Dimetotiazine

Dimetotiazine (INN) is a phenothiazine drug used for the treatment of migraine. It is a serotonin antagonist and histamine antagonist.[1]

Dimetotiazine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
IUPAC name
  • 10-(2-Dimethylaminopropyl)-N,N-dimethylphenothiazine-2-sulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.028.390
Chemical and physical data
FormulaC19H25N3O2S2
Molar mass391.55 g·mol−1
3D model (JSmol)
SMILES
  • CC(CN1C2=CC=CC=C2SC3=C1C=C(C=C3)S(=O)(=O)N(C)C)N(C)C
InChI
  • InChI=1S/C19H25N3O2S2/c1-14(20(2)3)13-22-16-8-6-7-9-18(16)25-19-11-10-15(12-17(19)22)26(23,24)21(4)5/h6-12,14H,13H2,1-5H3 N
  • Key:VWNWVCJGUMZDIU-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Synthesis
Thieme Patent:[2]

The Sandmeyer reaction on o-(4-Dimethylaminosulfonyl-2-nitrophenylthio)aniline [5510-56-5] (1) gives 4-[(2-Bromophenyl)-thio]-N,N'-dimethyl-3-nitro-benzenesulfonamide [5510-58-7] (2). The reduction of the nitro group gives 3-Amino-4-((2-bromophenyl)thio)-N,N-dimethylbenzenesulfonamide [5592-64-3] (3). Goldberg reaction gives the chief precursor, 2-Dimethylaminosulfonylphenthiazine [1090-78-4] (4). Alkylation of this with 1-chloro-N,N-dimethylpropan-2-amine [53309-35-6] (5) give Dimethothiazine (6).

References
  1. Shimazawa M, Hara H, Watano T, Sukamoto T (August 1995). "Effects of Ca2+ channel blockers on cortical hypoperfusion and expression of c-Fos-like immunoreactivity after cortical spreading depression in rats". British Journal of Pharmacology. 115 (8): 1359–68. doi:10.1111/j.1476-5381.1995.tb16624.x. PMC 1908864. PMID 8564192.
  2. GB 814512 (1959 to Rhone-Poulenc).
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