SDZ SER-082

{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 449587176 | drug_name = | image = SDZ SER-082.svg | image_class = skin-invert-image | width = 150px | caption =

<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = Selective serotonin 5-HT_2B and 5-HT_2C receptor antagonist or weak partial agonist | ATC_prefix = | ATC_suffix =

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<!-- Identifiers --> | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number = 141474-54-6 | CAS_supplemental = | PubChem = 9859407 | IUPHAR_ligand = 195 | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 8035107 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = M7FHF24Q22 | KEGG = | ChEBI = | ChEMBL = 316069 | NIAID_ChemDB = | PDB_ligand = | synonyms = SDZ SER-082; SDZ SER082

<!-- Chemical data --> | IUPAC_name = (2''R'',7''S'')-4-methyl-4,9-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),12(16),13-triene | C=15 | H=20 | N=2 | SMILES = CN1CC[C@@H]2CN3CCC4=C3C(=CC=C4)[C@@H]2C1 | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C15H20N2/c1-16-7-5-12-9-17-8-6-11-3-2-4-13(15(11)17)14(12)10-16/h2-4,12,14H,5-10H2,1H3/t12-,14-/m1/s1 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = YASBOGFWAMXINH-TZMCWYRMSA-N }}

'''SER-082''', or '''SDZ SER-082''', is a selective serotonin 5-HT_2B and 5-HT_2C receptor antagonist or weak partial agonist with an ergoline-like structure which is used in scientific research.<ref name="vanWijngaardenSoudijn1997">{{cite book | vauthors = van Wijngaarden I, Soudijn W | title=Pharmacochemistry Library | chapter=5-HT2A, 5-HT2B and 5-HT2C receptor ligands | publisher=Elsevier | volume=27 | date=1997 | isbn=978-0-444-82041-9 | doi=10.1016/s0165-7208(97)80013-x | pages=161–197}}</ref><ref name="OhHaChi2001">{{cite journal | vauthors = Oh SJ, Ha HJ, Chi DY, Lee HK | title = Serotonin receptor and transporter ligands - current status | journal = Current Medicinal Chemistry | volume = 8 | issue = 9 | pages = 999–1034 | date = July 2001 | pmid = 11472239 | doi = 10.2174/0929867013372599 }}</ref><ref name="NozulakKalkmanFloersheim1995">{{cite journal | vauthors = Nozulak J, Kalkman HO, Floersheim P, Hoyer D, Schoeffter P, Buerki HR | title = (+)-cis-4,5,7a,8,9,10,11,11a-octahydro-7H-10-methylindolo[1,7- bc][2,6]-naphthyridine: a 5-HT2C/2B receptor antagonist with low 5-HT2A receptor affinity | journal = Journal of Medicinal Chemistry | volume = 38 | issue = 1 | pages = 28–33 | date = January 1995 | pmid = 7837236 | doi = 10.1021/jm00001a007 }}</ref> It shows similar affinity for the serotonin 5-HT_2B and 5-HT_2C receptors and has ~40-fold higher affinity for the serotonin 5-HT_2C receptor over the closely related serotonin 5-HT_2A receptor.<ref name="vanWijngaardenSoudijn1997" /><ref name="NozulakKalkmanFloersheim1995" />

It has been used in animal studies into the behavioural effects of the different 5-HT₂ subtypes,<ref name="pmid9408213">{{cite journal | vauthors = Mora PO, Netto CF, Graeff FG | title = Role of 5-HT2A and 5-HT2C receptor subtypes in the two types of fear generated by the elevated T-maze | journal = Pharmacology, Biochemistry, and Behavior | volume = 58 | issue = 4 | pages = 1051–1057 | date = December 1997 | pmid = 9408213 | doi = 10.1016/S0091-3057(97)00057-9 | s2cid = 11115355 }}</ref><ref name="pmid11900808">{{cite journal | vauthors = Dave KD, Harvey JA, Aloyo VJ | title = A novel behavioral model that discriminates between 5-HT2A and 5-HT2C receptor activation | journal = Pharmacology, Biochemistry, and Behavior | volume = 72 | issue = 1–2 | pages = 371–378 | date = May 2002 | pmid = 11900808 | doi = 10.1016/S0091-3057(01)00767-5 | s2cid = 36921090 }}</ref><ref name="pmid18572227">{{cite journal | vauthors = Hawkins MF, Uzelac SM, Hearn JK, Baumeister AA | title = Effects of selective serotonin2 ligands on behaviors evoked by stress in the rat | journal = Pharmacology, Biochemistry, and Behavior | volume = 90 | issue = 4 | pages = 632–639 | date = October 2008 | pmid = 18572227 | doi = 10.1016/j.pbb.2008.05.006 | s2cid = 25959070 }}</ref> and how they influence the effects of other drugs such as cocaine.<ref name="pmid15131246">{{cite journal | vauthors = Filip M, Bubar MJ, Cunningham KA | title = Contribution of serotonin (5-hydroxytryptamine; 5-HT) 5-HT2 receptor subtypes to the hyperlocomotor effects of cocaine: acute and chronic pharmacological analyses | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 310 | issue = 3 | pages = 1246–1254 | date = September 2004 | pmid = 15131246 | doi = 10.1124/jpet.104.068841 | s2cid = 25809734 }}</ref><ref name="pmid15849375">{{cite journal | vauthors = Filip M | title = Role of serotonin (5-HT)2 receptors in cocaine self-administration and seeking behavior in rats | journal = Pharmacological Reports | volume = 57 | issue = 1 | pages = 35–46 | year = 2005 | pmid = 15849375 }}</ref><ref name="pmid16261316">{{cite journal | vauthors = Filip M, Bubar MJ, Cunningham KA | title = Contribution of serotonin (5-HT) 5-HT2 receptor subtypes to the discriminative stimulus effects of cocaine in rats | journal = Psychopharmacology | volume = 183 | issue = 4 | pages = 482–489 | date = January 2006 | pmid = 16261316 | doi = 10.1007/s00213-005-0197-y | s2cid = 23148827 }}</ref> The drug has been found to have no effect on anxiety in multiple paradigms in rodents.<ref name="BourinNicDhonnchadha2005">{{cite journal | vauthors = Bourin M, Nic Dhonnchadha BA | title=5-HT 2 receptors and anxiety | journal=Drug Development Research | volume=65 | issue=3 | date=2005 | issn=0272-4391 | doi=10.1002/ddr.20016 | pages=133–140}}</ref> In contrast to other serotonin 5-HT_2C receptor antagonists, SER-082 does not produce hyperlocomotion in rodents, and instead can produce hypolocomotion at high doses that is independent of the serotonin 5-HT_2C receptor.<ref name="FletcherTampakerasSinyard2009">{{cite journal | vauthors = Fletcher PJ, Tampakeras M, Sinyard J, Slassi A, Isaac M, Higgins GA | title = Characterizing the effects of 5-HT(2C) receptor ligands on motor activity and feeding behaviour in 5-HT(2C) receptor knockout mice | journal = Neuropharmacology | volume = 57 | issue = 3 | pages = 259–267 | date = September 2009 | pmid = 19501602 | doi = 10.1016/j.neuropharm.2009.05.011 }}</ref>

It fails to block the effects of serotonergic psychedelics in multiple behavioral paradigms, in contrast to serotonin 5-HT_2A receptor antagonists.<ref name="NicholsNichols2021">{{cite book | vauthors = Nichols D, Nichols CD | chapter=The Pharmacology of Psychedelics | veditors = Grob C, Grigsby J | title=Handbook of Medical Hallucinogens | publisher=Guilford Publications | year=2021 | isbn=978-1-4625-4544-5 | chapter-url=https://books.google.com/books?id=ebb2DwAAQBAJ&pg=PA3 | access-date=17 January 2025 | pages=3–28 | quote = M 100907, but not the 5-HT2C/2B antagonist SER-082, can block most of the behavioral effects of DOI in the BPM paradigm, which are therefore likely mediated by activation of 5-HT2A receptors (Krebs-Thomson, Paulus, & Geyer, 1998). [...] Furthermore, 5-HT2B antagonists (e.g., SB 200,646A, SB 206,553, and SER-082) and the selective 5-HT2C antagonist SB 242,084, consistently fail to block the effects of hallucinogens in a variety of behavioral paradigms (Halberstadt et al., 2016; Ouagazzal et al., 2001; Schreiber et al., 1994; Sipes & Geyer, 1995; Smith et al., 1999; Wettstein, Host, & Hitchcock, 1999; Winter, Rice, Amorosi, & Rabin, 2007).}}</ref><ref name="WillinsMeltzer1997">{{cite journal | vauthors = Willins DL, Meltzer HY | title = Direct injection of 5-HT2A receptor agonists into the medial prefrontal cortex produces a head-twitch response in rats | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 282 | issue = 2 | pages = 699–706 | date = August 1997 | pmid = 9262333 | doi = 10.1016/S0022-3565(24)36840-5}}</ref><ref name="Krebs-ThomsonPaulusGeyer1998">{{cite journal | vauthors = Krebs-Thomson K, Paulus MP, Geyer MA | title = Effects of hallucinogens on locomotor and investigatory activity and patterns: influence of 5-HT2A and 5-HT2C receptors | journal = Neuropsychopharmacology | volume = 18 | issue = 5 | pages = 339–351 | date = May 1998 | pmid = 9536447 | doi = 10.1016/S0893-133X(97)00164-4 }}</ref> However, the hypolocomotion induced by high doses of the phenethylamine psychedelic DOI can be attenuated by SER-082.<ref name="HalberstadtvanderHeijdenRuderman2009">{{cite journal | vauthors = Halberstadt AL, van der Heijden I, Ruderman MA, Risbrough VB, Gingrich JA, Geyer MA, Powell SB | title = 5-HT(2A) and 5-HT(2C) receptors exert opposing effects on locomotor activity in mice | journal = Neuropsychopharmacology | volume = 34 | issue = 8 | pages = 1958–1967 | date = July 2009 | pmid = 19322172 | pmc = 2697271 | doi = 10.1038/npp.2009.29 }}</ref> Conversely, the drug was ineffective against the hypolocomotion induced by the tryptamine psychedelic 5-MeO-DMT, whereas the serotonin 5-HT_1A receptor antagonist WAY-100635 was effective.<ref name="Krebs-ThomsonRuizMasten2006">{{cite journal | vauthors = Krebs-Thomson K, Ruiz EM, Masten V, Buell M, Geyer MA | title = The roles of 5-HT1A and 5-HT2 receptors in the effects of 5-MeO-DMT on locomotor activity and prepulse inhibition in rats | journal = Psychopharmacology | volume = 189 | issue = 3 | pages = 319–329 | date = December 2006 | pmid = 17013638 | doi = 10.1007/s00213-006-0566-1 }}</ref>

== See also == * Lysergine * JRT

== References == {{Reflist}}

{{Serotonin receptor modulators}}

Category:5-HT2B antagonists Category:5-HT2C antagonists Category:Indolonaphthyridines