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Reserpine

Overview Indications Mode of action Adverse reactions Warning and precautions References
Reserpine
Reserpine structure
CAS No.
50-55-5
Chemical Name:
Reserpine
Synonyms
H 520;R-e-s;Kitine;Rausan;reserp;Resine;rezide;Serpen;Anguil;Raucap
CBNumber:
CB4206679
Molecular Formula:
C33H40N2O9
Formula Weight:
608.68
MOL File:
50-55-5.mol

Reserpine Properties

Melting point:
~265 °C (dec.)
alpha 
D23 -118° (CHCl3); D26 -164° (c = 0.96 in pyridine); D26 -168° (c = 0.624 in DMF)
Boiling point:
655.12°C (rough estimate)
Density 
1.2336 (rough estimate)
refractive index 
177 ° (C=1, DMF)
Flash point:
22℃
storage temp. 
2-8°C
solubility 
Practically insoluble in water, very slightly soluble in ethanol (96 per cent).
pka
6.6(at 25℃)
form 
neat
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
CAS DataBase Reference
50-55-5
NIST Chemistry Reference
Reserpine(50-55-5)
EPA Substance Registry System
Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[(3,4,5- trimethoxybenzoyl)oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha., 18.beta.,20.alpha.)-(50-55-5)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  Xn,Xi
Risk Statements  22-67-36-10
Safety Statements  22-36/37/39-26
RIDADR  3077
WGK Germany  3
RTECS  ZG0350000
10-23
TSCA  Yes
PackingGroup  II
HS Code  29399990
Hazardous Substances Data 50-55-5(Hazardous Substances Data)
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H336 May cause drowsiness or dizziness Specific target organ toxicity,single exposure; Narcotic effects Category 3 Warning P261, P271, P304+P340, P312,P403+P233, P405, P501
Precautionary statements:
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P330 Rinse mouth.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Reserpine price More Price(14)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 06859 Reserpine certified reference material, TraceCERT 50-55-5 50mg $209 2018-11-22 Buy
Sigma-Aldrich 1601000 Reserpine United States Pharmacopeia (USP) Reference Standard 50-55-5 200mg $352.8 2018-11-20 Buy
TCI Chemical R0007 Reserpine >98.0%(HPLC)(T) 50-55-5 1g $96 2018-11-22 Buy
TCI Chemical R0007 Reserpine >98.0%(HPLC)(T) 50-55-5 5g $271 2018-11-22 Buy
Alfa Aesar L03506 Reserpine, 99% 50-55-5 5g $226 2018-11-13 Buy

Reserpine Chemical Properties,Uses,Production

Overview

Reserpine is an indole alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria[1]. It is an antipsychotic, and antihypertensive drug that used for the control of high blood pressure and for the relief of psychoticsymptoms[1-4]. However, its adverse effects have limited its clinical use[4]. The antihypertensive actions of reserpine results from its ability to deplete catecholamines(among other monoamine neurotransmitters) from peripheral sympathetic nerve endings[2-4]. Moreover, reserpine also has a peripheral action in many parts of the body, resulting in a preponderance of the effects of the cholinergic part of the autonomous nervous system on the GI tract, smooth muscles, blood vessels, etc[4].

Indications

Reserpine is a drug used for the treatment of hypertension[4, 5,7, 8] and schizophrenia[although rarely used nowadays][4, 6]. It can also be used as an anticholinergic drug to combat excessive cholinergic activity in many parts of the body as well as parkinsonism[9]. Reserpine can be used as sedative for horses in veterinary field. It is used as a long-acting tranquilizer to subdue excitable or difficult horses and has been used illicitly for the sedation of show horses, for-sale horses, and in other circumstances where a "quieter" horse might be desired[10]. In addition, it can be used frequently as a highly useful analytic reference standard in the field of mass spectrometry owing to its availability, ease of ionization under electrospray conditions and stability in solution[11].

Mode of action

Reserpine is an adrenergic blocking agent used to treat mild to moderate hypertension through disrupting the normal process norepinephrine vesicular storage. The antihypertensive actions of Reserpine are a result of its ability of depleting catecholamines from peripheral sympathetic nerve endings[12-14]. These substances are normally involved in controlling heart rate, force of cardiac contraction and peripheral resistance. Reserpine takes effect through inhibition of the ATP/Mg2+ pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron[13]. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase[MAO] causing a reduction in catecholamines[12, 14].

Adverse reactions

Some common adverse reactions of reserpine include dizziness, feeling sleepy, dry mouth, headache, muscle pain, stuff nose, upset stomach or throwing up, loose stools, anxiety, weight gain and nosebleed[15, 16]. More severe adverse reactions could occur as allergic reactions(such as rash, hives, itching, red, swollen, blistered with or without fever; wheezing; tightness in the chest or throat; trouble breathing, swallowing, or talking; unusual hoarseness; or swelling of the mouth, face, lips, tongue, or throat), chest pain or pressure, low mood(nervousness, suicidal mood, emotional ups and downs and anxiety), enlarged breasts, breast soreness, bad dreams, not hungry, swelling, lowered interest in sex, hearing loss, shortness of breath, trouble controlling body movements, pain when passing urine[16].

Warning and precautions

Patients of the following conditions should be disabled: being allergic, depression history, a history of suicidal thought, a stomach ulcer, ulcerative colitis and who are subjecting to treatment with electroconvulsive therapy. Patients should also seek advice from the doctors if he/she has gallstones, kidney disease, or a history of stomach problems or slow digestion, plan or has already become pregnant. Since reserpine can pass into breast milk and may do harm to a nursing baby, breast-feed is not allowed during taking this drug. Reserpine is only allowed for use in people older than 18 years old[16].

References

1. https://www.drugbank.ca/drugs/DB00206
2. Doyle, A. E., E. G. Mcqueen, and F. H. Smirk. "Treatment of hypertension with reserpine, with reserpine in combination with pentapyrrolidinium, and with reserpine in combination with Veratrum alkaloids." Circulation11.2(1955]:170.
3. Hughes, W. M., E. Dennis, and J. H. Moyer. "Treatment of hypertension with oral reserpine alone and in combination with hydralazine or hexamethonium. " American Journal of the Medical Sciences229.2(1955]:121-134.
4. The Columbia Encyclopedia, Sixth Edition. Copyright © 2001-05 Columbia University Press.
5. Kurland, A. A. "Comparison of chlorpromazine and reserpine in treatment of schizophrenia; a study of four hundred cases. " A.m.a.archives of Neurology & Psychiatry 75.5(1956]:510-513.
6. Braun, M. "Reserpine as a therapeutic agent in schizophrenia. " American Journal of Psychiatry 116.3(1960]:744.
7. Shamon SD, Perez MI[2009]. "Blood pressure lowering efficacy of reserpine for primary hypertension". Cochrane Database of Systematic Reviews. 4[4]: CD007655.
8. Chobanian AV, Bakris GL, Black HR, et al.[2003]. "The Seventh Report of the Joint National Committee on Prevention, Detection, Evaluation, and Treatment of High Blood Pressure: the JNC 7 report". JAMA. 289[19]: 2560–72.
9. Sharma, V. K., Harik, S. I., Ganapathi, M., Busto, R., & Banerjee, S. P.[1979]. Locus ceruleus lesion and chronic reserpine treatment: effect on adrenergic and cholinergic receptors in cerebral cortex and hippocampus. Experimental Neurology, 65(3], 685-690.
10. http://www.wedgewoodpetrx.com/learning-center/professional-monographs/reserpine-for-veterinary-use.html
11. Sharaf ElDin, M. M., et al. "Validated liquid chromatography-tandem mass spectrometry method for simultaneous determination of clopamide, reserpine and dihydroergotoxine: Application to pharmacokinetics in human plasma. " Journal of Pharmaceutical & Biomedical Analysis125(2016]:236-244.
12. Tsunoda, I.[1965]. A study on hypertension effects of reserpine and monoamine oxidase inhibitors on blood pressure and blood plasma catecholamines. Jpn J Nephrol, 7(3], 361-371.
13. Ahmed, N. A., Radwan, N. M., Al-Zahaby, A. S., & Abd el-Salam, M. M.[1997]. Reserpine effects on neurotransmitters in chick heart during growth. Journal of Physiology Paris, 91(2], 81.
14. Häggendal, J., & Malmfors, T.[2010]. The effect of nerve stimulation on catecholamines taken up in adrenergic nerves after reserpine pretreatment. Acta Physiologica, 75(1-2], 33-38.
15. AJ Giannini, HR Black. Psychiatric, Psychogenic, and Somatopsychic Disorders Handbook. Garden City, NY. Medical Examination Publishing, 1978. Pg. 233. ISBN 0-87488-596-5.
16. https://www.drugs.com/sfx/reserpine-side-effects.html

Chemical Properties

off-white crystalline powder

Chemical Properties

Reserpine is a white to pale buff to slightly yellow crystalline substance that darkens on exposure to light.

Uses

Reserpine occurs in the roots of Rauwolfiaserpentina and other Rauwolfia species, suchas R. micrantha, R. canescens, and R. vomitoria Hook. It is used therapeutically as anantihypertensive agent and a tranquilizer. Itsuse has been reduced significantly because oftoxic side effects.

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.

Uses

An inhibitor of transport of biogenic amines into adrenal chromaffin granules

Definition

ChEBI: An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.

brand name

Rau-Sed (Bristol-Myers Squibb); Sandril (Lilly); Serpasil (Novartis).

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.

General Description

Reserpine, a prototypicaland historically important drug, is an indole alkaloid obtainedfrom the root of Rauwolfia serpentina found in India.As is typical of many indole alkaloids, reserpine is susceptibleto decomposition by light and oxidation. Reserpine isextensively metabolized through hydrolysis of the esterfunction at position and yields methyl reserpate and3,4,5-trimethoxybenzoic acid. It not only depletes the vesiclestorage of NE in sympathetic neurons in PNS, neuronsof the CNS, and E in the adrenal medulla, but also depletesthe storage of serotonin and DA in their respective neuronsin the brain. Reserpine binds extremely tightly with andblocks VMAT that transports NE and other biogenic aminesfrom the cytoplasm into the storage vesicles. Thus in sympatheticneurons, NE, which normally is transported into thestorage vesicles, is instead metabolized by mitochondrialMAO in the cytoplasm. In addition, there is a gradual loss ofvesicle-stored NE as it is used up by release resulting fromsympathetic nerve activity so that the storage vesicles eventuallybecome dysfunctional. The end result is a depletion ofNE in the sympathetic neuron. Analogous effects are seen inthe adrenal medulla with E and with 5-HT in serotonergicneurons.

General Description

White or cream to slightly yellow crystals or crystalline powder. Odorless with a bitter taste.

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.

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.

Clinical Use

When reserpine is given orally, its maximum effect is seenafter a couple of weeks. A sustained effect up to severalweeks is seen after the last dose has been given. This isbecause the tight binding of reserpine to storage vesicles continuesfor a prolonged time, and recovery of sympatheticfunction requires synthesis of new vesicles over a period ofdays to weeks after discontinuation of the drug. Most adverseeffects of reserpine (log P=4.37) are caused by CNS effectsbecause it readily enters the CNS. Sedation and inability toconcentrate or perform complex tasks are the most commonadverse effects. More serious is the occasional psychoticdepression that can lead to suicide, which support monoaminetheory of pathology of depression. Agents with fewer sideeffects have largely replaced reserpine in clinical use.

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.

First aid

Skin Contact: Flood all areas of body that have contacted the substance with water. Don’t wait to remove contaminated clothing; do it under the water stream. Use soap to help assure removal. Isolate contaminated cloth- ing when removed to prevent contact by others . Eye Contact: Remove any contact lenses at once. Immediately flush eyes well with copious quantities of water or normal saline for at least 20?30 minutes. Seek medical attention. Inhalation: Leave contaminated area immediately; breathe fresh air. Proper respiratory protec- tion must be supplied to any rescuers. If coughing, diffi- cult breathing, or any other symptoms develop, seek medical attention at once, even if symptoms develop many hours after exposure. Ingestion: Contact a physi- cian, hospital, or poison center at once. If the victim is unconscious or convulsing, do not induce vomiting or give anything by mouth. Assure that the patient’s airway is open and lay him on his side with his head lower than his body and transport immediately to a medical facility. If conscious and not convulsing, give a glass of water to dilute the substance. Vomiting should not be induced without a physician’s advice.

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.

Reserpine Preparation Products And Raw materials

Raw materials

Preparation Products


Reserpine Suppliers

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View Lastest Price from Reserpine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-16 Reserpine
50-55-5
US $8.00 / kg 1kg 98% 10MT career henan chemical co

Reserpine Spectrum


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