8-OH-DPAT

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8-OH-DPAT

IUPAC name 8-Hydroxy-2-(di-n-propylamino)tetralin^{[citation needed]}
Systematic name 7-(Dipropylamino)-5,6,7,8-tetrahydronaphthalen-1-ol^[1]
Identifiers
Abbreviations	8-OH-DPAT
CAS number	78950-78-4^N
PubChem	1220, 6603866 (R), 10125797 (S)
ChemSpider	1183^Y, 5036174 (R)^Y, 8301316 (S)^Y
MeSH	8-Hydroxy-2-(di-N-propylamino)tetralin
ChEMBL	CHEMBL56^Y
IUPHAR ligand	7
Jmol-3D images	Image 1 Image 2
SMILES CCCN(CCC)C1CCc2cccc(O)c2C1 CCCN(CCC)C1CCC2=C(C1)C(O)=CC=C2
InChI InChI=1S/C16H25NO/c1-3-10-17(11-4-2)14-9-8-13-6-5-7-16(18)15(13)12-14/h5-7,14,18H,3-4,8-12H2,1-2H3^Y Key: ASXGJMSKWNBENU-UHFFFAOYSA-N^Y InChI=1/C16H25NO/c1-3-10-17(11-4-2)14-9-8-13-6-5-7-16(18)15(13)12-14/h5-7,14,18H,3-4,8-12H2,1-2H3 Key: ASXGJMSKWNBENU-UHFFFAOYAY
Properties
Molecular formula	C₁₆H₂₅NO
Molar mass	247.38 g mol⁻¹
Exact mass	247.193614427 g mol^-1
log P	3.711
Acidity (pK_a)	10.539
Basicity (pK_b)	3.458
Pharmacology
Elimination half-life	1.5 hours
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

8-OH-DPAT is a research chemical of the aminotetralin chemical class which was developed in the 1980s and has been widely used to study the function of the 5-HT_1A receptor. It was one of the first major 5-HT_1A receptor agonists to be discovered.

Originally believed to be selective for the 5-HT_1A receptor, 8-OH-DPAT was later found to act as a 5-HT₇ receptor agonist and serotonin reuptake inhibitor/releasing agent as well.^[2]^[3]^[4]^[5]^[6]

In animal studies, 8-OH-DPAT has been shown to possess antidepressant,^[7] anxiolytic,^[8] serenic,^[9] anorectic,^[10] antiemetic,^[11] hypothermic,^[12] hypotensive,^[13] bradycardic,^[13] hyperventilative,^[14]^[15]^[16] and analgesic effects.^[17]

References

^ "8-hydroxy-2-(di-N-propylamino)tetralin - PubChem Public Chemical Database". The PubChem Project. USA: National Center for Biotechnology Information. http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=1220.
^ Larsson LG, Rényi L, Ross SB, Svensson B, Angeby-Möller K (February 1990). "Different effects on the responses of functional pre- and postsynaptic 5-HT1A receptors by repeated treatment of rats with the 5-HT1A receptor agonist 8-OH-DPAT". Neuropharmacology 29 (2): 85–91. doi:10.1016/0028-3908(90)90047-U. PMID 1691832.
^ Sprouse J, Reynolds L, Li X, Braselton J, Schmidt A (January 2004). "8-OH-DPAT as a 5-HT7 agonist: phase shifts of the circadian biological clock through increases in cAMP production". Neuropharmacology 46 (1): 52–62. doi:10.1016/j.neuropharm.2003.08.007. PMID 14654097. http://linkinghub.elsevier.com/retrieve/pii/S0028390803003472.
^ "IUPHAR DATABASE - 5-Hydroxytryptamine receptors - 5-HT₇". http://www.iuphar-db.org/GPCR/ReceptorDisplayForward?receptorID=2337.
^ Assié MB, Koek W (November 1996). "Possible in vivo 5-HT reuptake blocking properties of 8-OH-DPAT assessed by measuring hippocampal extracellular 5-HT using microdialysis in rats". British Journal of Pharmacology 119 (5): 845–50. PMC 1915946. PMID 8922730. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1915946.
^ Wölfel R, Graefe KH (February 1992). "Evidence for various tryptamines and related compounds acting as substrates of the platelet 5-hydroxytryptamine transporter". Naunyn-Schmiedeberg's Archives of Pharmacology 345 (2): 129–36. doi:10.1007/BF00165727. PMID 1570019.
^ Luscombe GP, Martin KF, Hutchins LJ, Gosden J, Heal DJ (March 1993). "Mediation of the antidepressant-like effect of 8-OH-DPAT in mice by postsynaptic 5-HT1A receptors". British Journal of Pharmacology 108 (3): 669–77. PMC 1908013. PMID 8467355. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1908013.
^ Schreiber R, De Vry J (November 1993). "Neuronal circuits involved in the anxiolytic effects of the 5-HT1A receptor agonists 8-OH-DPAT ipsapirone and buspirone in the rat". European Journal of Pharmacology 249 (3): 341–51. doi:10.1016/0014-2999(93)90531-L. PMID 7904566.
^ de Boer SF, Koolhaas JM (December 2005). "5-HT1A and 5-HT1B receptor agonists and aggression: a pharmacological challenge of the serotonin deficiency hypothesis". European Journal of Pharmacology 526 (1–3): 125–39. doi:10.1016/j.ejphar.2005.09.065. PMID 16310183.
^ Dourish CT, Hutson PH, Curzon G (October 1985). "Characteristics of feeding induced by the serotonin agonist 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT)". Brain Research Bulletin 15 (4): 377–84. doi:10.1016/0361-9230(85)90005-X. PMID 2933126. http://linkinghub.elsevier.com/retrieve/pii/0361-9230(85)90005-X.
^ Lucot JB (February 1994). "Antiemetic effects of flesinoxan in cats: comparisons with 8-hydroxy-2-(di-n-propylamino)tetralin". European Journal of Pharmacology 253 (1–2): 53–60. doi:10.1016/0014-2999(94)90756-0. PMID 8013549.
^ O'Connell MT, Sarna GS, Curzon G (July 1992). "Evidence for postsynaptic mediation of the hypothermic effect of 5-HT1A receptor activation". British Journal of Pharmacology 106 (3): 603–9. PMC 1907559. PMID 1387027. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1907559.
^ ^a ^b Fozard JR, Mir AK, Middlemiss DN (March 1987). "Cardiovascular response to 8-hydroxy-2-(di-n-propylamino) tetralin (8-OH-DPAT) in the rat: site of action and pharmacological analysis". Journal of Cardiovascular Pharmacology 9 (3): 328–47. doi:10.1097/00005344-198703000-00010. PMID 2437400.
^ Sahibzada N, Ferreira M, Wasserman AM, Taveira-DaSilva AM, Gillis RA (February 2000). "Reversal of morphine-induced apnea in the anesthetized rat by drugs that activate 5-hydroxytryptamine(1A) receptors". The Journal of Pharmacology and Experimental Therapeutics 292 (2): 704–13. PMID 10640309.
^ Meyer LC, Fuller A, Mitchell D (February 2006). "Zacopride and 8-OH-DPAT reverse opioid-induced respiratory depression and hypoxia but not catatonic immobilization in goats". American Journal of Physiology. Regulatory, Integrative and Comparative Physiology 290 (2): R405–13. doi:10.1152/ajpregu.00440.2005. PMID 16166206.
^ Guenther U, Manzke T, Wrigge H, Dutschmann M, Zinserling J, Putensen C, Hoeft A (April 2009). "The counteraction of opioid-induced ventilatory depression by the serotonin 1A-agonist 8-OH-DPAT does not antagonize antinociception in rats in situ and in vivo". Anesthesia and Analgesia 108 (4): 1169–76. doi:10.1213/ane.0b013e318198f828. PMID 19299781.
^ Xu W, Qiu XC, Han JS (June 1994). "Serotonin receptor subtypes in spinal antinociception in the rat". The Journal of Pharmacology and Experimental Therapeutics 269 (3): 1182–9. PMID 8014862. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=8014862.

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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 Lubazodone 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)	Amitifadine Bicifadine Brasofensine BTS-74,398 Cocaine Diclofensine DOV-21,947 DOV-102,677 DOV-216,303 EXP-561 Fezolamine JNJ-7925476 NS-2359 PRC200-SS Pridefine SEP-225,289 SEP-227,162 Tesofensine

Norepinephrine reuptake inhibitors (NRIs)	Amedalin Atomoxetine/Tomoxetine Binedaline Ciclazindol Daledalin Esreboxetine Lortalamine 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 Nefazodone 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

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 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 Befol Berberine Brofaromine Cimoxatone Esuprone 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

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	Emylcamate • 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

Others	Chlormezanone • Ethanol (Alcohol) • Etifoxine • Kavalactones (Kava Kava) • Skullcap • Valerenic Acid (Valerian)

α₂δ VDCC Blockers

Gabapentin • Pregabalin

5-HT_1A Agonists

Azapirones: Buspirone • Gepirone • Tandospirone; Others: Flesinoxan • Oxaflozane

H₁ Antagonists

Diphenylmethanes: Captodiame • Hydroxyzine; Others: Brompheniramine • Chlorpheniramine • Pheniramine

CRH₁ Antagonists

Antalarmin • CP-154,526 • Pexacerfont • Pivagabine

NK₂ Antagonists

GR-159,897 • Saredutant

MCH₁ antagonists

ATC-0175 • SNAP-94847

mGluR₂_/₃ Agonists

DAA-1097 • DAA-1106 • Emapunil • FGIN-127 • FGIN-143

σ₁ agonists

Afobazole • Opipramol

Others

Benzoctamine • Carbetocin • Demoxytocin • Mephenoxalone • Mepiprazole • Oxanamide • Oxytocin • Promoxolane • Tofisopam • Trimetozine • WAY-267,464

^#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)

v t e Serenics (Antiaggressive Agents)

Serotonin Reuptake Inhibitors	SSRIs • SNRIs • SNDRIs • TCAs • .....

Serotonin Releasing Agents	4-MTA • AET • AMT • Aminorex • Chlorphentermine • Fenfluramine • IAP • MDxx • MMA • PMA • .....

Monoamine Oxidase Inhibitors	Isocarboxazid • Moclobemide • Nialamide • Phenelzine • Tranylcypromine • .....

Serotonin Synthesis Precursors	L-Tryptophan • L-5-HTP

5-HT_1A Receptor Agonists	8-OH-DPAT • Batoprazine • Buspirone • Eltoprazine • Fluprazine • Gepirone • Ipsapirone • S-15535 • Tandospirone • .....

5-HT_1B Receptor Agonists	Batoprazine • Eltoprazine • Fluprazine • .....

Oxytocin Receptor Agonists	Carbetocin • Demoxytocin • Oxytocin • WAY-267,464

Miscellaneous	Antiandrogens • Atypical Antipsychotics • Benzodiazepines • Beta Blockers • Clonidine • Lithium • Medetomidine • .....

Analgesics (N02A, N02B)

Opioids
See also: Opioids template

Opium & alkaloids thereof	Codeine^# Morphine^# Opium Laudanum Paregoric

Semi-synthetic opium derivatives	Acetyldihydrocodeine Benzylmorphine Buprenorphine Desomorphine Dihydrocodeine Dihydromorphine Ethylmorphine Diamorphine Hydrocodone Hydromorphinol Hydromorphone Nicocodeine Nicodicodeine Nicomorphine Oxycodone Oxymorphone

Synthetic opioids	Alphaprodine Anileridine Butorphanol Dextromoramide Dextropropoxyphene Dezocine Fentanyl Ketobemidone Levorphanol Methadone Meptazinol Nalbuphine Pentazocine Propoxyphene Propiram Pethidine Phenazocine Piminodine Piritramide Tapentadol Tilidine Tramadol

Pyrazolones

Cannabinoids

Anilides

Non-steroidal
anti-inflammatories
See also: NSAIDs template

Propionic acid class	Fenoprofen Flurbiprofen Ibuprofen^# Ketoprofen Naproxen Oxaprozin

Oxicam class	Meloxicam Piroxicam

Acetic acid class	Diclofenac Indometacin Ketorolac Nabumetone Sulindac Tolmetin

COX-2 inhibitors	Celecoxib Rofecoxib Valdecoxib Parecoxib Lumiracoxib

Anthranilic acid (fenamate) class	Meclofenamate Mefenamic acid

Salicylates	Aspirin (Acetylsalicylic acid)^# Benorylate Diflunisal Ethenzamide Magnesium salicylate Salicin Salicylamide Salsalate Trisalate Wintergreen (Methyl salicylate)

Atypical, adjuvant and potentiators,
Metabolic agents and miscellaneous

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

M: CNS

anat(n/s/m/p/4/e/b/d/c/a/f/l/g)/phys/devp

noco(m/d/e/h/v/s)/cong/tumr, sysi/epon, injr

proc, drug(N1A/2AB/C/3/4/7A/B/C/D)

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 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 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 PRX-00023 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 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 CP-286,601 GR-46611 L-694,247 L-772,405 PNU-109,291 PNU-142,633 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 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 2C-C-NBOMe 2C-E 2C-I 2C-TFM-NBOMe 2C-T-2 2C-T-7 2C-T-21 2CBCB-NBOMe 2CBFly-NBOMe Bromo-DragonFLY DOB DOC DOI DOM MDA MDMA Mescaline 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 Dimemebfe Medifoxamine Oxaflozane PNU-22394 RH-34 Antagonists: Atypical antipsychotics: Amperozide Aripiprazole Carpipramine Clocapramine Clorotepine Clozapine Gevotroline Iloperidone Melperone Mosapramine Olanzapine Paliperidone Pimozide Quetiapine Risperidone Sertindole Ziprasidone Zotepine; Typical antipsychotics: Loxapine Pipamperone; Antidepressants: Amitriptyline Amoxapine Aptazapine Etoperidone Mianserin Mirtazapine Nefazodone Teniloxazine Trazodone; Others: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin AMDA APD-215 Blonanserin Cinanserin CSP-2503 Cyproheptadine Deramciclane Dotarizine Eplivanserin Esmirtazapine Fananserin Flibanserin 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 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 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 CP-809,101 Dimemebfe Lorcaserin Medifoxamine MK-212 Org 12,962 ORG-37,684 Oxaflozane PNU-22394 Ro60-0175 Ro60-0213 Vabicaserin WAY-629 WAY-161,503 YM-348 Antagonists: Atypical antipsychotics: Clorotepine Clozapine Iloperidone Melperone Olanzapine Paliperidone Pimozide Quetiapine Risperidone Sertindole Ziprasidone Zotepine; Typical antipsychotics: Chlorpromazine Loxapine Pipamperone; Antidepressants: Agomelatine Amitriptyline Amoxapine Aptazapine Etoperidone Fluoxetine Mianserin Mirtazapine Nefazodone Nortriptyline Tedatioxetine Trazodone; Others: Adatanserin 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 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 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 Clorotepine Clozapine Olanzapine Risperidone Sertindole Tiospirone Ziprasidone Zotepine; Typical antipsychotics: Chlorpromazine Loxapine; Others: Butaclamol EGIS-12,233 Ketanserin LY-215,840 Metitepine/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 Vortioxetine

Reuptake inhibitors

SERT	Selective serotonin reuptake inhibitors (SSRIs): Alaproclate Citalopram Dapoxetine Desmethylcitalopram Desmethylsertraline Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Litoxetine Lubazodone Panuramine Paroxetine Pirandamine RTI-353 Seproxetine Sertraline Tedatioxetine 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 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 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)
Flephedrone
IAP
IMP
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
2-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
Befol
Brofaromine
Cimoxatone
Clorgiline
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

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