Basic information
- CAS
1198-47-6- Standard SMILES
CSc1nc(N)nc2nc[nH]c12- InChIKey
YEGKYFQLKYGHAR-UHFFFAOYSA-N- Molecular formula
- C6H7N5S
- Average molar mass
- 181.22 g/mol
- Monoisotopic mass
- 181.04221622
Overview
6-methylthioguanine is a metabolite of thioguanine, a drug used in cancer chemotherapy. It has a role as a human xenobiotic metabolite. It is a member of 2-aminopurines and a thiopurine. It is functionally related to a tioguanine.
Names & identifiers
- Preferred name
- 6-Methylthioguanine
- IUPAC
- 6-methylsulfanyl-7H-purin-2-amine
- English name
- 6-Methylthioguanine
- Molecular formula
- C6H7N5S
- Molecular weight
- 181.22
Names & synonyms
6-Methylthioguanine1198-47-6QNV75HJN3ANSC-29420s6-methylthioguanineDTXSID60152594RefChem:544051DTXCID4075085214-833-42-Amino-6-methylmercaptopurine6-(methylthio)-7H-purin-2-amine2-Amino-6-methylthiopurine
Show more names
RMA-349NSC 29420TIMTEC-BB SBB000228S-Methyl-6-thioguanineMercaptopurine Impurity 296-Methylthioguanine USP/EP/BP
6-methylsulfanyl-7H-purin-2-amine6-(methylsulfanyl)-7H-purin-2-aminePurine, 2-amino-6-(methylthio)-1H-Purin-2-amine, 6-(methylthio)-6-(methylsulfanyl)-9H-purin-2-amine9H-Purin-2-amine, 6-(methylthio)-S6-Methyl-6-thioguanine6-(Methylthio)-1H-purin-2-amine
Database identifiers
- CAS
1198-47-6- PubChem CID
- 70976
- DTXSID
DTXSID60152594- ChEMBL
CHEMBL1172777- ChEBI
CHEBI:140528- UNII
Properties
Computed structural properties
- XLogP
- 0.3
- Topological polar surface area
- 106 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 166
Physicochemical properties
- Melting point
- 235.5 °C · 235.5°C
- Density
- 1.403 · 1.403 (estimate)
- refractive index
- 1.4606 · 1.4606 (estimate)
- storage temp.
- -20 °C · -20°C Freezer
- solubility
- DMSO (Slightly), Methanol (Slightly, Sonicated)
- form
- solid
- color
- White to Off-White
- InChI
- 1S/C6H7N5S/c1-12-5-3-4(9-2-8-3)10-6(7)11-5/h2H,1H3,(H3,7,8,9,10,11)
- InChIKey
- YEGKYFQLKYGHAR-UHFFFAOYSA-N
- SMILES
- [H]n1cnc2c(SC)nc(N)nc12
- FDA UNII
- 75 HJN3A · QNV75HJN3A
- UNSPSC Code
- 41106305 · 41106305
- NACRES
- 51 · NA.51
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H315-H318-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information1H-Purin-2-amine, 6-(methylthio)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- hs_code
- 29335995
- risk_code
- 22-37/38-41
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xn
- safety_code
- 24/25-39-26
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H318-H335
Chemistry & industry
Applications
Uses2-Amino-6-methylmercaptopurine is a 2-amino-6-alkyldithiopurine that has been used with other 6-position carbon analogues to study brain specific diazepam binding.
UsesAs a metabolite of 2’-Deoxy-6-thio Guanosine (D281650) and 6-Thioguanine, 6-Methylthioguanine can be used as an effective immunosuppressant and anticancer agent, however chronic exposure can be mutagenic in human cells as long-term use of thiopurines was found to be associated with a significantly increased risk of various types of cancer.
Upstream & downstream products
Downstream products
Suppliers54 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
上海毕得医药科技股份有限公司400-1647117 13681763483 · [email protected]
陕西缔都新材料有限公司029-63373950 17392216152 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
毕佳索（上海毕得医药科技股份有限公司）
Related reactions
3 records
Compound notes
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