2β-Propanoyl-3β-(2-naphthyl)-tropane
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| Pharmacokinetic data | |
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| Bioavailability | High[medical citation needed] |
| Elimination half-life | Slow[medical citation needed] |
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| Chemical and physical data | |
| Formula | C21H25NO |
| Molar mass | 307.437 g·mol−1 |
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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.
WF-23 is made from methyl-ferruginine i.e. PC10080982 [152668-77-4].
See also
[edit]References
[edit]- ↑ US 6008227, Davies HM, Childers SR, Bennett B, "Process for blocking 5-HT and dopamine uptake with biologically active tropane derivatives", issued 28 December 1999, assigned to Wake Forest University Health Sciences
- ↑ Bennett BA, Wichems CH, Hollingsworth CK, Davies HM, Thornley C, Sexton T, et al. (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.
Further reading
[edit]- Singh S (March 2000). "Chemistry, design, and structure-activity relationship of cocaine antagonists" (PDF). Chemical Reviews. 100 (3): 925–1024. doi:10.1021/cr9700538. PMID 11749256.