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Product Name: Inosine, 6-thio-
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574-25-4

574-25-4 structure

Name: 6-mercaptopurine riboside
Chemical Name: 6-Mercaptopurine-9-D-riboside
CAS Number: 574-25-4
Molecular Formula: C₁₀H₁₂N₄O₄S
Molecular Weight: 284.29200
Catalog: Biochemical Nucleoside drugs Nucleoside intermediate
Create Date: 2018-09-21 05:25:50
Modify Date: 2026-07-13 19:09:39
6-Thioinosine (6TI) is a purine antimetabolite, acts as an anti-adipogenesis agent, downregulates mRNA levels of PPAR γ and C/EBPα, as well as PPAR γ target protein such as LPL, CD36, aP2, and LXRα[1][2].

Name	6-Mercaptopurine-9-D-riboside
Synonyms	9-β-D-Ribofuranosylpurine-6-thione 6H-Purine-6-thione, 1,9-dihydro-9-beta-D-ribofuranosyl (2R,3S,4R,5R)-2-(Hydroxymethyl)-5-(6-mercapto-9H-purin-9-yl)tetrahydrofuran-3,4-diol 6-Mercaptopurine riboside\|\|\|6TI 6-MERCAPTOPURINE RIBONUCLEOSIDE Ribosyl-6-thiopurine 6-Mercaptopurine riboside, 6-Purinethiol riboside, 6-Thioinosine 6-THIO-9-BETA-D-RIBOFURANOSIDE 6-thiopurineriboside Thionosine 6-Mercapto-9-(b-D-ribofuranosyl)purine 6-mercaptoinosine 6-MERCAPTOPURINE RIBOSIDE 9-β-D-Ribofuranosyl-9H-purine-6(1H)-thione Nucleoside Antimetabolite/Analog,6 Thioinosine,6-Thioinosine,inhibit,Inhibitor,6Thioinosine 9-β-D-Ribofuranosylpurine-6-thiol 9H-Purine-6-thiol, 9-β-D-ribofuranosyl- (6CI) 6-Mercaptopurine-9-β-D-ribofuranoside (~) 6-Thio-9-b-D-ribofuranoside 6-Thioinosine 9H-Purine-6(1H)-thione, 9-β-D-ribofuranosyl- (7CI, 8CI) 6-PURINETHIOL RIBOSIDE 6TI 9-beta-d-ribofuranosyl-9h-purine-6-thio 6-Mercaptopurine-9-beta-D-ribofuranoside >= (HPLC) 6-MP-Riboside Inosine, 6-thio 6-thiopurineribonucleoside 6-MERCAPTOPURINE-9-D-RIBOSIDE 6-Mercaptopurine Riboside(6-Mercaptopurine-9-β-D-ribofuranoside) 6-THIOINOSINE MERCAPTOPURINE-9-D-RIBOSIDE 6-Thiopurine riboside MFCD00005743 6-MERCAPTOPURINE RIBOSIDE //BP 6H-Purine-6-thione, 1,9-dihydro-9-β-D-ribofuranosyl 9-beta-d-ribofuranosyl-9h-purine-6(1h)-thion 9-[BETA-D-RIBOFURANOSYL]-6-THIOPURINE 6-Thio-9-D-ribofuranoside6-Thioinosine 9-β-D-Ribofuranosyl-9H-purine-6-thiol 9-beta-D-Ribofuranosyl-9H-purine-6-thiol 9H-Purine-6-thiol, 9-beta-D-ribofuransoyl MERCAPTOPURINE-9-D-RIBOSIDE, 6 9-β-D-Ribofuranosyl-9H-purine-6-thione 9H-Purine-6-thiol, 9-beta-D-ribofuranosyl 9H-Purine-6(1H)-thione, 9-beta-D-ribofuranosyl 6-mercaptopurine-9-β-d-ribofuranoside EINECS 209-371-5 9-β-D-Ribofuranosyl-6-mercaptopurine 6-MPR Thioinosine 6-MERCAPTOPURINE-9-B-D-RIBOFURANOSIDE 6-MERCAPTOPURINE RIBONUCLEOSIDE ABOUT 6-Thiopurineribose Mercaptopurine Impurity 22 6-Mercapto-9-β-D-ribofuranosyl-9H-purine 6-Thiopurine ribonucleoside 6-MERCAPTOPURINE-9-BETA-D-RIBOFURANOSIDE Tioinosine

Description	6-Thioinosine (6TI) is a purine antimetabolite, acts as an anti-adipogenesis agent, downregulates mRNA levels of PPAR γ and C/EBPα, as well as PPAR γ target protein such as LPL, CD36, aP2, and LXRα[1][2].
Related Catalog	Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog Research Areas >> Metabolic Disease
References	[1]. Lee J, et al. Anti-adipogenesis by 6-thioinosine is mediated by downregulation of PPAR gamma through JNK-dependent upregulation of iNOS. Cell Mol Life Sci. 2010 Feb;67(3):467-81. [2]. Neubert D, et al. Interference of 6-mercaptopurine riboside, 6-methylmercaptopurine riboside and azathioprine with the morphogenetic differentiation of mouse extremities in vivo and in organ culture. Naunyn Schmiedebergs Arch Pharmacol. 1977 Jun;298(2):93-105.

Density	2.02g/cm3
Boiling Point	714.7ºC at 760mmHg
Melting Point	220-223ºC(lit.)
Molecular Formula	C₁₀H₁₂N₄O₄S
Molecular Weight	284.29200
Flash Point	386ºC
Exact Mass	284.05800
PSA	148.51000
Index of Refraction	1.6270 (estimate)
Storage condition	-20°C
Stability	Store in Cool Dry Place

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UP0710000

CHEMICAL NAME :: 9H-Purine-6-thiol, 9-beta-D-ribofuranosyl-

CAS REGISTRY NUMBER :: 574-25-4

LAST UPDATED :: 199606

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C10-H12-N4-O4-S

MOLECULAR WEIGHT :: 284.32

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ ISH D- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1240 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1310 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1270 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1840 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1250 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 350 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - skin and skin appendages Reproductive - Specific Developmental Abnormalities - homeostasis

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 175 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 42 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 87500 ug/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 21 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Specific Developmental Abnormalities - skin and skin appendages

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 42 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 87500 ug/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - homeostasis

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 200 ug/plate

REFERENCE :: TAKHAA Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. (Takeda Yakuhin Kogyo K.K., 2-17-85 Jusohon-machi, Yodogawa-ku, Osaka 532, Japan) V.29- 1970- Volume(issue)/page/year: 44,96,1985

Hazard Codes	Xn
Risk Phrases	22
Safety Phrases	S22;S24/25
WGK Germany	3
RTECS	UP0710000

157930-09-1

58-96-8

~55%

574-25-4

Literature: Trelles; Fernandez; Lewkowicz; Iribarren; Sinisterra Tetrahedron Letters, 2003 , vol. 44, # 12 p. 2605 - 2609

108321-99-9

157930-09-1

~91%

574-25-4

Literature: Taverna-Porro, Marisa; Bouvier, Leon A.; Pereira, Claudio A.; Montserrat, Javier M.; Iribarren, Adolfo M. Tetrahedron Letters, 2008 , vol. 49, # 16 p. 2642 - 2645

3021-21-4

~94%

574-25-4

Literature: Meier, Lidiane; Monteiro, Gustavo C.; Baldissera, Rodrigo A.M.; Sa, Marcus Mandolesi Journal of the Brazilian Chemical Society, 2010 , vol. 21, # 5 p. 859 - 866

1146104-45-1

574-25-4

Literature: European Journal of Medicinal Chemistry, , vol. 45, # 5 p. 1912 - 1918

67-56-1

38048-32-7

107-03-9

100-27-6

Detail

Literature: Journal of Organic Chemistry, , vol. 57, # 22 p. 5968 - 5976

Precursor 8
157930-09-1 58-96-8 108321-99-9 3021-21-4
1146104-45-1 67-56-1 38048-32-7 107-03-9
DownStream 5
3021-21-4 550-33-4 71052-74-9 92035-03-5
6165-03-3

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