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Phenylephrine
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Name

Phenylephrine

 EINECS 200-424-8
CAS No. 59-42-7 Density 1.159 g/cm3
PSA 52.49000 LogP 1.03590
Solubility N/A Melting Point 171°C
Formula C9H13NO2 Boiling Point 341.1 °C at 760 mmHg
Molecular Weight 167.208 Flash Point 163.4 °C
Transport Information N/A Appearance N/A
Safety 26-36-45 Risk Codes 22-36/37/38
Molecular Structure Molecular Structure of 59-42-7 (Phenylephrine) Hazard Symbols Xn
Synonyms

m-Methylaminoethanolphenol;m-Oxedrine;m-Sympathol;Benzenemethanol,3-hydroxy-a-[(methylamino)methyl]-, (R)-;Benzyl alcohol, m-hydroxy-a-[(methylamino)methyl]-, (-)- (7CI,8CI);(-)-Phenylephrine;(-)-m-Hydroxy-a-(methylaminomethyl)benzylalcohol;(-)-m-Oxedrine;(-)-m-Synephrine;(R)-(-)-Phenylephrine;(R)-Phenylephrine;L-Phenylephedrine;Mesaton;Mesatone;Metaoxedrin;Metaoxedrine;Metasympatol;Metasynephrine;Mezaton;Neo-Synephrine;Phenylephrine;R(-)-Mezaton;Visadron;l-m-Hydroxy-a-[(methylamino)methyl]benzylalcohol;m-Sympatol;m-Synephrine;

Article Data 15

Phenylephrine Synthetic route

614-03-9

(S)-phenylephrine

59-42-7

Phenylephrin

Conditions
ConditionsYield
Stage #1: (S)-phenylephrine With sulfuric acid; acetic anhydride at 105℃; for 12h; Walden inversion;
Stage #2: With water at 95℃; for 3h; Walden inversion; optical yield given as %ee; enantioselective reaction;		99%
With sulfuric acid; acetic anhydride und Erhitzen des Reaktionsprodukts mit wss.Salzsaeure und anschliessend mit wss.Ammoniak;
1280541-42-5

(R)-phenylephrine-(R)-naproxen

59-42-7

Phenylephrin

Conditions
ConditionsYield
Stage #1: (R)-phenylephrine-(R)-naproxen With hydrogenchloride In water; toluene at 75 - 80℃; for 0.5h; pH=< 2;
Stage #2: With ammonium hydroxide In water at 1 - 15℃; pH=~ 9; Product distribution / selectivity;		90%

α-methylamino-m-hydroxy-acetophenone sulfate

59-42-7

Phenylephrin

Conditions
ConditionsYield
Stage #1: α-methylamino-m-hydroxy-acetophenone sulfate With hydrogen; (((R)-1-diphenylphosphino-2-[((S)-α-(N,N-dimethylamino)-o-diphenylphosphino-phenyl)methyl]ferrocene)-η5-2,4-dimethyl-pentadienyl)-ruthenium(II) iodide In methanol at 70℃; under 23272.3 Torr; for 48h;
Stage #2: With ammonium hydroxide In water at 65℃; for 0.0833333h; pH=~ 4.8 - 9;		88.7%
1477-63-0

Phenylephrine

59-42-7

Phenylephrin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Lg-tartaric acid
2: acetic acid anhydride; sulfuric acid / und Erhitzen des Reaktionsprodukts mit wss.Salzsaeure und anschliessend mit wss.Ammoniak
View Scheme
Multi-step reaction with 2 steps
1.1: methanol / 2 h / 20 - 65 °C / Resolution of racemate
2.1: hydrogenchloride / toluene; water / 0.5 h / 75 - 80 °C / pH < 2
2.2: 1 - 15 °C / pH ~ 9
View Scheme
94240-17-2

3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride

A

614-03-9

(S)-phenylephrine

B

59-42-7

Phenylephrin

Conditions
ConditionsYield
With potassium hydroxide; hydrogen; [(R)-P-Phos RuCl2 (R)-DAIPEN] In water; isopropyl alcohol at 65℃; under 21002.1 Torr; for 1h; Product distribution / selectivity;A n/a
B n/a
With hydrogen; [(S)-Cl-MeO-Biphep RuCl2](dmf)n In methanol at 75℃; under 22502.3 Torr; for 18h; Product distribution / selectivity;A n/a
B n/a
With hydrogen; [RuCl-(S)-P-Phos(p-cymene)]Cl In methanol at 75℃; under 22502.3 Torr; for 18h; Product distribution / selectivity;A n/a
B n/a
94240-17-2

3-Hydroxyphenyl-ω-methylaminoacetophenone hydrochloride

59-42-7

Phenylephrin

Conditions
ConditionsYield
With RuCl2[(S)-xylyl-2,2,6,6’-tetramethoxy-4,4’-bis(diphenylphosphino)-3,3-bipyridine][(R)-1,1-bis(4-methoxyphenyl)-3-methyl-1,2-butanediamine]; hydrogen; potassium hydroxide In water; isopropyl alcohol at 65℃; under 21752.2 - 24752.5 Torr; for 2.25h; Autoclave; optical yield given as %ee; enantioselective reaction;

(R)-1-(3-methoxyphenyl)-2-nitroethanol

59-42-7

Phenylephrin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 5%-palladium/activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr
2: dichloromethane / 0 °C
3: boron tribromide / dichloromethane / 24 h / 0 °C
View Scheme
747358-03-8

C10H15NO2

59-42-7

Phenylephrin

Conditions
ConditionsYield
With boron tribromide In dichloromethane at 0℃; for 24h;
591-31-1

3-methoxy-benzaldehyde

59-42-7

Phenylephrin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2,6-dimethylpyridine; copper(II) choride dihydrate; C50H54N2O6 / ethanol; dichloromethane / 30 h / 20 °C
2: 5%-palladium/activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr
3: dichloromethane / 0 °C
4: boron tribromide / dichloromethane / 24 h / 0 °C
View Scheme

(R)-2-N-tert-butoxycarbonyl-N-methylamino-1-(3-nitrophenyl)ethanol

59-42-7

Phenylephrin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper acetylacetonate; sodium tetrahydroborate / isopropyl alcohol; ethanol / 17 h / 30 °C / Inert atmosphere
2: hydrogenchloride; sodium nitrite / water / 0 - 120 °C
View Scheme

Phenylephrine Consensus Reports

 Phenylephrine (59-42-7) is reported in EPA TSCA Inventory.

Phenylephrine Specification

Phenylephrine with the CAS NO. 59-42-7 has the Synonyms of (-)-Phenylephrine;phenylephrine base; (-)-M-hydroxy-alpha-(methylaminomethyl)benzyl alcohol; (-)-M-hydroxy-alpha-(methylaminomethyl)benzylalcohol; (-)-M-oxedrine; (R)-3-hydroxy-alpha-[(methylamino)methyl]benzenemethanol hydrochloride; (R)-benzenemethano;(r)-phenylephrine. Phenylephrine is a selective α1-adrenergic receptor agonist used primarily as a decongestant, as an agent to dilate the pupil, and to increase blood pressure.

Physical properties about Phenylephrine are: (1)ACD/LogP: 0.117; (2)ACD/LogD (pH 5.5): -2.91; (3)ACD/LogD (pH 7.4): -1.78; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.572; (12)Molar Refractivity: 47.449 cm3; (13)Molar Volume: 144.258 cm3; (14)Polarizability: 18.81 10-24cm3; (15)Surface Tension: 49.1800003051758 dyne/cm; (16)Density: 1.159 g/cm3; (17)Flash Point: 163.4 °C; (18)Enthalpy of Vaporization: 61.709 kJ/mol; (19)Boiling Point: 341.068 °C at 760 mmHg

Uses of Phenylephrine: Phenylephrine is used as a decongestant sold as an oral medicine, as a nasal spray, or as eye drops. Phenylephrine is now the most common over-the-counter (OTC) decongestant in the United States. Phenylephrine is sometimes used as a vasopressor to increase the blood pressure in unstable patients with hypotension. It is used as an eye drop to dilate the pupil in order to facilitate visualization of the retina. It is often used in combination with tropicamide. Narrow-angle glaucoma is a contraindication to phenylephrine use.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);

You can still convert the following datas into molecular structure:
(1)InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1;
(2)InChIKey=SONNWYBIRXJNDC-VIFPVBQESA-N;
(3)Smilesc1([C@H](CNC)O)cc(ccc1)O;

 The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
infant TDLo ocular 5500ug/kg (5.5mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Anesthesiology. Vol. 36, Pg. 187, 1972.
 
mouse LD50 intravenous 38mg/kg (38mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP		 Acta Pharmacologica et Toxicologica. Vol. 38, Pg. 474, 1976.
 
mouse LD50 subcutaneous 875mg/kg (875mg/kg)   Farmakologiya i Toksikologiya Vol. 28, Pg. 46, 1965.
 
mouse LDLo intraperitoneal 60mg/kg (60mg/kg) CARDIAC: OTHER CHANGES Journal of Pharmacology and Experimental Therapeutics. Vol. 160, Pg. 22, 1968.
 
rat LD50 intraduodenal 65mg/kg (65mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969.
 
rat LD50 oral 350mg/kg (350mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969.
 
rat LD50 subcutaneous 28mg/kg (28mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 85, Pg. 119, 1945.
women TDLo ocular 188ug/kg (.188mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION Anesthesiology. Vol. 36, Pg. 187, 1972.
 

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