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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

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
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

rac N-Demethyl Promethazine Hydrochloride, TRC

CAS: 60113-77-1 Molecular Formula: C16 H18 N2 S . Cl H Molecular Weight (g/mol): 306.85 Synonym: (2RS)-N-Methyl-1-(10H-phenothiazin-10-yl)propan-2-amine Hydrochloride,Promethazine Hydrochloride Imp. C (EP) as Hydrochloride,Norpromethazine Hydrochloride,10H-Phenothiazine-10-ethanamine, N,α-dimethyl-, hydrochloride (1:1),10H-Phenothiazine-10-ethanamine, N,α-dimethyl-, monohydrochloride (9CI) IUPAC Name: N-methyl-1-phenothiazin-10-ylpropan-2-amine;hydrochloride SMILES: Cl.CNC(C)CN1c2ccccc2Sc3ccccc13

CAS 60113-77-1
Molecular Weight (g/mol) 306.85
SMILES Cl.CNC(C)CN1c2ccccc2Sc3ccccc13
Synonym (2RS)-N-Methyl-1-(10H-phenothiazin-10-yl)propan-2-amine Hydrochloride,Promethazine Hydrochloride Imp. C (EP) as Hydrochloride,Norpromethazine Hydrochloride,10H-Phenothiazine-10-ethanamine, N,α-dimethyl-, hydrochloride (1:1),10H-Phenothiazine-10-ethanamine, N,α-dimethyl-, monohydrochloride (9CI)
IUPAC Name N-methyl-1-phenothiazin-10-ylpropan-2-amine;hydrochloride
Molecular Formula C16 H18 N2 S . Cl H
4

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
5

N-(3,5-Dimethyl-2(3H)-thiazolylidene)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide, TRC

CAS: 1145656-36-5 Molecular Formula: C15 H15 N3 O4 S2 Molecular Weight (g/mol): 365.43 Synonym: 2H-1,2-Benzothiazine-3-carboxamide, N-(3,5-dimethyl-2(3H)-thiazolylidene)-4-hydroxy-2-methyl-, 1,1-dioxide,N-[3,5-Dimethylthiazol-2(3H)-ylidene]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide,(EZ)-N'-Methylmeloxicam,(EZ)-N-(3,5-dimethylthiazol-2(3H)-ylidene)-4-hydroxy-2-methyl-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide IUPAC Name: N-(3,5-dimethyl-1,3-thiazol-2-ylidene)-4-hydroxy-2-methyl-1,1-dioxo-1λ^{6},2-benzothiazine-3-carboxamide SMILES: CN1C=C(C)SC1=NC(=O)C2=C(O)c3ccccc3S(=O)(=O)N2C

CAS 1145656-36-5
Molecular Weight (g/mol) 365.43
SMILES CN1C=C(C)SC1=NC(=O)C2=C(O)c3ccccc3S(=O)(=O)N2C
Synonym 2H-1,2-Benzothiazine-3-carboxamide, N-(3,5-dimethyl-2(3H)-thiazolylidene)-4-hydroxy-2-methyl-, 1,1-dioxide,N-[3,5-Dimethylthiazol-2(3H)-ylidene]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide,(EZ)-N'-Methylmeloxicam,(EZ)-N-(3,5-dimethylthiazol-2(3H)-ylidene)-4-hydroxy-2-methyl-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide
IUPAC Name N-(3,5-dimethyl-1,3-thiazol-2-ylidene)-4-hydroxy-2-methyl-1,1-dioxo-1λ^{6},2-benzothiazine-3-carboxamide
Molecular Formula C15 H15 N3 O4 S2
6

Thermo Scientific Chemicals Giemsa Stain

CAS: 51811-82-6 Molecular Formula: C14H14ClN3S Molecular Weight (g/mol): 291.80 MDL Number: MFCD00012112,MFCD00081642 InChI Key: NALREUIWICQLPS-UHFFFAOYSA-N Synonym: azure a,dimethylthionine,giemsa stain,azur a,n,n-dimethylthionine,3-amino-7-dimethylamino phenothiazin-5-ium chloride,methylene azure a,giemsa solution,3-amino-7-dimethylaminophenazathionium chloride,unii-m731v243ef PubChem CID: 13735 IUPAC Name: (7-aminophenothiazin-3-ylidene)-dimethylazanium;chloride SMILES: [Cl-].C[N+](C)=C1C=CC2=NC3=CC=C(N)C=C3SC2=C1

PubChem CID 13735
CAS 51811-82-6
Molecular Weight (g/mol) 291.80
MDL Number MFCD00012112,MFCD00081642
SMILES [Cl-].C[N+](C)=C1C=CC2=NC3=CC=C(N)C=C3SC2=C1
Synonym azure a,dimethylthionine,giemsa stain,azur a,n,n-dimethylthionine,3-amino-7-dimethylamino phenothiazin-5-ium chloride,methylene azure a,giemsa solution,3-amino-7-dimethylaminophenazathionium chloride,unii-m731v243ef
IUPAC Name (7-aminophenothiazin-3-ylidene)-dimethylazanium;chloride
InChI Key NALREUIWICQLPS-UHFFFAOYSA-N
Molecular Formula C14H14ClN3S
7

7-Nitro-3,4-dihydro-2H-1,4-benzothiazine, 97%, Thermo Scientific Chemicals

CAS: 69373-37-1 Molecular Formula: C8H8N2O2S Molecular Weight (g/mol): 196.22 MDL Number: MFCD23379852 InChI Key: LCOAYUPAESYAHF-UHFFFAOYSA-N Synonym: 7-nitro-3,4-dihydro-2h-benzo b 1,4 thiazine PubChem CID: 20496121 IUPAC Name: 7-nitro-3,4-dihydro-2H-1,4-benzothiazine SMILES: [O-][N+](=O)C1=CC2=C(NCCS2)C=C1

PubChem CID 20496121
CAS 69373-37-1
Molecular Weight (g/mol) 196.22
MDL Number MFCD23379852
SMILES [O-][N+](=O)C1=CC2=C(NCCS2)C=C1
Synonym 7-nitro-3,4-dihydro-2h-benzo b 1,4 thiazine
IUPAC Name 7-nitro-3,4-dihydro-2H-1,4-benzothiazine
InChI Key LCOAYUPAESYAHF-UHFFFAOYSA-N
Molecular Formula C8H8N2O2S
8

Azure I

CAS: 531-55-5 Molecular Formula: C15H16ClN3S Molecular Weight (g/mol): 305.824 MDL Number: MFCD00011935 InChI Key: DNDJEIWCTMMZBX-UHFFFAOYSA-N Synonym: azure b,azure i,methylene azure b,3-dimethylamino-7-methylamino phenothiazin-5-ium chloride,trimethylthionine chloride,azur i,methyleneazure,methylene azure van,unii-7c8bel8wqv,modr kresylova bb czech PubChem CID: 68275 IUPAC Name: dimethyl-[7-(methylamino)phenothiazin-3-ylidene]azanium;chloride SMILES: CNC1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2.[Cl-]

PubChem CID 68275
CAS 531-55-5
Molecular Weight (g/mol) 305.824
MDL Number MFCD00011935
SMILES CNC1=CC2=C(C=C1)N=C3C=CC(=[N+](C)C)C=C3S2.[Cl-]
Synonym azure b,azure i,methylene azure b,3-dimethylamino-7-methylamino phenothiazin-5-ium chloride,trimethylthionine chloride,azur i,methyleneazure,methylene azure van,unii-7c8bel8wqv,modr kresylova bb czech
IUPAC Name dimethyl-[7-(methylamino)phenothiazin-3-ylidene]azanium;chloride
InChI Key DNDJEIWCTMMZBX-UHFFFAOYSA-N
Molecular Formula C15H16ClN3S
9

Thermo Scientific Chemicals Meloxicam, 99-101%

CAS: 71125-38-7 Molecular Formula: C14H13N3O4S2 Molecular Weight (g/mol): 351.40 MDL Number: MFCD00868752 InChI Key: DWMREKMVXIFPFM-ACCUITESSA-N Synonym: meloxicam,mobic,metacam,movalis,meloxicamum,mobicox,mobec,meloxicam mobic,movatec,parocin PubChem CID: 54677470 ChEBI: CHEBI:6741 IUPAC Name: 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide SMILES: CN1\C(=C(\O)NC2=NC=C(C)S2)C(=O)C2=CC=CC=C2S1(=O)=O

PubChem CID 54677470
CAS 71125-38-7
Molecular Weight (g/mol) 351.40
ChEBI CHEBI:6741
MDL Number MFCD00868752
SMILES CN1\C(=C(\O)NC2=NC=C(C)S2)C(=O)C2=CC=CC=C2S1(=O)=O
Synonym meloxicam,mobic,metacam,movalis,meloxicamum,mobicox,mobec,meloxicam mobic,movatec,parocin
IUPAC Name 4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-1$l^{6},2-benzothiazine-3-carboxamide
InChI Key DWMREKMVXIFPFM-ACCUITESSA-N
Molecular Formula C14H13N3O4S2
10

6-Bromo-3,4-dihydro-2H-1,4-benzothiazine, 97%

CAS: 187604-75-7 Molecular Formula: C8H8BrNS Molecular Weight (g/mol): 230.123 MDL Number: MFCD23379863 InChI Key: AUIBYERXYVUBIL-UHFFFAOYSA-N Synonym: 6-bromo-3,4-dihydro-2h-benzo b 1,4 thiazine PubChem CID: 67172430 IUPAC Name: 6-bromo-3,4-dihydro-2H-1,4-benzothiazine SMILES: C1CSC2=C(N1)C=C(C=C2)Br

PubChem CID 67172430
CAS 187604-75-7
Molecular Weight (g/mol) 230.123
MDL Number MFCD23379863
SMILES C1CSC2=C(N1)C=C(C=C2)Br
Synonym 6-bromo-3,4-dihydro-2h-benzo b 1,4 thiazine
IUPAC Name 6-bromo-3,4-dihydro-2H-1,4-benzothiazine
InChI Key AUIBYERXYVUBIL-UHFFFAOYSA-N
Molecular Formula C8H8BrNS
11

Iso Promethazine Hydrochloride, TRC

CAS: 5568-90-1 Molecular Formula: C17 H20 N2 S . Cl H Molecular Weight (g/mol): 320.88 Synonym: (2RS)-N,N-Dimethyl-2-(10H-phenothiazin-10-yl)propan-1-amine Hydrochloride,Promethazine Hydrochloride Imp. B (EP) as Hydrochloride,Isopromethazine Hydrochloride,10H-Phenothiazine-10-ethanamine, N,N,β-trimethyl-, hydrochloride (1:1),10H-Phenothiazine-10-ethanamine, N,N,β-trimethyl-, monohydrochloride (9CI),Phenothiazine, 10-[2-(dimethylamino)-1-methylethyl]-, monohydrochloride (8CI) IUPAC Name: N,N-dimethyl-2-phenothiazin-10-ylpropan-1-amine;hydrochloride SMILES: Cl.CC(CN(C)C)N1c2ccccc2Sc3ccccc13

CAS 5568-90-1
Molecular Weight (g/mol) 320.88
SMILES Cl.CC(CN(C)C)N1c2ccccc2Sc3ccccc13
Synonym (2RS)-N,N-Dimethyl-2-(10H-phenothiazin-10-yl)propan-1-amine Hydrochloride,Promethazine Hydrochloride Imp. B (EP) as Hydrochloride,Isopromethazine Hydrochloride,10H-Phenothiazine-10-ethanamine, N,N,β-trimethyl-, hydrochloride (1:1),10H-Phenothiazine-10-ethanamine, N,N,β-trimethyl-, monohydrochloride (9CI),Phenothiazine, 10-[2-(dimethylamino)-1-methylethyl]-, monohydrochloride (8CI)
IUPAC Name N,N-dimethyl-2-phenothiazin-10-ylpropan-1-amine;hydrochloride
Molecular Formula C17 H20 N2 S . Cl H
12

7-Bromo-3,4-dihydro-2H-1,4-benzothiazine, 97%, Thermo Scientific Chemicals

CAS: 193414-60-7 Molecular Formula: C8H8BrNS Molecular Weight (g/mol): 230.12 MDL Number: MFCD11847754 InChI Key: QWWYGAWGUCQKDL-UHFFFAOYSA-N Synonym: 7-bromo-3,4-dihydro-2h-benzo b 1,4 thiazine PubChem CID: 83823811 IUPAC Name: 7-bromo-3,4-dihydro-2H-1,4-benzothiazine SMILES: BrC1=CC2=C(NCCS2)C=C1

PubChem CID 83823811
CAS 193414-60-7
Molecular Weight (g/mol) 230.12
MDL Number MFCD11847754
SMILES BrC1=CC2=C(NCCS2)C=C1
Synonym 7-bromo-3,4-dihydro-2h-benzo b 1,4 thiazine
IUPAC Name 7-bromo-3,4-dihydro-2H-1,4-benzothiazine
InChI Key QWWYGAWGUCQKDL-UHFFFAOYSA-N
Molecular Formula C8H8BrNS
13

Moclobemide, TRC

CAS: 71320-77-9 Molecular Formula: C13 H17 Cl N2 O2 Molecular Weight (g/mol): 268.74 Synonym: Moclobemide,Benzamide, 4-chloro-N-[2-(4-morpholinyl)ethyl]- (9CI, ACI),4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide (ACI),4-Chloro-N-(2-morpholin-4-ylethyl)benzamide,4-Chloro-N-(2-morpholinoethyl)benzamide,Auromid,Aurorix,Manerix,MeSH ID: D020912,Moclaime,Moclobemide,p-Chloro-N-(2-morpholinoethyl)-benzamide,Ro 11-1163,Ro 11-1163/000 IUPAC Name: 4-chloro-N-(2-morpholin-4-ylethyl)benzamide SMILES: Clc1ccc(cc1)C(=O)NCCN2CCOCC2

CAS 71320-77-9
Molecular Weight (g/mol) 268.74
SMILES Clc1ccc(cc1)C(=O)NCCN2CCOCC2
Synonym Moclobemide,Benzamide, 4-chloro-N-[2-(4-morpholinyl)ethyl]- (9CI, ACI),4-Chloro-N-[2-(4-morpholinyl)ethyl]benzamide (ACI),4-Chloro-N-(2-morpholin-4-ylethyl)benzamide,4-Chloro-N-(2-morpholinoethyl)benzamide,Auromid,Aurorix,Manerix,MeSH ID: D020912,Moclaime,Moclobemide,p-Chloro-N-(2-morpholinoethyl)-benzamide,Ro 11-1163,Ro 11-1163/000
IUPAC Name 4-chloro-N-(2-morpholin-4-ylethyl)benzamide
Molecular Formula C13 H17 Cl N2 O2
14

Methylene Blue Hydrate, TRC

CAS: 122965-43-9 Molecular Formula: C16 H18 Cl N3 S x H2 O Molecular Weight (g/mol): 319.85 Synonym: Methylene blue hydrate,3,7-Bis(dimethylamino)phenothiazin-5-ium Chloride Hydrate; IUPAC Name: 3-N,3-N,7-N,7-N-tetramethylphenothiazin-5-ium-3,7-diamine;chloride;hydrate SMILES: O.[Cl-].CN(C)c1ccc2nc3ccc(cc3[s+]c2c1)N(C)C

CAS 122965-43-9
Molecular Weight (g/mol) 319.85
SMILES O.[Cl-].CN(C)c1ccc2nc3ccc(cc3[s+]c2c1)N(C)C
Synonym Methylene blue hydrate,3,7-Bis(dimethylamino)phenothiazin-5-ium Chloride Hydrate;
IUPAC Name 3-N,3-N,7-N,7-N-tetramethylphenothiazin-5-ium-3,7-diamine;chloride;hydrate
Molecular Formula C16 H18 Cl N3 S x H2 O
15

Promethazine Sulfoxide, TRC

CAS: 7640-51-9 Molecular Formula: C17 H20 N2 O S Molecular Weight (g/mol): 300.42 Synonym: (2RS)-N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine S-Oxide,Promethazine Hydrochloride Imp. D (EP),Promethazine Sulphoxide IUPAC Name: N,N-dimethyl-1-(5-oxophenothiazin-10-yl)propan-2-amine SMILES: CC(CN1c2ccccc2S(=O)c3ccccc13)N(C)C

CAS 7640-51-9
Molecular Weight (g/mol) 300.42
SMILES CC(CN1c2ccccc2S(=O)c3ccccc13)N(C)C
Synonym (2RS)-N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-amine S-Oxide,Promethazine Hydrochloride Imp. D (EP),Promethazine Sulphoxide
IUPAC Name N,N-dimethyl-1-(5-oxophenothiazin-10-yl)propan-2-amine
Molecular Formula C17 H20 N2 O S