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154-42-7

Basic Information
CAS No.: 154-42-7
Name: 6-Thioguanine
Article Data: 16
Molecular Structure:
Molecular Structure of 154-42-7 (6-Thioguanine)
Formula: C5H5N5S
Molecular Weight: 167.194
Synonyms: 6H-Purine-6-thione,2-amino-1,7-dihydro- (9CI);Purine-6(1H)-thione, 2,3-dihydro-2-imino- (6CI);Purine-6-thiol, 2-amino- (8CI);2-Amino-9H-purine-6(1H)-thione;2-Aminopurine-6-thiol;6-TG;Guanine, thio-;Lanvis;NSC 752;NSC 76504;Tabloid;Thioguanine;
EINECS: 205-827-2
Density: 2.08 g/cm3
Melting Point: ≥300 °C(lit.)
Boiling Point: 555.4 °C at 760 mmHg
Flash Point: 289.7 °C
Solubility: soluble in water
Appearance: Odorless or almost odorless pale yellow crystalline powder
Hazard Symbols: ToxicT,IrritantXi
Risk Codes: 25-23/24/25
Safety: 28-36/37/39-45-28A
Transport Information: UN 2811 6.1/PG 3
PSA: 119.28000
LogP: 0.80500
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Specification

The IUPAC name of 2-Aminopurine-6-thiol is 2-amino-3,7-dihydropurine-6-thione. With the CAS registry number 154-42-7, it is also named as Thioguanine. The product's categories are Pyridines, Pyrimidines, Purines and Pteredines; Purine; All Inhibitors; Antitumors for Research and Experimental Use; Biochemistry; Chemical Reagents for Pharmacology Research; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents; Sulfur & Selenium Compounds. It is odorless or almost odorless pale yellow crystalline powder which is soluble in water, insoluble in ethanol, acetone and other organic solvents. What's more, this chemical may be sensitive to prolonged exposure to air and incompatible with strong oxidizing agents. When heated to decomposition it emits very toxic fumes of SOx and NOx. Additioanlly, this chemical should be sealed in the container and stored in the cool, ventilate and dry place. As a guanine analogue, 2-Aminopurine-6-thiol is transformed inside the cell into 6-thioguanilyic acid (TGMP), which, by pseudofeedback interference with purine biosynthesis, interferes with the synthesis of guanine nucleotides.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -0.16; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.16; (4)ACD/LogD (pH 7.4): -0.16; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 19.56; (8)ACD/KOC (pH 7.4): 19.52; (9)#H bond acceptors: 5; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 2.07; (13)Molar Refractivity: 41.94 cm3; (14)Molar Volume: 80.2 cm3; (15)Polarizability: 16.62×10-24 cm3; (16)Surface Tension: 98.6 dyne/cm; (17)Enthalpy of Vaporization: 83.67 kJ/mol; (18)Vapour Pressure: 2.25E-12 mmHg at 25°C; (19)Tautomer Count: 26; (20)Exact Mass: 167.026566; (21)MonoIsotopic Mass: 167.026566; (22)Topological Polar Surface Area: 111; (23)Heavy Atom Count: 11; (24)Complexity: 225.

Preparation of 2-Aminopurine-6-thiol: It can be obtained by the replacement reaction of guanine through phosphorus pentasulfide at the presence of ammonium hydroxide.

Uses of 2-Aminopurine-6-thiol: It is a drug that is used in the treatment of cancer, coronary atherosclerosis and hepatitis. Its principal use is in acute leukaemias and chronic myeloid leukaemia. And it has been investigated for use in treatment of psoriasis. When use a large amount of this drug, it may canuse drowsiness, dizziness, vertigo, fatigue, loss of appetite, nausea, vomiting, etc. In addition, 2-Aminopurine-6-thiol can react with 2-bromo-1-(4-nitro-phenyl)-ethanone to get 2-(2-amino-9H-purin-6-ylsulfanyl)-1-(4-nitro-phenyl)-ethanone. This reaction needs reagent NaOH. The yield is 90%.

When you are using this chemical, please be cautious about it as the following:
It is toxic by inhalation, in contact with skin and if swallowed. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:S=C2/N=C(\Nc1ncnc12)N
2. InChI:InChI=1/C5H5N5S/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11) 
3. InChIKey:WYWHKKSPHMUBEB-UHFFFAOYAY

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 23720ug/kg (23.72mg/kg) SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Cancer Vol. 9, Pg. 1092, 1956.
 
mouse LD10 unreported 1600mg/kg (1600mg/kg) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.
mouse LD50 intraperitoneal 54mg/kg (54mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: HEMORRHAGE
Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 9, Pg. 56, 1980.
mouse LD50 oral 160mg/kg (160mg/kg) GASTROINTESTINAL: OTHER CHANGES

BLOOD: HEMORRHAGE
Eksperimental'naya i Klinicheskaya Farmakoterapiya. Vol. 9, Pg. 56, 1980.
rat LD50 intraperitoneal 300mg/kg (300mg/kg)   Journal of Reproduction and Fertility. Vol. 4, Pg. 291, 1962.