Chlorproethazine

From Wikipedia, the free encyclopedia
Chlorproethazine
Chlorproethazine.svg
Names
IUPAC name
3-(2-chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine
Other names
RP-4909
Identifiers
  • 84-01-5 YesY
  • 4611-02-3 N
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL2105938 N
ChemSpider
  • 59173 N
ECHA InfoCard 100.001.373
KEGG
  • D07308 YesY
PubChem CID
  • 65750
  • 65750
UNII
  • 960NX27Z07 YesY
Properties
C19H23ClN2S
Molar mass 346.91732 g/mol
Pharmacology
N05AA07 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Chlorproethazine, sold under the brand name Neuriplege, is a drug of the phenothiazine group described as a muscle relaxant or tranquilizer which is or has been marketed in Europe as a topical cream for the treatment of muscle pain.[1][2][3][4][5] It has been associated with photoallergic contact dermatitis.[6][7]

Chemistry

Synthesis

Chlorproethazine can be synthesized from a diphenylsulfide derivative. The general scheme is sufficiently flexible to permit the interchange of the order of some of the steps.

Chlorproethazine synthesis.svg

Thus alkylation of aniline thioether () with 3-chloro-1-diethylaminopropane leads to the intermediate (). Ring closure as above by nucleophilic aromatic displacement leads to the antipsychotic drug chlorproethazine.[8]

References

  1. ^ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 264–. ISBN 978-1-4757-2085-3. 
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 222–. ISBN 978-3-88763-075-1. 
  3. ^ I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 74–. ISBN 978-94-011-4439-1. 
  4. ^ William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 989–. ISBN 978-0-8155-1856-3. 
  5. ^ https://www.drugs.com/international/chlorproethazine.html
  6. ^ Robert L. Rietschel; Joseph F. Fowler; Alexander A. Fisher (2008). Fisher's Contact Dermatitis. PMPH-USA. pp. 249–. ISBN 978-1-55009-378-0. 
  7. ^ Jeanne Duus Johansen; Peter J. Frosch; Jean-Pierre Lepoittevin (29 September 2010). Contact Dermatitis. Springer Science & Business Media. pp. 373–. ISBN 978-3-642-03827-3. 
  8. ^ Buisson, P.; Gailliot, P.; 1956, U.S. Patent 2,769,002



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