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Imiquimod
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Name

Imiquimod

 EINECS 619-387-8
CAS No. 99011-02-6 Density 1.28 g/cm3
PSA 56.73000 LogP 3.40390
Solubility Soluble in dimethyl sulfoxide and dimethyl formamide. Slightly soluble in water. Insoluble in ethanol. Melting Point 292-294 °C
Formula C14H16N4 Boiling Point 456.7 °C at 760 mmHg
Molecular Weight 240.308 Flash Point 230 °C
Transport Information UN 2811 6.1/PG 3 Appearance White to off white crystalline powder
Safety 26-45-36/37/39-27 Risk Codes 25-36/37/38
Molecular Structure Molecular Structure of 99011-02-6 (Imiquimod) Hazard Symbols ToxicT, IrritantXi
Synonyms

Aldara;4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline;1H-Imidazo(4,5-c)quinolin-4-amine, 1-(2-methylpropyl)-;

Article Data 25

Imiquimod Synthetic route

201030-96-8

4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline

99011-02-6

imiqimod

Conditions
ConditionsYield
With hydrogenchloride; sodium formate; palladium 10% on activated carbon In water for 84h; Product distribution / selectivity; Heating / reflux;98%
Stage #1: 4-Hydrazino-1-(2-methylpropyl)-1H-imidazo [4,5-c]quinoline With hydrogenchloride; sodium formate; palladium 10% on activated carbon In water for 84h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 20℃;
Stage #3: With ammonia In water at 20℃; Product distribution / selectivity;		98%
132206-92-9

4-chloro-1H-imidazo[4,5-c]-quinoline

99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: formamide With potassium tert-butylate In dimethyl sulfoxide for 0.5h;
Stage #2: 4-chloro-1H-imidazo[4,5-c]-quinoline In dimethyl sulfoxide at 105℃; for 2h;
Stage #3: With hydrogenchloride In water; dimethyl sulfoxide pH=8; Product distribution / selectivity;		98%

N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide

99011-02-6

imiqimod

Conditions
ConditionsYield
With ethylenediamine In water at 70 - 95℃; for 4h;91.8%
Stage #1: N-(1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)-phthalimide With hydrazine In water at 70℃;
Stage #2: With 2,4,4-trimethylpentan-1-ol In water at 94 - 95℃; for 5h;
Stage #3: In methanol; water at 60℃; for 0.25h; Heating / reflux;		63.3%

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline fumarate

99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia; water In methanol Product distribution / selectivity;90%
960254-02-8

5-(2-aminophenyl)-1-(2-methylpropyl)-1H-imidazole-4-carbonitrile

99011-02-6

imiqimod

Conditions
ConditionsYield
With sodium amide In toluene at 20 - 100℃; for 2h;90%

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate

99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: 4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline maleate In methanol; water at 75℃; for 0.5h;
Stage #2: With ammonia In water		89.7%
With ammonia; water In methanol Product distribution / selectivity;89.7%

4-amino-1-isobutyl-1H-imidazo-[4,5-c]-quinoline oxalate

99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia; water In methanol Product distribution / selectivity;88%
896106-15-3

4-iodo-1-isobutyl-1H-imidazo-[4,5-c]-quinoline

99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia In methanol at 150 - 155℃; Autoclave (ca. 20 kg pressure);86%
With ammonia In methanol at 150 - 155℃; under 14711.4 Torr; Product distribution / selectivity; Autoclave;86%
99010-64-7

4-Chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

99011-02-6

imiqimod

Conditions
ConditionsYield
With ammonia In dimethyl sulfoxide at 20 - 150℃; under 1875.19 - 3750.38 Torr; for 6 - 12h; Product distribution / selectivity;85.7%
With ammonia at 150℃; for 7h;82%
With ammonia; formamide at 145℃; for 20 - 25h; Product distribution / selectivity;78%

imiquimod hydrochloride

99011-02-6

imiqimod

Conditions
ConditionsYield
Stage #1: imiquimod hydrochloride With sodium hydrogensulfide; pyrographite In water at 85 - 90℃; for 0.333333h;
Stage #2: With ammonium hydroxide In water at 20 - 80℃; Purification / work up;		80.5%
With sodium hydroxide In water at 20℃; for 0.5h; Product distribution / selectivity;

Imiquimod Chemical Properties

Molecular Structure of Imiquimod (CAS NO.99011-02-6):

IUPAC Name: 1-(2-methylpropyl)imidazo[4,5-c]quinolin-4-amine 
Empirical Formula: C14H16N4
Molecular Weight: 240.3036
H bond acceptors: 4
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 33.95 Å2
Index of Refraction: 1.681
Molar Refractivity: 71.02 cm3
Molar Volume: 187.7 cm3
Surface Tension: 48.8 dyne/cm
Density: 1.28 g/cm3
Flash Point: 230 °C
Enthalpy of Vaporization: 71.67 kJ/mol
Boiling Point: 456.7 °C at 760 mmHg
Vapour Pressure: 1.58E-08 mmHg at 25°C
Melting point: 292-294°C
Stability: Incompatible with strong oxidizing agents
InChl
InChI=1/C14H16N4/c1-9(2)7-18-8-16-12-13(18)10-5-3-4-6-11(10)17-14(12)15/h3-6,8-9H,7H2,1-2H3,(H2,15,17)
Smiles
c12c3c(nc(c1ncn2CC(C)C)N)cccc3
Product Categories: Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals

Imiquimod History

  The original FDA approval was on February 27, 1997, FDA Application No. (NDA) 020723, by 3M.

Imiquimod Uses

  Imiquimod (CAS NO.99011-02-6) is a prescription medication that acts as an immune response modifier. Imiquimod is approved to treat actinic keratosis, superficial basal cell carcinoma, and external genital warts. It has also been tested for treatment of molluscum contagiosum, vulvar intraepithelial neoplasia, common warts that have proven difficult to treat and vaginal intraepithelial neoplasia.Outstanding cosmetic result has resulted from the treatment of both large superficial basal cell carcinoma and squamous cell carcinoma in-situ, but the morbidity and discomfort of the treatment can be severe. Focal recurrence of tumor has been seen after imiquimod treatment, but appear to be amenable to surgical excision.

  Imiquimod can also cause subclinical lesions to become visible. This unmasking effect is felt to be of clinical benefit as lesions that may have otherwise have been missed are being treated. Photographs of actinic keratosis and basal cell carcinomas before, during and after treatment show the unmasking of subclinical disease.

Imiquimod Safety Profile

Safety Information about Imiquimod (CAS NO.99011-02-6):
Hazard Codes: ToxicT,IrritantXi
Risk Statements: 25-36/37/38
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-45-36/37/39-27
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S27:Take off immediately all contaminated clothing.
RIDADR: UN 2811 6.1/PG 3
Adverse side effects have been reported, in some cases serious and systemic, resulting in the revision of warning labels.

Imiquimod Specification

  Imiquimod , with CAS number of 99011-02-6, can be called 4-Amino-1-isobutyl-1H-imidazo(4,5-c)quinoline ; 1H-Imidazo(4,5-c)quinolin-4-amine, 1-(2-methylpropyl)- ; 1H-Imidazo[4,5-c]quinolin-4-amine, 1-(2-methylpropyl)- . It is a white to off white crystalline powder.

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