2β-Propanoyl-3β-(2-naphthyl)-tropane Chemical compound
Pharmaceutical compound
2β-Propanoyl-3β-(2-naphthyl)-tropane Bioavailability High[medical citation needed Elimination half-life Slow[medical citation needed
1-[(1S,3S,4R,5R)-8-methyl-3-naphthalen-2-yl-8-azabicyclo[3.2.1]octan-4-yl]propan-1-one
PubChem CID ChemSpider Formula C 21 H 25 N O Molar mass −1 3D model (JSmol )
CCC(=O)[C@H]1[C@H]2CC[C@@H](C[C@@H]1c3ccc4ccccc4c3)N2C
InChI=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
Key: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 .[ 1]
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;[ 2] [ 3] [ 4]
See also
External links
References
^ U.S. patent 6,008,227 ^ Bennett BA, Wichems CH, Hollingsworth CK, Davies HM, Thornley C, Sexton T, Childers SR (March 1995). "Novel 2-substituted cocaine analogs: uptake and ligand binding studies at dopamine, serotonin and norepinephrine transport sites in the rat brain" . The Journal of Pharmacology and Experimental Therapeutics . 272 (3): 1176–1186. PMID 7891330 . ^ Daunais JB, Hart SL, Smith HR, Letchworth SR, Davies HM, Sexton T, et al. (June 1998). "Long-acting blockade of biogenic amine transporters in rat brain by administration of the potent novel tropane 2beta-propanoyl-3beta-(2-Naphthyl)-tropane" . The Journal of Pharmacology and Experimental Therapeutics . 285 (3): 1246–1254. PMID 9618429 . ^ Kimmel HL, Carroll FI, Kuhar MJ (January 2003). "Withdrawal from repeated cocaine alters dopamine transporter protein turnover in the rat striatum". The Journal of Pharmacology and Experimental Therapeutics . 304 (1): 15–21. doi :10.1124/jpet.102.038018 . PMID 12490570 . S2CID 27253009 .
DAT Tooltip Dopamine transporter (DRIs Tooltip Dopamine reuptake inhibitors )
NET Tooltip Norepinephrine transporter (NRIs Tooltip Norepinephrine reuptake inhibitors )
Others: Antihistamines (e.g., brompheniramine , chlorphenamine , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., ketamine , phencyclidine )Dopexamine Ephenidine Ginkgo biloba Indeloxazine Nefazodone Opioids (e.g., desmetramadol , methadone , pethidine (meperidine) , tapentadol , tramadol , levorphanol )
SERT Tooltip Serotonin transporter (SRIs Tooltip Serotonin reuptake inhibitors )
Others: A-80426 Amoxapine Antihistamines (e.g., brompheniramine , chlorphenamine , dimenhydrinate , diphenhydramine , mepyramine (pyrilamine) , pheniramine , tripelennamine )Antipsychotics (e.g., loxapine , ziprasidone )Arylcyclohexylamines (e.g., 3-MeO-PCP , esketamine , ketamine , methoxetamine , phencyclidine )Cyclobenzaprine Delucemine Dextromethorphan Dextrorphan Efavirenz Hypidone Medifoxamine Mesembrine Mifepristone MIN-117 (WF-516) N-Me-5-HT Opioids (e.g., dextropropoxyphene , methadone , pethidine (meperidine) , levorphanol , tapentadol , tramadol )Roxindole
VMATs Tooltip Vesicular monoamine transporters Others
2-Carboxymethyl Esters (3,4-Disubstituted Phenyl)-tropanes Arylcarboxy Carboxyalkyl Acyl β,α Stereochemistry α,β Stereochemistry Heterocycles: 3-Substituted-isoxazol-5-yl Heterocycles: 3-Substituted-1,2,4-oxadiazole N-alkyl N-replaced (S,O,C) Irreversible Nortropanes (N-demethylated)
