Phenylephrine Hydrochloride
PHENYLEPHRINE HCL · PHENYLEPHRINE HYDROCHLORIDE · Phenylephrine Hydrochlorid · (R)-PHENYLEPHRINE HYDROCHLORIDE · (R)-(-)-PHENYLEPHRINE HYDROCHLORIDE · L-PHENYLEPHRINE HYDROCHLORIDE · Phenylephrine hydrochloride CRS · L(-)-PHENYLEPHRINE HYDROCHLORIDE
Identifiers & Physical Properties
| CAS No. | 61-76-7 |
|---|---|
| Molecular formula | C9H13NO2.ClH |
| Average molar mass | 203.66 g/mol |
| Monoisotopic mass | 203.0713064 g/mol |
| SMILES | CNC[C@H](O)c1cccc(O)c1.Cl |
| InChIKey | OCYSGIYOVXAGKQ-FVGYRXGTSA-N |
| PubChem CID | 5284443 |
| ChEMBL | CHEMBL1200339 |
| EC No. | 200-517-3 |
| DTXSID | DTXSID3021142 |
Chemical & Physical Properties
| Topological polar surface area | 52.5 |
|---|---|
| Hydrogen bond donors | 4 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 3 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 130 |
| Solubility | greater than or equal to 100 mg/mL at 70 °F (NTP, 1992)Freely soluble in water and in ethanol (96 per cent).>=10 g/100 mL at 21 ºC |
| Human Drugs | Breast FeedingLactationMilk, HumanAdrenergic AgentsAdrenergic Alpha-AgonistsAntiglaucoma AgentsSympathomimeticsVasoconstrictor AgentsNasal DecongestantsFDA approved drugs -> Active ingredient |
| Melting point | 284 to 293 °F (NTP, 1992)143-145 °C(lit.) |
| Physical Description | Phenylephrine hydrochloride is an odorless white microcrystalline powder. Bitter taste. pH (1% aqueous solution) about 5. (NTP, 1992) |
| Collision Cross Section | 133 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| alpha | -47 º (c=2, H2O) |
| Density | 1.2652 g/cm³(Temp: 25 °CPress: 750 Torr) |
| Refractive index | -45.5 ° (C=1, H2O) |
| Flash point | 9℃ |
| Storage conditions | 2-8°C |
| Physical state | Crystalline Powder |
| pKa (acidity coefficient) | pK1 8.77pK2 9.84(at 25℃) |
| Color | White to almost white |
| pH | pH (10g/L, 25℃) : 4.5～5.5 |
| Merck | 14,7286 |
| BRN | 4158948 |
| Stability | Hygroscopic |
| Major applications | pharmaceutical (small molecule) |
| InChI | 1S/C9H13NO2.ClH/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H31H/t9-/m0./s1 |
| InChIKey | OCYSGIYOVXAGKQ-FVGYRXGTSA-N |
| SMILES | OC1=CC([C@H](CNC)O)=CC=C1.Cl |
| LogP (partition coefficient) | -0.310 |
| Toxicology and Carcinogenesis | Toxicology and Carcinogenesis Studies of Phenylephrine Hydrochloride (CASRN 61-76-7) in F344/N Rats and B6C3F1 Mice (Feed Studies) |
| FDA 21 CFR | 341.20 |
| CAS DataBase Reference | 61-76-7(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 04JA59TNSJ |
| EPA Substance Registry System | Phenylephrine hydrochloride (61-76-7) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H302-H317 |
| GHS precautionary statements | P261-P264-P270-P280-P301+P312-P302+P352 |
| Hazard symbols | Xn,T,F |
| Risk statements (R) | 22-36/37/38-39/23/24/25-23/24/25-11 |
| Safety statements (S) | 26-36-37/39-45-36/37-16-7 |
| UN transport number | 3249 |
| Water hazard class (WGK) | 3 |
| RTECS number | DO7525000 |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1(b)Acute Tox. 4 OralSkin Sens. 1B |
| Packing group | III |
| Customs code | 29225090 |
| Storage class | 11 - Combustible Solids |
| Toxicity | LD50 in rats (mg/kg): 17 ±1.1 i.p.33 ±2.0 s.c. (Warren, Werner) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 0.3% (1 of 387) of reports.WarningH302 (90.2%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 387 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | REACH registered substance: Phenylephrine hydrochloride (EC: 200-517-3)Phenylephrine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard |
| Other safety information | IMAP assessments - Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-, hydrochloride, (R)-: Environment tier I assessment |
| Fire hazards | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Health hazards | SYMPTOMS: Symptoms of exposure to this compound may include tremor, insomnia and palpitations. Other symptoms include excessive central nervous system stimulation resulting in excitement and restlessnesstachycardia, hypertension, pallor, mydriasis, hyperglycemia and urinary retention. Severe overdosage may cause tachypnea or hyperpnea, hallucinations, convulsions and delirium. In some cases it may cause central nervous system depression with somnolence, stupor and respiratory depression. Arrhythmias (including ventricular fibrillation) may lead to hypotension and circulatory collapse. Severe hypokalemia can occur. Other symptoms include blanching and a feeling of coolness of the skin, pressor response, anxiety, nervousness, weakness, headache, dizziness and vomiting. It has an adverse effect on intraocular pressure, corneas, conjunctiva and lids. Trembling and perspiration may occur. Exposure to this compound may cause peripheral vasoconstriction, an increase in arterial pressure, reflex bradycardia and a rise in blood pressure Extravasation of the injection may cause tissue necrosis. Exposure may also cause ventricular dysrrhythmias, a sensation of fullness in the head, tingling, irritation, local discomfort at the site of application, cardiac arrhythmia or cardiac arrests, and death. It has caused acute pulmonary edema with associated hypertension in infants. Hypersensitive persons may experience mild stinging (transient). |
| Reactive group | Alcohols and Polyols |
| Reactivity Profile | PHENYLEPHRINE HYDROCHLORIDE is incompatible with acids, acid chlorides, acid anhydrides and oxidizing agents. It is also incompatible with butacaine, alkalis and ferric salts. (NTP, 1992) |
| Air and Water Reactions | May be sensitive to prolonged exposure to air and light. Water soluble. |
| Hazard Classes and Categories | Acute Tox. 4 (90.2%) |
| Fire fighting | Fires involving this chemical can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| First aid | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Carcinogen Classification | Phenylephrine HydrochlorideTR-322: Toxicology and Carcinogenesis Studies of Phenylephrine Hydrochloride (CASRN 61-76-7) in F344/N Rats and B6C3F1 Mice (Feed Studies) (1987 )03/26/86No Evidence |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | DO7525000 |
| UN transport number | 3249 |
| Customs code | 29225090 |
| Toxicity | LD50 in rats (mg/kg): 17 ±1.1 i.p.33 ±2.0 s.c. (Warren, Werner) |
| Risk statements (R) | 22-36/37/38-39/23/24/25-23/24/25-11 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xn,T,F |
| Safety statements (S) | 26-36-37/39-45-36/37-16-7 |
| Hazard class | 6.1(b)Acute Tox. 4 OralSkin Sens. 1B |
| Storage class | 11 - Combustible Solids |
| Packing group | III |
| GHS hazard statements | H302-H317 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P264-P270-P280-P301+P312-P302+P352 |
Applications & Uses
Description
R-(-)-Phenylephrine is an adrenergic α1A receptor agonist (Ki = 1.4 μM) that demonstrates selectivity against the α1B and α1C receptor subtypes (Kis = 23.9 and 47.8 μM, respectively). By stimulating adrenergic α1 receptors, L-phenylephrine can induce aortic smooth muscle contractions, although reported relative affinity and potency values in rabbit are 5-fold weaker compared to that of L-norepinephrine . This compound is frequently used to precontract smooth muscle in preparations designed to study the properties of various vasodilator agents.
Uses
(R)-Phenylephrine Hydrochloride is an α-Adrenergic agonist. Mydriatic; decongestant.
Uses
DECONGESTANTS
Uses
Phenylephrine hydrochloride is used medically as a vasoconstrictor and pressor drug. It is chemically related to epinephrine and ephedrine. Actions are usually longer lasting than the latter two drugs. The action of phenylephrine hydrochloride contrasts sharply with epinephrine and ephedrine, in that its action on the heart is to slow the rate and to increase the stroke output, inducing no disturbance in the rhythm of the pulse. In therapeutic doses, it produces little if any stimulation of either the spinal cord or cerebrum. The drug is intended for the maintenance of an adequate level of blood pressure during spinal and inhalation anesthesia and for the treatment of vascular failure in shock, shock-like states, and drug-induced hypotension, or hypersensitivity. It is also used to overcome paroxysmal supraventricular tachycardia, to prolong spinal anesthesia, and as a vasoconstrictor in regional analgesia. Caution is required in the administration of phenylephrine hydrochloride to elderly persons, or to patients with hyperthyroidism, bradycardia, partial heart block, myocardial disease, or severe arteriosclerosis. The brand name Neo-Synephrine is also used to designate another product (nose drops) which does not contain phenylephrine hydrochloride. The nose drops contain xylometazoline hydrochloride.
General Description
Odorless white microcrystalline powder. Bitter taste. pH (1% aqueous solution) about 5.