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58-55-9

Basic Information
CAS No.: 58-55-9
Name: Theophylline
Article Data: 105
Molecular Structure:
Molecular Structure of 58-55-9 (Theophylline)
Formula: C7H8N4O2
Molecular Weight: 180.166
Synonyms: 1H-Purine-2,6-dione,3,7-dihydro-1,3-dimethyl- (9CI);Theophylline (8CI);1,3-Dimethylxanthine;Accurbron;Aerobin;Aerolate;Afonilm;Apnecut;Armophylline;Asmax;Austyn;Bilordyl;Brochoretard;Bronkodyl;Cetraphylline;Chronophyllin;Diffumal;Duraphyl;Egifilin;Elixophyllin;Etheophyl;Euphylong;LaBID;Lanophyllin;Nuelin;Optiphyllin;Parkophyllin;Physpan;Pro-Vent;PulmiDur;Pulmo-Timelets;Quibron T/SR;Respbid;Respicur;Solosin;SomophyllinCRT;Somophyllin T;Spophyllin retard;Sustaire;Talotren;Telb-DS;Telbans;Telbans Dry Syrup;Teonova;Theo 24;Theo-Dur;Theo-Sav;Theobid;Theobid Duracap;Theoclear;Theodel;Theodrip;Theodur Dry Syrup;Theograd;Theolair;Theona P;Theopek;Theoplus;Theostat;Theotard;Theovent;Throphylline;Unicontin CR;Unilong;Uniphyl;Uniphyllin;Xanthium;Zydus;1H-Purine-2,6-dione,3,9-dihydro-1,3-dimethyl-;
EINECS: 200-385-7
Density: 1.466 g/cm3
Melting Point: 271-273 °C
Boiling Point: 454.091 °C at 760 mmHg
Flash Point: 228.426 °C
Solubility: 8.3 g/L (20 °C) in water
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn, ToxicT, FlammableF, IrritantXi
Risk Codes: 22-39/23/24/25-23/24/25-11-36/37/38
Safety: 7-16-36/37-45-36-26
Transport Information: UN 2811 6.1/PG 3
PSA: 72.68000
LogP: -1.03970
Synthetic route
7597-60-6

1,3-dimethyl-4-amino-5-(formylamino)uracil

58-55-9

theophylline

Conditions
ConditionsYield
With triethylamine; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In water at 75℃; under 4500.45 Torr; for 0.916667h; Pressure; Temperature; Autoclave;97.7%
With sodium hydroxide; sodium chloride
With sodium hydroxide
at 250 - 260℃;
With sulfuric acid at 90℃; pH=5; pH-value; Temperature; Reagent/catalyst;
107-31-3

Methyl formate

57533-87-6

1,3-Dimethylxanthine potassium salt

A

58-55-9

theophylline

B

58-08-2

3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione

Conditions
ConditionsYield
In methanolA 97.5%
B n/a
81281-58-5

7-amino-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione

58-55-9

theophylline

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite In water at 5℃; for 1h;95%

7-(2,4-dimethoxybenzyl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione

58-55-9

theophylline

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃;87%
226386-40-9

(1,3-Dimethyl-2,6(1H,3H)-dioxopurin-7-yl)(phenyl)methyl acetate

58-55-9

theophylline

Conditions
ConditionsYield
With hydrogenchloride In methanol Ambient temperature;78%
124093-03-4

1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-9H-purine-9-carbonitrile

58-55-9

theophylline

Conditions
ConditionsYield
In water for 1h; Reflux;77%
624734-82-3

N-(1,3-dimethyl-6-nitro-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-formamide

58-55-9

theophylline

Conditions
ConditionsYield
With iron; acetic acid for 0.5h; Heating;75%
64210-71-5

2,2-dimethyl-propionic acid 1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-ylmethyl ester

58-55-9

theophylline

Conditions
ConditionsYield
68%
80035-38-7, 80035-40-1, 80035-42-3

7-(2-acetamido-4,6-di-O-acetyl-2,3-dideoxy-D-threo-hex-2-enopyranosyl)theophylline

A

58-55-9

theophylline

B

70800-68-9

7-(methyl 2-acetamido-6-O-acetyl-2,3,4-trideoxy-α-D-threo-hex-2-enopyranosid-4-yl)theophylline

C

70675-25-1

7-(methyl 2-acetamido-6-O-acetyl-2,3,4-trideoxy-β-D-erythro-hex-2-enopyranosid-4-yl)theophylline

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In methanol for 0.25h; Heating;A n/a
B 54%
C 12%
64-18-6

formic acid

5440-00-6

4,5-Diamino-1,3-dimethyluracil

58-55-9

theophylline

Conditions
ConditionsYield
at 110 - 300℃; for 2.33333h;51%
With hydrogenchloride; sodium hydroxide at 90℃; Yield given;
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History

Around 1888,Theophylline was first extracted from tea leaves  by the German biologist Albrecht Kossel.
In 1888,Theophylline was first identified chemically.
At later,Theophylline was synthesized by another German scientist Wilhelm Traube.
In the 1950s,Theophylline was first used in asthma treatment as a drug.
In 2008, theophylline was used in anosmia treatment

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

1. Introduction of Theophylline

The IUPAC name of Theophylline is 1,3-dimethyl-7H-purine-2,6-dione. With the CAS registry number 58-55-9 and EINECS 200-385-7, it is also named as 1,3-Dimethylxanthine. The product's categories are Alkaloids; Alkaloids (Others); Biochemistry; Alkaloids Forensic and Veterinary Standards; Chemical Structure; Drugs of Abuse; Drugs & Metabolites; Neat Compounds Drugs of Abuse; API's. It is white to light yellow crystal powder which is soluble in water (1:120), ethanol (1:18), chloroform (1:86), hydrogen oxidation lye, ammonia, dilute hydrochloric acid and dilute nitric acid, slightly soluble in ether at room temperature. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

2. Properties of Theophylline

The other characteristics of this product can be summarized as: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 23.175; (5)ACD/KOC (pH 7.4): 21.837; (6)#H bond acceptors: 6; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 69.3 Å2; (10)Index of Refraction: 1.62; (11)Molar Refractivity: 43.15 cm3; (12)Molar Volume: 122.913 cm3; (13)Polarizability: 17.106×10-24 cm3; (14)Surface Tension: 67.638 dyne/cm; (15)Enthalpy of Vaporization: 71.361 kJ/mol; (16)Vapour Pressure: 0 mmHg at 25°C; (17)Tautomer Count: 4; (18)Exact Mass: 180.064726; (19)MonoIsotopic Mass: 180.064726; (20)Topological Polar Surface Area: 69.3; (21)Heavy Atom Count: 13; (22)Complexity: 267.

3. Structure Descriptors of Theophylline

You could convert the following datas into the molecular structure:
1). SMILES:Cn1c2c(c(=O)n(c1=O)C)[nH]cn2
2). InChI:InChI=1/C7H8N4O2/c1-10-5-4(8-3-9-5)6(12)11(2)7(10)13/h3H,1-2H3,(H,8,9)
3). InChIKey:ZFXYFBGIUFBOJW-UHFFFAOYAT

4. Toxicity of Theophylline

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo intramuscular 50mg/kg (50mg/kg) BEHAVIORAL: EXCITEMENT

CARDIAC: CHANGE IN RATE

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Journal of Pediatrics. Vol. 90, Pg. 827, 1977.
child TDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: HEADACHE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

GASTROINTESTINAL: NAUSEA OR VOMITING
Southern Medical Journal. Vol. 78, Pg. 1000, 1985.
guinea pig LD50 oral 183mg/kg (183mg/kg)   United States Patent Document. Vol. #4089959,
guinea pig LDLo subcutaneous 170mg/kg (170mg/kg)   "Handbook of Toxicology," 4 vols., Philadelphia, W.B. Saunders Co., 1956-59Vol. 5, Pg. 168, 1959.
human TDLo intravenous 10mg/kg/D (10mg/kg) BEHAVIORAL: TREMOR

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

GASTROINTESTINAL: NAUSEA OR VOMITING
JAMA, Journal of the American Medical Association. Vol. 235, Pg. 1983, 1976.
human TDLo oral 5mg/kg (5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 92, 1969.
human TDLo rectal 6mg/kg (6mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 92, 1969.
human TDLo subcutaneous 3500ug/kg (3.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 92, 1969.
infant TDLo oral 348mg/kg/4D-I (348mg/kg) BEHAVIORAL: ANOREXIA (HUMAN

BEHAVIORAL: IRRITABILITY

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Pediatric Pharmacology. Vol. 5, Pg. 209, 1985.
man LDLo intravenous 3429ug/kg (3.429mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
JAMA, Journal of the American Medical Association. Vol. 136, Pg. 397, 1948.
man LDLo parenteral 12mg/kg (12mg/kg)   Deutsches Archiv fuer Klinische Medizin. Vol. 80, Pg. 510, 1904.
man TDLo oral 66mg/kg (66mg/kg) CARDIAC: CHANGE IN RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

GASTROINTESTINAL: NAUSEA OR VOMITING
American Journal of Emergency Medicine. Vol. 11, Pg. 609, 1993.
man TDLo oral 66mg/kg (66mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

GASTROINTESTINAL: CONTRACTION (ISOLATED TISSUE)

GASTROINTESTINAL: NAUSEA OR VOMITING
Medical Journal of Australia. Vol. 156, Pg. 512, 1992.
man TDLo oral 86mg/kg (86mg/kg) CARDIAC: CHANGE IN RATE

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Annals of Emergency Medicine. Vol. 20, Pg. 1143, 1991.
man TDLo oral 129mg/kg (129mg/kg) ENDOCRINE: HYPERGLYCEMIA Annals of Internal Medicine. Vol. 104, Pg. 284, 1986.
mouse LD50 intramuscular 271mg/kg (271mg/kg)   Drugs in Japan Vol. 6, Pg. 34, 1982.
mouse LD50 intraperitoneal 70mg/kg (70mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD British Journal of Pharmacology. Vol. 73, Pg. 887, 1981.
mouse LD50 intravenous 136mg/kg (136mg/kg)   Pharmaceutica Acta Helvetiae. Vol. 48, Pg. 133, 1973.
mouse LD50 oral 235mg/kg (235mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 45, Pg. 569, 1995.
mouse LD50 rectal 166mg/kg (166mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Pediatric Research. Vol. 11, Pg. 783, 1977.
mouse LD50 subcutaneous 138mg/kg (138mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 328, 1953.
mouse LD50 unreported 400mg/kg (400mg/kg)   United States Patent Document. Vol. #4767763,
rabbit LD50 intravenous 150mg/kg (150mg/kg)   Drugs in Japan Vol. 6, Pg. 34, 1982.
rabbit LD50 oral 350mg/kg (350mg/kg)   "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 865, 1986.
rat LD50 intraperitoneal 150mg/kg (150mg/kg)   United States Patent Document. Vol. #4120947,
rat LD50 oral 225mg/kg (225mg/kg)   United States Patent Document. Vol. #4089959,
rat LD50 unreported 300mg/kg (300mg/kg)   United States Patent Document. Vol. #4767763,
rat LDLo intravenous 240mg/kg (240mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 259, 1973.
rat LDLo subcutaneous 325mg/kg (325mg/kg)   European Patent Application. Vol. #0134762,
women LDLo oral 130mg/kg (130mg/kg)   Annals of Internal Medicine. Vol. 101, Pg. 457, 1984.
women TDLo intravenous 120mg/kg/3D-C (120mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE Drug Intelligence and Clinical Pharmacy. Vol. 16, Pg. 877, 1982.
women TDLo oral 5mg/kg (5mg/kg) BEHAVIORAL: COMA

CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)

GASTROINTESTINAL: NAUSEA OR VOMITING
British Medical Journal. Vol. 288, Pg. 1497, 1984.
women TDLo oral 108mg/kg (108mg/kg) ENDOCRINE: HYPERGLYCEMIA American Journal of Emergency Medicine. Vol. 3, Pg. 408, 1985.
women TDLo oral 281mg/kg/4W (281mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) British Medical Journal. Vol. 281, Pg. 1322, 1980.
women TDLo oral 388mg/kg (388mg/kg) BEHAVIORAL: COMA

CARDIAC: CHANGE IN RATE
Annals of Emergency Medicine. Vol. 20, Pg. 1135, 1991.

5. Safety Information of Theophylline

When you are using this chemical, please be cautious about it as the following:
It is highly flammable, so people should keep it away from sources of ignition. What's more, it is not only toxic by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. And it has danger of very serious irreversible effects. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing and gloves. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 

6. Preparation and Use of Theophylline

Preparation of Theophylline: It can be obtained by starting from dimethylurea and ethyl 2-cyanoacetate.


Uses of Theophylline: It has main actions, such as relaxing bronchial smooth muscle, increasing blood pressure and renal blood flow, increasing heart muscle contractility and efficiency; as a positive inotropic, increasing heart rate: positive chronotropic, some anti-inflammatory effects, central nervous system stimulatory effect mainly on the medullary respiratory center. It also can react with bromoethane to get 7-ethyl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione. This reaction needs reagent 10percent aq. NaOH, catalytic agent bromure de tetra-n-butylammonium and solvent CH2Cl2 at temperature of 40 °C. The reaction time is 24 hours. The yield is 96%.

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