Phenoxybenzamine Hydrochloride
PHENOXYBENZAMINE · PHENOXYBENZAMINE HCL · dibenzyline · 688A · Bensylyt · benzylyt · SKF-688A · dibenylin
Identifiers & Physical Properties
| CAS No. | 63-92-3 |
|---|---|
| Molecular formula | C18H22ClNO.ClH |
| Average molar mass | 340.3 g/mol |
| Monoisotopic mass | 339.1156697 g/mol |
| SMILES | CC(COc1ccccc1)N(CCCl)Cc1ccccc1.Cl |
| InChIKey | VBCPVIWPDJVHAN-UHFFFAOYSA-N |
| PubChem CID | 5284441 |
| ChEMBL | CHEMBL1200787 |
| ChEBI | CHEBI:8078 |
| EC No. | 200-569-7 |
| DTXSID | DTXSID0021127 |
Chemical & Physical Properties
| Topological polar surface area | 12.5 |
|---|---|
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 8 |
| Heavy atoms | 22 |
| Formal charge | 0 |
| Complexity | 262 |
| Solubility | less than 0.1 mg/mL at 65.3 °F (NTP, 1992)45.8 [ug/mL] (The mean of the results at pH 7.4)soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide (DMF).<0.01 g/100 mL at 18.5 ºC |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Melting point | 280 to 284 °F (NTP, 1992)137.5°C |
| Physical Description | Phenoxybenzamine hydrochloride is a white crystalline powder. Melting point 137.5-140 °C. Used as an antihypertensive drug. |
| Collision Cross Section | 194.2 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Storage conditions | 15-25°C |
| pKa (acidity coefficient) | pKa 4.4 (Uncertain) |
| Physical state | powder |
| Color | white |
| Merck | 14,7256 |
| Stability | Stable for 2 years as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months. |
| InChI | 1S/C18H22ClNO.ClH/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17/h2-11,16H,12-15H2,1H3 |
| InChIKey | VBCPVIWPDJVHAN-UHFFFAOYSA-N |
| SMILES | Cl[H].CC(COc1ccccc1)N(CCCl)Cc2ccccc2 |
| Toxicology and Carcinogenesis | Bioassay of Phenoxybenzamine Hydrochloride for Possible Carcinogenicity (CASRN 63-92-3) |
| CAS DataBase Reference | 63-92-3(CAS DataBase Reference) |
| FDA UNII | X1IEG24OHL |
| IARC | 2B (Vol. 24, Sup 7) 1987 |
| Proposition 65 List | Phenoxybenzamine |
| NCI Drug Dictionary | Dibenzyline |
| ATC code | C04AX02 |
| EPA Substance Registry System | N-(2-Chloroethyl)-N-(1-methyl-2-phenoxyethyl)benzylamine hydrochloride (63-92-3) |
| UNSPSC Code | 41116107 |
| NACRES | NA.77 |
| Biological half-life | 24 (IV) / - |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Warning |
| GHS hazard statements | H302-H351 |
| GHS precautionary statements | P201-P301+P312+P330-P308+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | Xn |
| Risk statements (R) | 22-40 |
| Safety statements (S) | 22-36/37/39-45 |
| Water hazard class (WGK) | 3 |
| RTECS number | DP3750000 |
| Customs code | 2922299000 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Acute Tox. 4 OralCarc. 2 |
Safety & Regulations
| GHS classification | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH350: May cause cancer [Danger Carcinogenicity] |
|---|---|
| Regulatory information | Hazard Traits - CarcinogenicityBenzenemethanamine, N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)-, hydrochloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Other safety information | IMAP assessments - Benzenemethanamine, N-(2-chloroethyl)-N-(1-methyl-2-phenoxyethyl)-, hydrochloride: Human health tier I assessment |
| Fire hazards | Flash point data are not available for this chemical, but it is probably combustible. (NTP, 1992) |
| Health hazards | SYMPTOMS: Symptoms of exposure to this compound include nasal congestion, miosis, postural hypotension, tachycardia, gastrointestinal irritation, drowsiness and fatigue. |
| Reactive group | Ethers |
| Air and Water Reactions | Light sensitive and may be sensitive to exposure to air (NTP, 1992). Insoluble in water. |
| Hazard Classes and Categories | Acute Tox. 4 (100%)Acute toxicity (Oral) - Category 5Carcinogenicity - Category 1B |
| Fire fighting | Fires involving this compound should be controlled using 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. |
Applications & Uses
Description
Phenoxybenzamine hydrochloride (dibenzyline) is an orally effective, long-acting non-selective (alpha1 and alpha2) alpha-adrenoceptor blocking agent. It is used for the control of episodes of hypertension associated withpheochromocytoma. It literally produces a "chemical sympathectomy". It increases blood flow to the skin, mucosa and abdominal viscera, and lowers both supine and erect blood pressures. It has no effect on the parasympathetic system. The initialdose is 10 mg/day, increased by 10 mg every 4 days till the desired response is attained.The usual dosage range is 20-60mg/day.
Uses
Phenoxybenzamine is used in treating pheochromocytoma, swelling of the medullary layer of the adrenal glands, during which a large quantity of epinephrine is produced, which leads to a significant elevation of blood pressure.
Uses
Phenoxybenzamine (5.0 to 60.0 mg/day) is used in order to control episodes of hypertension and sweating, it has a relatively slow onset and prolonged effect when compared to alternative α-blockers. If tachycardia is excessive, it may also be necessary to use a betablocker concomitantly. In addition, phenoxybenzamine has been tested for its efficacy in micturition disorders resulting from neurogenic bladder, functional outlet obstruction, and partial prostatic obstruction.
General Description
Phenoxybenzamine hydrochloride is a white crystalline powder. Melting point 137.5-140°C. Used as an antihypertensive drug.