Palazestrant - Wikipedia

Palazestrant
Clinical data

Other names	OP-1250
Identifiers
IUPAC name (1R,3R)-2-(2-fluoro-2-methyl-propyl)-3-methyl-1-[4-(1-propylazetidin-3-yl)oxyphenyl]-1,3,4,9-tetrahydropyrido[3,4-b]indole
CAS Number	2092925-89-6
PubChem CID	135351887
DrugBank	DB18971
ChemSpider	128922074
UNII	VU35KM56Q4
KEGG	D12827
ChEMBL	ChEMBL5314475
Chemical and physical data
Formula	C₂₈H₃₆FN₃O
Molar mass	449.614 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCN1CC(C1)OC2=CC=C(C=C2)[C@@H]3C4=C(C[C@H](N3CC(C)(C)F)C)C5=CC=CC=C5N4
InChI InChI=1S/C28H36FN3O/c1-5-14-31-16-22(17-31)33-21-12-10-20(11-13-21)27-26-24(23-8-6-7-9-25(23)30-26)15-19(2)32(27)18-28(3,4)29/h6-13,19,22,27,30H,5,14-18H2,1-4H3/t19-,27-/m1/s1 Key:LBSFUBLFDCAEKV-XHCCPWGMSA-N

Palazestrant is an investigational new drug which is being evaluated for the treatment of estrogen receptor-positive (ER+) breast cancer, with a dual mechanism of action as both a complete estrogen receptor antagonist (CERAN) and a selective estrogen receptor degrader (SERD). This orally bioavailable small molecule has demonstrated potent activity against both wild-type and mutant forms of the estrogen receptor.^[1]

References

[edit]

↑ Parisian AD, Barratt SA, Hodges-Gallagher L, Ortega FE, Peña G, Sapugay J, et al. (March 2024). "Palazestrant (OP-1250), A Complete Estrogen Receptor Antagonist, Inhibits Wild-type and Mutant ER-positive Breast Cancer Models as Monotherapy and in Combination". Molecular Cancer Therapeutics. 23 (3): 285–300. doi:10.1158/1535-7163.MCT-23-0351. PMC 10911704. PMID 38102750.

Estrogen receptor modulators

Agonists	Steroidal: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol 3α-Androstanediol 3α,5α-Dihydrolevonorgestrel 3β,5α-Dihydrolevonorgestrel 3α-Hydroxytibolone 3β-Hydroxytibolone 3β-Androstanediol 4-Androstenediol 4-Androstenedione 4-Fluoroestradiol 4-Hydroxyestradiol 4-Hydroxyestrone 4-Methoxyestradiol 4-Methoxyestrone 5-Androstenediol 7-Oxo-DHEA 7α-Hydroxy-DHEA 7α-Methylestradiol 7β-Hydroxyepiandrosterone 8,9-Dehydroestradiol 8,9-Dehydroestrone 8β-VE2 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED) 11β-Chloromethylestradiol 11β-Methoxyestradiol 15α-Hydroxyestradiol 16-Ketoestradiol 16-Ketoestrone 16α-Fluoroestradiol 16α-Hydroxy-DHEA 16α-Hydroxyestrone 16α-Iodoestradiol 16α-LE2 16β-Hydroxyestrone 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol) 17α-Estradiol (alfatradiol) 17α-Dihydroequilenin 17α-Dihydroequilin 17α-Epiestriol (16α-hydroxy-17α-estradiol) 17α-Ethynyl-3α-androstanediol 17α-Ethynyl-3β-androstanediol 17β-Dihydroequilenin 17β-Dihydroequilin 17β-Methyl-17α-dihydroequilenin Abiraterone Abiraterone acetate Alestramustine Almestrone Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites) Atrimustine Bolandiol Bolandiol dipropionate Butolame Clomestrone Cloxestradiol Cloxestradiol acetate Conjugated estriol Conjugated estrogens Cyclodiol Cyclotriol DHEA DHEA-S ent-Estradiol Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol) Epimestrol Equilenin Equilin ERA-63 (ORG-37663) Esterified estrogens Estetrol Estradiol Estradiol esters Lipoidal estradiol Polyestradiol phosphate Estramustine Estramustine phosphate Estrapronicate Estrazinol Estriol Estriol esters Polyestriol phosphate Estrofurate Estrogenic substances Estromustine Estrone Estrone esters Estrone methyl ether Estropipate Etamestrol (eptamestrol) Ethinylandrostenediol Ethandrostate Ethinylestradiol Ethinylestradiol 3-benzoate Ethinylestradiol sulfonate Ethinylestriol Ethylestradiol Etynodiol Etynodiol diacetate Hexolame Hippulin Hydroxyestrone diacetate Lynestrenol Lynestrenol phenylpropionate Mestranol Methylestradiol Moxestrol Mytatrienediol Nilestriol Norethisterone Noretynodrel Orestrate Pentolame Prodiame Prolame Promestriene RU-16117 Quinestradol Quinestrol Tibolone Nonsteroidal: (R,R)-THC (S,S)-THC 2,8-DHHHC β-LGND1 β-LGND2 (GTx-878) AC-186 Allenestrol Allenolic acid Benzestrol Bifluranol Bisdehydrodoisynolic acid Butestrol Carbestrol D-15414 DCW234 Diarylpropionitrile Dienestrol Dienestrol diacetate Diethylstilbestrol Diethylstilbestrol esters Dimestrol (dianisylhexene) Dimethylstilbestrol Doisynoestrol (fenocycline) Doisynolic acid Efavirenz Elacestrant ERB-196 (WAY-202196) Erteberel (SERBA-1, LY-500307) Estrobin (DBE) Fenestrel FERb 033 Fosfestrol (diethylstilbestrol diphosphate) Furostilbestrol (diethylstilbestrol difuroate) GTx-758 Hexestrol Hexestrol esters ICI-85966 (Stilbostat) M2613 meso-Butestrol meso-Hexestrol Mestilbol Methallenestril Methestrol Methestrol dipropionate OSU-ERβ-12 Paroxypropione Pentafluranol Phenestrol Prinaberel (ERB-041, WAY-202041) Propylpyrazoletriol Quadrosilan SC-3296 SC-4289 SERBA-2 SKF-82,958 Terfluranol Triphenylbromoethylene Triphenylchloroethylene Triphenyliodoethylene Triphenylmethylethylene (triphenylpropene) WAY-166818 WAY-169916 WAY-200070 WAY-204688 (SIM-688) WAY-214156 Unknown/unsorted: ERB-26 ERA-45 ERB-79 ZK-283197 Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole) Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone) Coumestans (e.g., coumestrol, psoralidin) Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, epicatechin, equol, formononetin, glabrene, glabridin, genistein, genistin, glycitein, kaempferol, liquiritigenin, mirificin, myricetin, naringenin, penduletin, pinocembrin, prunetin, puerarin, quercetin, tectoridin, tectorigenin) Lavender oil Lignans (e.g., enterodiol, enterolactone, nyasol (cis-hinokiresinol)) Metalloestrogens (e.g., cadmium) Pesticides (e.g., alternariol, dieldrin, endosulfan, fenarimol, HPTE, methiocarb, methoxychlor, triclocarban, triclosan) Phytosteroids (e.g., digitoxin (digitalis), diosgenin, guggulsterone) Phytosterols (e.g., β-sitosterol, campesterol, stigmasterol) Resorcylic acid lactones (e.g., zearalanone, α-zearalenol, β-zearalenol, zearalenone, zeranol (α-zearalanol), taleranol (teranol, β-zearalanol)) Steroid-like (e.g., deoxymiroestrol, miroestrol) Stilbenoids (e.g., resveratrol, rhaponticin) Synthetic xenoestrogens (e.g., alkylphenols, bisphenols (e.g., BPA, BPF, BPS), DDT, parabens, PBBs, PHBA, phthalates, PCBs) Others (e.g., agnuside, rotundifuran)
Mixed (SERMsTooltip Selective estrogen receptor modulators)	2-Phenylbenzofuran 2-Phenyl-1-benzothiophene 4'-Hydroxynorendoxifen 27-Hydroxycholesterol Acefluranol Acolbifene Afimoxifene Anordiol Anordrin Arzoxifene Bazedoxifene Brilanestrant Broparestrol Camizestrant Chlorotrianisene Clomifene Clomifenoxide CN-55945-27 Cyclofenil D-15413 Desmethylchlorotrianisene Droloxifene Enclomifene Endoxifen Etacstil (GW-5638, DPC-974) Ethamoxytriphetol (MER-25) Femarelle Fispemifene GW-7604 ICI-55548 Idoxifene Lasofoxifene Levormeloxifene LN-1643 LN-2299 LY-117018 Menerba Miproxifene Miproxifene phosphate MRL-37 Nafoxidine Nitromifene NNC 45-0095 NNC 45-0320 NNC 45-0781 NNC 45-1506 Ormeloxifene Ospemifene Panomifene Pipendoxifene Promensil Raloxifene Rimostil (P-081) Spironolactone SS1010 Tamoxifen TAS-108 (SR-16234) Toremifene Trioxifene TZE-5323 U-11555A U-11634 Y-134 Zindoxifene Zuclomifene
Antagonists	(R,R)-THC 7β-Hydroxy-DHEA Chloroindazole Cytestrol acetate EM-800 (SCH-57050) Epitiostanol ERA-90 ERB-88 Fulvestrant (ICI-182780) Glyceollins (I, II, III, IV) ICI-164384 MDL-101906 Mepitiostane Methylepitiostanol Methylpiperidinopyrazole MIBE Oxabicycloheptene sulfonate Phenytoin PHTPP Prochloraz RU-39411 RU-58668 SS1020 TAS-108 (SR-16234) ZB716 ZK-164015 ZK-191703 Coregulator-binding modulators: ERX-11 Noncompetitive inhibitors: Trilostane

GPER

Agonists	2-Methoxyestradiol 7β-Hydroxyepiandrosterone Afimoxifene (4-hydroxytamoxifen) Aldosterone Atrazine Bisphenol A Daidzein DDT (p,p'-DDT, o',p'-DDE) Diarylpropionitrile Equol Estradiol Ethinylestradiol Fulvestrant (ICI-182780) G-1 Genistein GPER-L1 GPER-L2 Hydroxytyrosol Kepone Nicotinic acid Nicotinamide Nonylphenol Oleuropein PCBs (2,2',5'-PCB-4-OH) Propylpyrazoletriol Quercetin Raloxifene Resveratrol STX Tamoxifen Tectoridin
Antagonists	CCL18 Estriol G-15 G-36 MIBE
Unknown	Diethylstilbestrol Zearalenone

See also: Receptor/signaling modulators; Estrogens and antiestrogens; Androgen receptor modulators; Progesterone receptor modulators; List of estrogens

v t e Tryptamines
Tryptamines	1-Benzoyl-DMT 1-Methyl-DMT (1,N,N-TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N,N-TMT (2-methyl-DMT) 3-IAAR 4-Bromo-DMT 4-Fluoro-DMT 4-Fluoro-T 4-MeS-DMT 4-Methyl-DMT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-NiPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-Nitro-T (Nitro-I) 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-Fluoro-T 7-HO-DMT 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T 7-Hydroxytryptophan Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) CPI-CG-8 DALT DAT DBT Desformylflustrabromine DET (T-9) DMT-d10 (HLP004; CYB004) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 GR-46611 HBL20016 (5-MeS-6-F-DMT) HBL20017 (4-F-5-MeS-DMT) Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N-Benzyltryptamine (T-NB, NB-T, NBnT) N-(2-Cyanoethyl)tryptamine (CE-T) N-DEAOP-NET N-DEAOP-NMT N-Phosphonooxymethyl-DMT (N-POM-DMT) NAT NBoc-DMT (NB-DMT) NcPT NET/NETP NPT NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan T-NBOMe TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 ZCZ-011 Zolmitriptan
4-Hydroxytryptamines and esters/ethers	1-Methylpsilocin (CMY-16) 4-AcO-DALT 4-AcO-DET (ethacetin, ethylacybin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin; O-acetylpsilocin) 4-AcO-DPT (depracetin) 4-AcO-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-AcO-NMT 4-AcO-TMT 4-HO-5-MeO-T 4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiBT 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-DsBT 4-HO-EiBT (eibucin) 4-HO-EiPT 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-MET (metocin) 4-HO-McPT 4-HO-McPeT 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-MsBT 4-HO-NALT 4-HO-NBnT 4-HO-NcHT 4-HO-NET 4-HO-NiPT 4-HO-NBT (4-HO-NnBT) 4-HO-NPT 4-HO-NtBT 4-HO-PiPT (piprocin) 4-HO-TMT 4-HT (dinorpsilocin) 4-MeO-DET 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Deupsilocin (HLP003; CYB003) EB-002 (EB-373) Ethocybin (4-PO-DET; CEY-19) Luvesilocin (4-GO-DiPT; RE-104; FT-104) MSP-1014 Norbaeocystin (4-PO-T) Norpsilocin (4-HO-NMT) O-4310 (1-iPrO-6-F-psilocin) Psilocin (4-HO-DMT; CX-59) Psilocybin (4-PO-DMT; CY-39) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) RE-109 (4-GO-DMT)
5-Hydroxy- and 5-methoxytryptamines	1-Acetyl-5-MeO-DMT 2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-DPT 5-HO-MET 5-HO-NiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N,N,O-TMS; O-methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MBT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O,N-DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine; O-methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MTP (cytoguardin) 5-NOT 5-PhO-T (OVT2) 5,6-DHT 5,6-DiMeO-DiPT (5,6-MeO-DiPT) 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ; N,N,N-TMS) Bufotenin (5-HO-DMT; N,N-DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) IS-159 Isamide (N-CA-5-MT) L-741604 MS-245 N-DEAOP-5-MeO-NET N-DEAOP-5-MeO-NMT N-Feruloylserotonin (moschamine) NB-5-MeO-DALT NB-5-MeO-DMT NB-5-MeO-MiPT Norbufotenin (5-HO-NMT; NMS) O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT)
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin (N-Ac-O-Me-serotonin; N-Ac-5-MeO-T) Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301 (LY-156735)
α-Alkyltryptamines	1-Methyl-AMT 2,α-DMT (2-Me-AMT) 4-HO-αET 4-HO-αMT (MP-14) 4-Methyl-αET 4-Methyl-αMT (MP-809) 5-Chloro-αET (PAL-526) 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212; PAL-544) 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Me-αET α-Methyltryptophan (αMTP) α,N-DMT (N-Me-αMT; SKF-7024, Ro 3-1715) α,N,N-TMT (α-Me-DMT; Alpha-N) αET (etryptamine; Monase) αMT (Indopan; IT-290; 3-API; 3-IT) IPAP (α,N-DPT) N-Hydroxy-AMT Soclenicant (BNC-210; Ile–Trp) 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O-DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 β-Keto-α-alkyltryptamines: BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT
α-Ketotryptamines	AB-CHMIATA ADB-FUBIATA (ADB-FUBIACA) ADB-IACA AFUBIATA CH-FUBIATA (CH-FUBIACA) CH-HEXIATA CH-IACA CH-PIATA CH-PIATA N-(4-carboxybutyl) CH-PIATA N-(4-hydroxypentyl) CHM-FUBIATA
Cyclized tryptamines	5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD) Harmala alkaloids and β-carbolines (e.g., 5-methoxyharmalan, norharmine 6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine, tabernanthine) Ibogalogs (e.g., catharanthalog, fluorogainalog, ibogainalog, ibogaminalog (DM-506), LS-22925, noribogainalog, noribogaminalog, PHA-57378, Pharm-136, PNU-22394, tabernanthalog) Imidazolylindoles (e.g., AGH-107, AGH-192, AH-494) Metralindole Morpholinylethylindoles (e.g., mor-T, 5-MeO-mor-T) Partial ergolines and lysergamides (e.g., NDTDI, RU-27849, RU-28251, RU-28306, FHATHBIN, LY-178210, LY-301317, Bay R 1531 (LY-197206), LY-293284, 10,11-seco-LSD, 10,11-secoergoline (α,N-Pip-T), CT-5252) Pertines (e.g., alpertine, milipertine, oxypertine, solypertine) Piperidinylethylindoles (e.g., pip-T, 5-MeO-pip-T, indoramin, indolylethylfentanyl) Pyrrolidinylethylindoles (e.g., pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, 4-F-5-MeO-pyr-T, L-760790) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-122288, CP-135807, eletriptan, MSP-2020) Tetrahydrocarbazolamines (e.g., ciclindole, flucindole, frovatriptan, LY-344864, ramatroban) Tetrahydropyridinylindoles (e.g., RS134-49, RU-28253, NEtPhOH-THPI) Tetrahydropyrroloquinolines (e.g., bufothionine, O-methylnordehydrobufotenine, dehydrobufotenine) Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine) Z5247692566
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT isoAMT (1-API; 1-IT; α-Me-isoT) isoDMT Isotryptamine (isoT) Ro60-0175 VER-3323 Zalsupindole (DLX-001, AAZ-A-154) Cyclized isotryptamines: DLX-0002700 JRT PNU-181731
Related compounds	1-Methylmedmain 2-Azapsilocin 2,3-Dihydro-L-tryptophan 2,3-Dihydrotryptamine 2,3-Dihydro-DMT 2,3-Dihydro-NMT 2,3-Dihydro-DET 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g., γ-carboline, 2MePI, 8MeO-2MePI, alosetron, gevotroline, latrepirdine, lurosetron, mebhydrolin, tiflucarbine) Amedalin Benzindopyrine Benzydamine Benzofurans (e.g., 3-APB (1-oxa-AMT), 5-MeO-DiBF (1-oxa-5-MeO-DiPT), BPAP, 3-F-BPAP, dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT), mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT), MiPBF (1-oxa-MiPT), oxa-noribogaine) Benzothiophenes (e.g., S-DMT (1-thia-DMT), 3-APBT (1-thia-AMT)) BMS-505130 Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g., HT, DMHT) I-32 IAL Indalpine Indazolethylamines (e.g., AL-34662, AL-38022A, O-methyl-AL-34662, VU6067416, YM-348) Indenylethylamines (e.g., C-DMT (1-carba-DMT)) Indolizinylethylamines (e.g., TACT908 (2ZEDMA), 1ZP2MA, 1Z2MAP1O) Indolylaminopropanes (e.g., 1-API, 2-API, 4-API, 5-API (5-IT; PAL-571), 6-API (6-IT), 7-API) Iprindole Masupirdine Medmain Methylindolylethylpyridine (IN-399) Molindone Non-tryptamine triptans (e.g., avitriptan, LY-334370, naratriptan) Ondansetron Oxazinopyridoindoles (e.g., IHCH-8134) Phenethylamines (e.g., phenethylamine, amphetamine) Piperazinylbenzisothiazoles (e.g., lurasidone, perospirone, tiospirone, ziprasidone) Piperidinylbenzimidazolines (e.g., benperidol, timiperone) Piperidinylbenzisoxazoles (e.g., iloperidone, milsaperidone, ocaperidone, paliperidone, risperidone) Piperidinylindoles (e.g., BRL-54443, LY-334370, naratriptan, sertindole, SN-22) Pirlindole Pyridinylbenzimidazoles (e.g., droperidol) Pyridinylindoles (e.g., tepirindole) Pyridopyrroloquinoxalines (e.g., IHCH-7113, IHCH-7079, IHCH-7086, lumateperone, deulumateperone, ITI-1549) Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA), 3-pyrrolylethylamine (3-NEA), 3-pyrrolylpropylamine) Pyrrolopyridinylethylamines (e.g., WAY-208466) Quinolinylethylamines (e.g., mefloquine) Ro60-0213 Roxindole (EMD-49980) Selisistat Tetrahydropyridinylindoles (e.g., EMD-386088, LY-367265, RU-24,969) Tetrahydropyridinylpyrrolopyridines (e.g., (R)-69 (3IQ), (R)-70, CP-93129, CP-94253) Tetrindole Tipindole Zilpaterol (RU-42173)
See also: Phenethylamines Ergolines and lysergamides Psychedelics Simple tryptamines and common derivatives

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