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Chemical 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 307.437 g·mol−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] 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),
[4] it may be that WF-23 largely or mostly binds to its transporters until they are degraded.
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 .
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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)