Chlorproethazine

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]

Chlorproethazine
Names
Preferred IUPAC name
3-(2-Chlorophenothiazin-10-yl)-N,N-diethylpropan-1-amine
Other names
RP-4909
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.373
KEGG
UNII
  • InChI=1S/C19H23ClN2S/c1-3-21(4-2)12-7-13-22-16-8-5-6-9-18(16)23-19-11-10-15(20)14-17(19)22/h5-6,8-11,14H,3-4,7,12-13H2,1-2H3 ☒N
    Key: DBOUGBAQLIXZLV-UHFFFAOYSA-N ☒N
  • InChI=1/C19H23ClN2S/c1-3-21(4-2)12-7-13-22-16-8-5-6-9-18(16)23-19-11-10-15(20)14-17(19)22/h5-6,8-11,14H,3-4,7,12-13H2,1-2H3
    Key: DBOUGBAQLIXZLV-UHFFFAOYAP
  • Clc2cc1N(c3c(Sc1cc2)cccc3)CCCN(CC)CC
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).
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Infobox references

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. 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. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 222–. ISBN 978-3-88763-075-1.
  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. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia. Elsevier. pp. 989–. ISBN 978-0-8155-1856-3.
  5. "Chlorproethazine". Drugs.com. Archived from the original on 27 September 2017.
  6. Rietschel RL, Fowler JF, Fisher AA (2008). Fisher's Contact Dermatitis. PMPH-USA. pp. 249–. ISBN 978-1-55009-378-0.
  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. US 2769002, Buisson P, Gailliot P, "Preparation of Phenothiazine Compounds", issued 30 October 1956, assigned to Rhône-Poulenc



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