Chloroethylnorapomorphine

Chloroethylnorapomorphine is a chemical once thought to be an irreversible dopamine D2 receptor antagonist;[1][2] however, it was later proved to be reversible.[3]

Chloroethylnorapomorphine
Names
Preferred IUPAC name
(6aR)-6-(2-Chloroethyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline-10,11-diol
Other names
(−)-N-(2-Chloroethyl)-norapomorphine
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C18H18ClNO2/c19-7-9-20-8-6-11-2-1-3-13-16(11)14(20)10-12-4-5-15(21)18(22)17(12)13/h1-5,14,21-22H,6-10H2/t14-/m1/s1 Y
    Key: RMKWDBUEXHJPRZ-CQSZACIVSA-N Y
SMILES
  • C1CN([C@@H]2CC3=C(C4=C2C1=CC=C4)C(=C(C=C3)O)O)CCCl
Properties
Chemical formula
 C18H18ClNO2
Molar mass 315.80 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References
  1. Cohen SA, Neumeyer J (Oct 1983). "Kinetics of solvolysis of N-(2-chloroethyl)norapomorphine, an irreversible dopamine receptor antagonist". Journal of Medicinal Chemistry. 26 (10): 1348–53. doi:10.1021/jm00364a003. PMID 6620296.
  2. Guan JH, Neumeyer JL, Filer CN, Ahern DG, Lilly L, Watanabe M, Grigoriadis D, Seeman P (Jun 1984). "N-(2-chloroethyl) [8,9-2H]norapomorphine, an irreversible ligand for dopamine receptors: synthesis and application". Journal of Medicinal Chemistry. 27 (6): 806–10. doi:10.1021/jm00372a019. PMID 6737423.
  3. Lehmann, J; Langer, SZ (1982). "Dopamine autoreceptors differ pharmacologically from postsynaptic dopamine receptors: Effects of (−)-N-(2-chloroethyl)-norapomorphine". European Journal of Pharmacology. 77 (1): 85–6. doi:10.1016/0014-2999(82)90542-8. PMID 7060630.


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