9H-purine-2,6-dithiol

Modify Date: 2025-08-26 21:03:43

9H-purine-2,6-dithiol Structure
9H-purine-2,6-dithiol structure
 Common Name 9H-purine-2,6-dithiol
CAS Number 5437-25-2 Molecular Weight 184.24
Density 1.8±0.1 g/cm3 Boiling Point 496.2±37.0 °C at 760 mmHg
Molecular Formula C5H4N4S2 Melting Point >350 °C(lit.)
MSDS N/A Flash Point 253.9±26.5 °C

 Use of 9H-purine-2,6-dithiol


2,6-Dithiopurine (2,6-Dimercaptopurine) is a nucleophilic scavenger for electrophilic carcinogens. 2,6-Dithiopurine abolishes both DNA adduct formation and the initiation of carcinogenesis[1].

 Names

Name 2,6-Dithiopurine
Synonym More Synonyms

 9H-purine-2,6-dithiol Biological Activity

Description 2,6-Dithiopurine (2,6-Dimercaptopurine) is a nucleophilic scavenger for electrophilic carcinogens. 2,6-Dithiopurine abolishes both DNA adduct formation and the initiation of carcinogenesis[1].
Related Catalog
References

[1]. Stephen Boulware, et al. 2,6-Dithiopurine, a nucleophilic scavenger, protects against mutagenesis in mouse skin treated in vivo with 2-(chloroethyl) ethyl sulfide, a mustard gas analog. Toxicol Appl Pharmacol. 2012 Sep 1;263(2):203-9.  

 Chemical & Physical Properties

Density 1.8±0.1 g/cm3
Boiling Point 496.2±37.0 °C at 760 mmHg
Melting Point >350 °C(lit.)
Molecular Formula C5H4N4S2
Molecular Weight 184.24
Flash Point 253.9±26.5 °C
Exact Mass 183.987732
PSA 132.06000
LogP -0.60
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.890
InChIKey VQPMXSMUUILNFZ-UHFFFAOYSA-N
SMILES S=c1[nH]c(=S)c2[nH]cnc2[nH]1
Storage condition −20°C
Water Solubility slightly soluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UO8475000
CHEMICAL NAME :
Purine-2,6-dithiol
CAS REGISTRY NUMBER :
5437-25-2
LAST UPDATED :
199712
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C5-H4-N4-S2
MOLECULAR WEIGHT :
184.25
WISWESSER LINE NOTATION :
T56 BM DN FN HNJ GSH ISH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
180 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#03045

 Safety Information

Safety Phrases S24/25
WGK Germany 3
RTECS UO8475000
HS Code 2933990090

 Synthetic Route

2-Thioxanthine structure

2-Thioxanthine

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9H-purine-2,6-dithiol Structure

9H-purine-2,6-d...

CAS#:5437-25-2

Literature: Journal of the American Chemical Society, , vol. 76, p. 5633,5635,5636
Formic Acid structure

Formic Acid

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2,4-Dimercapto-5,6-diaminopyrimidine structure

2,4-Dimercapto-...

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~%

9H-purine-2,6-dithiol Structure

9H-purine-2,6-d...

CAS#:5437-25-2

Literature: Journal of the American Chemical Society, , vol. 76, p. 5087
2,6-diiodo-7H-purine structure

2,6-diiodo-7H-purine

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~%

9H-purine-2,6-dithiol Structure

9H-purine-2,6-d...

CAS#:5437-25-2

Literature: Zhurnal Obshchei Khimii, , vol. 27, p. 1712,1715;engl.Ausg.S.1783,1785
2,6,8-trichloropurine structure

2,6,8-trichloro...

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~%

9H-purine-2,6-dithiol Structure

9H-purine-2,6-d...

CAS#:5437-25-2

Literature: Zhurnal Obshchei Khimii, , vol. 27, p. 1712,1715;engl.Ausg.S.1783,1785
1H-Purine-2,6-dione, 8-chloro-3,7-dihydro- (9CI) structure

1H-Purine-2,6-d...

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~%

9H-purine-2,6-dithiol Structure

9H-purine-2,6-d...

CAS#:5437-25-2

Literature: Zhurnal Obshchei Khimii, , vol. 27, p. 1712,1715;engl.Ausg.S.1783,1785
thiourea structure

thiourea

CAS#:17356-08-0

2,6-Dichloropurine structure

2,6-Dichloropurine

CAS#:5451-40-1

~%

9H-purine-2,6-dithiol Structure

9H-purine-2,6-d...

CAS#:5437-25-2

Literature: US2697709 , ;

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 9H-purine-2,6-dithiolBioassay

View more

Name: qHTS Assay for Substrates of Mammalian Selenoprotein Thioredoxin Reductase 1 (TrxR1):...
Source: NCGC
Target: thioredoxin reductase [Rattus norvegicus]
External Id: TRXR101
Name: qHTS for Inhibitors of Polymerase Iota
Source: NCGC
Target: DNA polymerase iota [Homo sapiens]
External Id: PolI100
Name: qHTS for Inhibitors of human tyrosyl-DNA phosphodiesterase 1 (TDP1): qHTS in cells in...
Source: NCGC
Target: TDP1 protein [Homo sapiens]
External Id: TDP1100
Name: qHTS for Stage-Specific Inhibitors of Vaccinia Orthopoxvirus: mCherry Reporter Primar...
Source: NCGC
Target: 67.9K protein [Vaccinia virus]
External Id: Vaccinia-p2mCherry
Name: qHTS for Inhibitors of human tyrosyl-DNA phosphodiesterase 1 (TDP1): qHTS in cells in...
Source: NCGC
Target: TDP1 protein [Homo sapiens]
External Id: TDP1101
Name: qHTS for Inhibitors of Polymerase Kappa
Source: NCGC
Target: DNA polymerase kappa [Homo sapiens]
External Id: PolK100
Name: qHTS Assay for Inhibitors of Mammalian Selenoprotein Thioredoxin Reductase 1 (TrxR1):...
Source: NCGC
Target: thioredoxin reductase [Rattus norvegicus]
External Id: TRXR100
Name: qHTS for Stage-Specific Inhibitors of Vaccinia Orthopoxvirus: Venus Reporter Primary ...
Source: NCGC
Target: 67.9K protein [Vaccinia virus]
External Id: Vaccinia-p2Venus
Name: HIV Cellular Data
Source: NIAID
Target: N/A
External Id: HIV Cellular Data
Name: qHTS for Inhibitors of TGF-b: Cytotox Counterscreen
Source: NCGC
Target: N/A
External Id: SMAD3201
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1
2

 Synonyms

MFCD00022644
9H-purine-2,6-dithiol
EINECS 226-608-8
3,7-dihydropurine-2,6-dithione
6-Sulfanyl-1,9-dihydro-2H-purine-2-thione
3,7-Dihydro-1H-purine-2,6-dithione
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