Chloroethylnorapomorphine

Chloroethylnorapomorphine
Names
	IUPAC name 12a-Chloro-12a-homo-6aβ-aporphine-10,11-diol
	Systematic 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	75946-94-0 ;
3D model (JSmol)	Interactive image ;
ChEMBL	ChEMBL283871 ;
ChemSpider	137707 ;
PubChem CID	156376 ;
UNII	VD4272R3UB ;
CompTox Dashboard (EPA)	DTXSID90226853 ;
	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 Key: RMKWDBUEXHJPRZ-CQSZACIVSA-N ;
	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). verify (what is ?) Infobox references

Last updated December 30, 2025

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]

References

↑ 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.
↑ 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.
↑ 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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[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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Names

IUPAC name 12a-Chloro-12a-homo-6aβ-aporphine-10,11-diol
Systematic 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	75946-94-0 ^N
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL283871 ^Y
ChemSpider	137707 ^Y
PubChem CID	156376
UNII	VD4272R3UB ^Y
CompTox Dashboard (EPA)	DTXSID90226853
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). N verify (what is ^YN ?) Infobox references