Dimetotiazine

Dimetotiazine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	By mouth
ATC code	N02CX05 (WHO) ;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 10-(2-Dimethylaminopropyl)-N,N-dimethylphenothiazine-2-sulfonamide;
CAS Number	7456-24-8 ;
PubChem CID	3089;
DrugBank	DB08967 ;
ChemSpider	2979 ;
UNII	1FTA475ZDB;
KEGG	D07854 ;
CompTox Dashboard (EPA)	DTXSID6023076 ;
ECHA InfoCard	100.028.390
Chemical and physical data
Formula	C19H25N3O2S2
Molar mass	391.55 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:VWNWVCJGUMZDIU-UHFFFAOYSA-N ;
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Dimetotiazine (INN) is a phenothiazine drug used for the treatment of migraine. It is a serotonin antagonist and histamine antagonist.^[1]

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

^ 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.
^ GB 814512 (1959 to Rhone-Poulenc).

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[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).

[1]

[2]

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	By mouth
ATC code	N02CX05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 10-(2-Dimethylaminopropyl)-N,N-dimethylphenothiazine-2-sulfonamide
CAS Number	7456-24-8^Y
PubChem CID	3089
DrugBank	DB08967^N
ChemSpider	2979^N
UNII	1FTA475ZDB
KEGG	D07854^Y
CompTox Dashboard (EPA)	DTXSID6023076
ECHA InfoCard	100.028.390
Chemical and physical data
Formula	C₁₉H₂₅N₃O₂S₂
Molar mass	391.55 g·mol⁻¹
3D model (JSmol)	Interactive image
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)