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2β-Propanoyl-3β-(2-naphthyl)-tropane

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
2β-Propanoyl-3β-(2-naphthyl)-tropane
Pharmacokinetic data
BioavailabilityHigh[medical citation needed]
Eliminationhalf-lifeSlow[medical citation needed]
Identifiers
  • 1-[(1S,3S,4R,5R)-8-methyl-3-naphthalen-2-yl-8-azabicyclo[3.2.1]octan-4-yl]propan-1-one
CAS Number
PubChemCID
ChemSpider
Chemical and physical data
FormulaC21H25NO
Molar mass307.437 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 orWF-23 (Wake Forest-23, named after the university where it was first created) is acocaineanalogue. It is several hundred times more potent than cocaine at being aserotonin-norepinephrine-dopamine reuptake inhibitor.[1]

As can be seen onPubMed, these acyl substituted phenyltropanes are highly potentMAT inhibitors and also have a very longhalf-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]
  1. ^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 
  2. ^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.
  3. ^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.
  4. ^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

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Adamantanes
Adenosine antagonists
Alkylamines
Ampakines
Arylcyclohexylamines
Benzazepines
Cathinones
Cholinergics
Convulsants
Eugeroics
Oxazolines
Phenethylamines
Phenylmorpholines
Piperazines
Piperidines
Phenethylpyrrolidines
Racetams
Psychedelics
Tropanes
Tryptamines
Others
DATTooltip Dopamine transporter
(DRIsTooltip Dopamine reuptake inhibitors)
NETTooltip Norepinephrine transporter
(NRIsTooltip Norepinephrine reuptake inhibitors)
SERTTooltip Serotonin transporter
(SRIsTooltip Serotonin reuptake inhibitors)
VMATsTooltip 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)
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