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Details

Stereochemistry ACHIRAL
Molecular Formula C16H18N3S.Cl.3H2O
Molecular Weight 373.898
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Methylene blue

SMILES

O.O.O.[Cl-].CN(C)C1=CC2=[S+]C3=CC(=CC=C3N=C2C=C1)N(C)C

InChI

InChIKey=XQAXGZLFSSPBMK-UHFFFAOYSA-M
InChI=1S/C16H18N3S.ClH.3H2O/c1-18(2)11-5-7-13-15(9-11)20-16-10-12(19(3)4)6-8-14(16)17-13;;;;/h5-10H,1-4H3;1H;3*1H2/q+1;;;;/p-1

HIDE SMILES / InChI
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C16H18N3S
Molecular Weight 284.399
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: http://www.mdpoison.com/media/SOP/mdpoisoncom/healthcareprofessionals/antidote-facts/Methylene%20Blue%20Antidote%20Facts.pdf | https://clinicaltrials.gov/ct2/show/NCT01797978 | https://www.pharmgkb.org/pathway/PA165980834

Methylene blue, also known as methylthioninium chloride, is a medication from WHO's list of essential medicines. Upon administration, methylene blue is converted to leukomethylene blue by erythrocyte methemoblobin reductase in the presence of NADPH. Leukomethylene blue than reduces methemoglobin to oxyhemoglobin, thus restoring oxygen carrying capacity of the blood. Methylene blue is also used as a dye for various diagnostic procedures, for treatment of ifosfamide toxicity and for in vitro staining. Historically, it was used as a photosensitizer for photodynamic therapy for topical treatment of dermatologic or mucocutaneous infections, as an antidote for cyanide poisoning, but these applications are no longer approved. Methylene blue is investigated in clinical trials for treatment of septic shock and Alzheimer's disease.

CNS Activity

CNS Penetrant
2588
Curator's Comment: When injected intraperitoneally into live rats, MB crosses the blood-brain barrier and selectively stains brain tissueand selectively stains brain tissue.

Originator

BASF
18
Curator's Comment: Methylene blue was first prepared in 1876 by Heinrich Caro at BASF.

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
NADH-cytochrome b5 reductase 3
6
Target ID: P00387|||Q9UL55
Gene ID: 1727.0
Gene Symbol: CYB5R3
Target Organism: Homo sapiens (Human)
Substrate
661
Inhibitor
8504
 5.3 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
METHYLENE BLUE

Approved Use

Used for methemoglobinemia associated with certain drugs (e.g., dapsone, benzocaine, lidocaine), occupational or other exposures to toxic chemicals (e.g., hydrazine, amine-substituted benzenes, nitro-substituted benzenes, nitrates, nitrites), or substance abuse (e.g., inhalation or ingestion of volatile nitrites).
Primary
Approved
8583
METHYLENE BLUE

Approved Use

Management of ifosfamide-induced encephalopathy
Diagnostic
Approved
8583
METHYLENE BLUE

Approved Use

Has been used as diagnostic (visualizing) dye in a variety of procedures, including sentinel lymph node biopsy in cancer patients (e.g., breast cancer patients), endoscopic evaluation of lesions in patients with GERD or Barrett's esophagus, urologic evaluation in patients with ureteral or renal pelvis injury, and thoroscopic procedures in patients with pulmonary nodules.
Primary
Approved
8583
METHYLENE BLUE

Approved Use

Has been used as a photosensitizer for photodynamic therapy for topical treatment of dermatologic or mucocutaneous infections (e.g., herpes labialis, eczema herpeticum, oral candidiasis, cutaneous leishmaniasis, chromoblastomycosis) or chronic dermatologic or mucocutaneous conditions (e.g., plaque psoriasis, oral lichen planus).
Primary
Phase III
665
Unknown

Approved Use

Unknown
Preventing
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10952480/
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLENE BLUE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2917 ng/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204630s006lbl.pdf
2 mg/kg single, intravenous
dose: 2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLENE BLUE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
134 μM × min
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10952480/
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLENE BLUE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
13977 ng × h/mL
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204630s006lbl.pdf
2 mg/kg single, intravenous
dose: 2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLENE BLUE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/10952480/
100 mg single, intravenous
dose: 100 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLENE BLUE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
24 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204630s006lbl.pdf
2 mg/kg single, intravenous
dose: 2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLENE BLUE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
6%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/204630s006lbl.pdf
2 mg/kg single, intravenous
dose: 2 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
METHYLENE BLUE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
72 mg/kg 4 times / day multiple, intravenous
Highest studied dose
Dose: 72 mg/kg, 4 times / day
Route: intravenous
Route: multiple
Dose: 72 mg/kg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17026773
unhealthy, 0.5-4.9
Health Status: unhealthy
Age Group: 0.5-4.9
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17026773
Other AEs: Anemia...
Other AEs:
Anemia (0.8%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/17026773
1 g single, intravenous
Overdose
Dose: 1 g
Route: intravenous
Route: single
Dose: 1 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/973698
healthy, 3
Health Status: healthy
Age Group: 3
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/973698
Disc. AE: Tachycardia, Cyanosis...
AEs leading to
discontinuation/dose reduction:
Tachycardia
Cyanosis
Sources:
https://pubmed.ncbi.nlm.nih.gov/973698
AEs

AEs

AESignificanceDosePopulation
Anemia 0.8%
72 mg/kg 4 times / day multiple, intravenous
Highest studied dose
Dose: 72 mg/kg, 4 times / day
Route: intravenous
Route: multiple
Dose: 72 mg/kg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/17026773
unhealthy, 0.5-4.9
Health Status: unhealthy
Age Group: 0.5-4.9
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/17026773
Cyanosis Disc. AE
1 g single, intravenous
Overdose
Dose: 1 g
Route: intravenous
Route: single
Dose: 1 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/973698
healthy, 3
Health Status: healthy
Age Group: 3
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/973698
Tachycardia Disc. AE
1 g single, intravenous
Overdose
Dose: 1 g
Route: intravenous
Route: single
Dose: 1 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/973698
healthy, 3
Health Status: healthy
Age Group: 3
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/973698
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P000KBE
1PlusChem LLC
1P0035Q5
1PlusChem LLC
1P00IKXL
A2B Chem
AI66137
AA Blocks
AA00IKE5
AAA Chemistry
AR-1K4257
ABI Chem
AC1L1HI1
ABI Chem
AC1Q4UZ6
AbovChem LLC
HY-14536
Acros Organics
12675
Acros Organics
22980
Acros Organics
41424
Acros Organics
41425
AK Scientific
6335AF
AK Scientific
6336AF
AK Scientific
6337AF
AK Scientific
6338AF
Alfa Chemistry
42771
Alfa Chemistry
A18174
Alfa Chemistry
ACM61734
Alfa Chemistry
ACM7220793
Alfa Chemistry
J60823
Alinda
IBS-E0000554
Ambinter
Amb19654466
http://www.ambinter.com/reference/19654466
Ambinter
Amb21855833
http://www.ambinter.com/reference/21855833
Angene
AGN-PC-0O0J7Q
Angene
AGN-PC-0OH2YS
Apollo Scientific
BIA4084
Aronis
M04821
AstaTech
43008
Aurora Fine Chemicals LLC
A12.866.455
http://online.aurorafinechemicals.com/info?ID=A12.866.455
BioSynth
M-3598
BLD Pharm
BD139888
BLD Pharm
BD305948
BLD Pharm
BD338910
BOC Sciences
122965-43-9
BOC Sciences
26283-09-0
BOC Sciences
37247-10-2
BOC Sciences
61-73-4
BOC Sciences
7220-79-3
Bosche Scientific
M2940
Bosche Scientific
M2943
Capot Chemical
35596
Chem-Impex International
210
Chem-Impex International
22930
Chem Scene
CS-0013101
Chem Scene
CS-2959
ChemDiv
0083-0118
ChemShuttle
141809
Chemspace
CSSS00160696622
https://chem-space.com/CSSS00160696622
Compound Cloud
104827
Compound Cloud
16211647
Compound Cloud
4139
Compound Cloud
6099
DC Chemicals
DC11091
http://www.dcchemicals.com/product_show-DC11091.html
eMolecules
207322640
eMolecules
271447134
eMolecules
28206441
eMolecules
56968286
eMolecules
66729975
Enamine
EN300-6504462
eNovation Chemicals
D329417
eNovation Chemicals
D394566
Fluorochem
468422
Fluorochem
492385
Hairui
HR144947
Hangzhou APIChem Technology
AC-15225
Hangzhou APIChem Technology
AC-8349
Hangzhou Yuhao Chemical Technology
HL3337
Hangzhou Yuhao Chemical Technology
JZ4569
Hangzhou Yuhao Chemical Technology
LT7437
Hangzhou Yuhao Chemical Technology
XJ6809
Hangzhou Yuhao Chemical Technology
YH15655
KeyOrganics
AS-35256
Lab Network
33
Lab Network
LN00193772
Lab Network
LN00194290
Lab Network
LN00237724
Lab Network
LN02135350
mcule
MCULE-6490213141
https://mcule.com/MCULE-6490213141/
MedChem Express
HY-14536
MedChem Express
HY-B1359
Molnova
M15760
Molnova
M18906
MolPort
MolPort-001-494-481
MolPort
MolPort-003-666-690
MolPort
MolPort-004-963-308
MolPort
MolPort-006-110-157
MolPort
MolPort-039-063-118
MuseChem
A000087
MuseChem
M057779
MuseChem
M060342
MuseChem
R037152
MuseChem
R045681
NCI Plated 2007
215213
NCI Plated 2007
3089
NCI Plated 2007
617593
Ryan Scientific
Diolane
Scientific Exchange
R-079267
Selleck Chemicals
S4535
Sigma Aldrich
66725
Sigma Aldrich
M1800900
Sigma Aldrich
M44907
Sigma Aldrich
M9140|SIAL
Sigma Aldrich
MB1
Smolecule
S564122
https://www.smolecule.com/products/s564122
TargetMol
T0006
TargetMol
T6888
Tetrahedron
TS78351
Tetrahedron
TS80135
TimTec
SBB060907
TimTec
ST093058
TimTec
ST50406156
TimTec
ST50406802
TimTec
ST50411628
Tocris
3213
Vitas-M Laboratory
STL483851
http://www.request.vitasmlab.com/index.php?option=com_search_stk&Itemid=22&stk=STL483851&?utm_source=pubchem&utm_medium=p_search_link&utm_campaign=pubchem_search&utm_content=pubchem_slink
W&J PharmaChem
50C912420
Yuhao Chemical
LT7437
http://www.chemyuhao.com/61-73-4.html
ZINC
ZINC000012414057
http://zinc15.docking.org/substances/ZINC000012414057
PubMed

PubMed

TitleDatePubMed
[The enhancement of formalin induced agitation behavior by intrathecal administration of prostaglandin E1].
1999 Aug
Spinal antinociceptive effect of epidural nonsteroidal antiinflammatory drugs on nitric oxide-induced hyperalgesia in rats.
1999 Jul
Methylene blue: the drug of choice for catecholamine-refractory vasoplegia after cardiopulmonary bypass?
2003 Jun
Methylene blue for lithium-induced refractory hypotension in off-pump coronary artery bypass graft: report of two cases.
2004 Feb
Evaluating risk factors for the development of ifosfamide encephalopathy.
2005 Jun
Dual action of phenylarsine oxide on the glucose transport activity of GLUT1.
2009 Dec 10
Patents

Patents

08691979
9
JP1062310A
6
JP2000211902A
6
JP2002162394A
6
JP2004189632A
6
JP2008157627A
6
JP2009136699A
6
JP2009504333A
6
JP2010261012A
6
JP2011529898A
7
JP2012500844A
19
JP4283546B2
11
JPH021535A
6
JPH04315049A
6
JPH06238226A
7
JPH08151327A
6
JPH08169885A
6
JPH1194745A
6
JPS05742625A
6
JPS53101086A
6
JPS5513860A
6
JPS5543428A
6
JPS5611791A
6
JPS5635996A
8
JPS568547A
6
JPS58208354A
6
JPS6110020A
6
JPS6344591A
6
JPS6451425A
6

Sample Use Guides

In Vivo Use Guide
Main route of adminitration is intravenous, 1-2 mg/kg by slow IV injection. Inject slowly over several minutes (usually 3–10 minutes). Historically was also administered orally, but oral preparations are no longer commercially available in US. As a photosensitizer is administered topically. For a diagnostic purposes is administered by local instillation or injection.
Route of Administration: Other
In Vitro Use Guide
Suspension of erytrocytes from acid/citrate/dextrose-treated blood were incubabed on air with 0.5M M-sodium nitrite solution in isoosmotic saline. The erytrocytes were separated by centrifugation, washed, and incubated at pH 7.4 and 37°C with 10 mM glucose and 10 uM Methylene Blue. Samples were taken at defined intervals and hemolysed with 10 vol of ice-cold water, after that the content of mehtemoglobin, hemoglobins intermediate and oxyhemoglobin was estimated.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:37:03 GMT 2025
Edited
by admin
on Mon Mar 31 17:37:03 GMT 2025
Record UNII
T42P99266K
Record Status Validated (UNII)
Record Version
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Name Type Language
METHYLTHIONINIUM CHLORIDE TRIHYDRATE
WHO-IP  
Preferred Name English
Methylene blue
HPUS   II   USP   VANDF  
Common Name English
NSC-759135
Code English
METHYLENE BLUE [HPUS]
Common Name English
METHYLENE BLUE TRIHYDRATE
MI  
Common Name English
METHYLENE BLUE [ORANGE BOOK]
Common Name English
METHYLENE BLUE [USP MONOGRAPH]
Common Name English
TETRAMETHYLTHIONINE CHLORIDE TRIHYDRATE
Systematic Name English
METHYLENE BLUE [VANDF]
Common Name English
METHYLTHIONINIUM CHLORIDE TRIHYDRATE [WHO-IP]
Common Name English
PROVAYBLUE
Brand Name English
METHYLENE BLUE TRIHYDRATE [MI]
Common Name English
BASIC BLUE 9 TRIHYDRATE
Common Name English
METHYLENE BLUE [IARC]
Common Name English
METHYLTHIONINII CHLORIDUM TRIHYDRATE [WHO-IP LATIN]
Common Name English
C.I. BASIC BLUE 9 TRIHYDRATE
Common Name English
METHYLENE BLUE [II]
Common Name English
PHENOTHIAZIN-5-IUM, 3,7-BIS(DIMETHYLAMINO)-, CHLORIDE, TRIHYDRATE
Systematic Name English
METHYLENE BLUE [USP-RS]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 345711
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
EPA PESTICIDE CODE 39505
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
NCI_THESAURUS C461
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
FDA ORPHAN DRUG 385512
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
FDA ORPHAN DRUG 357111
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
Code System Code Type Description
WIKIPEDIA
METHYLENE BLUE
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
ChEMBL
CHEMBL191083
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
FDA UNII
T42P99266K
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
RXCUI
6878
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY RxNorm
CAS
122965-43-9
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
NON-SPECIFIC STOICHIOMETRY
MESH
D008751
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
EPA CompTox
DTXSID0025600
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
RS_ITEM_NUM
1428008
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
CHEBI
6872
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
DRUG BANK
DB09241
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
CAS
7220-79-3
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
NCI_THESAURUS
C644
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
EVMPD
SUB08877MIG
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
DAILYMED
T42P99266K
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
MERCK INDEX
m7402
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY Merck Index
NSC
759135
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
METHYLENE BLUE
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY Other name: Methylene blue.Description: Dark green crystals with a metallic lustre or a dark green, crystalline powder; odourless or almost odourless. Solubility: Sparingly soluble in water; slightly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Antidote. Storage: Methylthioninium chloride should be kept in a tightly closed container, protected from light. Additional information: Methylthioninium chloride is hygroscopic. Definition: Methylthioninium chloride contains not less than 97.0% and not more than 101.0% of C16H18ClN3S, calculated with reference to the dried substance.
PUBCHEM
104827
Created by admin on Mon Mar 31 17:37:03 GMT 2025 , Edited by admin on Mon Mar 31 17:37:03 GMT 2025
PRIMARY
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