{{Short description|Chemical compound}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | IUPAC_name = 1-[(1S,3S,4R,5R)-8-methyl-3-naphthalen-2-yl-8-azabicyclo[3.2.1]octan-4-yl]propan-1-one | image=WF-23.svg | image_class = skin-invert-image | CAS_number_Ref = {{cascite|correct|CAS}} | CAS_number= 146877-60-3 | ATC_prefix= | ATC_suffix= | ChemSpiderID = 8623360 | PubChem= 10447943 | DrugBank= | C=21 | H=25 | N=1 | O=1 | bioavailability= High{{medcn|date=November 2023}} | metabolism = | elimination_half-life = Slow{{medcn|date=November 2023}} | excretion = | pregnancy_category = | legal_status = | routes_of_administration= | smiles = CCC(=O)[C@H]1[C@H]2CC[C@@H](C[C@@H]1c3ccc4ccccc4c3)N2C | StdInChI = 1S/C21H25NO/c1-3-20(23)21-18(13-17-10-11-19(21)22(17)2)16-9-8-14-6-4-5-7-15(14)12-16/h4-9,12,17-19,21H,3,10-11,13H2,1-2H3/t17-,18+,19+,21+/m0/s1 | StdInChIKey = WJVLEIDMFWNIAA-QEUVDIPISA-N }}
'''2β-Propanoyl-3β-(2-naphthyl)-tropane''' or '''WF-23''' (Wake Forest-23, named after the university where it was first created) is a cocaine analogue. It is several hundred times more potent than cocaine at being a serotonin-norepinephrine-dopamine reuptake inhibitor.<ref>{{cite patent | title = Process for blocking 5-HT and dopamine uptake with biologically active tropane derivatives | number = 6008227 | country = US | url = https://patents.google.com/patent/US6008227A/en?oq=US6008227 | assign1 = Wake Forest University Health Sciences | inventor = Davies HM, Childers SR, Bennett B | gdate = 28 December 1999 }}</ref>
As can be seen on PubMed, these acyl substituted phenyltropanes are highly potent MAT inhibitors and also have a very long half-life, spanning perhaps at least a few days;<ref>{{cite journal | vauthors = Bennett BA, Wichems CH, Hollingsworth CK, Davies HM, Thornley C, Sexton T, Childers SR | title = Novel 2-substituted cocaine analogs: uptake and ligand binding studies at dopamine, serotonin and norepinephrine transport sites in the rat brain | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 272 | issue = 3 | pages = 1176–1186 | date = March 1995 | pmid = 7891330 | url = http://jpet.aspetjournals.org/content/272/3/1176 }}</ref><ref>{{cite journal | vauthors = Daunais JB, Hart SL, Smith HR, Letchworth SR, Davies HM, Sexton T, Bennett BA, Childers SR, Porrino LJ | title = Long-acting blockade of biogenic amine transporters in rat brain by administration of the potent novel tropane 2beta-propanoyl-3beta-(2-Naphthyl)-tropane | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 285 | issue = 3 | pages = 1246–1254 | date = June 1998 | pmid = 9618429 | url = http://jpet.aspetjournals.org/content/285/3/1246.full }}</ref> as the half-life of the dopamine transporter in rats was found to be 2–3 days under normal conditions (with agonists, antagonists, and transporter inhibitors altering the half-life),<ref>{{cite journal | vauthors = Kimmel HL, Carroll FI, Kuhar MJ | title = Withdrawal from repeated cocaine alters dopamine transporter protein turnover in the rat striatum | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 304 | issue = 1 | pages = 15–21 | date = January 2003 | pmid = 12490570 | doi = 10.1124/jpet.102.038018 | s2cid = 27253009 }}</ref> it may be that WF-23 largely or mostly binds to its transporters until they are degraded.
WF-23 is made from methyl-ferruginine i.e. [https://pubchem.ncbi.nlm.nih.gov/compound/10080982 PC10080982] [152668-77-4]. == See also == * HDEP-28 * HDMP-28 * List of cocaine analogues *Ferruginine
== References == {{reflist}}
== Further reading == {{refbegin}} * {{cite journal | vauthors = Singh S | title = Chemistry, design, and structure-activity relationship of cocaine antagonists | journal = Chemical Reviews | volume = 100 | issue = 3 | pages = 925–1024 | date = March 2000 | pmid = 11749256 | doi = 10.1021/cr9700538 | url = https://www.erowid.org/archive/rhodium/pdf/cocaineanalogs.pdf }} {{refend}}
{{Stimulants}} {{Monoamine reuptake inhibitors}} {{Phenyltropanes}}
{{DEFAULTSORT:Propanoyl 3 beta 2 Naphthyl Tropane}} Category:Tropanes Category:Serotonin–norepinephrine–dopamine reuptake inhibitors Category:Stimulants Category:2-Naphthyl compounds Category:Ketones