Doxanthrine

Doxanthrine
Clinical data
ATC code	none;
Identifiers
	IUPAC name (6aS,12bR)-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline-2,3-diol;
PubChem CID	15981509;
ChemSpider	13112900;
Chemical and physical data
Formula	C16H15NO3
Molar mass	269.295 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c1ccc2c(c1)CN[C@H]3[C@H]2c4cc(c(cc4OC3)O)O;
	InChI InChI=1S/C16H15NO3/c18-13-5-11-15(6-14(13)19)20-8-12-16(11)10-4-2-1-3-9(10)7-17-12/h1-6,12,16-19H,7-8H2/t12-,16-/m1/s1; Key:QDUNOUQOKOYLCH-MLGOLLRUSA-N;
(verify)

Doxanthrine is a synthetic compound which is a potent and selective full agonist for the dopamine D₁ receptor.[1][2] Doxanthrine has been shown to be orally active in producing contralateral rotation in the 6-hydroxy-dopamine rat model of Parkinson's disease.[3]

References

Cueva JP, Giorgioni G, Grubbs RA, Chemel BR, Watts VJ, Nichols DE (November 2006). "trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist". Journal of Medicinal Chemistry. 49 (23): 6848–57. doi:10.1021/jm0604979. PMID 17154515.
Przybyla JA, Cueva JP, Chemel BR, Hsu KJ, Riese DJ, McCorvy JD, Chester JA, Nichols DE, Watts VJ (February 2009). "Comparison of the enantiomers of (±)-doxanthrine, a high efficacy full dopamine D1 receptor agonist, and a reversal of enantioselectivity at D1 versus alpha2C adrenergic receptors". European Neuropsychopharmacology. 19 (2): 138–46. doi:10.1016/j.euroneuro.2008.10.002. PMC 2636714. PMID 19028082.
McCorvey JD, Watts VJ, Nichols DE (July 2012). "Comparison of the D1 dopamine full agonists, dihydrexidine and doxanthrine, in the 6-OHDA rat model of Parkinson's disease". Psychopharmacology. 222 (1): 81–87. doi:10.1007/s00213-011-2625-5. PMID 22222862.

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[pmid17154515-1] Cueva JP, Giorgioni G, Grubbs RA, Chemel BR, Watts VJ, Nichols DE (November 2006). "trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist". Journal of Medicinal Chemistry. 49 (23): 6848–57. doi:10.1021/jm0604979. PMID 17154515.

[pmid19028082-2] Przybyla JA, Cueva JP, Chemel BR, Hsu KJ, Riese DJ, McCorvy JD, Chester JA, Nichols DE, Watts VJ (February 2009). "Comparison of the enantiomers of (±)-doxanthrine, a high efficacy full dopamine D1 receptor agonist, and a reversal of enantioselectivity at D1 versus alpha2C adrenergic receptors". European Neuropsychopharmacology. 19 (2): 138–46. doi:10.1016/j.euroneuro.2008.10.002. PMC 2636714. PMID 19028082.

[3] McCorvey JD, Watts VJ, Nichols DE (July 2012). "Comparison of the D1 dopamine full agonists, dihydrexidine and doxanthrine, in the 6-OHDA rat model of Parkinson's disease". Psychopharmacology. 222 (1): 81–87. doi:10.1007/s00213-011-2625-5. PMID 22222862.