| Identification | More | [Name]
Papaverine hydrochloride | [CAS]
61-25-6 | [Synonyms]
1-(3,4-DIMETHOXYBENZYL)-6,7-DIMETHOXYISOQUINOLINE HYDROCHLORIDE
1-[(3',4'-DIMETHOXYPHENYL)METHYL]-6,7-DIMETHOXYISOQUINOLINE HCL
6,7-DIMETHOXY-1-(3,4-DIMETHOXYBENZYL)-ISOQUINOLINE HYDROCHLORIDE
6,7-DIMETHOXY-1-VERATRYLISOQUINOLINE HCL
6,7-DIMETHOXY-1-VERATRYL-ISOQUINOLINE HYDROCHLORIDE
PAPAVERINE HCL
PAPAVERINE HYDROCHLORIDE
1-((3,4-dimethoxyphenyl)methyl)-6,7-dimethoxy-isoquinolinhydrochloride
1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-isoquinolinhydrochloride
6,7,3’,4’-tetramethoxy-1-benzylisoquinolinehydrochloride
6,7-dimethoxy-1-veratryl-isoquinolinhydrochloride
artegodan
cardoverina
cepaverin
cerespan
chlorhydratedepapaverine
dipav
dispamil
dynovas
lapav | [EINECS(EC#)]
200-502-1 | [Molecular Formula]
C20H22ClNO4 | [MDL Number]
MFCD00012745 | [Molecular Weight]
375.85 | [MOL File]
61-25-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
226°C (dec.) | [storage temp. ]
Amber Vial, Refrigerator | [solubility ]
H2O: 25 mg/mL
| [form ]
powder
| [color ]
white
| [PH]
pH (20g/l, 25℃) : 3.0～4.0 | [Stability:]
Stable, but may be light sensitive. | [Water Solubility ]
freely soluble | [Sensitive ]
Light Sensitive | [Usage]
Smooth muscle relaxant found in opium. Vasodilator (cerebral) | [Merck ]
14,7019 | [BRN ]
3921435 | [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,9H2,1-4H3;1H | [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 DataBase Reference]
61-25-6(CAS DataBase Reference) | [EPA Substance Registry System]
61-25-6(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H301 | [Precautionary statements ]
P264-P270-P301+P310-P405-P501 | [Hazard Codes ]
Xn,C,F | [Risk Statements ]
R22:Harmful if swallowed.
R34:Causes burns.
R11:Highly Flammable. | [Safety Statements ]
S22:Do not breathe dust .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S16:Keep away from sources of ignition-No smoking . | [RIDADR ]
UN 1544 6.1/PG 3
| [WGK Germany ]
1
| [RTECS ]
NW8575000
| [F ]
8 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29391900 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral | [Safety Profile]
Poison by ingestion, intraperitoneal, intraduodenal, intravenous, and subcutaneous routes. Human systemic effects: metabolic acidosis, pulse rate increase. An experimental teratogen. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and HCl. See also PAPAVERINE | [Hazardous Substances Data]
61-25-6(Hazardous Substances Data) | [Toxicity]
LD50 in mice, rats (mg/kg): 27.5, 20 i.v.; 150, 370 s.c. (Levis) |
| Hazard Information | Back Directory | [General Description]
White powder. pH (0.05 molar solution) 3.9. pH (2% aqueous solution) 3.3. | [Reactivity Profile]
This material is sensitive to light. . | [Air & Water Reactions]
Water soluble. | [Health Hazard]
SYMPTOMS: Symptoms of exposure to this compound may include sleepiness, slowed respiration and slowed heart beat. | [Fire Hazard]
Flash point data for this compound are not available, but PAPAVERINE HYDROCHLORIDE(61-25-6) is probably combustible. | [Description]
Papaverine mainly exists in the mature capsule shell of Papaveraceae poppy
(Papaver somniferum L). Opium poppy shell is proved to be poisonous and contains
more than 30 kinds of alkaloids including morphine, codeine, narcotine, and papaverine, the content of which varies greatly between different habitats and batches.
The main effects of papaverine are astringing the lung and intestine and relieving
the pain. The usage of opium poppy shell as medicine was recorded in the
Compendium of Materia Medica, Ben Cao Jing Shu, and Materia Medica of Seeking
Truth. Opium poppy shell can also be used for the treatment of chronic cough, diarrhea, archoptosis, and abdominal pain, but the long-term usage turns out to be
addictive easily.
As an annual or biennial herb, the cultivation of opium poppy requires certain
climate and regional conditions, generally in the altitude of 900–1300?m. Opium
poppy is native in Asia Minor, India, Armenia, and Iran, and Afghanistan is the largest origin of poppy flower in the world. In China, there is only a small amount of
cultivation of opium poppy for medicinal research in the herbal plantation.
Considering the low content and the low production rate of papaverine in the
opium poppy, the supply of papaverine by extracting from opium poppy can hardly
meet the clinical demand. To this end, the artificial synthesis of papaverine was
explored since 1909 , and Chinese established the synthetic method of papaverine hydrochloride by using guaiacol as starting material in the 1980s . | [Chemical Properties]
PAPAVERINE HYDROCHLORIDE is Crystalline Solid
| [Physical properties]
Appearance: colorless prismatic or acicular crystal. Melting point: 147–148? °C.
Relative density: 1.337 (20/4?°C). Solubility: very soluble in benzene, acetone, hot
ethanol, and glacial acetic acid; soluble in concentrated sulfuric acid; slightly soluble in ether, chloroform, and carbon tetrachloride; and insoluble in water. The common crystalline salt is hydrochloride salt, papaverine hydrochloride. | [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 et?al. 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 . | [Uses]
Anti-spasmodic, The treatment of erectile dysfunction | [Uses]
Smooth muscle relaxant found in opium. Vasodilator (cerebral) | [Uses]
Vasodilator;Phosphodiesterase inhibitor | [Indications]
Papaverine is mainly used for the treatment of ischemia caused by cerebral, cardiac,
and peripheral vascular spasm, as well as visceral spasm of the kidney, gallbladder,
or gastrointestinal tract. | [Brand name]
Pavabid (Hoechst Marion Roussel). | [Biochem/physiol Actions]
Papaverine is originally used to resolve male impotence. | [Pharmacology]
As a vasodilator, papaverine is a nonspecific antispasmodic drug of smooth muscle,
which is especially effective on pulmonary artery, coronary artery, and great vessels, producing systemic and nonspecific hypotensive and smooth muscle relaxation
effect. Papaverine has a direct effect on the smooth muscle cells by inhibiting phosphodiesterase, thus increasing the intracellular concentration of cyclic adenosine
monophosphate (cAMP), which further removes the catalase calcium from cytoplasmic of vascular smooth muscle, leading to the direct smooth muscle relaxation
without nerve. Papaverine can also inhibit the cardiac conduction, directly act on
myocardial cells, and prolong the refractory period. No effect of papaverine on the
central nervous system has been found. High dose of papaverine can cause hypotension and tachycardia. | [Clinical Use]
Papaverine hydrochloride is used for the treatment of ischemia induced by brain,
heart, and peripheral vascular spasm, as well as visceral spasm of the kidney, bladder, or gastrointestinal tract. Besides, papaverine is also suitable for angina and
arterial embolism, occasionally used for the treatment of erectile dysfunction. In
recent years, papaverine hydrochloride also combines with other drugs like nimodipine to treat the vasospasm and crisis triggered by subarachnoid hemorrhage and
calculi-induced acute renal colic. The main adverse effects of papaverine include
liver function damage, exaggerated respiration induced by rapid parenteral administration, facial flushing, heart rate acceleration, as well as hypotension with vertigo.
In addition, overdose of papaverine can lead to blurred vision, diplopia, lethargy,
and weakness. | [Purification Methods]
Recrystallise it from H2O. It sublimes at 140o/0.1mm. Its solubility in H2O is 5%. [Saunders & Srivastava J Pharm Pharmacol 3 78 1951, Biggs Trans Faraday Soc 50 800 1954.] The free base has m 148-150o, The picrate has m 186-189o(dec, 186-186.5o(dec) [Bobbitt J Org Chem 22 1729 1957]. [Beilstein 21 II 202, 21 III/IV 2788, 21/6 V 182.] |
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