Ethylbenzodioxolylbutanamine

From Wikipedia, the free encyclopedia

(Redirected from Ethyl-J)

Ethylbenzodioxolylbutanamine

IUPAC name	(1-Benzo[1,3]dioxol-5-ylmethyl-propyl)-ethyl-amine
Other names	3,4-Methenedioxy-α,N-diethyl-phenethylamine
Identifiers
CAS number	[167394-39-0]
SMILES	`C1=C2C(=CC=C1CC(CC)NCC)OCO2`
Properties
Molecular formula	C₁₃H₁₉NO₂
Molar mass	221.30 g/mol
Melting point	176–177 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Ethylbenzodioxolylbutanamine (EBDB; Ethyl-J) is a lesser-known entactogen, stimulant, and psychedelic. It is the N-ethyl analogue of benzodioxylbutanamine (BDB; "J"), and also the α-ethyl analogue of methylenedioxyethylamphetamine (MDEA; "Eve"). EBDB was first synthesized by Alexander Shulgin. In his book PiHKAL (Phenethylamines i Have Known And Loved)), the minimum dosage consumed was 90 mg, and the duration is unknown. MBDB produced few to no effects at the dosage range tested in PiHKAL, but at higher doses of several hundred milligrams it produces euphoric effects similar to those of methylbenzodioxylbutanamine (MBDB; "Eden", "Methyl-J"), although milder and shorter lasting. Very little data exists about the pharmacological properties, metabolism, and toxicity of EBDB.

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.

[edit] See Also

Benzodioxolylbutanamine (BDB; J)
Methylbenzodioxolylbutanamine (MBDB; Methyl-J; "Eden")

[edit] References

[edit] External links

Entactogens

Aminoindanes

Methylenedioxy-substituted: MDAI • MDMAI; Others: 5-IAI • MMAI

Phenethylamines

Methylenedioxy-substituted: MDPEA

Alpha-Methylated
(Amphetamines)

4-substituted: 4-FA • 4-FMA • 4-MTA • PMA • PMEA • PMMA; Methylenedioxy-substituted: 2-Me-MDA • 5-Me-MDA • MDA • MDEA • MDMA • MDOH • MMDA

Beta-Ketones
(Cathinones)

4-substituted: 4-FMC • 4-MMC; Methylenedioxy-substituted: bk-MDEA • bk-MDMA

Alpha-Ethylated

4-substituted: α-Et-DOM; Methylenedioxy-substituted: BDB • EBDB • MBDB

Beta-Ketones

Methylenedioxy-substituted: bk-MBDB • bk-DMBDB

Tryptamines

5-MeO-DALT • AET • AMT

Others

5-APDB • IAP

v • d • e Stimulants

Adamantanes	Adaphenoxate • Adapromine • Bromantane • Chlodantane • Gludantane • Memantine • Midantane

Alkylamines	Cyclopentamine • Geranamine • Heptaminol • Isometheptene • Octodrine • Propylhexedrine • Tuaminoheptane (Tuamine)

Cholinergics	ABT-089 • ABT-418 • Anabasine • Arecoline • Cotinine • Cytisine • Dianicline • Epibatidine • Epiboxidine • GTS-21 • Ispronicline • Nicotine • Rivanicline • TC-5619 • Tebanicline • Varenicline

Convulsants	Bicuculline • DMCM • Flurothyl • Gabazine • Pentetrazol • Picrotoxin • Strychnine • Thujone

Eugeroics	Adrafinil • Armodafinil • Carphedon • Modafinil

Phenethylamines	1-Phenyl-2-methylaminobutan-1-one • 2-Phenyl-3-aminobutane • 2-Phenyl-3-methylaminobutane • 4-Bromomethcathinone • 4-FA • 4-Fluoromethamphetamine • 4-Fluoromethcathinone • 4-Ethylamphetamine • 4-Hydroxyephedrine (Oxilofrine) • 4-Methylamphetamine • 4-Methylmethamphetamine • Mephedrone (4-MMC) • 4-MTA • Alfetamine • Alpha-ethyl-phenethylamine • Amfepentorex • Amphechloral • Amphetamine (Dextroamphetamine) • Amphetaminil • Benfluorex • Benzphetamine • β-Methylphenethylamine • Bupropion • Cathinone • Chlorphentermine • Clenbuterol • Clobenzorex • Clortermine • Diethylcathinone (Diethylpropion) • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone • Ephedrine • Epinephrine • Ethcathinone • Ethylamphetamine • Fenbutrazate • Fencamine • Fenethylline • Fenfluramine • Fenproporex • Fludorex • Furfenorex • Levomethamphetamine • MDMA (Ecstasy) • Mefenorex • Mephentermine • Methamphetamine • Methcathinone • Methoxyphedrine • Methoxyphenamine • Methylone • Norfenefrine • Octopamine • Ortetamine • Parahydroxyamphetamine • PCA • PIA • PMA • PMEA • PMMA • PPAP • Phendimetrazine • Phenmetrazine • Phenpentermine • Phenpromethamine • Phentermine • Phenylephrine • Phenylpropanolamine • Propylamphetamine • Pseudoephedrine • Selegiline • Synephrine • Tiflorex • Xylopropamine

Phenylaminooxazoles	4-Methylaminorex • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone

Piperazines	2C-B-BZP • BZP • DBL-583 • GBR-12783 • GBR-12935 • GBR-13069 • GBR-13098 • GBR-13119 • MeOPP • MBZP • Vanoxerine

Piperidines	2-Benzylpiperidine • 4-Benzylpiperidine • BTCP • Desoxypipradrol • Diphemethoxidine • Ethylphenidate • HDMP-28 • (-)-Methyl-1-methyl-4β-(2-naphthyl)piperidine-3β-carboxylate • Methylphenidate (Dexmethylphenidate) • Nocaine • Phacetoperane (Levofacetoperane) • Pipradrol (Meretran)

Pyrrolidinophenones	α-PPP • MDPPP • MDPV • MPBP • MPHP • MPPP • MOPPP • Pyrovalerone

Tropanes	3α-Bis-(4-fluorophenyl)methoxytropane • 3α-((4-Chlorophenyl)phenylmethoxy)tropane • 3-Pseudotropyl-4-fluorobenzoate • Altropane (IACFT) • Brasofensine • CFT (WIN 35,428) • β-CIT (RTI-55) • Cocaethylene • Cocaine • β-CPPIT • Dichloropane (RTI-111) • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (FPCIT) • Norcocaine • PIT • PTT • RTI-31 • RTI-32 • RTI-51 • RTI-112 • RTI-113 • RTI-121 (IPCIT) • RTI-126 • RTI-150 • RTI-171 • RTI-177 • RTI-336 • RTI-371 • RTI-386 • Tesofensine • Troparil (β-CPT, WIN 35,065-2) • Tropoxane • WF-23 • WF-33 • WF-60

Xanthines	Aminophylline • Caffeine • Dimethazan • Paraxanthine • Theobromine • Theophylline

Others	1-(Thiophen-2-yl)-2-aminopropane • 2-Aminoindane • 5-(2-Aminopropyl)indole • Amfonelic acid • Amineptine • Amiphenazole • Bemegride • Benzydamine • BPAP • BTQ • BTS 74,398 • Clofenciclan • Cropropamide • Crotetamide • Cypenamine • Cyprodenate • Diclofensine • Dimethocaine • Diphenylprolinol • Etamivan • Fencamfamine • Feprosidnine • Gilutensin • GYKI-52895 • Hexacyclonate • Indanorex • Indanylaminopropane • Indatraline • Lefetamine • Leptacline • LR-5182 • Manifaxine • Mazindol • Meclofexonate • Mefexamide • Mesocarb • Naphthylisopropylamine • Nikethamide • Nomifensine • O-2172 • Phthalimidopropiophenone • Prolintane • Sibutramine • Tametraline • UH-232 • Yohimbine • Zylofuramine

See also Sympathomimetic amines

Adrenergics (under construction)

Receptor
Ligands

α1	Agonists: Antagonists: Alfuzosin • Arotinolol • Carvedilol • Doxazosin • Indoramin • Labetalol • Moxisylyte • Nantenine • Phentolamine • Phenoxybenzamine • Prazosin • Silodosin • Tamsulosin • Terazosin • Tolazoline • Trimazosin • Urapidil

α2	Agonists: Nonselective; Clonidine • Dexmedetomidine • Lofexidine • Tizanidine • Xylazine; α_2A selective; Guanfacine • Octopamine; α_2C selective; (R)-3-Nitrobiphenyline Antagonists: Nonselective; Atipamezole • Efaroxan • Idazoxan • Mianserin • Mirtazapine • NAN-190 • Phentolamine • Phenoxybenzamine • Rauwolscine • SB-269,970 • Tolazoline • Yohimbine; α_2A selective; BRL-44408; α_2C selective; Spiroxatrine

β1	Agonists: Antagonists: Acebutolol • Alprenolol • Amosulalol • Arotinolol • Atenolol • Bupranolol • Carvedilol • Celiprolol • Betaxolol • Bisoprolol • Dichloroisoprenaline • Esmolol • Labetalol • Metipranolol • Metoprolol • Nadolol • Nebivolol • Oxprenolol • Penbutolol • Pindolol • Practolol • Pronethalol • Propranolol • Sotalol • Tertatolol • Timolol • Tilisolol

β2	Agonists: Antagonists: Alprenolol • Amosulalol • Arotinolol • Bupranolol • Butaxamine • Carvedilol • Dichloroisoprenaline • ICI 118551 • Labetalol • Metipranolol • Nadolol • Oxprenolol • Penbutolol • Pindolol • Pronethalol • Propranolol • Sotalol • Tertatolol • Timolol • Tilisolol

β3	Agonists: Amibegron • Arotinolol • Labetalol • Solabegron Antagonists: Carvedilol • SR 59230A

Reuptake
Inhibitors

Plasmalemmal

NET Inhibitors	Norepinephrine Reuptake Inhibitors: Atomoxetine • Ciclazindol • Mazindol • Nisoxetine • Reboxetine • Tandamine • Viloxazine; Norepinephrine-Dopamine Reuptake Inhibitors: Amineptine • Bupropion • Methylphenidate • Nomifensine • Radafaxine; Serotonin-Norepinephrine Reuptake Inhibitors: Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Sibutramine • Tramadol • Venlafaxine; Serotonin-Norepinephrine-Dopamine Reuptake Inhibitors: Brasofensine • Diclofensine • DOV 102,677 • DOV 21,947 • DOV 216,303 • NS2359 • SEP-225289 • SEP-227162 • Tesofensine; Tricyclic Antidepressants: Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants: Amoxapine • Maprotiline • Mianserin • Oxaprotiline; Others: Cocaine • Nefazodone • Ziprasidone

TRPC6 Activators	Adhyperforin • Hyperforin

Vesicular

VMAT Inhibitors

Ibogaine • Reserpine • Tetrabenazine

Releasing
Agents

Alkylamines: Cyclopentamine • Propylhexedrine; Aminopropanes: Indanylaminopropane • Naphthylaminopropane; Oxazolines: 4-Methylaminorex • Aminorex • Pemoline; Phenethylamines: 4-Fluoroamphetamine • 4-Fluoromethamphetamine • Amphetamine • Amphetaminil • Amfepentorex • Benzphetamine • Butylone • Cathine • Cathinone • Clobenzorex • Dextroamphetamine • Diethylcathinone • Dimethylamphetamine • Dimethylcathinone • Ephedrine • Ethylamphetamine • Ethylone • Fenethylline • Fenproporex • Flephedrone • Furfenorex • Lisdexamfetamine • MBDB • MDA • MDEA • MDMA • Mefenorex • Mephedrone • Methamphetamine • Methcathinone • Methylone • Phendimetrazine • Phenethylamine • Phenmetrazine • PMA • PMEA • PMMA • Phenylpropanolamine • Propylamphetamine • Pseudoephedrine • Tyramine • Xylopropamine; Piperazines: BZP • MBZP • MeOPP; Others: 4-Benzylpiperidine • Zylofuramine

Enzyme
Inhibitors

Anabolism

PAH Inhibitors	3,4-Dihydroxystyrene

TH Inhibitors	3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone

AAAD Inhibitors	Benserazide • Carbidopa

DBH Inhibitors	Disulfiram • Nepicastat • Tropolone

PNMT Inhibitors	CGS-19281A • SKF-64139 • SKF-7698

Catabolism

MAO Inhibitors	Nonselective: Iproclozide • Iproniazid • Isocarboxazid • Nialamide • Phenelzine • Pheniprazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline * Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.

COMT Inhibitors	Entacapone • Tolcapone

Others

Precursors	L-Phenylalanine • L-Tyrosine • L-DOPA • Dopamine

Cofactors	Ferrous Iron (Fe²⁺) • S-Adenosyl-L-Methionine • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc (Zn²⁺)

Others	Activity Enhancers: BPAP • PPAP; Release Blockers: Bretylium • Guanethidine

Dopaminergics

Receptor
Ligands

Agonists	Benzazepines: 6-Br-APB • Fenoldopam • SKF-38,393 • SKF-77,434 • SKF-81,297 • SKF-82,958 • SKF-83,959; Ergot-derivatives: Bromocriptine • Cabergoline • Dihydroergocryptine • Lisuride • LSD • Pergolide; Dihydrexidine-derivatives: A-86,929 • Dihydrexidine • Dinapsoline • Dinoxyline • Doxanthrine; Morphine-derivatives: Apomorphine • Propylnorapomorphine; Piperazines: Aripiprazole • Piribedil • WAY-100,635; Others: 7-OH-DPAT • A-68,930 • A-77,636 • A-412,997 • Aplindore • CY-208,243 • Memantine • Pramipexole • Pukateine • Quinpirole • RDS-127 • Ropinirole • Rotigotine

Antagonists	Typical Antipsychotics: Acepromazine • Azaperone • Benperidol • Bromperidol • Clopenthixol • Chlorpromazine • Chlorprothixene • Droperidol • Flupentixol • Fluphenazine • Fluspirilene • Haloperidol • Loxapine • Mesoridazine • Methotrimeprazine • Molindone • Penfluridol • Perazine • Periciazine • Perphenazine • Pimozide • Prochlorperazine • Promazine • Sulforidazine • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Trifluperidol • Zuclopenthixol; Atypical Antipsychotics: Amisulpride • Asenapine • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Perospirone • Quetiapine • Risperidone • Sertindole • Sulpiride • Ziprasidone • Zotepine; Antiemetics: AS-8112 • Alizapride • Bromopride • Clebopride • Domperidone • Metoclopramide • Thiethylperazine; Others: Amoxapine • Blonanserin • Buspirone • Butaclamol • N-Ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline • Ecopipam • Eticlopride • Fananserin • Mosapramine • Nafadotride • Nemonapride • Nuciferine • Raclopride • Remoxipride • SB-277,011-A • SCH-23,390 • SKF-83,566 • Spiperone • Spiroxatrine • Stepholidine • Tetrahydropalmatine • Tiapride • UH-232 • Yohimbine

Reuptake
Inhibitors

Plasmalemmal

DAT Inhibitors	Piperazines: DBL-583 • GBR-12,935 • Nefazodone • Vanoxerine; Piperidines: BTCP • Desoxypipradrol • Dextromethylphenidate • Ethylphenidate • HDMP-28 • Methylphenidate • Phencyclidine • Pipradrol; Pyrovalerones: MDPV • Pyrovalerone; Tropanes: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane • Lometopane • RTI-112 • RTI-113 • RTI-121 • RTI-126 • RTI-150 • RTI-177 • RTI-336 • Tenocyclidine • Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 • WF-31 • WF-33; Others: Amfonelic Acid • Amineptine • Benztropine • Bromantane • BTQ • BTS-74,398 • Bupropion • Cypenamine • Diclofensine • Dimethocaine • Diphenylprolinol • Dizocilpine • DOV-102,677 • DOV-21,947 • DOV-216,303 • Ethcathinone • Fencamfamine • GYKI-52,895 • Indatraline • Ketamine • Lefetamine • LR-5182 • Manifaxine • Mazindol • Medifoxamine • Mesocarb • Nisoxetine • Nomifensine • NS-2359 • O-2172 • Prolintane • Radafaxine • SEP-225,289 • SEP-227,162 • Sibutramine • Tametraline • Tripelennamine

TRPC6 Activators	Adhyperforin • Hyperforin

Vesicular

VMAT Inhibitors

Deserpidine • Ibogaine • Reserpine • Tetrabenazine

Releasing
Agents

Alkylamines: Cyclopentamine • Propylhexedrine; Aminopropanes: Indanylaminopropane • Naphthylaminopropane; Oxazolines: 4-Methylaminorex • Aminorex • Pemoline; Phenethylamines: 4-Fluoroamphetamine • 4-Fluoromethamphetamine • Amphetamine • Amphetaminil • Amfepentorex • Benzphetamine • Butylone • Cathine • Cathinone • Clobenzorex • Dextroamphetamine • Diethylcathinone • Dimethylamphetamine • Dimethylcathinone • Ethylamphetamine • Ethylone • Fenethylline • Fenproporex • Flephedrone • Furfenorex • MBDB • MDA • MDEA • MDMA • Mefenorex • Mephedrone • Methamphetamine • Methcathinone • Methylone • Phendimetrazine • Phenethylamine • Phenmetrazine • PMA • PMEA • PMMA • Propylamphetamine • Tyramine • Xylopropamine; Piperazines: BZP • MBZP • MeOPP; Others: 4-Benzylpiperidine • Zylofuramine

Enzyme
Inhibitors

Anabolism

PAH Inhibitors	3,4-Dihydroxystyrene

TH Inhibitors	3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone

AAAD / DDC Inhibitors	Benserazide • Carbidopa • Methyldopa

Catabolism

MAO Inhibitors (MAOIs)	Nonselective: Iproclozide • Iproniazid • Isocarboxazid • Nialamide • Phenelzine • Pheniprazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline

COMT Inhibitors	Entacapone • Tolcapone

DBH Inhibitors	Disulfiram • Nepicastat • Tropolone

Others

Precursors	L-Phenylalanine • L-Tyrosine • L-DOPA

Cofactors	Ferrous Iron (Fe²⁺) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc (Zn²⁺)

Others	Activity Enhancers: BPAP • PPAP; Others: Amantadine • Memantine • Rimantadine

Serotonergics

Receptor
Ligands

5-HT₁

5-HT_1A	Agonists: Azapirones: Alnespirone • Binospirone • Buspirone • Gepirone • Ipsapirone • Perospirone • Tandospirone • Tiospirone • Zalospirone; Lysergamides: Dihydroergotamine • Ergotamine • Methysergide • LSD; Phenethylamines: MDA • MDMA; Piperazines: Eltoprazine • Flesinoxan • Flibanserin; Tryptamines: 5-CT • 5-MeO-DMT • 5-MT • DMT • Psilocin • Psilocybin • Rauwolscine • Yohimbine; Atypical Antipsychotics: Aripiprazole • Asenapine • Clozapine • Quetiapine • Ziprasidone; Others: 8-OH-DPAT • Befiradol • F-11440 • Lesopitron • Lu AA21004 • LY-293,284 • LY-301,317 • MKC-242 • Osemozotan • Piclozotan • PRX-00023 • Repinotan • RU-24969 • S-15535 • Sarizotan • SSR-181,507 • Sunepitron • U-92016A • Urapidil • Vilazodone • Xaliproden Antagonists: Beta Blockers: Alprenolol • Cyanopindolol • Iodocyanopindolol • Oxprenolol • Pindobind • Pindolol • Propranolol; Piperazines: Nefazodone • Trazodone • WAY-100,135 • WAY-100,635; Others: AV965 • BMY-7378 • Dotarizine • GR-46611 • Isamoltane • Lecozotan • Methiothepin • MPPF • NAN-190 • Robalzotan • S-15535 • SB-649915 • SDZ 216-525 • Spiperone • Spiramide • Spiroxatrine • UH-301 • WAY-100,135 • WAY-100,635 • Xylamidine

5-HT_1B	Agonists: Lysergamides: Dihydroergotamine • Ergotamine • Methysergide; Piperazines: Eltoprazine • TFMPP; Triptans: Eletriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CP-93,129 • CP-94,253 • CP-135,807 • RU-24969 Antagonists: Lysergamides: Metergoline • Methiothepin; Tryptamines: Yohimbine; Others: AR-A000002 • GR-127,935 • Isamoltane • SB-216,641 • SB-224,289 • SB-236,057

5-HT_1D	Agonists: Lysergamides: Dihydroergotamine • Methysergide; Triptans: Almotriptan • Eletriptan • Frovatriptan • Naratriptan • Rizatriptan • Sumatriptan • Zolmitriptan; Tryptamines: 5-CT • 5-MT; Others: CP-135,807 • CP-286,601 • GR-46611 • L-694,247 • L-772,405 • PNU-109,291 • PNU-142,633 Antagonists: Lysergamides: Metergoline • Methiothepin; Tryptamines: Rauwolscine • Yohimbine; Others: BRL-15572 • GR-127,935 • Ketanserin • LY-310,762 • LY-367,642 • LY-456,219 • LY-456,220 • Ritanserin • Ziprasidone

5-HT_1E	Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: Tryptamine Antagonists: Methiothepin

5-HT_1F	Agonists: Triptans: Eletriptan • Naratriptan • Sumatriptan; Tryptamines: 5-MT; Others: LY-334,370 Antagonists: Methiothepin

5-HT₂

5-HT_2A	Agonists: Lysergamides: ALD-52 • Ergonovine • Lisuride • LA-SS-Az • LSD • Lysergic acid 2-butyl amide • Methysergide; Phenethylamines: 25I-NBMD • 25I-NBOH • 25I-NBOMe • 2C-B • 2C-B-FLY • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • 2CBCB-NBOMe • 2CBFly-NBOMe • Bromo-DragonFLY • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin • TCB-2 • TFMFly; Piperazines: BZP • Quipazine • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: AL-34662 • AL-37350A • PNU-22394 Antagonists: Atypical Antipsychotics: Amperozide • Aripiprazole • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical Antipsychotics: Loxapine • Pipamperone; Antidepressants: Amitriptyline • Amoxapine • Etoperidone • Mianserin • Mirtazapine • Nefazodone • Trazodone; Others: 5-I-R91150 • AC-90179 • Altanserin • AMDA • APD-215 • Blonanserin • Cinanserin • Cyproheptadine • Deramciclane • Dotarizine • Eplivanserin • Fananserin • Flibanserin • Ketanserin • KML-010 • Lubazodone • Methiothepin • Nantenine • Pimavanserin • Pizotifen • Ritanserin • Sarpogrelate • Setoperone • Spiperone • Spiramide • SR-46349B • Volinanserin • Xylamidine • Yohimbine

5-HT_2B	Agonists: Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines: Chlorphentermine • DOB • DOC • DOI • DOM • Fenfluramine • MDA • MDMA • Norfenfluramine; Tryptamines: 5-CT • 5-MT • α-Methyl-5-HT; Others: BW-723C86 • Cabergoline • mCPP • Pergolide • PNU-22394 • Ro60-0175 Antagonists: Agomelatine • Asenapine • EGIS-7625 • Ketanserin • Lisuride • LY-272,015 • Rauwolscine • Ritanserin • RS-127,445 • Sarpogrelate • SB-200,646 • SB-204,741 • SB-206,553 • SB-215,505 • SB-221,284 • SB-228,357 • SDZ SER-082 • Tegaserod • Yohimbine

5-HT_2C	Agonists: Phenethylamines: 2C-B • 2C-E • 2C-I • 2C-T-2 • 2C-T-7 • 2C-T-21 • DOB • DOC • DOI • DOM • MDA • MDMA • Mescaline • Myristicin; Piperazines: Aripiprazole • mCPP • TFMPP; Tryptamines: 5-CT • 5-MeO-α-ET • 5-MeO-α-MT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MT • α-ET • α-Methyl-5-HT • α-MT • Bufotenin • DET • DiPT • DMT • DPT • Psilocin • Psilocybin; Others: A-372,159 • AL-38022A • CP-809,101 • Lorcaserin • MK-212 • PNU-22394 • Ro60-0175 • Vabicaserin • WAY-629 • WAY-161,503 • YM-348 Antagonists: Atypical Antipsychotics: Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Pimozide • Quetiapine • Risperidone • Sertindole • Ziprasidone • Zotepine; Typical Antipsychotics: Loxapine • Pipamperone; Antidepressants: Agomelatine • Amitriptyline • Amoxapine • Etoperidone • Fluoxetine • Mianserin • Mirtazapine • Nefazodone • Trazodone; Others: Cinanserin • Deramciclane • Dimebolin • Dotarizine • Eltoprazine • FR-260,010 • Ketanserin • Pizotifen • Ritanserin • RS-102,221 • SB-200,646 • SB-206,553 • SB-221,284 • SB-228,357 • SB-242,084 • SB-243,213 • SDZ SER-082 • Xylamidine

5-HT₃

Agonists: Piperazines: BZP • Quipazine; Tryptamines: 2-Methyl-5-HT • 5-CT; Others: Chlorophenylbiguanide • RS-56812 • SR-57,227 • SR-57,227-A • YM-31636
Antagonists: Antiemetics: AS-8112 • Alosetron • Azasetron • Batanopride • Bemesetron • Cilansetron • Dolasetron • Granisetron • Lerisetron • Ondansetron • Palonosetron • Ramosetron • Renzapride • Tropisetron • Zacopride • Zatosetron; Atypical Antipsychotics: Clozapine • Olanzapine • Quetiapine; Tetracyclic Antidepressants: Amoxapine • Mianserin • Mirtazapine; Others: ICS-205,930 • Lu AA21004 • MDL-72,222 • Memantine • Ricasetron

5-HT₄

Agonists: Gastroprokinetic Agents: Cisapride • Metoclopramide • Mosapride • Prucalopride • Renzapride • Tegaserod • Zacopride; Others: 5-MT • BIMU-8 • CJ-033,466 • PRX-03140 • RS-67333 • RS-67506 • TD-5108
Antagonists: GR-113,808 • GR-125,487 • L-Lysine • Piboserod • RS-39604 • RS-67532 • SB-203,186

5-HT₅

5-HT_5A	Agonists: Lysergamides: Ergotamine • LSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: Asenapine • Dimebolin • Methiothepin • Ritanserin • SB-699,551

5-HT_5B*	Agonists: Lysergamides: Ergotamine • LSD Antagonists: Methiothepin * Note that the 5-HT_5B receptor is not functional in humans.

5-HT₆

Agonists: Lysergamides: Lisuride • LSD • Metergoline; Tryptamines: 5-CT • 5-MT • E-6801 • E-6837 • EMD-386,088 • EMDT • LY-586,713 • WAY-181,187 • WAY-208,466
Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Doxepin • Mianserin • Nortriptyline; Atypical Antipsychotics: Aripiprazole • Asenapine • Clozapine • Fluperlapine • Iloperidone • Olanzapine • Tiospirone; Typical Antipsychotics: Chlorpromazine • Loxapine; Others: BGC20-760 • BVT-5182 • BVT-74316 • Dimebolin • EGIS-12233 • GW-742,457 • Ketanserin • Methiothepin • MS-245 • PRX-07034 • Ritanserin • Ro 04-6790 • Ro 63-0563 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885

5-HT₇

Agonists: Lysergamides: LSD; Tryptamines: 5-CT • 5-MT; Others: 8-OH-DPAT • AS-19 • Bifeprunox • LP-12 • LP-44 • Sarizotan
Antagonists: Antidepressants: Amitriptyline • Amoxapine • Clomipramine • Imipramine • Maprotiline • Mianserin; Atypical Antipsychotics: Amisulpride • Aripiprazole • Clozapine • Olanzapine • Risperidone • Sertindole • Tiospirone • Ziprasidone • Zotepine; Typical Antipsychotics: Chlorpromazine • Loxapine; Others: EGIS-12233 • LY-215,840 • Mesulergine • Metergoline • Methiothepin • Pimozide • Ritanserin • SB-258,719 • SB-258,741 • SB-269,970 • SB-656,104 • SB-656,104-A • SB-691,673 • SLV-313 • SLV-314 • Spiperone • SSR-181,507

Reuptake
Inhibitors

Plasmalemmal

SERT Inhibitors	Selective Serotonin Reuptake Inhibitors (SSRIs): Alaproclate • Citalopram • Dapoxetine • Escitalopram • Femoxetine • Fluoxetine • Fluvoxamine • Indalpine • Litoxetine • Lubazodone • Paroxetine • Sertraline • Vilazodone • Zimelidine; Serotonin-Norepinephrine Reuptake Inhibitors (SNRIs): Bicifadine • Desvenlafaxine • Duloxetine • Milnacipran • Venlafaxine; Serotonin-Norepinephrine-Dopamine Reuptake Inhibitors (SNDRIs): Brasofensine • Diclofensine • DOV 102,677 • DOV 21,947 • DOV 216,303 • NS2359 • SEP-225289 • SEP-227162 • Tesofensine; Tricyclic Antidepressants (TCAs): Amitriptyline • Butriptyline • Cianopramine • Clomipramine • Desipramine • Dosulepin • Doxepin • Imipramine • Lofepramine • Nortriptyline • Protriptyline • Trimipramine; Tetracyclic Antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone • Trazodone; Tropanes: Cocaine; Antihistamines: Brompheniramine • Chlorpheniramine • Diphenhydramine • Mepyramine/Pyrilamine • Pheniramine • Tripelennamine; Opioids: Meperidine/Pethidine • Methadone • Propoxyphene • Tramadol; Others: Cyclobenzaprine • Dextromethorphan • Mesembrine • SB-649915 • Sibutramine • Ziprasidone

TRPC6 Activators	Adhyperforin • Hyperforin

Vesicular

VMAT Inhibitors

Ibogaine • Reserpine • Tetrabenazine

Releasing
Agents

Aminoindanes: ETAI • MDAI • MDMAI • MMAI • TAI; Aminopropanes: Indanylaminopropane • Naphthylaminopropane; Benzofurans: 5-APDB; Aminotetralins: 8-OH-DPAT; Oxazolines: 4-Methylaminorex • Aminorex; Phenethylamines: 2-Methyl-MDA • 3-Methoxy-4-methylamphetamine • 4-Bromomethcathinone • 4-Fluoroamphetamine • 4-Fluoromethamphetamine • 4-Methylamphetamine • 4-Methylmethamphetamine • 4-Methylthioamphetamine • 5-Methyl-MDA • BDB • BOH • Butylone • Chlorphentermine • Diethylcathinone • Dimethylcathinone • EBDB • Ethylone • Fenfluramine • Flephedrone • MBDB • MDA • MDEA • MDMA (Ecstasy) • MDOH • MDPEA • Mephedrone • Methylone • MMDA • MMDMA • Norfenfluramine • para-Bromoamphetamine • para-Chloroamphetamine • para-Chloromethamphetamine • para-Iodoamphetamine • para-Methoxyamphetamine • para-Methoxyethylamphetamine • para-Methoxymethamphetamine; Quinolines: PK 7059 • Viqualine; Tryptamines: α-ET • α-MT

Enzyme
Inhibitors

Anabolism

TPH Inhibitors	AGN-2979 • Fenclonine

AAAD Inhibitors	Benserazide • Carbidopa

Catabolism

MAO Inhibitors

Nonselective: Iproclozide • Iproniazid • Isocarboxazid • Nialamide • Phenelzine • Pheniprazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima

Others

Precursors	L-Tryptophan • 5-HTP

Cofactors	Ferrous Iron (Fe²⁺) • Magnesium (Mg²⁺) • Tetrahydrobiopterin • Vitamin B3 (Niacin, Nicotinamide → NADPH) • Vitamin B6 (Pyridoxine, Pyridoxamine, Pyridoxal → Pyridoxal Phosphate) • Vitamin B9 (Folic Acid → Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc (Zn²⁺)

Others	Activity Enhancers: BPAP • PPAP; Reuptake Enhancers: Tianeptine

Phenethylamines

2C-B • 2C-C • 2C-D • 2C-E • 2C-I • 2C-N • 2C-T-2 • 2C-T-21 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 3C-E • 4-FA • 4-FMA • 6-OHDA • Alfetamine • Amphetamine • β-methylphenethylamine • Br-DFLY • Bupropion • Butylone • Cathine • Cathinone • Clenbuterol • DESOXY • Dextroamphetamine • Diethylcathinone • Dimethylcathinone • DOB • DOC • DOI • DOM • Dopamine • Ephedrine • Epinephrine • Escaline • Etafedrine • Ethylone • Fenfluramine • Hordenine • Levosalbutamol • Levomethamphetamine • MBDB ("Eden") • MDA • MDMA ("Ecstasy") • MDEA ("Eve") • Mescaline • Methamphetamine • Methcathinone • Methylone • Methylphenidate • Norepinephrine • Octopamine • Phenethylamine • Phentermine • Phenylephrine • PMA • PMEA • PMMA • Pseudoephedrine • Salbutamol • Tyramine

v • d • e Methylenedioxyphenethylamines

Phenethylamines	bk-MDMPEA • bk-MDPEA • MDMPEA • MMDPEA (Lophophine, Homomyristicylamine) • MDPEA (Homopiperonylamine)

Amphetamines	2-Methyl-MDA • 3-Desoxy-MDA • 5-Methyl-MDA • 6-Methyl-MDA • DMMDA • DMMDA-2 • MADAM-2 • MADAM-6 • MDA (Tenamfetamine; "Hug Drug", "Love Drug", "Mellow Drug of America") • MDAL (MDAA) • MDBU (MDBA) • MDBZ (MDBZA) • MDCPM (MDCPMA, MDCA) • MDDM (MDDMA) • MDEA (MDE; "Eve") • MDIP (MDIPR, MDIPA) • MDMA (MDM; "Ecstasy", "Adam", "Empathy", "Molly", "E", "X", "XTC") • MDOH (MDH) • MDHOET (MDHET, MDHEA) • MDMEO (MDMEOA) • MDMEOET (MDMEOET, MDMEOEA, MDMEA) • MDMOH (MDMHO, MDMHA, MDMH; FLEA) • MDPR (MDPA) • MDPL (MDPLA) • MMDA • MMDMA

Cathinones	bk-MDA (MDC, MDCAT) • bk-MDEA (MDEC, MDECAT; Ethylone) • bk-MDMA (MDMC, MDMCAT; Methylone; "Explosion", "Ease")

Phentermines	MDMP (MDMPH, MDMPTM) • MDPH (MDPTM)

Butanamines	BDB (J) • bk-BDB (bk-J) • bk-DMBDB (Dibutylone) • bk-EDBD (Eutylone) • bk-MBDB (Butylone) • BOH • DMBDB (Dimethyl-J) • EBDB (Ethyl-J) • MBDB (Methyl-J; "Eden")

Pentylamines	bk-K • bk-Methyl-K • Ethyl-K • K • Methyl-K

Miscellaneous	Aminoindanes: MDAI • MDMAI; Pyrrolidinophenones: MDPPP • MDPV