Reserpine
- CAS No.
- 50-55-5
- Chemical Name:
- Reserpine
- Synonyms
- METHYL RESERPATE;Sandril;Rau-sed;Serpate;serpine;regroton;renese-r;serpalan;Serpasil;Hiserpia
- CBNumber:
- CB4206679
- Molecular Formula:
- C33H40N2O9
- Molecular Weight:
- 608.69
- MOL File:
- 50-55-5.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/25 20:04:51
| Melting point | ~265 °C (dec.) |
|---|---|
| Boiling point | 655.12°C (rough estimate) |
| alpha | D23 -118° (CHCl3); D26 -164° (c = 0.96 in pyridine); D26 -168° (c = 0.624 in DMF) |
| Density | 1.2336 (rough estimate) |
| refractive index | 177 ° (C=1, DMF) |
| Flash point | 22℃ |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | Practically insoluble in water, very slightly soluble in ethanol (96 per cent). |
| pka | 6.6(at 25℃) |
| form | Solid |
| color | Off-white |
| optical activity | [α]20/D 123±3°, c = 1% in chloroform |
| Water Solubility | Soluble in water. |
| Merck | 14,8145 |
| BRN | 102014 |
| Stability | Stable, but darkens slowly in light. Combustible. Incompatible with strong acids, reducing agents, oxidizing agents. |
| InChIKey | QEVHRUUCFGRFIF-MDEJGZGSSA-N |
| LogP | 4.050 (est) |
| CAS DataBase Reference | 50-55-5 |
| IARC | 3 (Vol. 24, Sup 7) 1987 |
| NIST Chemistry Reference | Reserpine(50-55-5) |
| EPA Substance Registry System | Reserpine (50-55-5) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |   GHS07,GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H302-H336-H351-H360D | |||||||||
| Precautionary statements | P201-P301+P312+P330-P308+P313 | |||||||||
| Hazard Codes | Xn,Xi | |||||||||
| Risk Statements | 22-67-36-10 | |||||||||
| Safety Statements | 22-36/37/39-26 | |||||||||
| RIDADR | 3077 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | ZG0350000 | |||||||||
| F | 10-23 | |||||||||
| TSCA | Yes | |||||||||
| PackingGroup | II | |||||||||
| HS Code | 29399990 | |||||||||
| Toxicity | LD50 oral in rat: 420mg/kg | |||||||||
| NFPA 704 |
|
Reserpine price More Price(13)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | R0875 | Reserpine | 50-55-5 | 1G | ₹15930 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 83580 | Reserpine crystallized, ≥99.0% (HPLC) | 50-55-5 | 1G | ₹6700.68 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR1750 | Reserpine Pharmaceutical Secondary Standard; Certified Reference Material | 50-55-5 | 1G | ₹15966.88 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 83580 | Reserpine crystallized, ≥99.0% (HPLC) | 50-55-5 | 5G | ₹12048.23 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 5.06130 | Reserpine - CAS 50-55-5 - Calbiochem | 50-55-5 | 250MG | ₹20010 | 2022-06-14 | Buy |
Reserpine Chemical Properties,Uses,Production
Description
Reserpine causes release of norepinephrine, dopamine, and serotonin at neuronal termini. It weakens the intracellular uptake of biogenic amines and decreases the ability to store them in vesicles.
Chemical Properties
Reserpine is a white to pale buff to slightly yellow crystalline substance that darkens on exposure to light.
Physical properties
Appearance: crystalline powder, colorless to yellowish brown, darker in case of light. Solubility: soluble in chloroform, slightly soluble in acetone, and almost insoluble in water, methanol, ethanol, or ether. Melting point: 264–265 °C. Specific optical rotation: ?117.7°.
History
In 1931, Indian scholar Sen discovered Indian Rauvolfia have the antihypertensive
and antipsychotic effects. The following studies in medicinal chemistry and pharmacology
found that the main active ingredient is reserpine and clarified th mechanism of lowering blood pressure. In 1952, reserpine was first isolated and won
an important status in treating hypertension and neurological and psychiatric disorders
because of its remarkable physiological attributes. The structure analysis of
reserpine peaked in 1955.The total synthesis of reserpine is completed in 1956.
There are no effective antihypertensive drugs in clinic at the initial stage in our
country, and the reserpine imported from India was scarce and expensive, which
could not meet the urgent needs of patients. In
1958, the Bureau of Drug Administration of Ministry of Health presided over the
work of identifying the total alkaloids in Rauvolfia and approved the first Chinese
antihypertensive drug commercially named “Verticil”. Large scales of studies about
Chinese Rauvolfia as well as the numerous participants promote the rapid progress
of natural medicine. It can be taken as the earliest study in plant medicine since the
founding of China, providing valuable experience to our later studies.
Uses
An indole alkaloid found in Rauwolfia serpentina. Inhibits vesicular uptake of catecholamines and serotonin. Reserpine is reasonably anticipated to be a human carcinogen. Antihypertensive.
Definition
ChEBI: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.
Biological Functions
Reserpine (Serpasil) is the prototypical drug interfering
with norepinephrine storage. Reserpine lowers blood
pressure by reducing norepinephrine concentrations in
the noradrenergic nerves in such a way that less norepinephrine
is released during neuron activation.
Reserpine does not interfere with the release process
per se as does guanethidine.
Reserpine also interferes with the neuronal storage
of a variety of central transmitter amines such that significant
depletion of norepinephrine, dopamine, and 5-
hydroxytryptamine (serotonin) occurs. This central
transmitter depletion is responsible for the sedation and
other CNS side effects associated with reserpine therapy.
The depletion of brain amines also may contribute
to the antihypertensive effects of reserpine.
General Description
Reserpine (Serpasil, Reserpoid, Rau-Sed, Sandril) is a white to light yellow, crystalline alkaloid,practically insoluble in water, obtained from various speciesof Rauwolfia. In common with other compounds with anindole nucleus, it is susceptible to decomposition by lightand oxidation, especially when in solution. In the dry state,discoloration occurs rapidly when reserpine is exposed tolight, but the loss in potency is usually small. In solution,reserpine may break down with no appreciable color changewhen exposed to light, especially in clear glass containers;thus, color change cannot be used as an index of the amountof decomposition.
Air & Water Reactions
Insoluble in water. Reacts slowly with air and water. Darkens slowly on exposure to light.
Reactivity Profile
Reserpine is a weak base and can form salts with strong acids. Incompatible with oxidizing agents and reducing agents.
Hazard
Questionable carcinogen.
Health Hazard
Reserpine produces sedative, hypotensive,
LD50 value, intraperitoneal (mice): 5 mg/kg
LD50 value, oral (mice): 200 mg/kgand tranquilizing effects. This is due to itsactions of causing depletion of monoaminesfrom presynaptic nerve terminals in central and peripheral nervous systems. Theadverse side effects are drowsiness, nightmare, depression, excessive salivation, nausea, diarrhea, increased gastric secretion,abdominal cramps, and hypotension.
Fire Hazard
Flash point data for Reserpine are not available; however, Reserpine is probably combustible.
Biological Activity
Binds the vesicular monoamine transporter (VMAT2) and inhibits transport of biogenic amines into adrenal chromaffin granules and synaptic vesicles. Causes depletion of biogenic amine stores. Antihypertensive and antipsychotic.
Mechanism of action
Reserpine acts to replace and deplete the adrenergic neurons of their stores of norepinephrine by inhibiting the active transport Mg-ATPase responsible for sequestering norepinephrine and dopamine within the storage vesicles. The norepinephrine and dopamine that are not sequestered in vesicles are destroyed by MAO. As a result, the storage vesicles contain little neurotransmitter, adrenergic transmission is dramatically inhibited, and sympathetic tone is decreased, leading to vasodilation. Reserpine has the same effect on epinephrine storage in the adrenal medulla. Reserpine readily enters the CNS, where it also depletes the stores of norepinephrine and serotonin. The CNS neurotransmitter depletion led to the use of reserpine in treating certain mental illnesses.
Pharmacology
Reserpine causes a breakdown of norepinephrine, dopamine, and serotonin in neuron endings. It weakens intracellular uptake of biogenic amines and reduces the ability if storing them in vesicles. It is possible that reserpine acts on membrane vesicles, irreversibly inhibiting ATP-Mg2 (adenosinetriphosphate) requiring process that is responsible for the uptake of biogenic amines in interneuronal vesicles. Breakdown of catecholamines is expressed by a decreased number of intraneuronal serotonin and dopamine.
Pharmacokinetics
Limited information is available regarding the pharmacokinetics of reserpine. Peak blood concentrations for reserpine occur within 2 hours following oral administration, and the full effects for reserpine usually are delayed for at least 2 to 3 weeks. Both CNS and cardiovascular effects may persist for several days to several weeks after chronic oral therapy is discontinued. Reserpine appears to be widely distributed in body tissues, especially adipose tissue; crosses the blood-brain barrier and the placenta; and is distributed into milk. The elimination of reserpine appears to be biphasic, with a plasma half-life averaging 4.5 hours during the first phase and approximately 11.3 days during the second phase. Reserpine is metabolized to unidentified inactive compounds. Unchanged reserpine and its metabolites are excreted slowly in urine and feces, with an average of 60% reserpine recovered in feces within 96 hours after oral administration of 0.25 mg of radiolabeled reserpine.
Clinical Use
Reserpine is effective orally and parenterally for thetreatment of hypertension. After a single intravenous dose,the onset of antihypertensive action usually begins in about1 hour. After intramuscular injection, the maximumeffect occurs within approximately 4 hours and lasts about10 hours. When it is given orally, the maximum effectoccurs within about 2 weeks and may persist up to 4 weeksafter the final dose. When used in conjunction with otherhypotensive drugs in the treatment of severe hypertension,the daily dose varies from 100 to 250μg.
Side effects
The most troublesome untoward effects of treatment
with reserpine involve the CNS. Sedation and depression
are the most common, although nightmares
and thoughts of suicide also occur. Reserpine treatment,
therefore, is contraindicated in patients with a history
of severe depression. The occasional report of reserpine-
induced extrapyramidal symptoms, which are
similar to those seen in patients with Parkinson’ s disease,
is believed to be a result of dopamine depletion
from neurons in the CNS.
Peripheral nervous system side effects are the result
of a reserpine-induced reduction of sympathetic function
and unopposed parasympathetic activity; symptoms
include nasal congestion, postural hypotension, diarrhea,
bradycardia, increased gastric secretion, and
occasionally impotence. Because of the increased gastric
secretion, reserpine is contraindicated for patients with peptic ulcer. In patients with little cardiac reserve,
reserpine must be administered with caution because of
its ability to interfere with sympathetic stimulation of
the heart.
Safety Profile
Confirmed human carcinogen producing tumors of the sh and brain. Poison by ingestion, intravenous, subcutaneous, and intraperitoneal routes. Mutation data reported. An experimental teratogen. Human and experimental reproductive effects by ingestion: sullbirth, reduced viability, and other neonatal measures or effects. In humans, 0.014 mg/kg causes psychotropic effects. A medicine with side effects. Used as an addltive permitted in the feed and drinking water of animals and/or for the treatment of food-producing animals. Also permitted in food for human consumption. A sedative. When heated to decomposition it emits toxic fumes of NOx.
Potential Exposure
Reserpine, a pharmaceutical, is a natu- rally occurring substance that is isolated from the roots of the plant rauwolfia serpentina. Insoluble in water. Reserpine is used as a hypertensive for humans and ani- mals; tranquilizer, and sedative. Permitted for use as an additive in food for human consumption, and the feed and drinking water of food-producing animals.
Carcinogenicity
Reserpine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
Environmental Fate
Reserpine is a naturally occurring alkaloid produced by several members of genus Rauwolfia, indigenous to India, Burma, Malaysia, Thailand, Nepal, and Indonesia. The release of reserpine to the environment through several waste streams is possible due to the manufacture of reserpine and/or excretion following therapeutic use. It has a pKb of 6.6 and is expected to be in a partially protonated state in the environment. Reserpine released into air at ambient temperature and pressure exists only in the particulate phase and is removed from the atmosphere by wet and dry deposition. Reserpine released to soil is available in oral dosage forms in combinations with hydralazine (a vasodilator) and/or hydrochlorothiazide (a thiazide diuretic). Occupational exposure would be expected to occur through inhalation or dermal contact.
Shipping
UN1544 Alkaloids, solid, n.o.s. or Alkaloid salts, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. UN3077 Environmentally haz- ardous substances, solid, n.o.s., Hazard class: 9; Labels: 9- Miscellaneous hazardous material, Technical Name Required.
Purification Methods
Crystallise reserpine from aqueous Me2CO or Et2O. [Woodward et al. Tertrahedron 2 155 1958, Beilstein 25 III/IV 1319.]
Incompatibilities
A weak acid; keep away from bases. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoa- cids, epoxides, and strong reducing agents such as hydri- deds and active metals. Compounds of the carboxyl group react with all bases, both inorganic and organic (i.e., amines) releasing substantial heat, water, and a salt that may be harmful. Incompatible with arsenic compounds (releases hydrogen cyanide gas), diazo compounds, dithio- carbamates, isocyanates, mercaptans, nitrides, sulfides (releasing heat, toxic, and possibly flammable gases),thiosulfates, and dithionites (releasing hydrogen sulfate and oxides of sulfur).
Waste Disposal
It is inappropriate and possi- bly dangerous to the environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding them to the trash. Household quanti- ties of expired or waste pharmaceuticals may be mixed with wet cat litter or coffee grounds, double-bagged in plastic, discard in trash. Larger quantities shall carefully take into consideration applicable DEA, EPA, and FDA regulations. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator. Consult with environmental regula- tory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/ mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
References
Muller, Schlittler, Bein., Experientia, 8,338 (1952)
Woodward et al., Tetrahedron, 2, 1 (1958)
Jilek e t aI., Collect. Czech. Chem. Commun., 26, 687 (1961)
Hakkesteegt., Pharm. Weekbl., 105,829 (1970)
Reserpine Preparation Products And Raw materials
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| JSK Chemicals | +919879767970 | Gujarat, India | 3756 | 58 | Inquiry |
| Himpharm | +91-9816648055 +91-9816664455 | Himachal Pradesh, India | 29 | 58 | Inquiry |
| Ralington Pharma | +91-7948911722 +91-9687771722 | Gujarat, India | 1350 | 58 | Inquiry |
| Inga Pharmaceuticals | +91-2228202932 +91-2228202932 | Maharashtra, India | 38 | 58 | Inquiry |
| Quad Lifesciences Pvt Ltd | +91-9810034045 +91-9810034045 | New Delhi, India | 23 | 58 | Inquiry |
| Indo Phytochem Pharmaceuticals | +91-9315656907 +91-9816687908 | Himachal Pradesh, India | 11 | 58 | Inquiry |
| S M Herbals Pvt Ltd | +91-1124624177 +91-1124624177 | New Delhi, India | 15 | 58 | Inquiry |
| Ambe Phytoextracts Private Limited | +91-1143764376 +91-1143764376 | New Delhi, India | 37 | 58 | Inquiry |
| Chemical Resources | +91-1725022460 +91-1725022460 | Haryana, India | 17 | 58 | Inquiry |
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| JSK Chemicals | 58 |
| Himpharm | 58 |
| Ralington Pharma | 58 |
| Inga Pharmaceuticals | 58 |
| Quad Lifesciences Pvt Ltd | 58 |
| Indo Phytochem Pharmaceuticals | 58 |
| S M Herbals Pvt Ltd | 58 |
| Ambe Phytoextracts Private Limited | 58 |
| Chemical Resources | 58 |
| TCI Chemicals (India) Pvt. Ltd. | 58 |
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