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Metergoline

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From Wikipedia, the free encyclopedia

Chemical compound

Pharmaceutical compound

Metergoline
Clinical data

Trade names	Contralac, Liserdol
Other names	Methergoline; FI-6337; [(8β)-1,6-Dimethylergolin-8-yl)methyl]carbamic acid phenylmethyl ester
Routes of administration	Oral
ATC code	G02CB05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name benzylN-[[(6aR,9S,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinolin-9-yl]methyl]carbamate
CAS Number	17692-51-2^N
PubChemCID	28693
IUPHAR/BPS	133
ChemSpider	26687^Y
UNII	1501393LY5
ChEBI	CHEBI:64216
ChEMBL	ChEMBL19215^Y
CompTox Dashboard(EPA)	DTXSID5042584
ECHA InfoCard	100.037.881
Chemical and physical data
Formula	C₂₅H₂₉N₃O₂
Molar mass	403.526 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(OCc1ccccc1)NC[C@@H]3C[C@@H]4c5cccc2c5c(cn2C)C[C@H]4N(C3)C
InChI InChI=1S/C25H29N3O2/c1-27-14-18(13-26-25(29)30-16-17-7-4-3-5-8-17)11-21-20-9-6-10-22-24(20)19(12-23(21)27)15-28(22)2/h3-10,15,18,21,23H,11-14,16H2,1-2H3,(H,26,29)/t18-,21+,23+/m0/s1^Y Key:WZHJKEUHNJHDLS-QTGUNEKASA-N^Y
^NY (what is this?) (verify)

Metergoline (INNTooltip INN,BANTooltip British Approved Name), also known asmethergoline and sold under the brand namesContralac (veterinary) andLiserdol (clinical), is amonoaminergic medication of theergoline group which is used as aprolactin inhibitor in the treatment ofhyperprolactinemia (highprolactin levels) and to suppresslactation.^[1]^[2]^[3]

Pharmacology

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Pharmacodynamics

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Metergoline is aligand of variousserotonin anddopamine receptors.^[4]^[5]^[6]^[7]^[8]^[9]

Activities of metergoline at various sites^[4]^[5]^[10]^[11]^[12]^[8]
Site	Affinity (K_i [nM])	Efficacy (E_max [%])	Action
5-HT_1A	4.3	?	Antagonist
5-HT_1B	5.2–36	?	Partial agonist
5-HT_1D	0.60–11.7	?	Partial agonist
5-HT_1E	776–1,122	?	?
5-HT_1F	339–341	?	?
5-HT_2A	0.12–2.3	?	Antagonist
5-HT_2B	0.71–1.8	?	Antagonist
5-HT_2C	0.18–1.8	?	Antagonist
5-HT₃	>5,000–7,400	?	?
5-HT₄	354	?	?
5-HT_5A	630	?	?
5-HT_5B	1,000	?	?
5-HT₆	61–400	?	?
5-HT₇	6.4–6.5	?	Antagonist
D₂	?	?	Agonist
Notes: All sites are human except 5-HT₃ (rat/pig), 5-HT₄ (pig), and 5-HT_5B (rat—no human counterpart).^[4]

References

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^Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 661–.ISBN 978-3-88763-075-1.
^Plumb DC (21 February 2018)."Metergoline".Plumb's Veterinary Drug Handbook: Pocket. John Wiley & Sons. pp. 1057–.ISBN 978-1-119-34649-4.
^Johson CA (2 December 2008)."False Pregnancy, Disorders of Pregnancy and Parturition, and Mismating". In Nelson RW, Couto CG (eds.).Small Animal Internal Medicine - E-Book. Elsevier Health Sciences. pp. 927–.ISBN 978-0-323-06512-2.
^^a ^b ^c"PDSP Database - UNC".pdsp.unc.edu. Archived fromthe original on 16 April 2021. Retrieved15 January 2022.
^^a ^bHoyer D, Clarke DE, Fozard JR, Hartig PR, Martin GR, Mylecharane EJ, et al. (June 1994). "International Union of Pharmacology classification of receptors for 5-hydroxytryptamine (Serotonin)".Pharmacological Reviews.46 (2):157–203.PMID 7938165.
^Hamon M, Mallat M, Herbet A, Nelson DL, Audinot M, Pichat L, Glowinski J (February 1981). "[3H]Metergoline: a new ligand of serotonin receptors in the rat brain".Journal of Neurochemistry.36 (2):613–626.doi:10.1111/j.1471-4159.1981.tb01634.x.PMID 7463079.S2CID 20259621.
^Miller KJ, King A, Demchyshyn L, Niznik H, Teitler M (September 1992). "Agonist activity of sumatriptan and metergoline at the human 5-HT_1D beta receptor: further evidence for a role of the 5-HT_1D receptor in the action of sumatriptan".European Journal of Pharmacology.227 (1):99–102.doi:10.1016/0922-4106(92)90149-P.PMID 1330643.
^^a ^bWebster J (December 1999). "Dopamine agonist therapy in hyperprolactinemia".The Journal of Reproductive Medicine.44 (12 Suppl):1105–1110.PMID 10649819.
^Glennon RA (January 1987). "Central serotonin receptors as targets for drug research".J Med Chem.30 (1):1–12.doi:10.1021/jm00384a001.PMID 3543362.Table II. Affinities of Selected Phenalkylamines for 5-HT1 and 5-HT2 Binding Sites
^Pertz H, Eich E (1999)."Ergot Alkaloids and their Derivatives as Ligands for Serotoninergic, Dopaminergic, and Adrenergic Receptors"(PDF).Ergot. pp. 432–462.doi:10.1201/9780203304198-21.ISBN 9780429219764. Archived fromthe original(PDF) on 2021-04-16.
^Pauwels PJ (September 1997). "5-HT 1B/D receptor antagonists".General Pharmacology.29 (3):293–303.doi:10.1016/s0306-3623(96)00460-0.PMID 9378233.
^Hutcheson JD, Setola V,Roth BL, Merryman WD (November 2011)."Serotonin receptors and heart valve disease--it was meant 2B".Pharmacology & Therapeutics.132 (2):146–157.doi:10.1016/j.pharmthera.2011.03.008.PMC 3179857.PMID 21440001.

External links

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Metergoline at the U.S. National Library of MedicineMedical Subject Headings (MeSH)

v t e Prolactin inhibitors andanti-inflammatory products forvaginal administration (G02CB–G02CC)
Prolactin inhibitors	Bromocriptine Cabergoline Ergoloid Lisuride Metergoline Pergolide Quinagolide Terguride
Anti-inflammatory products forvaginal administration	Benzydamine Ibuprofen Flunoxaprofen Naproxen

v t e Tocolytics/labor repressants (G02CA)
β₂ adrenoreceptor agonists	Bedoradrine Buphenine Dextrofemine Fenoterol Hexoprenaline Isoxsuprine Racefemine Ritodrine Terbutaline
Oxytocin antagonists	Atosiban
NSAIDs	Indometacin
Calcium channel blockers	Nifedipine
Myosin inhibitors	Magnesium sulfate

Pharmacodynamics

Dopamine receptor modulators

D₁-like

Agonists	Benzazepines:6-Br-APB Fenoldopam SKF-38,393 SKF-77,434 SKF-81,297 SKF-82,958 SKF-83,959 Trepipam Zelandopam Ergolines:Cabergoline CY-208,243 Dihydroergocryptine LEK-8829 Lisuride Pergolide Terguride Dihydrexidine derivatives:A-77636 A-86929 Adrogolide (ABT-431, DAS-431) Dihydrexidine Dinapsoline Dinoxyline Doxanthrine Phenethylamines:BCO-001 Deoxyepinephrine (N-methyldopamine, epinine) Dopexamine Etilevodopa Ibopamine L-DOPA (levodopa) Melevodopa L-Phenylalanine L-Tyrosine XP21279 Others:A-68930 Apomorphine Isocorypalmine Nuciferine PF-6649751 PF 6669571 Propylnorapomorphine Rotigotine SKF-89,145 SKF-89,626 Stepholidine Tavapadon Tetrahydropalmatine
PAMs	Tetrahydroisoquinolines:DETQ DPTQ Mevidalen
Antagonists	Typical antipsychotics:Butaclamol Chlorpromazine Chlorprothixene Flupentixol (flupenthixol) (+melitracen) Fluphenazine Loxapine Perphenazine (+amitriptyline) Pifluthixol Thioridazine Thiothixene Trifluoperazine (+tranylcypromine) Zuclopenthixol Atypical antipsychotics:Asenapine Clorotepine Clotiapine Clozapine DHA-clozapine Fluperlapine Iloperidone Norclozapine Norquetiapine Olanzapine (+fluoxetine) Paliperidone Quetiapine Risperidone Tefludazine Zicronapine Ziprasidone Zotepine Others:Berupipam Ecopipam EEDQ Metitepine (methiothepin) Odapipam Perlapine SCH-23390

D₂-like

Agonists

Phenethylamines:Deoxyepinephrine (N-methyldopamine, epinine)
Dopexamine
Etilevodopa
Ibopamine
L-DOPA (levodopa)
L-Phenylalanine
L-Tyrosine
Melevodopa
XP21279

Atypical antipsychotics:Alentemol (U-66444B)
Aripiprazole (+sertraline)
Aripiprazole lauroxil
Bifeprunox
Brexpiprazole
Brilaroxazine
Cariprazine
F-15063
Lumateperone
Norclozapine

Antagonists

Antiemetics/gastroprokinetics/sedatives:Aceprometazine
AS-8112
Alimemazine
Alizapride
Benzquinamide
Bromopride
Clebopride
Deudomperidone
Domperidone
Eticlopride
Hydroxyzine
Itopride
Metoclopramide
Metopimazine
Promethazine
Thiethylperazine
Trazpiroben
Trimethobenzamide

See also:Receptor/signaling modulators
Adrenergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

Prolactin receptor modulators

Agonists

Antagonists

Monoclonal antibodies:ABS-201
BAY-1158061 (HMI-115)

Indirect
modulators

Inhibitors	D₂ receptor agonists (e.g.,bromocriptine,cabergoline,lergotrile,lisuride,metergoline,pergolide,quinagolide,terguride) Indirectdopaminergic agents (e.g.,levodopa)
Releasers	D₂ receptor antagonists (e.g.,domperidone,metoclopramide,risperidone) Indirectantidopaminergic agents (e.g.,reserpine) Estrogens (e.g.,estradiol) Progestogens (e.g.,progesterone) Thyrotropin-releasing hormone andanalogues (e.g.,protirelin,taltirelin) Vasoactive intestinal peptide

Serotonin receptor modulators

5-HT₁

5-HT_1A

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,gepirone,perospirone,tandospirone) 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-11461 F-12826 F-13714 F-14679 F-15063 F-15599 Flesinoxan Flibanserin Flumexadol Hypidone 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) TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine
Positive allosteric modulators:Oleamide
Antagonists:Atypical antipsychotics (e.g.,iloperidone,risperidone,sertindole) AV965 Beta blockers (e.g.,alprenolol,carteolol,cyanopindolol,iodocyanopindolol,isamoltane,oxprenolol,penbutolol,pindobind,pindolol,propranolol,tertatolol) BMY-7378 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-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine
Unknown/unsorted:Acetryptine Carvedilol Ergolines (e.g.,ergometrine (ergonovine))

5-HT_1B

Agonists: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-12066A CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g.,bromocriptine,dihydroergotamine,ergotamine,methylergometrine (methylergonovine),methysergide,pergolide) mCPP Methylenedioxyphenethylamines (e.g.,MDMA,methylone) PZKKN-94 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 Beta blockers (e.g.,alprenolol,carteolol,isamoltane,oxprenolol,penbutolol,propranolol,tertatolol) 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-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,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:Acetryptine 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 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

5-HT₂

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.,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)
Positive allosteric modulators: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) Chlorprothixene Cinanserin CSP-2503 Deramciclane Dotarizine Eplivanserin Ergolines (e.g.,amesergide,LY-53857,LY-215840,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
Unknown/unsorted:Ergolines (e.g.,dihydroergotamine,nicergoline)

5-HT_2B

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: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) 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
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) 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
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 Eltoprazine Ergolines (e.g.,amesergide,bromocriptine,LY-53857,LY-215840,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
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 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:LY-53857 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-HT_5A

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 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 andreleasing agents
Monoamine metabolism modulators
Monoamine neurotoxins

v t e Ergolines
Ergolines (incl.lysergines)	13-Fluorolysergol Acetergamine Brazergoline Bromerguride (2-bromolisuride) Cianergoline Delergotrile Descarboxylysergic acid Dihydrolysergic acid Disulergine Dosergoside Ergolene Ergoline Etisulergine Lergotrile Lisuride Lysergic acid Lysergic acid methyl ester Lysergine Lysergol Mesulergine Metergoline Nicergoline Pergolide Pibocin B Proterguride Romergoline Sergolexole Terguride Tiomergine
Clavines (6,8-dimethylergolines)	6,8-Dimethylergoline (clavine) 9-Deacetoxyfumigaclavine C Agroclavine Costaclavin Elymoclavine Epoxyagroclavine Festuclavine Fumigaclavine A Fumigaclavine B Fumigaclavine C Penniclavine Setoclavine Partial ergolines and related:Chanoclavine Chanoclavine II Cycloclavine Paliclavine
Lysergamides (lysergic acid amides)	Non-hallucinogenic lysergamides:1P-BOL-148 2-Bromo-LSD (bromolysergide; BOL-148) 2-Iodo-LSD 2-Oxo-LSD (2-keto-LSD) 2-Oxo-3-hydroxy-LSD 9,10-Dihydro-LSD Amesergide AWD 52-39 Cabergoline Ergometrinine Iso-LSD (d-iso-LSD) l-Iso-LSD l-LSD Lumi-LSD LY-215,840 Lysergic acid cyclobutylamide (LAcB) Lysergic acid cyclopentylamide (cepentil; LCyP) Lysergic acid dibutylamide (LBB-66) MBL-61 (MOB-61; 1-methyl-2-bromo-LSD) MIL (1-methyl-2-iodo-LSD) PHENETHY-LAD SPT-348 Psychedelic lysergamides:1B-LSD 1cP-AL-LAD 1cP-LSD 1cP-MiPLA 1D-LSD 1DD-LSD 1F-LSD 1H-LSD 1P-AL-LAD 1P-ETH-LAD 1P-LSD 1P-MiPLA 1S-LSD 1T-AL-LAD 1T-LSD 1V-LSD 2,3-Dihydro-LSD AL-LAD ALA-10 (1-acetyl-LAE) ALD-52 (1-acetyl-LSD) BU-LAD CPM-LAD CYP-LAD Diallyllysergamide (DAL) Dimethyllysergamide (DAM-57) Diisopropyllysergamide (DiPLA) Dipropyllysergamide (DPL) Ergine (lysergic acid amide; LSA; LA-111; lysergamide) Ergometrine (ergonovine, ergobasine) ETH-LAD Ethylcyclopropyllysergamide (EcPLA) Ethylisopropyllysergamide (EiPLA) Ethylpropyllysergamide (EPLA; LEP-57) Ethyltrifluoroethyllysergamide (ETFELA) IP-LAD Isoergine (isolysergic acid amide; iso-LSA; iso-LA; isolysergamide) Isopropyllysergamide (iPLA; LAiP) Methylpropyllysergamide (LAMPA, LMP-55) Lysergic acid diethylamide (LSD;d-LSD; lysergide) Lysergic acid ethylamide (LAE-32, LAE) Lysergic acid hydroxyethylamide (LSH, LAH) Lysergic acid methylamide (LAM) Lysergic acid methylethylamide (LME-54) Lysergic acid morpholide (LSM-775) Lysergic acid propylamide (LAP) Lysergic acid pyrrolidide (LPD-824) Lysergic acid 2-butylamide (LSB) Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ, LA-Azetidine) Lysergic acid 3-pentylamide (LSP) Methylergometrine (methylergonovine, methylergobasine; Methergine) Methylisopropyllysergamide (MiPLA) Methysergide (1-methylmethylergonovine; UML-491) MLA-74 (1-methyl-LAE) MLD-41 (1-methyl-LSD) MPD-75 (1-methyllysergic acid pyrrolidide) NBOMe-LAD OML-632 (1-hydroxymethyl-LSD) PARGY-LAD PRO-LAD Unsorted lysergamides:1-Dimethylaminomethyl-LSD 12-Hydroxy-LSD 12-Methoxy-LSD 13-Fluoro-LSD 13-Hydroxy-LSD 14-Hydroxy-LSD 14-Methoxy-LSD CE-LAD Dihydroergometrine (dihydroergonovine, dihydroergobasine) FLUORETH-LAD FP-LAD Lysergic acid azepane (LA-Azepane) Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine) Lysergic acid amylamide Lysergic acid butylamide Lysergic acid ethyl-2-hydroxyethylamide (LEO) Lysergic acid ethyl-2-methoxyethylamide (LA-MeO) Lysergic acid piperidide (LA-Pip, LSD-Pip) Lysergic acid pyrrolinide (LPN) Lysergic acidtert-butylamide (LAtB) MAL-LAD Propisergide (1-methylergonovine)
Ergopeptines (peptide ergolines)	Bromocriptine Dihydroergocornine Dihydroergocristine Dihydroergocryptine Dihydroergosine Dihydroergotamine Epicriptine Ergocornine Ergocristine Ergocryptine Ergoloid (dihydroergotoxine; Hydergine) Ergonine Ergosine Ergostine Ergotamine Ergotoxine Ergovaline Fludihydroergotamine Mergocriptine Metergotamine
Partial ergolines	2-Aminotetralins (e.g.,8-OH-DPAT) 3,4-DMPEA-NDEPA 5-MeO-N-DEAOP-NET 5-MeO-N-DEAOP-NMT 10,11-Secoergoline (α,N-Pip-T) 10,11-Seco-LSD 25B-NAcPip 25D-NM-NDEAOP (25D-NM-NDEPA) Bay R 1531 (LY-197206) CT-5252 DEIMDHPCA (3,5-seco-LSD) DEMPDHPCA DEMPDHPCA-2C-D DEMPDHPCA-mescaline DEMPDHPCA-NAP DEMPDHPCA-PMA DOB-NDEPA DOI-NDEPA DOM-NDEPA DOTFM-NDEPA FAEFHI FHATHBIN LPH-5 LY-178210 LY-293284 M-NDEPA N-DEAOP-NMPEA (PEA-NM-NDEPA) N-DEAOP-NMT NDTDI (8,10-seco-LSD) Phenethylamines RU-27251 RU-27849 RU-28251 RU-28306 TMA-2-NDEPA Tryptamines WXVL_BT0793LQ2118 Related:Nikethamide Tochergamine
Related compounds	A-86929 Adrogolide CY-208,243 IHCH-7162 (centpyraquin) IHCH-7179 JRT Naxagolide Quinagolide SDZ SER-082 Voxergolide
Natural sources	Fungi:Clavicipitaceae Claviceps spp. (ergot) Claviceps paspali Claviceps purpurea Epichloë spp. Periglandula spp. Periglandula clandestina Periglandula ipomoeae Periglandula turbinae Plants (infected/symbiotic with the above fungi):Achnatherum robustum (sleepy grass) Convolvulaceae (morning glory) Argyreia nervosa (Hawaiian baby woodrose) Ipomoea asarifolia (ginger-leaf morning-glory) Ipomoea corymbosa (coaxihuitl, ololiúqui) Ipomoea tricolor (tlitliltzin, badoh negro)
See also:Tryptamines Phenethylamines Psychedelics

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