-4 ,TMA-5 )TOMSO ZDCM-04 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 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 )Natural sources Tryptamines: Acacia spp.Acacia acuminata Acacia confusa Ayahuasca andvinho de Jurema (e.g.,Psychotria viridis (chacruna)Dipolopterys cabrerana (chaliponga, chacruna)Mimosa tenuiflora (Mimosa hostilis ; jurema)Brosimum 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)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.Periglandula ipomoeae Periglandula clandestina
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 ,gepirone ,perospirone ,tandospirone )Bay R 1531 Befiradol 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 Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan 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 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
5-HT1B
Agonists: 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-12066A 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 )PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g.,avitriptan ,donitriptan ,eletriptan ,sumatriptan ,zolmitriptan )TFMPP Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,DMT )Vortioxetine
5-HT1D
Agonists: 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 ,naratriptan ,rizatriptan ,sumatriptan ,zolmitriptan )Tryptamines (e.g.,5-BT ,5-CT ,5-Et-DMT ,5-MT ,5-(nonyloxy)tryptamine ,DMT )
5-HT1E
5-HT1F
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 )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 )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 LY-393558 mCPP Medifoxamine Metitepine (methiothepin) MIN-117 (WF-516) Naftidrofuryl Nantenine Nelotanserin Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Serotonin antagonists and reuptake inhibitors (e.g.,etoperidone ,hydroxynefazodone ,lubazodone ,mepiprazole ,nefazodone ,triazoledione ,trazodone )SR-46349B TGBA01AD Teniloxazine Temanogrel Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )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
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
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 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 Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Vabicaserin WAY-629 WAY-161503 YM-348 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 FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 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
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 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
5-HT4
5-HT5A
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 )
5-HT7
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
DRAs Tooltip Dopamine releasing agents
NRAs Tooltip Norepinephrine releasing agents
SRAs Tooltip Serotonin releasing agents
Others
TAAR1 Tooltip Trace amine-associated receptor 1
TAAR5 Tooltip Trace amine-associated receptor 5
Notes: (1) TAAR1 activity of ligands varies significantly between species. Some agents that are TAAR1 ligands in some species are not in other species. This navbox includes all TAAR1 ligands regardless of species. (2) See the individual pages for references, as well as the
List of trace amines ,
TAAR , and
TAAR1 pages.
See also: Receptor/signaling modulators
Tryptamines 1-Methyl-DMT (1,N ,N -TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N ,N -TMT (2-methyl-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT MET MiPT MPT MsBT N -Benzyltryptamine (T-NB, NB-T)N -DEAOP-NETN -DEAOP-NMTNAT NBoc-DMT NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 Zolmitriptan 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines 2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-NiPT 5-HO-DPT 5-HTP (oxitriptan )5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N ,N -TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N ,N ,O -TMS;O -methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MET 5-MeO-MiPT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O ,N -DMS) 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine;O -methylserotonin) 5-MeO-T-NBOMe 5-MT-NB3OMe 5-NOT 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ;N ,N ,N -TMS) Bufotenin (5-HO-DMT;N ,N -DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)Norbufotenin (5-HO-NMT; NMS) O -Acetylbufotenine (5-AcO-DMT)O -Pivalylbufotenine (5-t -BuCO-DMT)Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT) N -Acetyltryptaminesα-Alkyltryptamines 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O -DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 Cyclized tryptamines 5-MeO-IsoqT Barettin Cyclic 3-OHM Ergolines andlysergamides (e.g.,LSD )Harmala alkaloidsβ-carbolines (e.g.,5-methoxyharmalan ,6-MeO-THH ,6-methoxyharmalan ,9-Me-BC ,β-carboline (norharman) ,fenharmane ,harmaline ,harmalol ,harmane ,harmine ,LY-266,097 ,pinoline ,tetrahydroharmine ,tryptoline )Iboga alkaloidsibogaine ,ibogamine ,noribogaine ,tabernanthine )Ibogalogs (e.g.,catharanthalog ,fluorogainalog ,ibogainalog ,ibogaminalog (DM-506) ,LS-22925 ,noribogainalog ,noribogaminalog ,PHA-57378 ,PNU-22394 ,tabernanthalog )Imidazolylindoles (e.g.,AGH-107 ,AGH-192 ,AH-494 )Metralindole Morpholinylethylindoles (e.g.,mor-T ,5-MeO-mor-T )Partial ergolines and lysergamides (e.g.,NDTDI ,RU-27849 ,RU-28251 ,RU-28306 ,FHATHBIN ,LY-178210 ,Bay R 1531 (LY-197206) ,LY-293284 ,10,11-seco-LSD ,10,11-secoergoline (α,N -Pip-T) ,CT-5252 )Pertines (e.g.,alpertine ,milipertine ,oxypertine ,solypertine )Piperidinylethylindoles (e.g.,pip-T ,5-MeO-pip-T ,indolylethylfentanyl )Pyrrolidinylethylindoles (e.g.,pyr-T ,4-HO-pyr-T ,5-MeO-pyr-T ,4-F-5-MeO-pyr-T )Pyrrolidinylmethylindoles (e.g.,MPMI ,4-HO-MPMI (lucigenol) ,5F-MPMI ,5-MeO-MPMI ,CP-122288 ,CP-135807 ,eletriptan )Tetrahydrocarbazolamines (e.g.,ciclindole ,flucindole ,frovatriptan ,LY-344864 ,ramatroban )Tetrahydropyridinylindoles (e.g.,RS134-49 ,RU-28253 ,NEtPhOH-THPI )Tetrahydropyrroloquinolines (e.g.,bufothionine ,O -methylnordehydrobufotenineYohimbans (e.g.,yohimbine ,rauwolscine ,spegatrine ,corynanthine ,ajmalicine ,reserpine ,deserpidine ,rescinnamine )Isotryptamines Related compounds 2-Azapsilocin 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g.,γ-carboline ,alosetron ,gevotroline ,latrepirdine ,lurosetron ,mebhydrolin ,tiflucarbine )Amedalin Benzindopyrine Benzofurans (e.g.,3-APB ,5-MeO-DiBF ,BPAP ,3-F-BPAP ,dimemebfe ,mebfap ,oxa-noribogaine )Benzothiophenes (e.g.,3-APBT )Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g.,HT ,DMHT )I-32 IAL IN-399 Indazolethylamines (e.g.,AL-34662 ,AL-38022A ,O -methyl-AL-34662VU6067416 ,YM-348 )Indenylethylamines (e.g.,C-DMT )Indolizinylethylamines (e.g.,TACT908 (2ZEDMA) ,1ZP2MA ,1Z2MAP1O )Indolylaminopropanes (e.g.,1-API ,2-API ,4-API ,5-API (5-IT; PAL-571) ,6-API (6-IT) ,7-API )Iprindole Masupirdine Medmain Molindone Non-tryptaminetriptans (e.g.,avitriptan ,LY-334370 ,naratriptan ) Ondansetron Oxazinopyridoindoles (e.g.,IHCH-8134 )Phenethylamines (e.g.,phenethylamine ,amphetamine )Piperidinylbenzimidazolines (e.g.,benperidol ,timiperone )Piperazinylbenzisothiazoles (e.g.,lurasidone ,perospirone ,tiospirone ,ziprasidone )Piperidinylbenzisoxazoles (e.g.,iloperidone ,milsaperidone ,ocaperidone ,paliperidone ,risperidone )Piperidinylindoles (e.g.,BRL-54443 ,LY-334370 ,naratriptan ,sertindole ,SN-22 )Pirlindole Pyridinylbenzimidazoles (e.g.,droperidol )Pyridinylindoles (e.g.,tepirindole )Pyridopyrroloquinoxalines (e.g.,IHCH-7113 ,IHCH-7079 ,IHCH-7086 ,lumateperone ,deulumateperone ,ITI-1549 )Pyrrolylethylamines (e.g.,2-pyrrolylethylamine (NEA) ,3-pyrrolylethylamine (3-NEA) ,3-pyrrolylpropylamine )Pyrrolopyridinylethylamines (e.g.,WAY-208466 )Quinolinylethylamines (e.g.,mefloquine )Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g.,EMD-386088 ,LY-367265 ,RU-24,969 )Tetrahydropyridinylpyrrolopyridines (e.g.,(R )-69 (3IQ) ,(R )-70 ,CP-94253 )Tetrindole Tipindole Zilpaterol (RU-42173)
