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73-24-5

Basic Information
CAS No.: 73-24-5
Name: Adenine
Article Data: 80
Cas Database
Molecular Structure:
Molecular Structure of 73-24-5 (Adenine)
Formula: C5H5N5
Molecular Weight: 135.128
Synonyms: USAF CB-18;1,6-Dihydro-6-iminopurine;Adenine [JAN];ADE;Pedatisectine B;6-Amino-1H-purine;Vitamin B4;6-Aminopurine;1H-Purine, 6-amino-;6-Amino-7H-purine;3, 6-Dihydro-6-iminopurine;9H-purin-6-amine;Adenine (8CI);Adeninimine;9H-Purine, 1, 6-dihydro-6-imino-;Purine, 6-amino-;Adenine (JAN/USP);6-Amino-9H-purine;Leuco-4;Adenin;Crytidine;6-Aminopurine (Adenine);5H-purin-6-amine;6-Amino-3H-purine;
EINECS: 200-796-1
Density: 1.612 g/cm3
Melting Point: >360 °C(lit.)
Boiling Point: 553.491 °C at 760 mmHg
Flash Point: 322.71 °C
Solubility: 0.5 g/L at 20 °C in water
Appearance: white to almost white crystalline powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 22-20/21/22
Safety: 26-36
Transport Information: UN 2811 6.1/PG 3
PSA: 80.48000
LogP: 0.51630
Synthetic route
118-70-7

4,5,6-triaminopyrimidine

73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
at 140 - 150℃; for 4h;81.8%
at 140 - 150℃; for 4h;81.8%
1198-83-0

2-(methylthio)-7H-purin-6-amine

73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
With water; nickel

6-azidopurine

73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
With water; nickel Hydrogenation;
5122-36-1

N-(4,6-diaminopyrimidin-5-yl)formamide

73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
at 230℃;
409110-30-1

N-(4,6-diamino-pyrimidin-5-yl)-thioformamide

73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
With water
With pyridine
With quinoline
3647-48-1

6-amino-3,7-dihydro-purine-2-thione

73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
With water; nickel
64-18-6

formic acid

98022-70-9

4,5,6-triamino-pyrimidine-2-sulfinic acid

73-24-5

7H-purin-6-ylamine

49721-45-1

4,5,6-triaminopyrimidine sulfate

73-24-5

7H-purin-6-ylamine

623-11-0

1-methyl-4-nitrosobenzene

73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
at 98℃; zeitlicher Verlauf.Hydrolysis;
at 100℃; zeitlicher Verlauf.Hydrolysis;
65758-94-3

2-amino-malonamidine; dihydrochloride

122-51-0

orthoformic acid triethyl ester

73-24-5

7H-purin-6-ylamine

Conditions
ConditionsYield
With N,N-dimethyl-formamide
With acetonitrile
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History

 Adenine was also called Vitamin B4.It is no longer considered a true vitamin or part of the Vitamin B complex. However, two B vitamins, niacin and riboflavin, bind with adenine to form the essential cofactors nicotinamide adenine dinucleotide  and flavin adenine dinucleotide , respectively. Hermann Emil Fischer was one of the early scientists to study Adenine.Some think that, at the origin of life on Earth, the first adenine was formed by the polymerization of five hydrogen cyanide  molecules. However, this has been criticized by some chemists.

Specification

The IUPAC name of Adenine is 7H-purin-6-amine. With the CAS registry number 73-24-5, it is also named as 1,6-Dihydro-6-iminopurine. The product's categories are Pyrimidine; Pharmaceutical Intermediates; Purines; Plant Growth Regulator; Nucleobases and their Analogs; Biochemistry; Cytokinins; Nucleosides, Nucleotides & Related Reagents; Nutritional Supplements; Nucleic Acids; Nucleic Acid Purification; Vitamin Ingredients, and the other registry numbers are 22051-90-7; 42911-33-1; 42911-34-2; 520-75-2; 66224-65-5. Besides, it is white to almost white crystalline powder, which should be stored in a cool, ventilated, dry place. This chemical is stable, and incompatible with strong oxidizing agents. In addition, its molecular formula is C5H5N5 and molecular weight is 135.13.

The other characteristics of this product can be summarized as: (1)EINECS: 200-796-1; (2)ACD/LogP: 0.02; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 7.4): 0.021; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 21.974; (8)ACD/KOC (pH 7.4): 24.421; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.837; (13)Molar Refractivity: 37.039 cm3; (14)Molar Volume: 83.823 cm3; (15)Surface Tension: 122.712 dyne/cm; (16)Density: 1.612 g/cm3; (17)Flash Point: 322.71 °C; (18)Melting Point: 360-365 °C; (19)Water solubility: 0.5 g/L at 20 °C; (20)Sublimation: 220 °C; (21)Enthalpy of Vaporization: 83.432 kJ/mol; (22)Boiling Point: 553.491 °C at 760 mmHg; (23)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Adenine: this chemical can be derived from the nucleotide inosine monophosphate (IMP) by using atoms from the amino acids glycine, glutamine, and aspartic acid, as well as fused with the enzyme tetrahydrofolate. Additionally, you can use 4,6-Dichloro-5-nitropyrimidine to produce 4,6-Diamino-5-nitropyrimidine by reaction with Ammonia. And then you would obtain this chemical by the cyclization of 4,6-Diamino-5-nitropyrimidine with Formamide, Formic acid and Sodium thiosulfate.

Uses of Adenine: this chemical is used in forming nucleotides of the nucleic acids. Furthermore, it can bind to Thymine via two hydrogen bonds to assist in stabilizing the nucleic acid structures in DNA. And it is used for protein synthesis, adenine binds to uracil in RNA. It also can be used to produce Adenosine, Adenosine triphosphate (ATP). Similarly, it can react with Fluoromethyl-oxirane to get 1-(6-Amino-purin-9-yl)-3-fluoro-propan-2-ol.



This reaction needs K2CO3 and Dimethylformamide at temperature of 70-75 °C for 6 hours. The yield is 63 %.

When you are using this chemical, please be cautious about it as the following: it is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. And you should wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
(1)SMILES: c1[nH]c2c(ncnc2n1)N
(2)InChI: InChI=1/C5H5N5/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H3,6,7,8,9,10)
(3)InChIKey: GFFGJBXGBJISGV-UHFFFAOYAT

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 intravenous > 30mg/kg (30mg/kg)   Drugs in Japan Vol. 6, Pg. 20, 1982.
mouse LD50 oral 783mg/kg (783mg/kg)   Drugs in Japan Vol. 6, Pg. 19, 1982.
mouse LDLo subcutaneous 1gm/kg (1000mg/kg)   Annals of the New York Academy of Sciences. Vol. 60, Pg. 251, 1954.
rat LD50 intraperitoneal 198mg/kg (198mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Journal of Pharmacology and Experimental Therapeutics. Vol. 104, Pg. 20, 1952.
rat LD50 oral 227mg/kg (227mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 47, Pg. 229, 1979.