# Mefway (18F)

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Chemical compound

Pharmaceutical compound

Mefway (18 F) Clinical data Pregnancy category N/A ATC code none Legal status Legal status Research compound Identifiers IUPAC name 4-[(18F)fluoromethyl]-N-{2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl}-N-(pyridin-2-yl)cyclohexane-1-carboxamide CAS Number 943962-60-5 PubChem CID 11963740 ChemSpider 10137857 UNII 0NM517978A CompTox Dashboard (EPA) DTXSID50241461 Chemical and physical data Formula C26H35FN4O2 Molar mass 454.590 g·mol−1 3D model (JSmol) Interactive image SMILES COC1=CC=CC=C1N2CCN(CC2)CCN(C3=CC=CC=N3)C(=O)C4CCC(CC4)C[18F] InChI InChI=1S/C26H35FN4O2/c1-33-24-7-3-2-6-23(24)30-17-14-29(15-18-30)16-19-31(25-8-4-5-13-28-25)26(32)22-11-9-21(20-27)10-12-22/h2-8,13,21-22H,9-12,14-20H2,1H3/i27-1 Key:BQGLPDFQLBNUGU-FMLNDMEQSA-N

**Mefway** is a serotonin [5-HT1A](/source/5-HT1A) [receptor antagonist](/source/Receptor_antagonist) used in medical research, usually in the form of **mefway ([18F](/source/Fluorine-18))** as a [positron emission tomography](/source/Positron_emission_tomography) (PET) [radiotracer](/source/Radiotracer).[1]

## Chemistry

Mefway is closely related to the research compound [WAY-100,635](/source/WAY-100%2C635). The compound adds a fluoromethyl group to the cyclohexyl ring of WAY-100,635 and it is effectively prepared with automation module.[2] There are two [isomers](/source/Isomers) with regard to the cyclohexane ring, of which the *[trans](/source/Cis%E2%80%93trans_isomerism)* conformation has the higher 5-HT1A specificity.[3]

## Animal PET studies

In one study the uptake and retention of mefway (18F) was found to be similar to that found for 11C-WAY-100,635. Head-to-head comparison of mefway (18F) and 11C-WAY-100,635 have been evaluated. Since 11C-WAY-100,635 is the current 'gold standard' and difficult to synthesize, a suitable fluorine-18 replacement as in mefway is highly desired.[4] In addition, mefway (18F) showed comparable brain uptake and the target-to-reference ratios compared to fcway(18F)[5]

The ability to separately measure dissociation constant, KD and receptor density Bmax has been shown to be of potential value rather than simply comparing binding potential, BPND. Multiple injection mefway PET experiments can be used for the in-vivo measurement of 5-HT1A receptor density.[6]

Imaging studies of mefway on in vivo and ex vivo rat brains indicate that the substance binds to the known 5-HT1A receptor regions including the dorsal raphe. These findings support that the dorsal raphe is measurable in rat PET studies.[7] Mefway (18F) undergoes in vivo defluorination in rodent brain and this phenomenon was effectively suppressed by cytochrome P450 inhibitor (i.e. fluconazole).[8] [Animal models of Parkinson's disease](/source/Animal_models_of_Parkinson's_disease) and the acute physical stress model exhibited significant decrement of binding potential in the hippocampus [9][10]

## Human PET studies

First-in-human studies have shown in vivo stability of mefway (18F) and its localization to 5-HT1A receptor-rich regions in the human brain, including the [raphe nucleus](/source/Raphe_nucleus).[11] Mefway (18F) is highly selective for the human serotonin 5-HT1A receptor and may therefore may be used to quantify serotonin 5-HT1A receptor distribution in brain regions for the study of various central nervous system disorders.[12]

## References

1. **[^](#cite_ref-1)** Saigal N, Pichika R, Easwaramoorthy B, Collins D, Christian BT, Shi B, et al. (October 2006). "Synthesis and biologic evaluation of a novel serotonin 5-HT1A receptor radioligand, 18F-labeled mefway, in rodents and imaging by PET in a nonhuman primate". *Journal of Nuclear Medicine*. **47** (10): 1697–706. [PMID](/source/PMID_(identifier)) [17015907](https://pubmed.ncbi.nlm.nih.gov/17015907).

1. **[^](#cite_ref-2)** Choi JY, Kim CH, Ryu YH, Seo YB, Truong P, Kim EJ, et al. (October 2013). "Optimization of the radiosynthesis of [(18) F]MEFWAY for imaging brain serotonin 1A receptors by using the GE TracerLab FXFN-Pro module". *Journal of Labelled Compounds & Radiopharmaceuticals*. **56** (12): 589–94. [doi](/source/Doi_(identifier)):[10.1002/jlcr.3067](https://doi.org/10.1002%2Fjlcr.3067). [PMID](/source/PMID_(identifier)) [24285234](https://pubmed.ncbi.nlm.nih.gov/24285234).

1. **[^](#cite_ref-3)** Wooten D, Hillmer A, Murali D, Barnhart T, Schneider ML, Mukherjee J, Christian BT (October 2011). ["An in vivo comparison of cis- and trans-\[18F\]mefway in the nonhuman primate"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3190069). *Nuclear Medicine and Biology*. **38** (7): 925–32. [doi](/source/Doi_(identifier)):[10.1016/j.nucmedbio.2011.04.001](https://doi.org/10.1016%2Fj.nucmedbio.2011.04.001). [PMC](/source/PMC_(identifier)) [3190069](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3190069). [PMID](/source/PMID_(identifier)) [21741252](https://pubmed.ncbi.nlm.nih.gov/21741252).

1. **[^](#cite_ref-4)** Wooten DW, Moraino JD, Hillmer AT, Engle JW, Dejesus OJ, Murali D, et al. (July 2011). ["In vivo kinetics of \[F-18\]MEFWAY: a comparison with \[C-11\]WAY100635 and \[F-18\]MPPF in the nonhuman primate"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3080024). *Synapse*. **65** (7): 592–600. [doi](/source/Doi_(identifier)):[10.1002/syn.20878](https://doi.org/10.1002%2Fsyn.20878). [PMC](/source/PMC_(identifier)) [3080024](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3080024). [PMID](/source/PMID_(identifier)) [21484878](https://pubmed.ncbi.nlm.nih.gov/21484878).

1. **[^](#cite_ref-5)** Choi JY, Kim BS, Kim CH, Kim DG, Han SJ, Lee K, et al. (December 2014). "18 F]FCWAY in rodents". *Synapse*. **68** (12): 595–603. [doi](/source/Doi_(identifier)):[10.1002/syn.21771](https://doi.org/10.1002%2Fsyn.21771). [PMID](/source/PMID_(identifier)) [25056144](https://pubmed.ncbi.nlm.nih.gov/25056144). [S2CID](/source/S2CID_(identifier)) [23706884](https://api.semanticscholar.org/CorpusID:23706884).

1. **[^](#cite_ref-6)** Wooten DW, Hillmer AT, Moirano JM, Ahlers EO, Slesarev M, Barnhart TE, et al. (August 2012). ["Measurement of 5-HT(1A) receptor density and in-vivo binding parameters of \[(18)F\]mefway in the nonhuman primate"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3421091). *Journal of Cerebral Blood Flow and Metabolism*. **32** (8): 1546–58. [doi](/source/Doi_(identifier)):[10.1038/jcbfm.2012.43](https://doi.org/10.1038%2Fjcbfm.2012.43). [PMC](/source/PMC_(identifier)) [3421091](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3421091). [PMID](/source/PMID_(identifier)) [22472611](https://pubmed.ncbi.nlm.nih.gov/22472611).

1. **[^](#cite_ref-7)** Saigal N, Bajwa AK, Faheem SS, Coleman RA, Pandey SK, Constantinescu CC, et al. (September 2013). ["Evaluation of serotonin 5-HT(1A) receptors in rodent models using \[18F\]mefway PET"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3744326). *Synapse*. **67** (9): 596–608. [doi](/source/Doi_(identifier)):[10.1002/syn.21665](https://doi.org/10.1002%2Fsyn.21665). [PMC](/source/PMC_(identifier)) [3744326](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3744326). [PMID](/source/PMID_(identifier)) [23504990](https://pubmed.ncbi.nlm.nih.gov/23504990).

1. **[^](#cite_ref-8)** Choi JY, Kim CH, Jeon TJ, Kim BS, Yi CH, Woo KS, et al. (December 2012). "Effective microPET imaging of brain 5-HT(1A) receptors in rats with [(18) F]MeFWAY by suppression of radioligand defluorination". *Synapse*. **66** (12): 1015–23. [doi](/source/Doi_(identifier)):[10.1002/syn.21607](https://doi.org/10.1002%2Fsyn.21607). [PMID](/source/PMID_(identifier)) [22927318](https://pubmed.ncbi.nlm.nih.gov/22927318). [S2CID](/source/S2CID_(identifier)) [5266871](https://api.semanticscholar.org/CorpusID:5266871).

1. **[^](#cite_ref-9)** Lee M, Ryu YH, Cho WG, Jeon TJ, Lyoo CH, Kang YW, et al. (December 2014). "Dopaminergic neuron destruction reduces hippocampal serotonin 1A receptor uptake of trans-[(18)F]Mefway". *Applied Radiation and Isotopes*. **94**: 30–34. [doi](/source/Doi_(identifier)):[10.1016/j.apradiso.2014.06.016](https://doi.org/10.1016%2Fj.apradiso.2014.06.016). [PMID](/source/PMID_(identifier)) [25064461](https://pubmed.ncbi.nlm.nih.gov/25064461).

1. **[^](#cite_ref-10)** Choi JY, Shin S, Lee M, Jeon TJ, Seo Y, Kim CH, et al. (August 2014). "Acute physical stress induces the alteration of the serotonin 1A receptor density in the hippocampus". *Synapse*. **68** (8): 363–8. [doi](/source/Doi_(identifier)):[10.1002/syn.21748](https://doi.org/10.1002%2Fsyn.21748). [PMID](/source/PMID_(identifier)) [24771590](https://pubmed.ncbi.nlm.nih.gov/24771590).

1. **[^](#cite_ref-11)** Hillmer AT, Wooten DW, Bajwa AK, Higgins AT, Lao PJ, Betthauser TJ, et al. (December 2014). ["First-in-human evaluation of 18F-mefway, a PET radioligand specific to serotonin-1A receptors"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4316674). *Journal of Nuclear Medicine*. **55** (12): 1973–9. [doi](/source/Doi_(identifier)):[10.2967/jnumed.114.145151](https://doi.org/10.2967%2Fjnumed.114.145151). [PMC](/source/PMC_(identifier)) [4316674](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4316674). [PMID](/source/PMID_(identifier)) [25453045](https://pubmed.ncbi.nlm.nih.gov/25453045).

1. **[^](#cite_ref-12)** Mukherjee J, Bajwa AK, Wooten DW, Hillmer AT, Pan ML, Pandey SK, et al. (May 2016). ["Comparative assessment of (18) F-Mefway as a serotonin 5-HT1A receptor PET imaging agent across species: Rodents, nonhuman primates, and humans"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4783179). *The Journal of Comparative Neurology*. **524** (7): 1457–71. [doi](/source/Doi_(identifier)):[10.1002/cne.23919](https://doi.org/10.1002%2Fcne.23919). [PMC](/source/PMC_(identifier)) [4783179](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4783179). [PMID](/source/PMID_(identifier)) [26509362](https://pubmed.ncbi.nlm.nih.gov/26509362).

v t e Serotonin receptor modulators 5-HT1 5-HT1A Agonists: 4-F-5-MeO-pyr-T 5-MeO-pip-T 5-MeO-pyr-T 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine) Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone) Azapirones (e.g., buspirone, eptapirone (F-11440), gepirone, perospirone, tandospirone) Bay R 1531 Befiradol (NLX-112; F-13640) BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine 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 (NLX-101) F-17464 Flesinoxan Flibanserin Flumexadol GR-46611 Hypidone Lesopitron LY-293284 LY-301317 LY-315712 mCPP Naluzotan NBUMP NLX-204 NLX-266 Osemozotan (MKC-242) 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) TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine Positive allosteric modulators: Cannabicyclol (CBL) Oleamide Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) AV965 AZD-3676 Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) Flopropione Lecozotan LY-206130 LY-297996 ((–)-LY206130) LY-426965 Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-272183 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine Unknown/unsorted: Acetryptine Carvedilol Ergolines (e.g., ergometrine (ergonovine)) 5-HT1B Agonists: Alniditan Anpirtoline AZ10419369 Benzofurans (e.g., 5-MAPB, 6-MAPB, BK-5-MAPB, BK-6-MAPB) Benzothiophenes (e.g., 5-MAPBT, 6-MAPBT, BK-5-MAPBT) CGS-12066 (CGS-12066A, CGS-12066B) CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) GR-46611 mCPP Methylenedioxyphenethylamines (e.g., MDMA, methylone) PGI-7043 PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g., avitriptan, donitriptan, eletriptan, IS-159, sumatriptan, zolmitriptan) TFMPP Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT) Vortioxetine Antagonists: AOP-208 (LB-208) AR-A000002 AZD-3676 Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol) Elzasonan Ergolines (e.g., metergoline) F-12682 F-14258 GR-127935 LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 SB-272183 SB-616234 Trelanserin Yohimbine Negative allosteric modulators: 5-HT-moduline Miscellaneous: HG1 (5-HT-moduline antagonist) Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride) 5-HT1D Agonists: Alniditan CGS-12066 (CGS-12066A, CGS-12066B) CP-122288 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) TGBA01AD Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, IS-159, naratriptan, rizatriptan, sumatriptan, zolmitriptan) Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT) Antagonists: BRL-15572 Elzasonan Ergolines (e.g., metergoline) F-12682 F-14258 GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin SB-272183 Yohimbine Ziprasidone Negative allosteric modulators: 5-HT-moduline Unknown/unsorted: Acetryptine Ergolines (e.g., lisuride, lysergol, pergolide) 5-HT1E 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-HT1F Agonists: BRL-54443 CP-122288 Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide) Lasmiditan LY-334370 LY-344864 Serotonin (5-HT) Triptans (e.g., eletriptan, naratriptan, sumatriptan) Tryptamines (e.g., 5-MT) Antagonists: Metitepine (methiothepin) Mianserin Unknown/unsorted: LY-53857 LY-86057 5-HT2 5-HT2A 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, BMB-202) 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 Aporphines and noraporphines (e.g., (S)-glaucine, 11-methoxyasimilobine, 2-hydroxy-11-(2-methylallyl)oxynoraporphine) BMB-201 Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g., DOB, DOC, DOI, DOM) Efavirenz Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergometrine (ergonovine), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide) Flumexadol IHCH-7113 Jimscaline Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP, VCU-1012) Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Positive allosteric modulators: AB0124 CTW0404 CTW0419 JPC0323 (R)-Glaucine Oleamide Antagonists: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine) AMDA Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine) Barettin Butanserin Chlorprothixene Cinanserin CSP-2503 Deramciclane DLX-2270 Dotarizine DSP-6745 Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Fananserin FCE-24379 Flibanserin Glemanserin Irindalone KB-128 Ketanserin KML-010 Landipirdine LY03017 LY-393558 mCPP Medifoxamine Metitepine (methiothepin) Metrenperone MIN-117 (WF-516) MT-1207 Naftidrofuryl Nantenine Nelotanserin NH130 Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin R-96544 R-102444 Rauwolscine Ritanserin Roluperidone S-14671 SpAMDA Sarpogrelate Seganserin Serotonin antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone) Temanogrel Teniloxazine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TGBA01AD Trelanserin Tricyclic antidepressants (e.g., amitriptyline) Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine) Volinanserin Xylamidine Yohimbine Unknown/unsorted: Ergolines (e.g., dihydroergotamine, nicergoline) 5-HT2B Agonists: 4-Methylaminorex Aminorex Amphetamines (e.g., 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) Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) Piperazines (e.g., TFMPP) 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: 1-Methylmedmain Agomelatine Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N-desalkylquetiapine (norquetiapine), N-desmethylclozapine (norclozapine), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone) Cyproheptadine EGIS-7625 Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine) KB-128 Ketanserin LY-393558 mCPP Medmain Metadoxine Metitepine (methiothepin) Minaprine MW073 Pirenperone Pizotifen 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, mirtazapine) Trazodone Typical antipsychotics (e.g., chlorpromazine) TIK-301 Yohimbine Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine)) 5-HT2C 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 Aporphines and noraporphines (e.g., MQ02-439, (S)-glaucine, nornuciferine, asimilobine, 11-chloroasimilobine, 11-methoxyasimilobine) ATHX-105 Bexicaserin BMB-101 BMB-105 BMB-201 Centhaquine CP-809101 Dimemebfe DLX-2270 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) Flumexadol KB-128 Lorcaserin Lumocaserin LY03020 MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) 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 PRX-00933 (BVT-933; GW-876167) Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine, CPI-CG-8) Vabicaserin VR-1065 WAY-629 WAY-161503 YM-348 Positive allosteric modulators: CTW0415 CYD-1-79 JPC0323 Oleamide PNU-69176E VA012 VA240 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 Desmetramadol Dotarizine DSP-6745 Eltoprazine Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fluoxetine FR260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) LY03017 Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SB-247853 SDZ SER-082 Seganserin Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TIK-301 Tramadol 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-HT3–7 5-HT3 Agonists: Alcohols (e.g., butanol, ethanol (alcohol), 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 Positive allosteric modulators: 5-Aminoindole 5-Chloroindole 5-Hydroxyindole Catechol Chloroform meta-Chlorophenylbiguanide (mCPBG) Colchicine Ethanol (alcohol) Halothane Indole Isoflurane TMPPAA Antagonists: Alosetron Anpirtoline Arazasetron AS-8112 Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine) Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Itasetron 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 Negative allosteric modulators: Bupropion Colchicine Hydroxybupropion Unknown/unsorted: Piperazines (e.g., naphthylpiperazine) 5-HT4 Agonists: 5-MT BIMU8 Capeserod Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Minesapride Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) Tegaserod Usmarapride Velusetrag Zacopride Antagonists: GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070 5-HT5A Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD) Serotonin (5-HT) Tryptamines (e.g., 5-CT) UCSF648 Valerenic acid Antagonists: Asenapine Latrepirdine (dimebolin) 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) Hypidone 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, ST-1936, 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 Landipirdine Latrepirdine (dimebolin) Masupirdine Metitepine (methiothepin) MS-245 PRX-07034 PZKKN-94 Ritanserin Ro 04-6790 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 LP-211 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, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine) Butaclamol DR-4485 DSP-6745 EGIS-12233 Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) JNJ-18038683 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 Negative allosteric modulators: Oleamide Unknown/unsorted: Ergolines (e.g., lisuride, pergolide) Piperazines (e.g., naphthylpiperazine) See also: Receptor/signaling modulators Adrenergics Dopaminergics Melatonergics Monoamine reuptake inhibitors and releasing agents Monoamine metabolism modulators Monoamine neurotoxins

v t e Arylpiperazines Phenylpiperazines 1-Phenylpiperazine (1-PP; PP) 3,4-CFP 2C-B-PP Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-7625 EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635 Benzylpiperazines 2C-B-BZP 3-Methylbenzylpiperazine Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP EGIS-7625 Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide NSI-189 Piberaline Piribedil RN-1747 Sunifiram Trimetazidine Vesnarinone Naphthylpiperazines 1-Naphthylpiperazine (1-NP) 2-Naphthylpiperazine (2-NP) CSP-2503 F-11,461 S-14,506 S-14671 Quinolinylpiperazines FPPQ 6-Nitroquipazine Isoquipazine Quipazine Diphenylalkylpiperazines AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine JJC8-088 Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine Pyrimidinylpiperazines Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone Pyridinylpiperazines Atevirdine Azaperone Delavirdine Mirtazapine ORG-12962 Pyridinylpiperazine Benzo(iso)thiazolylpiperazines Lurasidone Perospirone Revospirone Tiospirone Ziprasidone Tricyclic-linked piperazines Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol Others/uncategorized AP-238 Azimilide Bucinnazine Cinepazet Cinepazic acid Cinepazide CPD-1 Cyclohexylpiperazine Hexocyclium Indinavir JNJ-7777120 Lodenafil MK-212 Mirodenafil PB-28 Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VCU-1012 VUF-6002 WY-46824 Zipeprol ZINC000443438219

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Adapted from the Wikipedia article [Mefway (18F)](https://en.wikipedia.org/wiki/Mefway_(18F)) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Mefway_(18F)?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.