2β-Propanoyl-3β-(2-naphthyl)-tropane
Chemical compound
Pharmacokinetic data | |
---|---|
Bioavailability | high |
Metabolism | slow |
Identifiers | |
|
|
PubChem CID | |
ChemSpider | |
Chemical and physical data | |
Formula | C 21 H 25 N O |
Molar mass | 307.437 g·mol −1 |
3D model ( JSmol ) | |
|
|
|
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
- (Satendra Singh, 2000) Page 16-17
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 .
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) |