From Wikipedia, the free encyclopedia
Chlorproethazine
Names
Preferred IUPAC name
3-(2-Chlorophenothiazin-10-yl)-N ,N -diethylpropan-1-amine
Other names
RP-4909
Identifiers
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
C19 H23 ClN2 S
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).
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]
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
^ 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 .
^
Index Nominum 2000: International Drug Directory . Taylor & Francis. 2000. pp. 222–.
ISBN
978-3-88763-075-1 .
^ 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 .
^ William Andrew Publishing (22 October 2013).
Pharmaceutical Manufacturing Encyclopedia . Elsevier. pp. 989–.
ISBN
978-0-8155-1856-3 .
^
"Chlorproethazine" . Drugs.com . Archived from
the original on 27 September 2017.
^ Rietschel RL, Fowler JF, Fisher AA (2008).
Fisher's Contact Dermatitis . PMPH-USA. pp. 249–.
ISBN
978-1-55009-378-0 .
^ Johansen JD, Frosch PJ, Lepoittevin JP (29 September 2010).
Contact Dermatitis . Springer Science & Business Media. pp. 373–.
ISBN
978-3-642-03827-3 .
^
US 2769002 , Buisson P, Gailliot P, "Preparation of Phenothiazine Compounds", issued 30 October 1956, assigned to Rhône-Poulenc