Robalzotan

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Robalzotan

Systematic (IUPAC) name
(3R)-3-[di(cyclobutyl)amino]-8-fluoro-3,4-dihydro-2H-chromene-5-carboxamide
Clinical data
Legal status	Uncontrolled
Routes	Oral
Identifiers
CAS number	169758-66-1^Y
ATC code	None
PubChem	CID 3055171
ChemSpider	2316732
UNII	I18M56OGME^Y
Chemical data
Formula	C₁₈H₂₃F N₂O₂
Mol. mass	318.174 g/mol
SMILES C1CC(C1)N(C2CCC2)[C@@H]3CC4=C(C=CC(=C4OC3)F)C(=O)N
InChI InChI=1S/C18H23FN2O2/c19-16-8-7-14(18(20)22)15-9-13(10-23-17(15)16)21(11-3-1-4-11)12-5-2-6-12/h7-8,11-13H,1-6,9-10H2,(H2,20,22)/t13-/m1/s1 Key:MQTUXRKNJYPMCG-CYBMUJFWSA-N
Y (what is this?) (verify)

Robalzotan (NAD-299, AZD-7371) is a selective antagonist at the 5-HT_1A receptor.^[1] It was shown to completely reverse the autoreceptor-mediated inhibition of serotonin release induced by the administration of selective serotonin reuptake inhibitors like citalopram in rodent studies.^[2] It was subsequently investigated by AstraZeneca as a potential antidepressant but like many other 5-HT_1A ligands was discontinued.^[3] Later on it was researched for other indications such as irritable bowel syndrome but was dropped once again.^[4]

References

↑ Jerning E, Svantesson GT, Mohell N. (1998). "Receptor binding characteristics of [3H]NAD-299, a new selective 5-HT1A receptor antagonist.". Eur J Pharmacol. 360 (2-3): 219–225. doi:10.1016/S0014-2999(98)00667-0. PMID 9851589.
↑ Arborelius L, Wallsten C, Ahlenius S, Svensson TH. (1999). "The 5-HT(1A) receptor antagonist robalzotan completely reverses citalopram-induced inhibition of serotonergic cell firing.". Eur J Pharmacol. 382 (2): 133–138. doi:10.1016/S0014-2999(99)00592-0. PMID 10528148.
↑ Mucke HA. (2000). "Robalzotan AstraZeneca.". Curr Opin Investig Drugs. 1 (2): 236–240. PMID 11249580.
↑ Drossman DA, Danilewitz M, Naesdal J, Hwang C, Adler J, Silberg DG (October 2008). "Randomized, double-blind, placebo-controlled trial of the 5-HT1A receptor antagonist AZD7371 tartrate monohydrate (robalzotan tartrate monohydrate) in patients with irritable bowel syndrome". The American Journal of Gastroenterology 103 (10): 2562–9. doi:10.1111/j.1572-0241.2008.02115.x. PMID 18775020.

Antidepressants (N06A)

Specific reuptake inhibitors (RIs), enhancers (REs), and releasing agents (RAs)

Selective serotonin reuptake inhibitors (SSRIs)	Alaproclate Citalopram Escitalopram Femoxetine Fluoxetine^# Fluvoxamine Indalpine Ifoxetine Litoxetine Omiloxetine Panuramine Paroxetine Pirandamine Seproxetine Sertraline Zimelidine^‡

Serotonin–norepinephrine reuptake inhibitors (SNRIs)	Clovoxamine Desvenlafaxine Duloxetine Levomilnacipran Eclanamine Milnacipran Sibutramine Venlafaxine

Serotonin–norepinephrine–dopamine reuptake inhibitors (SNDRIs)	Adhyperforin Amitifadine Bicifadine Brasofensine BTS-74,398 Cocaine Diclofensine DOV-102,677 DOV-216,303 EXP-561 Fezolamine Hyperforin JNJ-7925476 NS-2359 PRC200-SS Pridefine SEP-225,289 SEP-227,162 Tesofensine

Norepinephrine reuptake inhibitors (NRIs)	Amedalin Atomoxetine/Tomoxetine Binedaline Ciclazindol Daledalin Edivoxetine Esreboxetine Lortalamine Maprotiline Mazindol Nisoxetine Reboxetine Talopram Talsupram Tandamine Viloxazine

Dopamine reuptake inhibitors (DRIs)	Medifoxamine Vanoxerine

Norepinephrine-dopamine reuptake inhibitors (NDRIs)	Amineptine Bupropion/Amfebutamone Cilobamine Manifaxine Methylphenidate Nomifensine Radafaxine Tametraline

Norepinephrine-dopamine releasing agents (NDRAs)	Amphetamine Befuraline Lisdexamfetamine Methamphetamine Phenethylamine Piberaline Tranylcypromine

Serotonin-norepinephrine-dopamine releasing agents (SNDRAs)	4-Methyl-αMT αET/Etryptamine αMT/Metryptamine

Selective serotonin reuptake enhancers (SSREs)	Tianeptine

Others	Indeloxazine Teniloxazine Tramadol Viqualine

Receptor antagonists and/or reuptake inhibitors

Serotonin antagonists and reuptake inhibitors (SARIs)	Etoperidone Lubazodone Nefazodone Mepiprazole Trazodone

Noradrenergic and specific serotonergic antidepressants (NaSSAs)	Aptazapine Esmirtazapine Mianserin Mirtazapine Setiptiline/Teciptiline

Norepinephrine-dopamine disinhibitors (NDDIs)	Agomelatine

Serotonin modulators and stimulators (SMSs)	Vortioxetine

Others	Tedatioxetine Vilazodone

Heterocyclic antidepressants (bi-, tri-, and tetracyclics)

Bicyclics	Tiazesim Tofenacin

Tricyclics	Amezepine Amineptine Amitriptyline^# Amitriptylinoxide Azepindole Butriptyline Cianopramine Clomipramine^# Cotriptyline Cyanodothiepin Demexiptiline Depramine/Balipramine Desipramine Dibenzepin Dimetacrine Dosulepin/Dothiepin Doxepin Enprazepine Fluotracen Hepzidine Homopipramol Imipramine Imipraminoxide Intriptyline Iprindole Ketipramine Litracen Lofepramine Losindole Mariptiline Melitracen Metapramine Mezepine Naranol Nitroxazepine Nortriptyline Noxiptiline Octriptyline Opipramol Pipofezine Propizepine Protriptyline Quinupramine Tampramine Tianeptine Tienopramine Trimipramine

Tetracyclics	Amoxapine Aptazapine Azipramine Ciclazindol Ciclopramine Esmirtazapine Maprotiline Mazindol Mianserin Mirtazapine Oxaprotiline Setiptiline/Teciptiline

Monoamine oxidase inhibitors (MAOIs)

Nonselective	Irreversible: Benmoxin Carbenzide Cimemoxin Domoxin Echinopsidine Iproclozide Iproniazid Isocarboxazid Mebanazine Metfendrazine Nialamide Octamoxin Phenelzine Pheniprazine Phenoxypropazine Pivalylbenzhydrazine Safrazine Tranylcypromine Reversible: Caroxazone Paraxazone Quercetin

MAO_A-Selective	Irreversible: Clorgiline Reversible: Amiflamine Bazinaprine Befloxatone Berberine Brofaromine Cimoxatone Esuprone Eprobemide Harmala Alkaloids (Harmine Harmaline Tetrahydroharmine Harman Norharman, etc) Methylene Blue Metralindole Minaprine Moclobemide Pirlindole Sercloremine Tetrindole Toloxatone Tyrima

MAO_B-Selective	Irreversible: Ladostigil Mofegiline Pargyline Rasagiline Selegiline Reversible: Lazabemide Milacemide

Azapirones and other 5-HT_1A receptor agonists

Alnespirone Aripiprazole Befiradol Buspirone Eptapirone Flesinoxan Flibanserin Gepirone Ipsapirone Oxaflozane Tandospirone Vilazodone Zalospirone

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc (eval/thrp), drug (N5A/5B/5C/6A/6B/6D)

Anxiolytics (N05B)

GABA_A
PAMs

non-N05B	Alcohols (2M2B, Ethanol (beverage), Ethchlorvynol, Methylpentynol) Chlormezanone Etifoxine Inhalants Kavalactones (Kava) Skullcap Valerenic acid (Valerian)

Benzodiazepine	Adinazolam Alprazolam Bretazenil Bromazepam Camazepam Chlordiazepoxide Clobazam Clonazepam Clorazepate Clotiazepam Cloxazolam Diazepam^# Ethyl Loflazepate Etizolam Fludiazepam Halazepam Imidazenil Ketazolam Lorazepam^# Medazepam Nordazepam Oxazepam Pinazepam Prazepam

Carbamates	Difebarbamate Emylcamate Febarbamate Mebutamate Meprobamate (Carisoprodol, Tybamate) Phenprobamate Procymate

Nonbenzodiazepines	Abecarnil Adipiplon Alpidem CGS-8216 CGS-9896 CGS-13767 CGS-20625 Divaplon ELB-139 Fasiplon GBLD-345 Gedocarnil L-838,417 NS-2664 NS-2710 Ocinaplon Pagoclone Panadiplon Pipequaline RWJ-51204 SB-205,384 SL-651,498 Taniplon TP-003 TP-13 TPA-023 Y-23684 ZK-93423

Pyrazolopyridines	Cartazolate Etazolate ICI-190,622 Tracazolate

α₂δ VDCC Blockers

CRH₁ Antagonists

mGluR₂_/₃ Agonists

mGluR5 NAMs

TSPO agonists

σ₁ agonists

Antidepressants

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

M: PSO/PSI

mepr

dsrd (o, p, m, p, a, d, s), sysi/epon, spvo

proc (eval/thrp), drug (N5A/5B/5C/6A/6B/6D)

Drugs for functional gastrointestinal disorders (A03)

Drugs for
functional
bowel disorders

Antimuscarinics

Tertiary amino group	Oxyphencyclimine Camylofin Mebeverine Trimebutine Rociverine Dicycloverine Dihexyverine Difemerine Piperidolate

Quaternary ammonium compounds	Benzilone Mepenzolate Pipenzolate Glycopyrronium Oxyphenonium Penthienate Methantheline Propantheline Otilonium Tridihexethyl Isopropamide Hexocyclium Poldine Bevonium Diphemanil Tiemonium Prifinium Timepidium Fenpiverinium

Phosphodiesterase
inhibitors

Acting on
serotonin receptors

Other

Belladonna
and derivatives
(antimuscarinics)

tertiary amines: Atropine
Hyoscyamine

Propulsives

M: DIG

anat (t, g, p)/phys/devp/enzy

noco/cong/tumr, sysi/epon

proc, drug (A2A/2B/3/4/5/6/7/14/16), blte

Serotonergics

5-HT₁ receptor ligands

5-HT_1A	Agonists: Azapirones: Alnespirone Binospirone Buspirone Enilospirone Eptapirone Gepirone Ipsapirone Perospirone Revospirone Tandospirone Tiospirone Umespirone Zalospirone; Antidepressants: Etoperidone Nefazodone Trazodone Vortioxetine; Antipsychotics: Aripiprazole Asenapine Clozapine Quetiapine Ziprasidone; Ergolines: Dihydroergotamine Bromocriptine Ergotamine Lisuride Methysergide LSD; Tryptamines: 5-CT 5-MeO-DMT 5-MT Bufotenin DMT Indorenate Psilocin Psilocybin; Others: 8-OH-DPAT Adatanserin Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Ebalzotan Eltoprazine F-11,461 F-12,826 F-13,714 F-14,679 F-15,063 F-15,599 Flesinoxan Flibanserin Lesopitron LY-293,284 LY-301,317 MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24,969 S 14,506 S-14,671 S-15,535 Sarizotan SSR-181,507 Sunepitron U-92,016-A Urapidil Vilazodone Xaliproden Yohimbine Antagonists: Antipsychotics: Iloperidone Risperidone Sertindole; Beta blockers: Alprenolol Cyanopindolol Iodocyanopindolol Oxprenolol Pindobind Pindolol Propranolol Tertatolol; Others: AV965 BMY-7,378 CSP-2503 Dotarizine Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine/Methiothepin MPPF NAN-190 Robalzotan S-15535 SB-649,915 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: Avitriptan Eletriptan Sumatriptan Zolmitriptan; Tryptamines: 5-CT 5-MT; Others: CGS-12066A Bromocriptine CP-93,129 CP-94,253 CP-135,807 RU-24,969 Vortioxetine Antagonists: Lysergamides: Metergoline; Others: AR-A000002 Elzasonan GR-127,935 Isamoltane Metitepine/Methiothepin SB-216,641 SB-224,289 SB-236,057 Yohimbine

5-HT_1D	Agonists: Lysergamides: Dihydroergotamine Methysergide; Triptans: Almotriptan Avitriptan Eletriptan Frovatriptan Naratriptan Rizatriptan Sumatriptan Zolmitriptan; Tryptamines: 5-CT 5-Ethyl-DMT 5-MT 5-(Nonyloxy)tryptamine; Others: CP-135,807 Bromocriptine CP-286,601 GR-46611 L-694,247 L-772,405 PNU-109,291 PNU-142633 Antagonists: Lysergamides: Metergoline; Others: Alniditan BRL-15,572 Elzasonan GR-127,935 Ketanserin LY-310,762 LY-367,642 LY-456,219 LY-456,220 Metitepine/Methiothepin Ritanserin Yohimbine Ziprasidone

5-HT_1E	Agonists: Lysergamides: Methysergide; Triptans: Eletriptan; Tryptamines: BRL-54443 Tryptamine Antagonists: Metitepine/Methiothepin

5-HT_1F	Agonists: Triptans: Eletriptan Naratriptan Sumatriptan; Tryptamines: 5-MT; Others: BRL-54443 Bromocriptine Lasmiditan LY-334,370 Antagonists: Metitepine/Methiothepin

5-HT₂ receptor ligands

5-HT_2A	Agonists: Lysergamides: ALD-52 Ergometrine Lisuride LA-SS-Az LSD LSD-Pip Lysergic acid 2-butyl amide Lysergic acid 3-pentyl amide Methysergide; Phenethylamines: 25I-NBF 25I-NBMD 25I-NBOH 25I-NBOMe 2C-B 2C-B-FLY 2CB-Ind 25B-NBOMe 25C-NBOMe 2C-E 2C-I 25TFM-NBOMe 2C-T-2 2C-T-7 2C-T-21 2CBCB-NBOMe 2CBFly-NBOMe Juncosamine Bromo-DragonFLY DOB DOC DOI DOM MDA MDMA Mescaline 25CN-NBOH 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 Bromocriptine Dimemebfe Medifoxamine O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 Antagonists: Atypical antipsychotics: Amperozide Aripiprazole Blonanserin Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Melperone Mosapramine Olanzapine Paliperidone Quetiapine Risperidone Sertindole Zicronapine Ziprasidone Zotepine; Typical antipsychotics: Loxapine Pipamperone; Antidepressants: Amitriptyline Amoxapine Aptazapine Etoperidone Mianserin Mirtazapine Nefazodone Pimozide Teniloxazine Trazodone; Others: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin AMDA APD-215 Cinanserin CSP-2503 Cyproheptadine Deramciclane Dotarizine Eplivanserin Esmirtazapine Fananserin Flibanserin Glemanserin Ketanserin KML-010 Lubazodone Mepiprazole Metitepine/Methiothepin Nantenine Pimavanserin Pizotifen Pruvanserin Rauwolscine Ritanserin S-14,671 Sarpogrelate Setoperone Spiperone Spiramide SR-46349B Volinanserin Xylamidine Yohimbine

5-HT_2B	Agonists: Oxazolines: 4-Methylaminorex Aminorex; Phenethylamines: Chlorphentermine Cloforex DOB DOC DOI DOM Fenfluramine (Dexfenfluramine, Levofenfluramine) MDA MDMA Norfenfluramine; Tryptamines: 5-CT 5-MT α-Methyl-5-HT; Others: BW-723C86 Bromocriptine Cabergoline mCPP Pergolide PNU-22394 Ro60-0175 Antagonists: Agomelatine Asenapine EGIS-7625 Ketanserin Lisuride LY-272,015 Metitepine/Methiothepin PRX-08066 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; 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 Alstonine Bromocriptine CP-809,101 Dimemebfe Lorcaserin Medifoxamine MK-212 Org 12,962 ORG-37,684 Oxaflozane PHA-57378 PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Vabicaserin WAY-629 WAY-161,503 YM-348 Antagonists: Atypical antipsychotics: Clorotepine Clozapine Iloperidone Melperone Olanzapine Paliperidone Quetiapine Risperidone Sertindole Ziprasidone Zotepine; Typical antipsychotics: Chlorpromazine Loxapine Pimozide Pipamperone; Antidepressants: Agomelatine Amitriptyline Amoxapine Aptazapine Etoperidone Fluoxetine Mianserin Mirtazapine Nefazodone Nortriptyline Tedatioxetine Trazodone; Others: Adatanserin CEPC Cinanserin Cyproheptadine Deramciclane Dotarizine Eltoprazine Esmirtazapine FR-260,010 Ketanserin Ketotifen Latrepirdine Metitepine/Methiothepin Methysergide Pizotifen Ritanserin RS-102,221 S-14,671 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 Butanol Ethanol Halothane Isoflurane RS-56812 SR-57,227 SR-57,227-A Toluene Trichloroethane Trichloroethanol Trichloroethylene YM-31636 Antagonists: Antiemetics: AS-8112 Alosetron Azasetron Batanopride Bemesetron Cilansetron Dazopride Dolasetron Galanolactone Granisetron Lerisetron Ondansetron Palonosetron Ramosetron Renzapride Tropisetron Zacopride Zatosetron; Atypical antipsychotics: Clozapine Olanzapine Quetiapine; Tetracyclic antidepressants: Amoxapine Mianserin Mirtazapine; Others: CSP-2503 ICS-205,930 MDL-72,222 Memantine Nitrous Oxide Ricasetron Sevoflurane Tedatioxetine Thujone Tropanserin Vortioxetine Xenon

5-HT₄	Agonists: Gastroprokinetic Agents: Cinitapride Cisapride Dazopride Metoclopramide Mosapride Prucalopride Renzapride Tegaserod Velusetrag Zacopride; Others: 5-MT BIMU8 CJ-033,466 PRX-03140 RS-67333 RS-67506 SL65.0155 Antagonists: GR-113,808 GR-125,487 L-Lysine Piboserod RS-39604 RS-67532 SB-203,186 SB-204,070

5-HT_5A	Agonists: Lysergamides: Ergotamine LSD; Tryptamines: 5-CT; Others: Valerenic Acid Antagonists: Asenapine Latrepirdine Metitepine/Methiothepin Ritanserin SB-699,551 * Note that the 5-HT_5B receptor is not functional in humans.

5-HT₆	Agonists: Lysergamides: Dihydroergotamine Ergotamine Lisuride LSD Mesulergine Metergoline Methysergide; Tryptamines: 2-Methyl-5-HT 5-BT 5-CT 5-MT Bufotenin E-6801 E-6837 EMD-386,088 EMDT LY-586,713 N-Methyl-5-HT Tryptamine; Others: WAY-181,187 WAY-208,466 Antagonists: Antidepressants: Amitriptyline Amoxapine Clomipramine Doxepin Mianserin Nortriptyline; Atypical antipsychotics: Aripiprazole Asenapine Clorotepine Clozapine Fluperlapine Iloperidone Olanzapine Tiospirone; Typical antipsychotics: Chlorpromazine Loxapine; Others: BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12,233 GW-742,457 Ketanserin Latrepirdine Lu AE58054 Metitepine/Methiothepin MS-245 PRX-07034 Ritanserin Ro04-6790 Ro 63-0563 SB-258,585 SB-271,046 SB-357,134 SB-399,885 SB-742,457

5-HT₇	Agonists: Lysergamides: LSD; Tryptamines: 5-CT 5-MT Bufotenin; Others: 8-OH-DPAT AS-19 Bifeprunox E-55888 LP-12 LP-44 RU-24,969 Sarizotan Antagonists: Lysergamides: 2-Bromo-LSD Bromocriptine Dihydroergotamine Ergotamine Mesulergine Metergoline Methysergide; Antidepressants: Amitriptyline Amoxapine Clomipramine Imipramine Maprotiline Mianserin; Atypical antipsychotics: Amisulpride Aripiprazole Asenapine Clorotepine Clozapine Olanzapine Risperidone Sertindole Tiospirone Ziprasidone Zotepine; Typical antipsychotics: Chlorpromazine Loxapine; Pimozide; Others: Butaclamol EGIS-12,233 Ketanserin LY-215,840 Metitepine/Methiothepin 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 Vortioxetine

Reuptake inhibitors

SERT	Selective serotonin reuptake inhibitors (SSRIs): Alaproclate Citalopram Dapoxetine Desmethylcitalopram Desmethylsertraline Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Litoxetine Lubazodone Omiloxetine Panuramine Paroxetine Pirandamine RTI-353 Seproxetine Sertraline Vilazodone Vortioxetine Zimelidine; Serotonin-norepinephrine reuptake inhibitors (SNRIs): Bicifadine Desvenlafaxine Duloxetine Eclanamine Levomilnacipran Milnacipran Sibutramine Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors (SNDRIs): Brasofensine Diclofensine DOV-102,677 DOV-21,947 DOV-216,303 NS-2359 SEP-225289 SEP-227,162 Tedatioxetine Tesofensine; Tricyclic antidepressants (TCAs): Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline Trimipramine; Tetracyclic antidepressants (TeCAs): Amoxapine; Piperazines: Nefazodone Trazodone; Antihistamines: Brompheniramine Chlorphenamine Diphenhydramine Mepyramine/Pyrilamine Pheniramine Tripelennamine; Opioids: Pethidine Methadone Propoxyphene; Others: Cocaine CP-39,332 Cyclobenzaprine Dextromethorphan Dextrorphan EXP-561 Fezolamine Mesembrine Nefopam PIM-35 Pridefine Roxindole SB-649,915 Tofenacin Ziprasidone

VMAT	Ibogaine Reserpine Tetrabenazine

Releasing agents

Aminoindanes: 5-IAI
AMMI
ETAI
MDAI
MDMAI
MMAI
TAI; Aminotetralins: 6-CAT
8-OH-DPAT
MDAT
MDMAT; Oxazolines: 4-Methylaminorex
Aminorex
Clominorex
Fluminorex; Phenethylamines (also Amphetamines, Cathinones, Phentermines, etc): 2-Methyl-MDA
4-CAB
4-FA
4-FMA
4-HA
4-MTA
5-APDB
5-Methyl-MDA
6-APDB
6-Methyl-MDA
AEMMA
Amiflamine
BDB
BOH
Brephedrone
Butylone
Chlorphentermine
Cloforex
Amfepramone
Metamfepramone
DCA
DFMDA
DMA
DMMA
EBDB
EDMA
Ethylone
Etolorex
Fenfluramine (Dexfenfluramine, Levofenfluramine)
Flephedrone
IAP
IMP
Iofetamine
Lophophine
MBDB
MDA
MDEA
MDHMA
MDMA
MDMPEA
MDOH
MDPEA
Mephedrone
Methedrone
Methylone
MMA
MMDA
MMDMA
MMMA
NAP
Norfenfluramine
4-TFMA
pBA
pCA
pIA
PMA
PMEA
PMMA
TAP; Piperazines: 2C-B-BZP
3-MeOPP
BZP
DCPP
MBZP
mCPP
MDBZP
MeOPP
Mepiprazole
pCPP
pFPP
pTFMPP
TFMPP; Tryptamines: 4-Methyl-αET
4-Methyl-αMT
5-CT
5-MeO-αET
5-MeO-αMT
5-MT
αET
αMT
DMT
Tryptamine (itself); Others: Indeloxazine
Tramadol
Viqualine

Enzyme inhibitors

Anabolism

TPH	AGN-2979 Fenclonine

AAAD	Benserazide Carbidopa Genistein Methyldopa

Catabolism

MAO

Nonselective: Benmoxin
Caroxazone
Echinopsidine
Furazolidone
Hydralazine
Indantadol
Iproclozide
Iproniazid
Isocarboxazid
Isoniazid
Linezolid
Mebanazine
Metfendrazine
Nialamide
Octamoxin
Paraxazone
Phenelzine
Pheniprazine
Phenoxypropazine
Pivalylbenzhydrazine
Procarbazine
Safrazine
Tranylcypromine; MAO-A Selective: Amiflamine
Bazinaprine
Befloxatone
Brofaromine
Cimoxatone
Clorgiline
Eprobemide
Esuprone
Harmala alkaloids (Harmine
Harmaline
Tetrahydroharmine
Harman
Norharman, etc)
Methylene Blue
Metralindole
Minaprine
Moclobemide
Pirlindole
Sercloremine
Tetrindole
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; Steroids: Anabolic-androgenic steroids

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Robalzotan

See also

References