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Benzothiazines

Aromatic organic heterocyclic compounds that consist of benzene fused with a thiazine; thiazines are six-membered rings that contain four carbon atoms, one nitrogen atom, and one sulfur atom.

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1

10H-Phenothiazine 5-Oxide, TRC

CAS: 1207-71-2 Molecular Formula: C12H9NOS Molecular Weight (g/mol): 215.27 Synonym: Phenothiazine 5-Oxide,NSC 3554,Phenothiazine S-Oxide IUPAC Name: 10H-phenothiazine 5-oxide SMILES: O=S1c2ccccc2Nc3ccccc13

CAS 1207-71-2
Molecular Weight (g/mol) 215.27
SMILES O=S1c2ccccc2Nc3ccccc13
Synonym Phenothiazine 5-Oxide,NSC 3554,Phenothiazine S-Oxide
IUPAC Name 10H-phenothiazine 5-oxide
Molecular Formula C12H9NOS
2

N-Propargyl Phenothiazine, TRC

CAS: 4282-78-4 Molecular Formula: C15H11NS Molecular Weight (g/mol): 237.32 Synonym: 10-Propargylphenothiazine,10-(2-Propyn-1-yl)-10H-phenothiazine IUPAC Name: 10-prop-2-ynylphenothiazine SMILES: C#CCN1c2ccccc2Sc3ccccc13

CAS 4282-78-4
Molecular Weight (g/mol) 237.32
SMILES C#CCN1c2ccccc2Sc3ccccc13
Synonym 10-Propargylphenothiazine,10-(2-Propyn-1-yl)-10H-phenothiazine
IUPAC Name 10-prop-2-ynylphenothiazine
Molecular Formula C15H11NS
3

Didesmethylchlorpromazine Hydrochloride, TRC

CAS: 3763-80-2 Molecular Formula: C15H16Cl2N2S Molecular Weight (g/mol): 327.27 Synonym: 10-(3-Aminopropyl)-2-chloro-phenothiazine Monohydrochloride,Didemethylchlorpromazine Hydrochloride,Didesmethylchlorpromazine Hydrochloride,SKF 4577A SMILES: Cl.NCCCN1c2ccccc2Sc3ccc(Cl)cc13

CAS 3763-80-2
Molecular Weight (g/mol) 327.27
SMILES Cl.NCCCN1c2ccccc2Sc3ccc(Cl)cc13
Synonym 10-(3-Aminopropyl)-2-chloro-phenothiazine Monohydrochloride,Didemethylchlorpromazine Hydrochloride,Didesmethylchlorpromazine Hydrochloride,SKF 4577A
Molecular Formula C15H16Cl2N2S
4

2-(1-Hydroxyethyl) Promazine Sulfoxide (mixture of diastereomers), TRC

Molecular Formula: C19H24N2O2S Molecular Weight (g/mol): 344.47 Synonym: 2-(1-Hydroxyethyl) Promazine Sulfoxide IUPAC Name: 1-[10-[3-(dimethylamino)propyl]-5-oxophenothiazin-2-yl]ethanol SMILES: CC(O)c1ccc2c(c1)N(CCCN(C)C)c3ccccc3S2=O

Molecular Weight (g/mol) 344.47
SMILES CC(O)c1ccc2c(c1)N(CCCN(C)C)c3ccccc3S2=O
Synonym 2-(1-Hydroxyethyl) Promazine Sulfoxide
IUPAC Name 1-[10-[3-(dimethylamino)propyl]-5-oxophenothiazin-2-yl]ethanol
Molecular Formula C19H24N2O2S
5

Methdilazine Hydrochloride, TRC

CAS: 1229-35-2 Molecular Formula: C18 H20 N2 S . Cl H Molecular Weight (g/mol): 332.89 Synonym: 10H-Phenothiazine, 10-[(1-methyl-3-pyrrolidinyl)methyl]-, hydrochloride (1:1), 10H-Phenothiazine, 10-[(1-methyl-3-pyrrolidinyl)methyl]-, monohydrochloride (9CI),Phenothiazine, 10-[(1-methyl-3-pyrrolidinyl)methyl]-, monohydrochloride (8CI),Dilosyn,Disyncran,Methdilazine hydrochloride,Methdilazine monohydrochloride,NSC 169091,Tacaryl,Tacaryl hydrochloride IUPAC Name: 10-[(1-methylpyrrolidin-3-yl)methyl]phenothiazine;hydrochloride SMILES: Cl.CN1CCC(CN2c3ccccc3Sc4ccccc24)C1

CAS 1229-35-2
Molecular Weight (g/mol) 332.89
SMILES Cl.CN1CCC(CN2c3ccccc3Sc4ccccc24)C1
Synonym 10H-Phenothiazine, 10-[(1-methyl-3-pyrrolidinyl)methyl]-, hydrochloride (1:1), 10H-Phenothiazine, 10-[(1-methyl-3-pyrrolidinyl)methyl]-, monohydrochloride (9CI),Phenothiazine, 10-[(1-methyl-3-pyrrolidinyl)methyl]-, monohydrochloride (8CI),Dilosyn,Disyncran,Methdilazine hydrochloride,Methdilazine monohydrochloride,NSC 169091,Tacaryl,Tacaryl hydrochloride
IUPAC Name 10-[(1-methylpyrrolidin-3-yl)methyl]phenothiazine;hydrochloride
Molecular Formula C18 H20 N2 S . Cl H
6

2-(1-Hydroxyethyl) Promazine, TRC

CAS: 73644-43-6 Molecular Formula: C19 H24 N2 O S Molecular Weight (g/mol): 328.47 Synonym: 10-[3-(Dimethylamino)propyl]-α-methyl-10H-phenothiazine-2-methanol,Phenothiazine-2-methanol, 10-(3-dimethylaminopropyl)-α-methyl- (6CI),10-[3-(Dimethylamino)propyl]-α-methyl-10H-phenothiazine-2-methanol,Dihydroacepromazine,2-(1-Hydroxyethyl) Promazine IUPAC Name: 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]ethanol SMILES: CC(O)c1ccc2Sc3ccccc3N(CCCN(C)C)c2c1

CAS 73644-43-6
Molecular Weight (g/mol) 328.47
SMILES CC(O)c1ccc2Sc3ccccc3N(CCCN(C)C)c2c1
Synonym 10-[3-(Dimethylamino)propyl]-α-methyl-10H-phenothiazine-2-methanol,Phenothiazine-2-methanol, 10-(3-dimethylaminopropyl)-α-methyl- (6CI),10-[3-(Dimethylamino)propyl]-α-methyl-10H-phenothiazine-2-methanol,Dihydroacepromazine,2-(1-Hydroxyethyl) Promazine
IUPAC Name 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]ethanol
Molecular Formula C19 H24 N2 O S
7

Azure B (Technical Grade), TRC

CAS: 531-55-5 Molecular Formula: C15 H16 N3 S . Cl Molecular Weight (g/mol): 305.83 Synonym: Azur I,Azure B Chloride,Azure I,C.I. 52010,Methylene Azure,Trimethylthionine Chloride,3-Methylamino-7-dimethylaminophenazathionium Chloride,Trimethylthionine,3-(Dimethylamino)-7-(methylamino)-phenothiazin-5-ium Chloride,3-(Dimethylamino)-7-(methylamino)phenothiazin-5-ylium Chloride IUPAC Name: 3-N,7-N,7-N-trimethylphenothiazin-5-ium-3,7-diamine;chloride SMILES: [Cl-].CNc1ccc2nc3ccc(cc3[s+]c2c1)N(C)C

CAS 531-55-5
Molecular Weight (g/mol) 305.83
SMILES [Cl-].CNc1ccc2nc3ccc(cc3[s+]c2c1)N(C)C
Synonym Azur I,Azure B Chloride,Azure I,C.I. 52010,Methylene Azure,Trimethylthionine Chloride,3-Methylamino-7-dimethylaminophenazathionium Chloride,Trimethylthionine,3-(Dimethylamino)-7-(methylamino)-phenothiazin-5-ium Chloride,3-(Dimethylamino)-7-(methylamino)phenothiazin-5-ylium Chloride
IUPAC Name 3-N,7-N,7-N-trimethylphenothiazin-5-ium-3,7-diamine;chloride
Molecular Formula C15 H16 N3 S . Cl
8

1,9-Dimethyl-methylene Blue Zinc Chloride Double Salt (Technical Grade), TRC

CAS: 931418-92-7 Molecular Formula: 2 C18 H22 N3 S . 2Cl . Zn Cl2 Molecular Weight (g/mol): 832.12 Synonym: 1,9-Dimethyl-Methylene Blue Zinc Chloride Double Salt IUPAC Name: bis(3,7-bis(dimethylamino)-1,9-dimethylphenothiazin-5-ium) zinc(II) chloride SMILES: CC1=C2C([S+]=C(C3=N2)C=C(C=C3C)N(C)C)=CC(N(C)C)=C1.CC4=C5C([S+]=C(C6=N5)C=C(C=C6C)N(C)C)=CC(N(C)C)=C4.Cl[Zn]Cl.[Cl-].[Cl-]

CAS 931418-92-7
Molecular Weight (g/mol) 832.12
SMILES CC1=C2C([S+]=C(C3=N2)C=C(C=C3C)N(C)C)=CC(N(C)C)=C1.CC4=C5C([S+]=C(C6=N5)C=C(C=C6C)N(C)C)=CC(N(C)C)=C4.Cl[Zn]Cl.[Cl-].[Cl-]
Synonym 1,9-Dimethyl-Methylene Blue Zinc Chloride Double Salt
IUPAC Name bis(3,7-bis(dimethylamino)-1,9-dimethylphenothiazin-5-ium) zinc(II) chloride
Molecular Formula 2 C18 H22 N3 S . 2Cl . Zn Cl2
9

Phenothiazine S,S-Dioxide, TRC

CAS: 1209-66-1 Molecular Formula: C12H9NO2S Molecular Weight (g/mol): 231.27 Synonym: 5,5-Dioxophenothiazine; IUPAC Name: 10H-phenothiazine 5,5-dioxide SMILES: O=S1(=O)c2ccccc2Nc3ccccc13

CAS 1209-66-1
Molecular Weight (g/mol) 231.27
SMILES O=S1(=O)c2ccccc2Nc3ccccc13
Synonym 5,5-Dioxophenothiazine;
IUPAC Name 10H-phenothiazine 5,5-dioxide
Molecular Formula C12H9NO2S
10

4-Chlorophenothiazine, TRC

CAS: 7369-69-9 Molecular Formula: C12 H8 Cl N S Molecular Weight (g/mol): 233.72 Synonym: 4-Chloro-10H-phenothiazine IUPAC Name: 4-chloro-10H-phenothiazine SMILES: Clc1cccc2Nc3ccccc3Sc12

CAS 7369-69-9
Molecular Weight (g/mol) 233.72
SMILES Clc1cccc2Nc3ccccc3Sc12
Synonym 4-Chloro-10H-phenothiazine
IUPAC Name 4-chloro-10H-phenothiazine
Molecular Formula C12 H8 Cl N S
11

Propionylpromazine Hydrochloride, TRC

CAS: 7681-67-6 Molecular Formula: C20 H24 N2 O S . Cl H Molecular Weight (g/mol): 376.94 Synonym: Propionylpromazine Hydrochloride,1-Propanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-, monohydrochloride (9CI),1-Propanone, 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]-, hydrochloride (7CI),1-Propanone, 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]-, monohydrochloride (8CI),2-Propionyl-10-(3-dimethylaminopropyl)phenothiazine hydrochloride,Propiopromazine hydrochloride,Tranvet,1-Propanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-, hydrochloride (1:1) IUPAC Name: 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]propan-1-one;hydrochloride SMILES: Cl.CCC(=O)c1ccc2Sc3ccccc3N(CCCN(C)C)c2c1

CAS 7681-67-6
Molecular Weight (g/mol) 376.94
SMILES Cl.CCC(=O)c1ccc2Sc3ccccc3N(CCCN(C)C)c2c1
Synonym Propionylpromazine Hydrochloride,1-Propanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-, monohydrochloride (9CI),1-Propanone, 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]-, hydrochloride (7CI),1-Propanone, 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]-, monohydrochloride (8CI),2-Propionyl-10-(3-dimethylaminopropyl)phenothiazine hydrochloride,Propiopromazine hydrochloride,Tranvet,1-Propanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-, hydrochloride (1:1)
IUPAC Name 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]propan-1-one;hydrochloride
Molecular Formula C20 H24 N2 O S . Cl H
12

1-[10-[2-(Dimethylamino)propyl]phenothiazin-2-yl-1-propanone (>90%), TRC

CAS: 362-29-8 Molecular Formula: C20 H24 N2 O S Molecular Weight (g/mol): 340.48 Synonym: 1-Propanone, 1-[10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-,1-Propanone, 1-[10-[2-(dimethylamino)propyl]phenothiazin-2-yl]- (6CI,7CI,8CI),1-[10-[2-(Dimethylamino)propyl]-10H-phenothiazin-2-yl]-1-propanone,(±)-Propiomazine,1-[10-[2-(Dimethylamino)propyl]phenothiazin-2-yl]-1-propanone,2-Propionyl-10-[2-(dimethylamino)propyl]phenothiazine,Propiomazine,Propionylpromethazine,Wy 1359 IUPAC Name: 1-[10-[2-(dimethylamino)propyl]phenothiazin-2-yl]propan-1-one SMILES: CCC(=O)c1ccc2Sc3ccccc3N(CC(C)N(C)C)c2c1

CAS 362-29-8
Molecular Weight (g/mol) 340.48
SMILES CCC(=O)c1ccc2Sc3ccccc3N(CC(C)N(C)C)c2c1
Synonym 1-Propanone, 1-[10-[2-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-,1-Propanone, 1-[10-[2-(dimethylamino)propyl]phenothiazin-2-yl]- (6CI,7CI,8CI),1-[10-[2-(Dimethylamino)propyl]-10H-phenothiazin-2-yl]-1-propanone,(±)-Propiomazine,1-[10-[2-(Dimethylamino)propyl]phenothiazin-2-yl]-1-propanone,2-Propionyl-10-[2-(dimethylamino)propyl]phenothiazine,Propiomazine,Propionylpromethazine,Wy 1359
IUPAC Name 1-[10-[2-(dimethylamino)propyl]phenothiazin-2-yl]propan-1-one
Molecular Formula C20 H24 N2 O S
13

Acepromazine Maleate, TRC

CAS: 3598-37-6 Molecular Formula: C19 H22 N2 O S . C4 H4 O4 Molecular Weight (g/mol): 442.53 Synonym: Acepromazine Maleate,Ethanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-, (2Z)-2-butenedioate (1:1),Ethanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-, (Z)-2-butenedioate (1:1),Ketone, 10-[3-(dimethylamino)propyl]phenothiazin-2-yl methyl, maleate (1:1) (8CI),Ketone, 10-[3-(dimethylamino)propyl]phenothiazin-2-yl methyl, maleate (6CI,7CI),Maleic acid, compd. with 10-(3-dimethylaminopropyl)phenothiazin-2-yl methyl ketone (6CI),Acepran,Acepromazine monomaleate,Acetopromazine maleate salt,Acetylpromazine maleate,Anatran,Atravet,Calmivet,Calmo Neosan,NSC 264522,Notensil,Notenzil,Plegicil,Sedalin,Soprontin IUPAC Name: 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]ethanone SMILES: CN(C)CCCN1c2ccccc2Sc3ccc(cc13)C(=O)C.OC(=O)\C=C/C(=O)O

CAS 3598-37-6
Molecular Weight (g/mol) 442.53
SMILES CN(C)CCCN1c2ccccc2Sc3ccc(cc13)C(=O)C.OC(=O)\C=C/C(=O)O
Synonym Acepromazine Maleate,Ethanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-, (2Z)-2-butenedioate (1:1),Ethanone, 1-[10-[3-(dimethylamino)propyl]-10H-phenothiazin-2-yl]-, (Z)-2-butenedioate (1:1),Ketone, 10-[3-(dimethylamino)propyl]phenothiazin-2-yl methyl, maleate (1:1) (8CI),Ketone, 10-[3-(dimethylamino)propyl]phenothiazin-2-yl methyl, maleate (6CI,7CI),Maleic acid, compd. with 10-(3-dimethylaminopropyl)phenothiazin-2-yl methyl ketone (6CI),Acepran,Acepromazine monomaleate,Acetopromazine maleate salt,Acetylpromazine maleate,Anatran,Atravet,Calmivet,Calmo Neosan,NSC 264522,Notensil,Notenzil,Plegicil,Sedalin,Soprontin
IUPAC Name 1-[10-[3-(dimethylamino)propyl]phenothiazin-2-yl]ethanone
Molecular Formula C19 H22 N2 O S . C4 H4 O4
14

Promethazine N-Oxide, TRC

CAS: 81480-39-9 Molecular Formula: C17 H20 N2 O S Molecular Weight (g/mol): 300.4185 Synonym: N,N,α-Trimethyl-10H-phenothiazine-10-ethanamine N-Oxide IUPAC Name: N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine oxide SMILES: CC(CN1c2ccccc2Sc3ccccc13)[N+](C)(C)[O-]

CAS 81480-39-9
Molecular Weight (g/mol) 300.4185
SMILES CC(CN1c2ccccc2Sc3ccccc13)[N+](C)(C)[O-]
Synonym N,N,α-Trimethyl-10H-phenothiazine-10-ethanamine N-Oxide
IUPAC Name N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine oxide
Molecular Formula C17 H20 N2 O S
15

rac N-Demethyl Promethazine-d3 Hydrochloride, TRC

CAS: 1330173-19-7 Molecular Formula: C16H16D3ClN2S Molecular Weight (g/mol): 309.87 Synonym: N,α-Dimethyl-10H-phenothiazine-10-ethanamine-d3 Hydrochloride,Nor1-Promethazine-d3 Monohydrochloride SMILES: CC(NC([2H])([2H])[2H])CN1C2=C(C=CC=C2)SC3=CC=CC=C31.Cl

CAS 1330173-19-7
Molecular Weight (g/mol) 309.87
SMILES CC(NC([2H])([2H])[2H])CN1C2=C(C=CC=C2)SC3=CC=CC=C31.Cl
Synonym N,α-Dimethyl-10H-phenothiazine-10-ethanamine-d3 Hydrochloride,Nor1-Promethazine-d3 Monohydrochloride
Molecular Formula C16H16D3ClN2S