Pharmaceutical compound
Methallylescaline (MAL ), also known as4-methylallyloxy-3,5-dimethoxyphenethylamine , is apsychedelic drug of thephenethylamine andscaline families related tomescaline .[ 1] [ 3] orally .[ 1] [ 3]
The drug acts as aserotonin 5-HT2 receptor agonist , including of the serotonin5-HT2A receptor .[ 4] [ 5] structurally related to mescaline and to other scalines likeescaline andallylescaline .[ 5]
Methallylescaline was first described byAlexander Shulgin in his 1991 bookPiHKAL Phenethylamines I Have Known and Loved ).[ 3] [ 1] designer drug by 2013.[ 6] [ 7] [ 8]
In his bookPiHKAL Phenethylamines I Have Known and Loved ),Alexander Shulgin lists the dose range of methallylescaline as 40 to 65 mg and itsduration as 12 to 16 hours.[ 1] [ 9] [ 10] [ 1] [ 9] [ 10] dose–response curve , such that a small increase in dose can result in an unexpectedly large increase in effects.[ 11] [ 12] times thepotency of mescaline, which has a much higher listed dose range of 200 to 400 mg.[ 9] [ 10] [ 1] onset is within 1 hour and peak effects occur within 2 hours.[ 1]
Shulgin has described methallylescaline as a "mixed bag" in terms ofexperience reports .[ 1] closed-eye visuals , "visual theater",open-eye visuals includingvisual distortions , visual depth and movement effects,kaleidoscopic neon colors ,watercolors ,fantasy ,mental imagery ,feelings of unreality , easy childhoodmemory recall , self-connectedness,eroticism , initialdiscomfort ,overload , feeling overwhelmed, shades of possibleamnesia , loss of contact, extremerestlessness ,trouble sleeping , and enhanceddreams .[ 1] body effects ,diuretic effects, and slightlyreduced heart rate .[ 1] [ 1] [ 1] visual imagery than otherscalines likecyclopropylmescaline andallylescaline .[ 1]
Others have noted that methallylescaline has strongvisual effects, as well as prominentnausea ,vomiting , andbody load , including feeling "overstimulated .[ 11] mescaline .[ 11]
Methallylescaline activities Target Affinity (Ki , nM) 5-HT1A 5,100–>10,000 5-HT1B >10,000 5-HT1D 2,754 5-HT1E >10,000 5-HT1F ND 5-HT2A 72–955 (Ki )EC50 Tooltip half-maximal effective concentration )Emax Tooltip maximal efficacy ) 5-HT2B 110 (Ki )EC50 ) Emax ) 5-HT2C 5.1–520 (Ki )EC50 ) Emax ) 5-HT3 >10,000 5-HT4 ND 5-HT5A >10,000 5-HT6 >10,000 5-HT7 >10,000 α1A –α1D >10,000 α2A 550–1,500 α2B ,α2C >10,000 β1 –β3 >10,000 D1 –D5 >10,000 H1 –H4 >10,000 M1 –M5 >10,000 TAAR1 1,000 (Ki ) (rat)i ) (mouse)EC50 ) (rodent) EC50 ) (human) I1 ND σ1 >10,000 σ2 5,248 SERT Tooltip Serotonin transporter >10,000 (Ki )ND ( IC50 Tooltip half-maximal inhibitory concentration ) NET Tooltip Norepinephrine transporter >10,000 (Ki )ND ( IC50 ) DAT Tooltip Dopamine transporter >10,000 (Ki )ND ( IC50 ) Notes: The smaller the value, the more avidly the drug binds to the site. All proteins are human unless otherwise specified.Refs: [ 4] [ 5] [ 13] [ 14]
Methallylescaline acts as apotent agonist of theserotonin 5-HT2A ,5-HT2B , and5-HT2C receptors , among other actions.[ 4] [ 5] [ 13] [ 14] 2B receptor agonist in one study,[ 5] [ 4] receptor interactions of methallylescaline have been studied.[ 4]
The drug produces thehead-twitch response (HTR), a behavioral proxy ofpsychedelic effects, in rodents.[ 14] selective serotonin 5-HT2C receptorantagonist SB-242084 but not by the serotonin 5-HT2A receptor antagonistketanserin .[ 14]
In addition to its psychedelic-like effects, methallylescaline produceshyperlocomotion (astimulant -like effect),conditioned place preference (CPP; arewarding effect), and modestself-administration (areinforcing effect ) in rodents, among other effects.[ 15]
Methallylescaline, along withBOD andDOI , has been reported to produceserotonergic neurotoxicity in rodents at high doses given repeatedly.[ 14] preclinical research .[ 16] [ 17] [ 18]
Themetabolism of methallylescaline has been studied.[ 19] [ 20]
Methallylescaline, also known as 4-methylallyloxy-3,5-dimethoxyphenethylamine, is asubstituted phenethylamine andscaline .[ 1] [ 3] [ 9] [ 10] synthetic derivative ofmescaline (3,4,5-trimethoxyphenethylamine) with ameth allyl oxy group instead ofmethoxy group at the 4 position.[ 1] [ 3] [ 9] [ 10]
Thechemical synthesis of methallylescaline has been described.[ 1]
Analogues of methallylescaline includemescaline ,escaline ,allylescaline , andcyclopropylmescaline , among others.[ 1] [ 3] [ 9] [ 10] [ 21] 3C-MAL ,2C-T-3 ,2C-O-3 , andMMALM .[ 1] [ 3] [ 21]
Methallylescaline was first described in the literature byAlexander Shulgin in his 1991 bookPiHKAL Phenethylamines I Have Known and Loved ).[ 3] [ 1] [ 9] hallucinogenic effects were discovered by him in 1982.[ 22] [ 10] PiHKAL , but not in Shulgin's 2011 bookThe Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds [ 3] designer drug inEurope by 2013.[ 6] [ 7] [ 8] pharmacology was described byMatthias Liechti andDaniel Trachsel and colleagues in 2021.[ 5] [ 11]
Society and culture [ edit ] Alexander Shulgin described the name ofmethallylescaline (MAL ) as "completely unsound".[ 1] meth allyl group withescaline .[ 1] mescaline with a 2-propene group attached to themethyl of themethoxy group at the 4 position.[ 1] [ 1] 4-methylallyldesmethylmescaline (MAD ).[ 1] MAD to be disagreeable and ultimately preferredMAL .[ 1]
Methallylescaline is not acontrolled substance inCanada as of 2025.[ 23]
Methallylescaline is illegal in Sweden as of 26 January 2016.[ 24]
Methallylescaline is not explicitly scheduled under theControlled Substances Act .[ 25] mescaline , it could potentially be prosecuted under theFederal Analogue Act if sold for human consumption.
^a b c d e f g h i j k l m n o p q r s t u v w x y z aa ab "Methallylescaline" .PiHKAL .^ 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 h i Shulgin A, Manning T, Daley PF (2011)."#91. Mescaline" .The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds ISBN 978-0-9630096-3-0 OCLC 709667010 .[...] Homologues and Analogues [...] Name: MAL. CAS #: [207740-41-8]. Ref: (30,31). [...] (30) Synthesis (Shulgin and Shulgin, 1991). (31) Orally active in humans at 40-65 mg; duration 12-16 hours (Shulgin and Shulgin, 1991). ^a b c d e Jain MK, Gumpper RH, Slocum ST, Schmitz GP, Madsen JS, Tummino TA, et al. (October 2025). "The polypharmacology of psychedelics reveals multiple targets for potential therapeutics".Neuron .113 (19): 3129–3142.e9.doi :10.1016/j.neuron.2025.06.012 .PMID 40683247 . ^a b c d e f Kolaczynska KE, Luethi D, Trachsel D, Hoener MC, Liechti ME (2021)."Receptor Interaction Profiles of 4-Alkoxy-3,5-Dimethoxy-Phenethylamines (Mescaline Derivatives) and Related Amphetamines" .Frontiers in Pharmacology .12 794254.doi :10.3389/fphar.2021.794254 PMC 8865417 PMID 35222010 . ^a b King LA (2014). "New phenethylamines in Europe".Drug Testing and Analysis .6 (7– 8):808– 818.doi :10.1002/dta.1570 .PMID 24574327 . ^a b "EMCDDA–Europol 2013 Annual Report on the implementation of Council Decision 2005/387/JHA" .www.euda.europa.eu . 2 July 2024. Retrieved9 October 2025 .^a b Coelho Neto J (July 2015). "Rapid detection of NBOME's and other NPS on blotter papers by direct ATR-FTIR spectrometry".Forensic Science International .252 :87– 92.doi :10.1016/j.forsciint.2015.04.025 .PMID 25965305 . ^a b c d e f g Jacob P, Shulgin AT (1994)."Structure-activity relationships of the classic hallucinogens and their analogs" (PDF) .NIDA Research Monograph .146 :74– 91.PMID 8742795 . Archived fromthe original (PDF) on August 5, 2023. ^a b c d e f g Shulgin AT (2003)."Basic Pharmacology and Effects" . In Laing RR (ed.).Hallucinogens: A Forensic Drug Handbook 67– 137.ISBN 978-0-12-433951-4 . Retrieved1 February 2025 . ^a b c d "Weekly Briefing Issue 181" .National Drug Early Warning System (NDEWS) . 10 May 2024. Retrieved5 January 2026 .^ "SATA Early Warning System of the Americas" . Archived fromthe original on 2025-06-19.[United States National Drug Early Warning System (NDEWS)] issued an alert about the substance methallylescaline, a synthetic analog of mescaline and a 5-HT receptor agonist. Discussions in online forums often warn of methallylescaline's steep dose-response curve, where small dosage changes can dramatically alter the experience. Some of the effects discussed are nausea and "body load". Those who experiment with polysubstance use, combine methallylescaline with other substances, such as etizolam. ^a b Wang S, Zhu A, Paudel S, Jang CG, Lee YS, Kim KM (March 2023)."Structure-Activity Relationship and Evaluation of Phenethylamine and Tryptamine Derivatives for Affinity towards 5-Hydroxytryptamine Type 2A Receptor" .Biomolecules & Therapeutics .31 (2):176– 182.doi :10.4062/biomolther.2022.096 .PMC 9970836 PMID 36224112 . ^a b c d e Custodio RJ, Ortiz DM, Lee HJ, Sayson LV, Kim M, Lee YS, et al. (July 2025). "Serotonin 2C receptors are also important in head-twitch responses in male mice".Psychopharmacology .242 (7):1585– 1605.doi :10.1007/s00213-023-06482-9 .PMID 37882810 . ^ Custodio RJ, Sayson LV, Botanas CJ, Abiero A, Kim M, Lee HJ, et al. (September 2020). "Two newly-emerging substituted phenethylamines MAL and BOD induce differential psychopharmacological effects in rodents".Journal of Psychopharmacology .34 (9):1056– 1067.doi :10.1177/0269881120936458 .PMID 32648801 . ^ Rudin D, Liechti ME, Luethi D (September 2021). "Molecular and clinical aspects of potential neurotoxicity induced by new psychoactive stimulants and psychedelics".Experimental Neurology .343 113778.doi :10.1016/j.expneurol.2021.113778 .PMID 34090893 . ^ Capela JP, Ruscher K, Lautenschlager M, Freyer D, Dirnagl U, Gaio AR, et al. (2006). "Ecstasy-induced cell death in cortical neuronal cultures is serotonin 2A-receptor-dependent and potentiated under hyperthermia".Neuroscience .139 (3):1069– 1081.doi :10.1016/j.neuroscience.2006.01.007 .PMID 16504407 . ^ Capela JP, Carmo H, Remião F, Bastos ML, Meisel A, Carvalho F (June 2009). "Molecular and cellular mechanisms of ecstasy-induced neurotoxicity: an overview".Molecular Neurobiology .39 (3):210– 271.doi :10.1007/s12035-009-8064-1 .PMID 19373443 .To further corroborate the fact that MDMA agonistic properties at the 5-HT2A receptor could produce neuronal death, DOI, a prototypical agonist of that receptor was added to cortical neurons [289]. DOI (10 to 100 μM for 24 or 48 h) also induced a dose- and time-dependent apoptotic cortical neuronal apoptosis, which was attenuated by ketanserin and R-96544 [289]. Ketanserin and R-96544 are competitive selective 5-HT2A receptor antagonists and only attenuated MDMA-induced cortical neurodegeneration. However, an antibody raised against the 5-HT2A-receptor, an "irreversible" non-competitive 5-HT2A receptor blocker, prevented almost completely MDMA- and DOI-induced cortical neurotoxicity [289, 290]. Neuronal apoptosis mediated by MDMA is accompanied by activation of caspase 3, which could be blocked by the antibody raised against the 5-HT2A receptor [290]. Therefore, it is likely that DOI- and MDMA-induced neuronal apoptosis arises from direct stimulation of the 5-HT2A receptor [289, 290]. ^ Tang Y, Xu L, Guo Z, Zhao J, Xiao Y, Xiang P, et al. (June 2025). "Metabolism study of two phenethylamine - derived new psychoactive substances using in silico, in vivo, and in vitro approaches".Archives of Toxicology .99 (6):2367– 2378.doi :10.1007/s00204-025-04010-6 .PMID 40064698 . ^ Kim S, Kim JH, Kim DK, Lee J, In S, Lee HS (30 September 2018). "In vitro Metabolism of Methallylescaline in Human Hepatocytes Using Liquid Chromatography-High Resolution Mass Spectrometry".Mass Spectrometry Letters .9 (3):86– 90.doi :10.5478/MSL.2018.9.3.86 . ^a b Trachsel D, Lehmann D, Enzensperger C (2013).Phenethylamine: von der Struktur zur Funktion Phenethylamines: From Structure to Function ]. Nachtschatten-Science (in German) (1 ed.). Solothurn: Nachtschatten-Verlag.ISBN 978-3-03788-700-4 OCLC 858805226 . Archived fromthe original on 21 August 2025. ^ Alexander Shulgin (1981),Pharmacology Lab Notes #4 (PDF) ^ "Controlled Drugs and Substances Act" .Department of Justice Canada . Retrieved19 January 2026 .^ "31 nya ämnen kan klassas som narkotika eller hälsofarlig vara" (in Swedish). Folkhälsomyndigheten. November 2015.^ Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) (PDF) ,United States : U.S.Department of Justice :Drug Enforcement Administration (DEA): Diversion Control Division, January 2026
Tryptamines
No ring subs. 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Other ring subs. α-Alkyltryptamines Others Cyclized Ergolines /lysergamides (e.g.,LSD )Ibogalogs (e.g.,ibogainalog ,tabernanthalog )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 ,MSP-2020 )Tetrahydropyridinylindoles (e.g.,RU-28253 (5-MeO-THPI) ,NEtPhOH-THPI )Bioisosteres Benzofurans (e.g.,5-MeO-DiBF (1-oxa-5-MeO-DiPT) ,dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) ,mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) )Benzothiophenes (e.g.,3-APBT (1-thia-AMT) )Indazolethylamines (e.g.,AL-38022A ,O -methyl-AL-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 ,BOHB )HOT-x HOT-2 ,HOT-7 ,HOT-17 )N -Ethyl-2C-BTWEETIOs 2CB-2-EtO ,2CD-2-EtO ,2CD-5-EtO ,2CE-5-EtO ,2CE-5iPrO ,2CT2-5-EtO ,ASR-2001 (2CB-5-PrO) )3C-x DOx 4C-x Ψ-PEA MDxx FLY 25x-NB (NBOMes) Others 25B-NAcPip 2-DM-DOM 4-HA 5-DM-DOM Benzofurans (e.g.,5-APB ,5-APDB ,6-APB ,6-APDB ,F ,F-2 ,F-22 )Benzothiophenes (e.g.,5-APBT ,6-APBT )CT-5172 DMAs (e.g.,2,4-DMA ,3,4-DMA )Fenfluramine MMA (3-MeO-4-MA) Norfenfluramine PEA-NDEPAs 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 TMA-3 ,TMA-4 ,TMA-5 )ZDCM-04 (DOC-fenethylline) 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 (F-11440) ,gepirone ,perospirone ,tandospirone )Bay R 1531 Befiradol (NLX-112; F-13640) BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g.,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,lisuride ,LSD ,methylergometrine (methylergonovine) ,methysergide ,pergolide )F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 (NLX-101) Flesinoxan Flibanserin Flumexadol Hypidone Lesopitron LY-293284 LY-301317 mCPP Naluzotan NBUMP NLX-204 NLX-266 Osemozotan (MKC-242) Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g.,5-CT ,5-MeO-DMT ,5-MT ,bufotenin ,DMT ,indorenate ,N-Me-5-HT ,psilocin ,psilocybin )TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine 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: Alniditan Anpirtoline AZ10419369 Benzofurans (e.g.,5-MAPB ,6-MAPB ,BK-5-MAPB ,BK-6-MAPB )Benzothiophenes (e.g.,5-MAPBT ,6-MAPBT ,BK-5-MAPBT )CGS-12066 (CGS-12066A, CGS-12066B) CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine ,dihydroergotamine ,ergotamine ,methylergometrine (methylergonovine) ,methysergide ,pergolide )mCPP Methylenedioxyphenethylamines (e.g.,MDMA ,methylone )PGI-7043 PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g.,avitriptan ,donitriptan ,eletriptan ,IS-159 ,sumatriptan ,zolmitriptan )TFMPP Tryptamines (e.g.,5-BT ,5-CT ,5-MT ,DMT )Vortioxetine
5-HT1D
Agonists: Alniditan CGS-12066 (CGS-12066A, CGS-12066B) CP-122288 CP-135807 CP-286601 Ergolines (e.g.,bromocriptine ,cabergoline ,dihydroergotamine ,ergotamine ,LSD ,methysergide )GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g.,almotriptan ,avitriptan ,donitriptan ,eletriptan ,frovatriptan ,IS-159 ,naratriptan ,rizatriptan ,sumatriptan ,zolmitriptan )Tryptamines (e.g.,5-BT ,5-CT ,5-Et-DMT ,5-MT ,5-(nonyloxy)tryptamine ,DMT )
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 )Butanserin Chlorprothixene Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g.,amesergide ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Landipirdine LY03017 LY-393558 mCPP Medifoxamine Metitepine (methiothepin) Metrenperone MIN-117 (WF-516) MT-1207 Naftidrofuryl Nantenine Nelotanserin NH130 Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin Roluperidone S-14671 Sarpogrelate Seganserin Serotonin antagonists and reuptake inhibitors (e.g.,etoperidone ,hydroxynefazodone ,lubazodone ,mepiprazole ,nefazodone ,triazoledione ,trazodone )Temanogrel Teniloxazine Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )TGBA01AD Trelanserin Tricyclic antidepressants (e.g.,amitriptyline )Typical antipsychotics (e.g.,chlorpromazine ,fluphenazine ,haloperidol ,loxapine ,perphenazine ,pimozide ,pipamperone ,prochlorperazine ,setoperone ,spiperone ,spiramide ,thioridazine ,thiothixene ,trifluoperazine )Volinanserin Xylamidine Yohimbine
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 ATHX-105 Centhaquine CP-809101 Dimemebfe DOx (e.g.,DOB ,DOC ,DOI ,DOM )Ergolines (e.g.,ALD-52 ,cabergoline ,dihydroergotamine ,ergine (LSA) ,ergotamine ,lisuride ,LA-SS-Az ,LSB ,LSD ,LSD-Pip ,LSH ,LSP ,pergolide )Flumexadol Lorcaserin MDxx (e.g.,MDA (tenamfetamine) ,MDMA (midomafetamine) ,MDOH ,MMDA )MK-212 ORG-12962 ORG-37684 Oxaflozane PHA-57378 Phenethylamines (e.g.,lophophine ,mescaline )Piperazines (e.g.,aripiprazole ,BZP ,mCPP ,quipazine ,TFMPP )PNU-22394 PNU-181731 PRX-00933 (BVT-933; GW-876167) Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g.,5-BT ,5-CT ,bufotenin ,DET ,DiPT ,DMT ,DPT ,psilocin ,psilocybin ,tryptamine )Vabicaserin VR-1065 WAY-629 WAY-161503 YM-348 Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g.,asenapine ,clorotepine ,clozapine ,fluperlapine ,iloperidone ,melperone ,olanzapine ,paliperidone ,quetiapine ,risperidone ,sertindole ,ziprasidone ,zotepine )Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine Eltoprazine Ergolines (e.g.,amesergide ,bromocriptine ,LY-53857 ,LY-215840 ,mesulergine ,metergoline ,methysergide ,sergolexole )Etoperidone Fluoxetine FR260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) LY03017 Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SB-247853 SDZ SER-082 Seganserin Tedatioxetine Tetracyclic antidepressants (e.g.,amoxapine ,aptazapine ,esmirtazapine ,maprotiline ,mianserin ,mirtazapine )TIK-301 Tramadol Trazodone Tricyclic antidepressants (e.g.,amitriptyline ,nortriptyline )Typical antipsychotics (e.g.,chlorpromazine ,loxapine ,pimozide ,pipamperone ,thioridazine )Xylamidine
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
Phenethylamines Amphetamines Phentermines Cathinones Phenylisobutylamines (and further-extended) Catecholamines (and close relatives) Cyclized
Phenylalkylpyrrolidines 2-Benzylpiperidines (phenidates ) Phenylmorpholines (phenmetrazines) Phenyloxazolamines (aminorexes) Isoquinolines andtetrahydroisoquinolines 2-Aminoindanes 2-Aminotetralins Others / unsorted 1-Aminomethylindanes (e.g.,2CB-Ind ,AMMI ,bromojimscaline ,jimscaline )2-ADN 2-Benzhydrylpyrrolidine 2C-B-5-hemiFLY-α6 (BNAP) 2C-B-PYR 2CBecca 2CB7 2CJP 2CLisaB 2CLisaH 3-Benzazepines (e.g.,fenoldopam ,lorcaserin ,7-chlorolorcaserin ,SCHEMBL5334361 )3-Benzhydrylmorpholine 3-Phenylpiperidines (e.g.,3-phenylpiperidine ,3-PPP ,OSU-6162 (PNU-96391) ,LPH-5 ,LPH-48 ,2C-B-3PIP ,2C-B-3PIP-NBOMe ,2C-B-3PIP-POMe ,Z3517967757 (Z7757) )6-AB AL-1095 Aminochromes (e.g.,adrenochrome ,adrenolutin )Benzocyclobutenes (e.g.,2CBCB-NBOMe ,bromotomscaline ,S33005 ,TCB-2 ,tomscaline )Benzoxepins (e.g.,BBOX ,IBOX ,TFMBOX )Butyltolylquinuclidine Camfetamine Cypenamine (trans -2-phenylcyclopentylamine) Diphenidine Diphenylprolinol Ergolines (e.g.,LSD )Fencamfamin GYKI-52895 HDMP-29 Ivabradine Methoxphenidine Methylmorphenate Milnacipran MT-45 2-Naphthylamine Org 6582 Partial ergolines (e.g.,NDTDI ,RU-27849 ,DEIMDHPCA ,DEMPDHPCA ,DEMPDHPCA-2C-D ,RU-27251 )PF-592,379 Phenylcyclopropylamines (e.g.,DMCPA ,TMT ,tranylcypromine )Phenylpiracetams (e.g.,phenylpiracetam ,MRZ-9547 ,RGPU-95 )Pyridopyrroloquinoxalines (e.g.,lumateperone ,deulumateperone ,IHCH-7079 ,IHCH-7086 ,IHCH-7113 ,ITI-1549 )Tetrahydrobenzopyranylamines (e.g.,CT-5126 )Tolazoline Tricyclics (e.g.,AMDA ,AMDH ,benzoctamine ,dizocilpine ,SpAMDA )ZC-B
Related compounds 2-Furylethylamine 2-Pyrrolylethylamine 3-Pyrrolylethylamine 3-Pyrrolylpropylamine 2-Tetrahydrofurylethylamine 4-Benzylpiperidine 7-AB Alkylamines (e.g.,1,3-DMBA Tooltip 1,3-dimethylbutylamine ,1,4-DMAA Tooltip 1,4-dimethylamylamine ,heptaminol ,iproheptine ,isometheptene ,methylhexanamine/ 1,3-DMAA ,octodrine ,oenethyl ,tuaminoheptane )Benzylamines (e.g.,benzylamine ,α-methylbenzylamine ,MDM1EA ,ALPHA ,M-ALPHA ,pargyline )Benzylpiperazines (e.g.,benzylpiperazine ,MDBZP ,fipexide )Cyclohexylaminopropanes (e.g.,propylhexedrine ,norpropylhexedrine )Cyclopentylaminopropanes (e.g.,isocyclamine ,cyclopentamine )Phenoxyethylamines (e.g.,3,4,5-trimethoxyphenoxyethylamine ,CT-4719 ,ORG-37684 )Phenylalkenylamines (e.g.,phenylbutenamine )Phenylalkynylamines (e.g.,phenylbutynamine )Phenylpiperazines (e.g.,1-phenylpiperazine ,mCPP Tooltip meta-chlorophenylpiperazine ,TFMPP Tooltip trifluoromethylphenylpiperazine ,oMPP Tooltip ortho-methylphenylpiperazine ,pFPP Tooltip para-fluorophenylpiperazine ,pMeOPP Tooltip para-methoxyphenylpiperazine )Phenylpropylamines (e.g.,phenylpropylamine ,homo-MDA ,homo-MDMA )Thienylaminopropanes (thiopropamines) (e.g.,thiopropamine ,methiopropamine ,thiothinone )Phenylbutylamines (e.g.,4-Phenylbutylamine ,4-Phenylpentan-1-amine )
