Chlorproethazine

Chlorproethazine

Chlorproethazine

Chemical compound

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]

Quick Facts Names, Identifiers ...

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.

Patent:[8]

Thus alkylation of 2-(2-bromo-phenylsulfanyl)-5-chloro-aniline [105790-02-1] (1) with 3-chloro-1-diethylaminopropane [104-77-8] (2) leads to the intermediate (3). Ring closure as above by nucleophilic aromatic displacement leads to the antipsychotic drug chlorproethazine (4).

The last step uses copper powder and is a form of the Ullmann condensation (i.e. the Goldberg reaction).

References

  1. [1]
    Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 264–. ISBN 978-1-4757-2085-3.
  2. [2]
    Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 222–. ISBN 978-3-88763-075-1.
  3. [3]
    Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 74–. ISBN 978-94-011-4439-1.
  4. [4]
    William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 989–. ISBN 978-0-8155-1856-3.
  5. [5]
    "Chlorproethazine". Drugs.com. Archived from the original on 27 September 2017.
  6. [6]
    Rietschel RL, Fowler JF, Fisher AA (2008). Fisher's Contact Dermatitis. PMPH-USA. pp. 249–. ISBN 978-1-55009-378-0.
  7. [7]
    Johansen JD, Frosch PJ, Lepoittevin JP (29 September 2010). Contact Dermatitis. Springer Science & Business Media. pp. 373–. ISBN 978-3-642-03827-3.
  8. [8]
    US 2769002, Buisson P, Gailliot P, "Preparation of Phenothiazine Compounds", issued 30 October 1956, assigned to Rhône-Poulenc



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