O-4310

O-4310
Systematic (IUPAC) name

3-[2-(dimethylamino)ethyl]-6-fluoro-1-isopropyl-1H-indol-4-ol
Clinical data
Identifiers
CAS Registry Number	885671-63-6^N
PubChem	CID 68541087
Chemical data
Formula	C₁₅H₂₁F N₂O
Molecular mass	264.34 g/mol
SMILES CC(C)N1C2=CC(F)=CC(O)=C2C(CCN(C)C)=C1

O-4310 (1-isopropyl-6-fluoro-psilocin) is a tryptamine derivative developed by Organix which acts as a serotonin receptor agonist. It is claimed to have an EC₅₀ of 5nM at 5-HT_2A with 89% efficacy vs 5-HT, and 100x selectivity over 5-HT_2C, while being apparently inactive at the 5-HT_2B antitarget.^[1]

References

↑ Govindaraj Kumaran, Cynthia Morency, Bryan Roth, Sard Howard P, Louis Shuster, Liang Xu. Indole compounds useful as serotonin selective agents. Patent US 7655691

Serotonergics

5-HT₁ receptor ligands

5-HT_1A	Agonists: 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g., etoperidone, nefazodone, trazodone, vilazodone, vortioxetine) Atypical antipsychotics (e.g., aripiprazole, asenapine, clozapine, lurasidone, quetiapine, ziprasidone) Azapirones (e.g., buspirone, eptapirone, gepirone, perospirone, tandospirone) Bay R 1531 Befiradol BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide) F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Lesopitron LY-293284 LY-301317 mCPP MKC-242 Naluzotan NBUMP Osemozotan Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin) U-92016A Urapidil Vilazodone Xaliproden Yohimbine Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) AV965 Beta blockers (e.g., alprenolol, cyanopindolol, iodocyanopindolol, oxprenolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) Flopropione GR-46611 Isamoltane Lecozotan Mefway Metitepine (methiothepin) MIN-117 MPPF NAN-190 Robalzotan S-15535 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

5-HT_1B	Agonists: CGS-12066A CP-93129 CP-94253 CP-135807 Eltoprazine Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) mCPP RU-24969 Serotonin (5-HT) Triptans (e.g., avitriptan, donitriptan, eletriptan, sumatriptan, zolmitriptan) TFMPP Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT) Vortioxetine Antagonists: AR-A000002 Elzasonan Ergolines (e.g., metergoline) GR-127935 Isamoltane LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 Yohimbine Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride)

5-HT_1D	Agonists: 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) Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, naratriptan, rizatriptan, sumatriptan, zolmitriptan) Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT) Antagonists: Alniditan BRL-15572 Elzasonan Ergolines (e.g., metergoline) GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin Yohimbine Ziprasidone Unknown/unsorted: Ergolines (e.g., lisuride, lysergol, pergolide)

5-HT_1E	Agonists: BRL-54443 Ergolines (e.g., methysergide) Serotonin (5-HT) Triptans (e.g., eletriptan) Tryptamines (e.g., tryptamine) Antagonists: Metitepine (methiothepin) Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine)

5-HT_1F	Agonists: BRL-54443 Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide) Lasmiditan LY-334370 Serotonin (5-HT) Triptans (e.g., eletriptan, naratriptan, sumatriptan) Tryptamines (e.g., 5-MT) Antagonists: Mianserin Metitepine (methiothepin)

5-HT₂ receptor ligands

5-HT_2A	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., ALD-52, bromocriptine, cabergoline, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide) Jimscaline MDxx (e.g., MDA, MDMA, MDOH, MMDA) Medifoxamine O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, mCPP, 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 AMDA APD-215 Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, melperone, mosapramine, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine) Cinanserin CSP-2503 Cyproheptadine Deramciclane Dotarizine Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fananserin Flibanserin Glemanserin Irindalone Ketanserin KML-010 Lubazodone LY-393558 Mepiprazole Metitepine (methiothepin) MIN-101 Nantenine Nefazodone Pimavanserin Pirenperone Pizotifen Pruvanserin Rauwolscine Ritanserin S-14671 Sarpogrelate Setoperone Spiperone Spiramide SR-46349B Teniloxazine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) Trazodone Tricyclic antidepressants (e.g., amitriptyline) Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, thioridazine, thiothixene, trifluoperazine) Volinanserin Xylamidine Yohimbine Unknown/unsorted: Ergolines (e.g., dihydroergotamine, ergometrine (ergonovine), nicergoline)

5-HT_2B	Agonists: 4-Methylaminorex Aminorex Amphetamines (eg., 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) MDxx (e.g., MDA, MDMA, MDOH, MMDA) Piperazines (e.g., mCPP) 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 Asenapine Cyproheptadine EGIS-7625 Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine) Ketanserin LY-393558 Metadoxine Metitepine (methiothepin) Pirenperone 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) Yohimbine Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine))

5-HT_2C	Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) A-372159 AL-38022A Alstonine CP-809101 Dimemebfe DOx (e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide) Lorcaserin MDxx (e.g., MDA, MDMA, MDOH, MMDA) Medifoxamine MK-212 Org 12962 Org 37684 Oxaflozane PHA-57378 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP) PNU-22394 PNU-181731 Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Vabicaserin WAY-629 WAY-161503 YM-348 Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine) Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Dotarizine Eltoprazine Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fluoxetine FR-260010 Irindalone Ketanserin Ketotifen Latrepirdine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SDZ SER-082 Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) Trazodone Tricyclic antidepressants (e.g., amitriptyline, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine) Xylamidine Unknown/unsorted: Efavirenz Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine))

5-HT₃	Agonists: Alcohols (e.g., butanol, ethanol, 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 AS-8112 Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine) Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron ICS-205930 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 Unknown/unsorted: LY-53857 Piperazines (e.g., naphthylpiperazine)

5-HT₄	Agonists: 5-MT BIMU8 Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) SL65.0155 Tegaserod Velusetrag Zacopride Antagonists: GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070

5-HT_5A	Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD) Serotonin (5-HT) Tryptamines (e.g., 5-CT) Valerenic Acid Antagonists: Asenapine Latrepirdine Metitepine (methiothepin) Ritanserin SB-699551 Unknown/unsorted: Ergolines (e.g., metergoline, methysergide) Piperazines (e.g., naphthylpiperazine)

5-HT₆	Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide) 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, 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 Latrepirdine Metitepine (methiothepin) MS-245 PRX-07034 Ritanserin Ro04-6790 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) Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide) Piperazines (e.g., naphthylpiperazine)

5-HT₇	Agonists: 8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g., LSD) LP-12 LP-44 RU-24969 Sarizotan Serotonin (5-HT) Triptans (e.g., frovatriptan) Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT) Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, 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) 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 Unknown/unsorted: Ergolines (e.g., lisuride, pergolide) Piperazines (e.g., naphthylpiperazine)

Reuptake inhibitors

SERT	Selective serotonin reuptake inhibitors (SSRIs): Alaproclate Citalopram Dapoxetine Desmethylcitalopram Escitalopram Femoxetine Fluoxetine Fluvoxamine Indalpine Ifoxetine Litoxetine Lubazodone Omiloxetine Panuramine Paroxetine Pirandamine RTI-353 Seproxetine Sertraline Zimelidine Serotonin-norepinephrine reuptake inhibitors (SNRIs): Bicifadine BTS-54505 Desvenlafaxine Duloxetine Eclanamine Levomilnacipran McN-5652 Milnacipran N-Methyl-PPPA PPPA SEP-227162 Sibutramine Venlafaxine WY-45233 Serotonin-norepinephrine-dopamine reuptake inhibitors (SNDRIs): (S)-Duloxetine Brasofensine Dasotraline Desmethylsertraline Diclofensine DOV-102677 DOV-21947 DOV-216303 Liafensine NS-2359 Perafensine SEP-228431 SEP-228432 Tedatioxetine Tesofensine Tricyclic antidepressants (TCAs): Amitriptyline Butriptyline Cianopramine Clomipramine Desipramine Dosulepin Doxepin Imipramine Lofepramine Nortriptyline Pipofezine Protriptyline Trimipramine Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine, chlorphenamine, dimenhydrinate, diphenhydramine, mepyramine (pyrilamine), pheniramine, tripelennamine) Arylcyclohexylamines (e.g., ketamine, phencyclidine) CP-39332 Cyclobenzaprine Dextromethorphan Dextrorphan Efavirenz Etoperidone EXP-561 Fezolamine LY-393558 Litoxetine Loxapine Lubazodone Mesembrine Mifepristone MIN-117 N-Me-5-HT Nefazodone Nefopam Opioids (e.g., dextropropoxyphene, methadone, pethidine (meperidine)) PIM-35 Pridefine Roxindole SB-649915 Tofenacin Trazodone Tropanes (e.g., cocaine) Vilazodone Vortioxetine Ziprasidone

VMATs	Amiodarone Amphetamines (e.g., amphetamine, methamphetamine, MDMA) APP AZIK Bietaserpine Deserpidine Dihydrotetrabenazine Efavirenz GBR-12935 GZ-793A Ibogaine Ketanserin Lobeline Methoxytetrabenazine NBI-98854 Reserpine Rose bengal SD-809 Tetrabenazine Vanoxerine (GBR-12909)

Releasing agents

Aminoindanes: 5-IAI
AMMI
ETAI
MDAI
MDMAI
MMAI
TAI

Aminotetralins: 6-CAT
8-OH-DPAT
MDAT
MDMAT

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

Enzyme inhibitors

TPH	AGN-2979 Fenclonine (PCPA)

AAAD	Benserazide Carbidopa Genistein Methyldopa

MAO	Non-selective: 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 (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine) 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⁺)

Neurotoxins	3-CA 4-CAB 5,7-DHT α-Me-DA (3,4-DHA) αET αMT DCA MDA MDMA PBA PCA PIA

Others	Activity enhancers: BPAP PPAP

See also	Serotonin syndrome

See also: Adrenergics • Dopaminergics • Melatonergics

Tryptamines