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A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
N -[2-[4-(2-Methoxyphenyl)-1-piperazinyl]ethyl]-N -(2-pyridyl)cyclohexanecarboxamide
Chemical and physical data
C 25 H 34 N 4 O 2
422.573 g·mol−1
COC1=CC=CC=C1N2CCN(CC2)CCN(C3=CC=CC=N3)C(=O)C4CCCCC4
InChI=1S/C25H34N4O2/c1-31-23-12-6-5-11-22(23 )28-18-15-27(16-19-28)17-20-29(24-13-7-8-14-26-24)25(30 )21-9-3-2-4-10-21/h5-8,11-14,21H,2-4,9-10,15-20H2,1H3 N
Key:SBPRIAGPYFYCRT-UHFFFAOYSA-N N
WAY-100635 is a piperazine drug and research chemical widely used in scientific studies. It was originally believed to act as a selective 5-HT1A receptor antagonist , but subsequent research showed that it also acts as potent full agonist at the D 4 receptor.[1] [2] [3] It is sometimes referred to as a silent antagonist at the former receptor.[4] It is closely related to WAY-100135 .
In light of its only recently discovered dopaminergic activity, conclusions drawn from studies that employed WAY-100635 as a selective 5-HT1A antagonist may need to be re-evaluated.[5]
Human PET studies [ edit ]
In human PET studies WAY-100635 shows high binding in the cerebral cortex , hippocampus , raphe nucleus and amygdaloid nucleus , while lower in thalamus and basal ganglia .[6]
One study described a single case with relatively high binding in the cerebellum.[7]
In relating its binding to subject variables one Swedish study found WAY-100635 binding in raphe brain region correlating with self-transcendence and spiritual acceptance personality traits .[8]
WAY-100635 binding has also been assessed in connection with clinical depression , where there has been disagreement about the presence and direction of the 5-HT1A receptor binding.[9]
In healthy subjects WAY-100635 binding has been found to decline with age ,[10]
— though not all studies have found this relationship.[11] [12]
Human WAY-100635 binding neuroimaging studies (patients compared to healthy control subjects).
Subjects
Ref.
Global decrease and particularly in parietal cortex and dorsolateral prefrontal cortex
19
[10]
No correlation found
61
[11]
No correlation detected
25
[12]
Higher binding in females
25
[12]
Positive correlation in raphe region
15 males
[8]
Negative correlation
25
[12]
Positive correlation in the raphe nuclei and hippocampus
12 males
[13]
Result
Subjects
Ref.
No difference found
35
[14]
Lower binding in "all brain regions" for SS or SL genotypes compared to LL
35
[14]
Result
Subjects
Ref.
Depressive (with primary, recurrent, familial mood disorders)
Reduction in raphe nucleus and mesiotemporal cortex
12+8
[15]
Reduction in "many of the regions examined"
25+18
[16]
Reducing in binding in raphe in both treated and untreated. Reduced binding in global postsynaptic regions for untreated, while no or little reduction for treated.
9+7+19
[17]
Decrease in right medial temporal cortex
10+10
[18]
Radioligands [ edit ]
Labeled with the radioisotope carbon-11 it is used as a radioligand in positron emission tomography (PET) studies to determine neuroreceptor binding in the brain .[19]
WAY-100635 may be labeled in different ways with carbon-11:
As [carbonyl-11 C ]WAY-100635 or [O-methyl-11 C ]WAY-100635, with [carbonyl-11 C ]WAY-100635 regarded as "far superior".[20]
Labeled with tritium WAY-100635 may also be used in autoradiography .[21]
WAY-100635 has higher 5-HT1A affinity than 8-OH-DPAT .[22]
Other actions [ edit ]
WAY-100635 has also been found to increase the analgesic effects of opioid drugs in a dose-dependent manner, in contrast to 5-HT1A agonists such as 8-OH-DPAT which were found to reduce opioid analgesia.[23] [24] However, since 5-HT1A agonists were also found to reduce opioid-induced respiratory depression and WAY-100635 was found to block this effect,[25] it is likely that 5-HT1A antagonists might worsen this side effect of opioids. Paradoxically, chronic administration of the very high efficacy 5-HT1A agonist befiradol results in potent analgesia following an initial period of hyperalgesia , an effect most likely linked to desensitisation and/or downregulation of 5-HT1A receptors (i.e. analogous to a 5-HT1A antagonist-like effect).[26] [27] [28] As with other 5-HT1A silent antagonists such as UH-301 and robalzotan , WAY-100635 can also induce a head-twitch response in rodents.[29]
See also [ edit ]
External links [ edit ]
References [ edit ]
^ Chemel BR, Roth BL , Armbruster B, Watts VJ, Nichols DE (October 2006). "WAY-100635 is a potent dopamine D4 receptor agonist". Psychopharmacology . 188 (2 ): 244–251. doi :10.1007/s00213-006-0490-4 . PMID 16915381 . S2CID 24194034 .
^ Marona-Lewicka D, Nichols DE (February 2009). "WAY 100635 produces discriminative stimulus effects in rats mediated by dopamine D(4 ) receptor activation". Behavioural Pharmacology . 20 (1 ): 114–118. doi :10.1097/FBP.0b013e3283242f1a . PMID 19179855 . S2CID 43332577 .
^ Fletcher A, Forster EA, Bill DJ, Brown G, Cliffe IA, Hartley JE, et al. (1996). "Electrophysiological, biochemical, neurohormonal and behavioural studies with WAY-100635, a potent, selective and silent 5-HT1A receptor antagonist". Behavioural Brain Research . 73 (1–2): 337–353. doi :10.1016/0166-4328(96 )00118-0 . PMID 8788530 . S2CID 18229202 .
^ Chemel BR, Roth BL, Armbruster B, Watts VJ, Nichols DE (October 2006). "WAY-100635 is a potent dopamine D4 receptor agonist". Psychopharmacology . 188 (2 ): 244–251. doi :10.1007/s00213-006-0490-4 . PMID 16915381 . S2CID 24194034 .
^ Ito H, Halldin C, Farde L (January 1999). "Localization of 5-HT1A receptors in the living human brain using [carbonyl-11C]WAY-100635: PET with anatomic standardization technique" . Journal of Nuclear Medicine . 40 (1 ): 102–109. PMID 9935065 .
^ Hirvonen J, Kajander J, Allonen T, Oikonen V, Någren K, Hietala J (January 2007). "Measurement of serotonin 5-HT1A receptor binding using positron emission tomography and [carbonyl-(11 )C]WAY-100635-considerations on the validity of cerebellum as a reference region" . Journal of Cerebral Blood Flow and Metabolism . 27 (1 ): 185–195. doi :10.1038/sj.jcbfm.9600326 . PMID 16685258 .
^ a b Borg J, Andrée B, Soderstrom H, Farde L (November 2003). "The serotonin system and spiritual experiences". The American Journal of Psychiatry . 160 (11 ): 1965–1969. doi :10.1176/appi.ajp.160.11.1965 . PMID 14594742 . S2CID 5911066 .
^ Drevets WC, Thase ME, Moses-Kolko EL, Price J, Frank E, Kupfer DJ, Mathis C (October 2007). "Serotonin-1A receptor imaging in recurrent depression: replication and literature review" . Nuclear Medicine and Biology . 34 (7 ): 865–877. doi :10.1016/j.nucmedbio.2007.06.008 . PMC 2702715 . PMID 17921037 .
^ a b Tauscher J, Verhoeff NP, Christensen BK, Hussey D, Meyer JH, Kecojevic A, et al. (May 2001). "Serotonin 5-HT1A receptor binding potential declines with age as measured by [11C]WAY-100635 and PET" . Neuropsychopharmacology . 24 (5 ): 522–530. doi :10.1016/S0893-133X(00 )00227-X . PMID 11282252 .
^ a b Rabiner EA, Messa C, Sargent PA, Husted-Kjaer K, Montgomery A, Lawrence AD, et al. (March 2002). "A database of [(11 )C]WAY-100635 binding to 5-HT(1A) receptors in normal male volunteers: normative data and relationship to methodological, demographic, physiological, and behavioral variables". NeuroImage . 15 (3 ): 620–632. doi :10.1006/nimg.2001.0984 . PMID 11848705 . S2CID 42080193 .
^ a b c d Parsey RV, Oquendo MA, Simpson NR, Ogden RT, Van Heertum R, Arango V, Mann JJ (November 2002). "Effects of sex, age, and aggressive traits in man on brain serotonin 5-HT1A receptor binding potential measured by PET using [C-11]WAY-100635". Brain Research . 954 (2 ): 173–182. doi :10.1016/S0006-8993(02 )03243-2 . PMID 12414100 . S2CID 20650203 .
^ Lundberg J, Borg J, Halldin C, Farde L (December 2007). "A PET study on regional coexpression of 5-HT1A receptors and 5-HTT in the human brain". Psychopharmacology . 195 (3 ): 425–433. doi :10.1007/s00213-007-0928-3 . PMID 17874074 . S2CID 22272672 .
^ a b David SP, Murthy NV, Rabiner EA, Munafó MR, Johnstone EC, Jacob R, et al. (March 2005). "A functional genetic variation of the serotonin (5-HT) transporter affects 5-HT1A receptor binding in humans" . The Journal of Neuroscience . 25 (10 ): 2586–2590. doi :10.1523/JNEUROSCI.3769-04.2005 . PMC 1942077 . PMID 15758168 .
^ Drevets WC, Frank E, Price JC, Kupfer DJ, Holt D, Greer PJ, et al. (November 1999). "PET imaging of serotonin 1A receptor binding in depression". Biological Psychiatry . 46 (10 ): 1375–1387. doi :10.1016/S0006-3223(99 )00189-4 . PMID 10578452 . S2CID 719822 .
^ Sargent PA, Kjaer KH, Bench CJ, Rabiner EA, Messa C, Meyer J, et al. (February 2000). "Brain serotonin1A receptor binding measured by positron emission tomography with [11C]WAY-100635: effects of depression and antidepressant treatment". Archives of General Psychiatry . 57 (2 ): 174–180. doi :10.1001/archpsyc.57.2.174 . PMID 10665620 .
^ Nash JR, Sargent PA, Rabiner EA, Hood SD, Argyropoulos SV, Potokar JP, et al. (September 2008). "Serotonin 5-HT1A receptor binding in people with panic disorder: positron emission tomography study" . The British Journal of Psychiatry . 193 (3 ): 229–234. doi :10.1192/bjp.bp.107.041186 . PMID 18757983 .
^ Lanctôt KL, Hussey DF, Herrmann N, Black SE, Rusjan PM, Wilson AA, et al. (October 2007). "A positron emission tomography study of 5-hydroxytryptamine-1A receptors in Alzheimer disease". The American Journal of Geriatric Psychiatry . 15 (10 ): 888–898. doi :10.1097/JGP.0b013e3180488325 . PMID 17567932 .
^ Pike VW, McCarron JA, Lammerstma AA, Hume SP, Poole K, Grasby PM, et al. (September 1995). "First delineation of 5-HT1A receptors in human brain with PET and [11C]WAY-100635". European Journal of Pharmacology . 283 (1–3): R1–R3. doi :10.1016/0014-2999(95 )00438-Q . PMID 7498295 .
^ Pike VW, McCarron JA, Lammertsma AA, Osman S, Hume SP, Sargent PA, et al. (April 1996). "Exquisite delineation of 5-HT1A receptors in human brain with PET and [carbonyl-11 C]WAY-100635". European Journal of Pharmacology . 301 (1–3): R5–R7. doi :10.1016/0014-2999(96 )00079-9 . PMID 8773468 .
^ Hume SP, Ashworth S, Opacka-Juffry J, Ahier RG, Lammertsma AA, Pike VW, et al. (December 1994). "Evaluation of [O-methyl-3H]WAY-100635 as an in vivo radioligand for 5-HT1A receptors in rat brain". European Journal of Pharmacology . 271 (2–3): 515–523. doi :10.1016/0014-2999(94 )90813-3 . PMID 7705452 .
^ Burnet PW, Eastwood SL, Harrison PJ (June 1997). "[3H]WAY-100635 for 5-HT1A receptor autoradiography in human brain: a comparison with [3H]8-OH-DPAT and demonstration of increased binding in the frontal cortex in schizophrenia". Neurochemistry International . 30 (6 ): 565–574. doi :10.1016/S0197-0186(96 )00124-6 . PMID 9152998 . S2CID 21135585 .
^ Bardin L, Colpaert FC (June 2004). "Role of spinal 5-HT(1A) receptors in morphine analgesia and tolerance in rats". European Journal of Pain . 8 (3 ): 253–261. doi :10.1016/j.ejpain.2003.09.002 . PMID 15109976 . S2CID 25580572 .
^ Berrocoso E, De Benito MD, Mico JA (July 2007). "Role of serotonin 5-HT1A and opioid receptors in the antiallodynic effect of tramadol in the chronic constriction injury model of neuropathic pain in rats". Psychopharmacology . 193 (1 ): 97–105. doi :10.1007/s00213-007-0761-8 . PMID 17393145 . S2CID 21898521 .
^ 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 ): 704–713. PMID 10640309 .
^ Bardin L, Assié MB, Pélissou M, Royer-Urios I, Newman-Tancredi A, Ribet JP, et al. (March 2005). "Dual, hyperalgesic, and analgesic effects of the high-efficacy 5-hydroxytryptamine 1A (5-HT1A) agonist F 13640 [(3-chloro-4-fluoro-phenyl)-[4-fluoro-4-{[(5-methyl-pyridin-2-ylmethyl)-amino]-methyl}piperidin-1-yl]methanone, fumaric acid salt]: relationship with 5-HT1A receptor occupancy and kinetic parameters". The Journal of Pharmacology and Experimental Therapeutics . 312 (3 ): 1034–1042. doi :10.1124/jpet.104.077669 . PMID 15528450 . S2CID 42446435 .
^ Assié MB, Lomenech H, Ravailhe V, Faucillon V, Newman-Tancredi A (September 2006). "Rapid desensitization of somatodendritic 5-HT1A receptors by chronic administration of the high-efficacy 5-HT1A agonist, F13714: a microdialysis study in the rat" . British Journal of Pharmacology . 149 (2 ): 170–178. doi :10.1038/sj.bjp.0706859 . PMC 2013794 . PMID 16921393 .
^ Buritova J, Berrichon G, Cathala C, Colpaert F, Cussac D (February 2009). "Region-specific changes in 5-HT1A agonist-induced Extracellular signal-Regulated Kinases 1/2 phosphorylation in rat brain: a quantitative ELISA study". Neuropharmacology . 56 (2 ): 350–361. doi :10.1016/j.neuropharm.2008.09.004 . PMID 18809418 . S2CID 45068116 .
^ Fox MA, Stein AR, French HT, Murphy DL. Functional interactions between 5-HT2A and presynaptic 5-HT1A receptor-based responses in mice genetically deficient in the serotonin 5-HT transporter (SERT). Br J Pharmacol . 2010 Feb;159(4 ):879-87. Fox MA, Stein AR, French HT, Murphy DL (February 2010). "Functional interactions between 5-HT2A and presynaptic 5-HT1A receptor-based responses in mice genetically deficient in the serotonin 5-HT transporter (SERT)" . British Journal of Pharmacology . 159 (4 ): 879–887. doi :10.1111/j.1476-5381.2009.00578.x . PMC 2829213 . PMID 20128812 .
Bay R 1531
Befiradol
BMY-14802
Cannabidiol
Dimemebfe
Dopamine
Ebalzotan
Eltoprazine
Enciprazine
Ergolines (e.g., bromocriptine , cabergoline , dihydroergotamine , ergotamine , lisuride , LSD , methylergometrine (methylergonovine) , methysergide , pergolide )
F-11,461
F-12826
F-13714
F-14679
F-15063
F-15,599
Flesinoxan
Flibanserin
Flumexadol
Hypidone
Lesopitron
LY-293284
LY-301317
mCPP
MKC-242
Naluzotan
NBUMP
Osemozotan
Oxaflozane
Pardoprunox
Piclozotan
Rauwolscine
Repinotan
Roxindole
RU-24,969
S-14,506
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
U-92,016-A
Urapidil
Vilazodone
Xaliproden
Yohimbine
Beta blockers (e.g., alprenolol , carteolol , cyanopindolol , iodocyanopindolol , isamoltane , oxprenolol , penbutolol , pindobind , pindolol , propranolol , tertatolol )
BMY-7,378
CSP-2503
Dotarizine
Ergolines (e.g., metergoline )
FCE-24379
Flopropione
GR-46611
Isamoltane
Lecozotan
Mefway
Metitepine (methiothepin)
MIN-117 (WF-516)
MPPF
NAN-190
Robalzotan
S-15535
SB-649,915
SDZ 216-525
Spiperone
Spiramide
Spiroxatrine
UH-301
WAY-100135
WAY-100635
Xylamidine
Ergolines (e.g., ergometrine (ergonovine) )
CP-122,288
CP-135807
Eltoprazine
Ergolines (e.g., bromocriptine , dihydroergotamine , ergotamine , methylergometrine (methylergonovine) , methysergide , pergolide )
mCPP
RU-24,969
Serotonin (5-HT)
Triptans (e.g., avitriptan , donitriptan , eletriptan , sumatriptan , zolmitriptan )
TFMPP
Tryptamines (e.g., 5-BT , 5-CT , 5-MT , DMT )
Vortioxetine
Elzasonan
Ergolines (e.g., metergoline )
GR-127935
Isamoltane
LY-393558
Metitepine (methiothepin)
SB-216641
SB-224289
SB-236057
Yohimbine
GR-46611
L-694247
L-772405
mCPP
PNU-109291
PNU-142633
Serotonin (5-HT)
TGBA01AD
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 )
Elzasonan
Ergolines (e.g., metergoline )
GR-127935
Ketanserin
LY-310762
LY-367642
LY-393558
LY-456219
LY-456220
Metitepine (methiothepin)
Mianserin
Ritanserin
Yohimbine
Ziprasidone
Tryptamines (e.g., tryptamine )
LY-334370
Serotonin (5-HT)
Triptans (e.g., eletriptan , naratriptan , sumatriptan )
Tryptamines (e.g., 5-MT )
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., 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 )
Serotonin (5-HT)
TCB-2
TFMFly
Tryptamines (e.g., 5-BT , 5-CT , bufotenin , DET , DiPT , DMT , DPT , psilocin , psilocybin , tryptamine )
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 )
Chlorprothixene
Cinanserin
CSP-2503
Deramciclane
Dotarizine
Eplivanserin
Ergolines (e.g., amesergide , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
Fananserin
Flibanserin
Glemanserin
Irindalone
Ketanserin
KML-010
Landipirdine
LY-393558
mCPP
Medifoxamine
Metitepine (methiothepin)
MIN-117 (WF-516)
Naftidrofuryl
Nantenine
Nelotanserin
Opiranserin (VVZ-149)
Pelanserin
Phenoxybenzamine
Pimavanserin
Pirenperone
Pizotifen
Pruvanserin
Rauwolscine
Ritanserin
Roluperidone
S-14671
Sarpogrelate
Serotonin antagonists and reuptake inhibitors (e.g., etoperidone , hydroxynefazodone , lubazodone , mepiprazole , nefazodone , triazoledione , trazodone )
SR-46349B
TGBA01AD
Teniloxazine
Temanogrel
Tetracyclic antidepressants (e.g., amoxapine , aptazapine , esmirtazapine , maprotiline , mianserin , mirtazapine )
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
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 )
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 )
Ketanserin
LY-393558
mCPP
Metadoxine
Metitepine (methiothepin)
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
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 )
Flumexadol
Lorcaserin
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
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
Atypical antipsychotics (e.g., asenapine , clorotepine , clozapine , fluperlapine , iloperidone , melperone , olanzapine , paliperidone , quetiapine , risperidone , sertindole , ziprasidone , zotepine )
Captodiame
CEPC
Cinanserin
Cyproheptadine
Deramciclane
Desmetramadol
Dotarizine
Eltoprazine
Ergolines (e.g., amesergide , bromocriptine , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
Etoperidone
Fluoxetine
FR-260010
Irindalone
Ketanserin
Ketotifen
Latrepirdine (dimebolin)
Medifoxamine
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 )
TIK-301
Tramadol
Trazodone
Tricyclic antidepressants (e.g., amitriptyline , nortriptyline )
Typical antipsychotics (e.g., chlorpromazine , loxapine , pimozide , pipamperone , thioridazine )
Xylamidine
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
Arazasetron
AS-8112
Atypical antipsychotics (e.g., clozapine , olanzapine , quetiapine )
Azasetron
Batanopride
Bemesetron (MDL-72222)
Bupropion
Cilansetron
CSP-2503
Dazopride
Dolasetron
Galanolactone
Granisetron
Hydroxybupropion
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
Cisapride
CJ-033466
Dazopride
Metoclopramide
Minesapride
Mosapride
Prucalopride
PRX-03140
Renzapride
RS-67,333
RS-67,506
Serotonin (5-HT)
Tegaserod
Usmarapride
Velusetrag
Zacopride
L-Lysine
Piboserod
RS-39604
RS-67532
SB-203186
SB-204070
Metitepine (methiothepin)
Ritanserin
SB-699551
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
AVN-101
AVN-211
AVN-322
AVN-397
BGC20-760
BVT-5182
BVT-74316
Cerlapirdine
EGIS-12,233
GW-742457
Idalopirdine
Ketanserin
Landipirdine
Latrepirdine (dimebolin)
Masupirdine
Metitepine (methiothepin)
MS-245
PRX-07034
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 )
Ergolines (e.g., LSD )
LP-12
LP-44
LP-211
RU-24,969
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
EGIS-12,233
Ergolines (e.g., 2-Br-LSD (BOL-148) , amesergide , bromocriptine , cabergoline , dihydroergotamine , ergotamine , LY-53857 , LY-215,840 , mesulergine , metergoline , methysergide , sergolexole )
JNJ-18038683
Ketanserin
LY-215,840
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
Dopaminergics
Melatonergics
Monoamine reuptake inhibitors and releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins
SKF-77,434
SKF-81,297
SKF-82,958
SKF-83,959
Trepipam
Zelandopam
Tetrahydroisoquinolines : DETQ
DPTQ
Mevidalen
Chlorpromazine
Chlorprothixene
Flupentixol (flupenthixol) (+melitracen )
Fluphenazine
Loxapine
Perphenazine (+amitriptyline )
Pifluthixol
Thioridazine
Thiothixene
Trifluoperazine (+tranylcypromine )
Zuclopenthixol
Acetophenazine
Azaperone
Benperidol
Bromperidol
Butaclamol
Butaperazine
Chloracizine
Chlorproethazine
Chlorpromazine
Chlorprothixene
Ciclindole
Clopenthixol
Clothixamide
Clopimozide
Droperidol
Fluacizine
Fluanisone
Flucindole
Fluotracen
Flupentixol (flupenthixol) (+melitracen )
Fluphenazine
Fluprothixene
Fluspirilene
Haloperidol
Homopipramol
Lenperone
Levomepromazine (methotrimeprazine)
Levosulpiride
Loxapine
Mesoridazine
Moperone
Naranol
Nemonapride
Penfluridol
Perathiepin
Perazine
Pericyazine (periciazine)
Perphenazine (+amitriptyline )
Piflutixol (pifluthixol)
Pimozide
Pipamperone
Preclamol
Prochlorperazine
Promazine
Prothipendyl
Spiperone (spiroperidol)
Sulforidazine
Sulpiride
Sultopride
Teflutixol
Thiopropazate
Thioproperazine
Thioridazine
Thiothixene
Timiperone
Trifluoperazine (+tranylcypromine )
Triflupromazine
Trifluperidol
Zetidoline
Zuclopenthixol
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins
Simple piperazines(no additional rings)
Diethylcarbamazine
HEPPS
Midafotel
Piperazine
PIPES
3,4-CFP
Acaprazine
Antrafenine
Aripiprazole
Batoprazine
Bifeprunox
BRL-15,572
Ciprofloxacin
CSP-2503
Dapiprazole
DCPP
DMPP
Diphenylpiperazine
Dropropizine
EGIS-12,233
Elopiprazole
Eltoprazine
Enpiprazole
Ensaculin
Etoperidone
Flesinoxan
Fluanisone
Flibanserin
Fluprazine
Itraconazole
Ketoconazole
Levodropropizine
Lorpiprazole
mCPP
Mefway
MeOPP
Mepiprazole
Naftopidil
Naluzotan
Naphthylpiperazine
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
3-Methylbenzylpiperazine
Befuraline
Bifeprunox
Buclizine
BZP
Chlorbenzoxamine
DBZP
Fipexide
Imatinib
MBZP
MDBZP
Meclozine
Methoxypiperamide
NSI-189
Piberaline
Piribedil
RN-1747
Sunifiram
Trimetazidine
Vesnarinone
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
Lidoflazine
Manidipine
Meclozine
MT-45
Oxatomide
SNC-80
Vanoxerine
Dasatinib
Eptapirone
Gepirone
Ipsapirone
Piribedil
Prazitone
Pyrimidinylpiperazine
Revospirone
Tandospirone
Tirilazad
Trimazosin
Umespirone
Zalospirone
Azaperone
Delavirdine
Mirtazapine
ORG-12962
Pyridinylpiperazine
Perospirone
Revospirone
Tiospirone
Ziprasidone
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
AP-238
Azimilide
Bucinnazine
Cinepazet
Cinepazic acid
Cinepazide
CPD-1
Cyclohexylpiperazine
EGIS-7625
Hexocyclium
Indinavir
JNJ-7777120
Lodenafil
MK-212
Mirodenafil
PB-28
Quipazine
Ranolazine
SA-4503
Sildenafil
Tadalafil
Vardenafil
VUF-6002
WY-46824
Zipeprol
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=WAY-100635&oldid=1171071985 "
C a t e g o r i e s :
● D o p a m i n e a g o n i s t s
● N - ( 2 - m e t h o x y p h e n y l ) p i p e r a z i n e s
● C a r b o x a m i d e s
● 2 - P y r i d y l c o m p o u n d s
● S e r o t o n i n r e c e p t o r a n t a g o n i s t s
H i d d e n c a t e g o r i e s :
● A r t i c l e s w i t h s h o r t d e s c r i p t i o n
● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● A r t i c l e s w i t h c h a n g e d C h e m S p i d e r i d e n t i f i e r
● A r t i c l e s w i t h c h a n g e d E B I i d e n t i f i e r
● A r t i c l e s w i t h c h a n g e d I n C h I i d e n t i f i e r
● C h e m i c a l p a g e s w i t h o u t D r u g B a n k i d e n t i f i e r
● A r t i c l e s w i t h o u t K E G G s o u r c e
● D r u g s m i s s i n g a n A T C c o d e
● D r u g s w i t h n o l e g a l s t a t u s
● D r u g b o x e s w h i c h c o n t a i n c h a n g e s t o v e r i f i e d f i e l d s
● D r u g b o x e s w h i c h c o n t a i n c h a n g e s t o w a t c h e d f i e l d s
● T h i s p a g e w a s l a s t e d i t e d o n 1 8 A u g u s t 2 0 2 3 , a t 2 2 : 0 2 ( U T C ) .
● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n .
● P r i v a c y p o l i c y
● A b o u t W i k i p e d i a
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● C o n t a c t W i k i p e d i a
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● M o b i l e v i e w