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550-99-2

Basic Information
CAS No.: 550-99-2
Name: 1H-Imidazole,4,5-dihydro-2-(1-naphthalenylmethyl)-, hydrochloride (1:1)
Molecular Structure:
Molecular Structure of 550-99-2 (1H-Imidazole,4,5-dihydro-2-(1-naphthalenylmethyl)-, hydrochloride (1:1))
Formula: C14H14N2.HCl
Molecular Weight: 246.76
Synonyms: 1H-Imidazole,4,5-dihydro-2-(1-naphthalenylmethyl)-, monohydrochloride (9CI);2-Imidazoline,2-(1-naphthylmethyl)-, monohydrochloride (8CI);Naphazoline hydrochloride(6CI);2-(1-Naphthylmethyl)-2-imidazoline hydrochloride;2-(a-Naphthylmethyl)-2-imidazoline hydrochloride;Ak-Con;Albalon;Allerest Eye Drops;Coldan;Degest 2;Iridina Due;Naphazoline chloride;Naphcon;Niazol;Ocumethyl;Opcon;Privine (American);Privine hydrochloride;Rhinantin;Rhinoperd;Sanorin-Spofa;Strictylon;Stricylon;Vasocon;
EINECS: 208-989-2
Density: 1.15 g/cm3
Melting Point: 254-260 °C
Boiling Point: 440.5 °C at 760 mmHg
Flash Point: 220.2 °C
Solubility: water: 170 g/L (20 °C)
Appearance: white crystalline powder
Hazard Symbols: ToxicT,HarmfulXn
Risk Codes: 25-23/24/25-20/21/22
Safety: 45-36/37/39-24/25
Transport Information: UN 2811 6.1/PG 2
PSA: 24.39000
LogP: 2.95040
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Specification

The IUPAC name of Niazol is 2-(naphthalen-1-ylmethyl)-4,5-dihydro-1H-imidazole hydrochloride. With the CAS registry number 550-99-2, it is also named as Naphazoline. The product's categorie is Adrenoceptor. It is white crystalline powder which is soluble in ethanol, slightly soluble in chloroform, insoluble in benzene and ether. This product is vasoconstrictor drug. When heated to decomposition it emits very toxic fumes of NOx and HCl.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 3.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.88; (4)ACD/LogD (pH 7.4): 1.94; (5)ACD/BCF (pH 5.5): 5.25; (6)ACD/BCF (pH 7.4): 5.94; (7)ACD/KOC (pH 5.5): 30.82; (8)ACD/KOC (pH 7.4): 34.89; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Flash Point: 220.2 °C; (13)Enthalpy of Vaporization: 67.07 kJ/mol; (14)Boiling Point: 440.5 °C at 760 mmHg; (15)Vapour Pressure: 1.52E-07 mmHg at 25°C; (16)Rotatable Bond Count: 2; (17)Exact Mass: 246.092376; (18)MonoIsotopic Mass: 246.092376; (19)Topological Polar Surface Area: 24.4; (20)Heavy Atom Count: 17; (21)Complexity: 272.

Preparation of Niazol: The condensation and cyclization of ethylenediamine and α-naphthylacetic acid to get 2-(1-naphthylmethyl) imidazoline (C14H14N2, [CAS NO.835-31-4]), and then salifing to obtain Niazol. Adding α-naphthylacetic acid and ethylenediamine into the reaction pot, stirring and heating to 120 °C for 1 hour, then heating to 130 °C for 1 hour. Distilling out ethylenediamine and water, collecting 180-240 °C (1.33-4 kPa) fractions to get 2-(1- naphthylmethyl) imidazoline. Then dissolved in the mixture of acetone and ethanol, leading to hydrogen chloride gas in the 10-12 °C to salify, then we can obtain Niazol crystals.

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, so people should avoid contact with skin and eyes. 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:Cl.N\1=C(\NCC/1)Cc2cccc3c2cccc3
2. InChI:InChI=1/C14H14N2.ClH/c1-2-7-13-11(4-1)5-3-6-12(13)10-14-15-8-9-16-14;/h1-7H,8-10H2,(H,15,16);1H

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 2uL/kg (0.002mL/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Japanese Journal of Toxicology. Vol. 9, Pg. 295, 1996.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 28, Pg. 761, 1993.
mouse LD50 intravenous 16500ug/kg (16.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 113, Pg. 341, 1955.
 
mouse LD50 subcutaneous 170mg/kg (170mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 280, 1946.
rabbit LD50 intramuscular 950ug/kg (0.95mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 284, 1946.
rabbit LD50 intravenous 800ug/kg (0.8mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 284, 1946.
rabbit LD50 oral 50mg/kg (50mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941.
rabbit LD50 subcutaneous 4mg/kg (4mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941.
rat LD50 intraperitoneal 50mg/kg (50mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 86, Pg. 284, 1946.
rat LD50 intravenous 6mg/kg (6mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Pharmacology and Experimental Therapeutics. Vol. 113, Pg. 341, 1955.
 
rat LD50 subcutaneous 200mg/kg (200mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION Schweizerische Medizinische Wochenschrift. Vol. 71, Pg. 554, 1941.