1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyiso-chinolin-hydrochlorid
PAPAVERINE HCL · paph · dipav · BOC-azide · 1-(3,4-DIMETHOXYBENZYL)-6,7-DIMETHOXYISOQUINOLINE HYDROCHLORIDE · lapav · vasal · dynovas
Identifikatoren & physikalische Daten
| CAS No. | 61-25-6 |
|---|---|
| Summenformel | C20H21NO4.ClH |
| Durchschnittliche Molmasse | 375,8 g/mol |
| Monoisotopische Masse | 375,12373586 g/mol |
| SMILES | COc1ccc(Cc2nccc3cc(OC)c(OC)cc23)cc1OC.Cl |
| InChIKey | UOTMYNBWXDUBNX-UHFFFAOYSA-N |
| PubChem CID | 6084 |
| ChEMBL | CHEMBL98123 |
| EC No. | 200-502-1 |
| DTXSID | DTXSID9025825 |
| Lokaler Name | 1-((3,4-Dimethoxyphenyl)methyl)-6,7-dimethoxyiso-chinolin-hydrochlorid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 49,8 |
|---|---|
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 26 |
| Formalladung | 0 |
| Komplexität | 407 |
| Löslichkeit | Soluble (>=10 mg/ml at 70 °F) (NTP, 1992)H2O: 25 mg/mLfreely soluble |
| Schmelzpunkt | 435 to 437 °F (decomposes) (NTP, 1992)226°C (dec.) |
| Physical Description | Papaverine hydrochloride is a white powder. pH (0.05 molar solution) 3.9. pH (2% aqueous solution) 3.3. (NTP, 1992) |
| Collision Cross Section | 185.8 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Lagerbedingungen | Amber Vial, Refrigerator |
| Aggregatzustand | powder |
| Farbe | white |
| pH | pH (20g/l, 25℃) : 3.0～4.0 |
| Merck | 14,7019 |
| BRN | 3921435 |
| Stabilität | Stable, but may be light sensitive. |
| InChI | InChI=1S/C20H21NO4.ClH/c1-22-17-6-5-13(10-18(17)23-2)9-16-15-12-20(25-4)19(24-3)11-14(15)7-8-21-16/h5-8,10-12H,9H2,1-4H31H |
| InChIKey | UOTMYNBWXDUBNX-UHFFFAOYSA-N |
| SMILES | C1(CC2=CC=C(OC)C(OC)=C2)=C2C(C=C(OC)C(OC)=C2)=CC=N1.[H]Cl |
| CAS Datenbank | 61-25-6(CAS DataBase Reference) |
| EPA chemische Informationen | Papaverine hydrochloride (61-25-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (47%): Toxic if swallowed [Danger Acute toxicity, oral]P264, P270, P301+P316, P301+P317, P321, P330, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 132 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-, hydrochloride: Environment tier I assessment |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this compound are not available, but it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include sleepiness, slowed respiration and slowed heart beat. (NTP, 1992) |
| Reaktive Gruppe | Ethers |
| Reactivity Profile | This material is sensitive to light. (NTP, 1992). |
| Air and Water Reactions | Water soluble. |
| Hazard Classes and Categories | Acute Tox. 3 (47%) |
| Brandbekämpfung | Fires involving this compound should be controlled with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992) |
| Erste Hilfe | 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. |
| Freisetung ohne Brand | 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 strong 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| 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) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Papaverine hydrochloridevMost-DILI-concern5Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1544 6.1/PG 3 |
| Zollcode | 29391900 |
| RTECS-Nr. | NW8575000 |
| R-Sätze (R) | 22-34-11 |
| Toxizität | LD50 in mice, rats (mg/kg): 27.5, 20 i.v.150, 370 s.c. (Levis) |
| Gefahrensymbole | Xn,C,F |
| Sicherheitshinweise (S) | 22-45-36/37/39-26-16 |
| Gefahrenklasse | 6.1Acute Tox. 3 Oral |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
Anwendungen & Verwendung
Beschreibung
Papaverine Hydrochloride, USP, is the hydrochloride of an alkaloid obtained from opium or prepared synthetically. It belongs to the benzylisoquinoline group of alkaloids. It does not contain a phenanthrene group as do morphine and codeine.Papaverine Hydrochloride, USP, is 6,7-dimethoxy-1-veratrylisoquinoline hydrochloride and contains, on the dried basis, not less than 98.5% of CHNO.HCI. The molecular weight is 375.85. The structural formula is as shown.Papaverine Hydrochloride occurs as white crystals or white crystalline powder. One gram dissolves in about 30 mL of water and in 120 mL of alcohol. It is soluble in chloroform and practically insoluble in ether.Papaverine Hydrochloride Injection, USP, is a clear, colorless to pale-yellow solution.Papaverine Hydrochloride, for parenteral administration, is a smooth-muscle relaxant that is available in vials containing 30 mg/mL. Each vial also contains edetate disodium 0.005%. The 10 mL vials also contain chlorobutanol 0.5% as a preservative. pH may be adjusted with sodium citrate and/or citric acid.
History
Human beings have a long history of using opium poppy as food and narcotics, which can be dated back to the Neolithic age. The opium, which is the dried product of the opium poppy juice, is widely used as analgesics in the old and new civilizations of the old continent except the Chinese civilization. In 1848, German chemist Georg Merck successfully isolated a new alkaloid from the opium liquor for the first time and named it as “papaverine” . He also determined the correct molecular formula of papaverine as C20 H21NO4 and prepared the papaverine hydrochloride and nitrate by recrystallization method. Then, Goldschmiedt etal. put forward the molecular structure of papaverine by studying its oxidation products in 1883 and determined the isoquinoline ring as the core structure of papaverine in 1888 . Since the content of papaverine in plants is very low (less than 1%) and can hardly meet the clinical needs, so Pictet and Gams proposed a synthetic method of papaverine in 1909, which makes the large-scale industrialized production of papaverine possible . Study on the pharmacology of papaverine was first published in 1914 by Professor Pal of Vienna, who found that papaverine possessed smooth muscle relaxation effect without causing smooth muscle paralysis and can be used for the treatment of hypertension, angina, and acute uremia .
Verwenden
Papaverine hydrochloride is as effective as sodium diclofenac for the short-term relief of acute renal colic pain and may be advantageous in patients with contraindications for nonsteroidal anti-inflammatory drugs. However, sodium diclofenac appears to provide a longer effective analgesia.Papaverine hydrochloride belongs to the group of benzylisoquinoline alkaloid. It is obtained from opium poppy.Papaverine hydrochloride has been used:in oxygenated Krebs solution for tissue mechanics analysisas a vasodilator in heparinized horse serum in tissue uptake techniqueas an inhibitor of H-MPP+ uptake into stably transfected 293 cells expressing either extraneuronal monoamine transporter (EMT) human or EMT rat