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Product Name:
Vinpocetine
CAS No:
42971-09-5
Usage:
ADF
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Product Introduction

Basic information of Vinpocetine(CAS 42971-09-5):
Empirical Formula: C22H26N2O2
Molecular Weight: 350.454
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 4
Polar Surface Area: 34.47 ?2
Index of Refraction: 1.665
Molar Refractivity: 101.5 cm3
Molar Volume: 273 cm3
Surface Tension: 49 dyne/cm
Density: 1.28 g/cm3
Flash Point: 207.5 °C
Enthalpy of Vaporization: 67.32 kJ/mol
Boiling Point: 419.5 °C at 760 mmHg
Vapour Pressure: 3.02E-07 mmHg at 25°C
EINECS: 256-028-0
Melting point: 147-153 °C dec
Solubility: DMSO: 5 mg/mL
Appearance: White Crystalline Solid
Categories: Active Pharmaceutical Ingredients; All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Cyclic Nucleotide related

Safety Profile of Vinpocetine(CAS 42971-09-5):
Poison by intravenous and intraperitoneal routes. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: Xn
Risk Statements: 22
22:  Harmful if swallowed
Safety Statements: 36
36:  Wear suitable protective clothing
WGK Germany: 3
RTECS: JW4792000

Specification of Vinpocetine(CAS 42971-09-5):
Vinpocetine(CAS 42971-09-5), with CAS number of 42971-09-5, can be called Ethyl (+)-cis-apovincaminate ; Ethyl(+)-apovincaminate ; cis-Apovincaminic acid ethylester ; Apovincaminic acid ethyl ester ; (+)-cis-Apovincaminic acid ethyl ester ; 1H-Indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridine,eburnamenine-14-carboxylic acid deriv ; (+)-Apovincaminic acid ethyl ester . It is a white crystalline solid, Vinpocetine(CAS 42971-09-5) (CAS NO.42971-09-5) is used as a vasodilator.

Vinpocetine(CAS 42971-09-5) is a semi-synthetic derivative of vincamine, an alkaloid derived from the Vinca minor L.plant, that has been used since the 1970s in Japan, Europe, Mexico, and Russia for the treatment of cerebrovascular and cognitive disorders. Vinpocetine(CAS 42971-09-5) can also be derived from tabersonine, the alkaloid extract of Voacanga seeds found mostly in West Africa. In the United States, it is commonly sold as a dietary supplement for the general population either alone or with other ingredients. Its numerous proposed uses include for improvement of brain function, rapid weight/fat loss, increases in energy, enhancement in focus and visual acuity, prevention of motion sickness, and treatment of menopausal symptoms, chronic fatigue syndrome, and hearing and eye disorders. According to the Physicians' Desk Reference for Nutritional Supplements, doses may range from 5-20 mg/day. Adverse reactions associated with its consumption include nausea, dizziness, dry mouth, transient hypo- and hyper-tension, headaches, heartburn, and changes in blood pressure and blood glucose levels. Pharmacokinetic absorption, distribution, metabolism, and excretion studies have been conducted in humans as well as rats via the oral, intravenous (i.v.), and/or intraperitoneal (i.p.) route. Vinpocetine(CAS 42971-09-5) and apovincaminic acid, the main metabolite, have been detected. Acute toxicity values (LD50s) for vinpocetine(CAS 42971-09-5) were similar for mice and rats. Oral LD50s were 534 and 503 mg/kg, respectively. F or both species, values ranged from 43-59mg/kg via the i.v. route and from 117-240 mg/kg via the i.p. route; lethal doses of vinpocetine(CAS 42971-09-5) produced ataxia and clonic convulsions. In short-term studies with rats, effects of oral administration of vinpocetine(CAS 42971-09-5) for up to five weeks included a decrease in bronchial blood flow and increases in salivation, urine volume, and liver and thyroid weights. When 25 mg/kg vinpocetine(CAS 42971-09-5) was given via i.v. injection for up to three months, 3/8 males and 2/8 females died; death was attributed to severe confluent fibroblastic peritonitis and ascites. However, doses of 25-100 mg/kg vinpocetine(CAS 42971-09-5) given via gastric intubation for up to six months did not result in mortality or adverse effects on a variety of endpoints. Vinpocetine(CAS 42971-09-5) inhibits cell proliferation in human breast cancer cell lines (i.e., MDA-MB-231, MDA-MB-468, MCF-7, and ZR-75-1). A dditionally, it inhibited tumor growth in a xenograft model of breast cancer in nude mice. Vinpocetine(CAS 42971-09-5) did not affect male or female mating ability or fertility when orally administered for eight weeks prior to mating, but uterine bleeding was a common finding in studies with pregnant rats.

Nontoxicological Data of Vinpocetine(CAS 42971-09-5):
Vinpocetine(CAS 42971-09-5) is a semi-synthetic derivative of vincamine, an alkaloid derived from the Vinca minor L.plant, that has been used since the 1970s in Japan, Europe, Mexico, and Russia for the treatment of cerebrovascular and cognitive disorders. An example of synthesis is transesterification of vincamine in ethanol using Lewis acids. It can also be derived from tabersonine, the alkaloid extract of Voacanga seeds found mostly in West Africa. In general, analysis of vinpocetine(CAS 42971-09-5) in matrices is via highperformance liquid chromatography. Vinpocetine(CAS 42971-09-5) is available from countries all around the world, from the United States to China to Italy to Korea. Although a p harmaceutical agent in Japan, Europe, and Mexico, it is commonly sold as a dietary supplement for the U.S. general population either alone or as one of several ingredients in dietary supplement products. Similar standards for identity and quality of vinpocetine(CAS 42971-09-5) products have been specified by the United States, British, and European Phamacopoeias. The marketed uses include improvement of brain function, rapid weight/fat loss, increases in energy, and enhancement in visual acuity, memory, and focus. These make vinpocetine(CAS 42971-09-5) a product for athletes too. Additional reported uses of vinpocetine(CAS 42971-09-5) are the prevention of motion sickness and the treatment of menopausal symptoms, chronic fatigue syndrome, seizure disorders, and hearing and eye disorders. Patents also claim additional applications of vinpocetine(CAS 42971-09-5), such as its use in a topical application to increase female sexual response. Despite these uses, no regulatory body has approved vinpocetine(CAS 42971-09-5) for the treatment of cognitive impairment. In the United States, it is regulated under the Dietary Supplement Health and Education Act of 1994.

Human Data of Vinpocetine(CAS 42971-09-5):
Vinpocetine(CAS 42971-09-5) exposure typically occurs through oral consumption. According to the Physicians' Desk Reference for Nutritional Supplements, doses may range from 5-20 mg/day.
Adverse reactions associated with vinpocetine(CAS 42971-09-5) consumption include nausea, dizziness, dry mouth,transient hypo- and hyper-tension, headaches, and heartburn. A lterations in blood pressure and blood glucose levels were observed with prolonged use. P otential for development of tachycardia was also noted. In an elder Japanese man, vinpocetine(CAS 42971-09-5) was reported to produce agranulocytosis.
In absorption, distribution, metabolism, and excretion (ADME) studies, volunteers were orally exposed to radiolabeled vinpocetine(CAS 42971-09-5). Radioactivity concentration decreased in the stomach and increased in the liver, blood, and kidneys. Unchanged vinpocetine(CAS 42971-09-5) levels in urine decreased to 4% after 60 minutes. Heterogenous brain distribution was noted; greatest uptake was observed in the thalamus, occipital cortex, basal ganglia, and some cortical structures. After intravenous (i.v.) administration of vinpocetine(CAS 42971-09-5), vinpocetine(CAS 42971-09-5) and apovincaminic acid were detected in cerebrospinal fluid. In another i.v. study, total brain uptake of vinpocetine(CAS 42971-09-5), peaked 2 minutes after administration and represented 3.71% of the total radioactivity administered. The greatest amount was present in the thalamus.
Pharmacokinetic studies on vinpocetine(CAS 42971-09-5) and apovincaminic acid, the main metabolite after vinpocetine(CAS 42971-09-5) consumption, have been conducted after oral consumption and i.v. administration of vinpocetine(CAS 42971-09-5). The half-life of vinpocetine(CAS 42971-09-5) after oral administration ranged from 1.73 t o 2.9 hou rs, while the half-life of apovincaminic acid after oral vinpocetine(CAS 42971-09-5) administration was calculated to be 1.25 h ours. A fter intravenous vinpocetine(CAS 42971-09-5) administration, the half-lives of vinpocetine(CAS 42971-09-5) and apovincaminic acid were 2.1 to 17 hours and 2.8 hours, respectively.

Toxicological Data of Vinpocetine(CAS 42971-09-5):
Studies regarding carcinogenicity, initiation/promotion, genotoxicity, cogenotoxicity, cytotoxicity, and immunotoxicity were not located.
Chemical Disposition, Metabolism, and Toxicokinetics
In rats orally administered tritiated-vinpocetine(CAS 42971-09-5), the majority of the urinary radioactivity was associated with apovincaminic acid. Unchanged vinpocetine(CAS 42971-09-5) was also identified in urine. In plasma, the majority of the radioactivity was excreted as either apovincaminic acid or vinpocetine(CAS 42971-09-5). In a separate study in which male and female Wistar rats were orally administered tritiated-vinpocetine(CAS 42971-09-5), maximal concentrations occurred approximately two hours after administration, with the greatest amounts in the liver and small intestine. By 48 hours after administration, vinpocetine(CAS 42971-09-5) levels were minimal in most organs except the liver and kidneys. Within 48 hours of administration 80% of the administered radioactivity was recovered in the feces and urine and <5% in the bile after nine hours. In blood, a majority of the vinpocetine(CAS 42971-09-5) was present in the plasma fraction bound to proteins. When Wistar rats were orally administered vinpocetine(CAS 42971-09-5) for five days and then tritiated-vinpocetine(CAS 42971-09-5) on day 5, ~75% of the administered radiolabel was excreted in the urine and feces within 48 h ours. This was also seen following intraperitoneal (i.p.) injection of vinpocetine(CAS 42971-09-5). A dditionally, four metabolites were identified: ethyl vincaminate, 10-hydroxyvinpocetine(CAS 42971-09-5), and a dihydroxylated, glycine-conjugate of apovincaminic acid; one could not be structurally identified.
Pharmacokinetic studies have been conducted after oral consumption and i.v. administration of vinpocetine(CAS 42971-09-5). In rats, the half-life of vinpocetine(CAS 42971-09-5) after oral administration ranged from 1.73-2.9 hours. Comparatively, the half-life of vinpocetine(CAS 42971-09-5) after i.v. administration ranged from 15.2 minutes to 17 hours.
Acute Exposure
Acute toxicity values (LD50s) for vinpocetine(CAS 42971-09-5) were similar for mice and rats. Oral LD50s were 534 and 503 mg/kg, respectively. For both species, values ranged from 43-59 mg/kg via the i.v. route and from 117-240 mg/kg via the i.p. route; lethal doses of vinpocetine(CAS 42971-09-5) produced ataxia and clonic convulsions. At doses of 0.5-8 mg/kg, i.p. injection of vinpocetine(CAS 42971-09-5) resulted in increased sensitivity to environmental stimuli; at higher doses (16-64 mg/kg), clonic convulsions and decreases in spontaneous motility, orientation hypermotility, and locomotor activity were seen. When rats were orally administered 1-30mg/kg vinpocetine(CAS 42971-09-5), mean arterial pressure was increased at the highest dose, while cerebral blood flow was decreased at the lowest dose.
Short-Term and Subchronic Exposure
When male CD rats were orally administered 25 or 100 mg/kg vinpocetine(CAS 42971-09-5) over a four-week period, no deaths or changes in body weight gain were noted. At the higher dose, increases in salivation and liver and thyroid weights were observed. In Sprague-Dawley rats orally administered 3, 10, o r 30 m g/kg vinpocetine(CAS 42971-09-5) for five days, mean arterial pressure was not altered, but cardiac output was increased at the high dose. Additionally, decreased bronchial blood flow and increased splanchnic blood flow were noted after administration of the low and high dose, respectively. In rats orally administered vinpocetine(CAS 42971-09-5) [dose n.p.] for five weeks, observed effects included fluid intake, increased urine volume, and weight loss or decreased weight gain. Male and female Wistar rats were administered 5 or 25 mg/kg vinpocetine(CAS 42971-09-5) by i.p. injection five times per week for three months. At the high dose, three of eight males and two of eight females died; death was attributed to severe confluent fibroblastic peritonitis and ascites.
Chronic Exposure
Male and female CFY rats were administered 25, 50, or 100 mg/kg vinpocetine(CAS 42971-09-5) by gastric intubation five times per week for six months. No vinpocetine(CAS 42971-09-5) associated deaths, adverse effects, or changes in relative organ weights were observed. During treatment, animals were agitated. Mild tubular degeneration was observed in some mid-dose animals. In a separate study, rats were orally administered vinpocetine(CAS 42971-09-5) for 26 weeks. Observed effects included changes in liver and adrenal weight and increased urine volume.
Synergistic/Antagonistic Effects
Synergistic and antagonistic effects of vinpocetine(CAS 42971-09-5) have been described in a v ariety of systems. Vinpocetine(CAS 42971-09-5) was reported to antagonize liver injury induced by carbon tetrachloride in rats and the effects produced by postnatal alcohol exposure in mice and rats. Vinpocetine(CAS 42971-09-5) antagonized lead-induced hyperactivity in female mice pups, electroshock- and metrazol-induced convulsions in mice, and streptozotocin-induced effects on learning and memory in male rats.
Reproductive and Teratological Effects
Vinpocetine(CAS 42971-09-5) had no effects on male or female CFY rat fertility and mating ability after oral administration of 10 or 50 mg/kg vinpocetine(CAS 42971-09-5) for eight weeks prior to mating. However, high-dose males did have a decreased relative prostate weight. Although vinpocetine(CAS 42971-09-5) had no teratogenic effect in rats, uterine bleeding and death was observed in pregnant rats administered vinpocetine(CAS 42971-09-5).
Other Data
Vinpocetine(CAS 42971-09-5) inhibited tumor necrosis factor (TNF)-α induced activation of nuclear factor-κB. In a xenograft model of breast cancer, i.p. administration inhibited tumor growth in vivo. In vitro, vinpocetine(CAS 42971-09-5) inhibited migration of MDA-MB-231 cells. Vinpocetine(CAS 42971-09-5) was active in 52 tests from 917 different bioassays indexed by PubChem. P rotein targets included the KCNQ potassium channel family and euchromatic histone-lysine N-methyltransferase 2. Vinpocetine(CAS 42971-09-5) inhibited the cellular proliferation of four human breast cancer cell lines: MDA-MB-231, MDA-MB-468, MCF-7, and ZR-75-1. It also induced apoptosis in MDA-MB-231 and MCF-7 cells. Comparatively, it did not affect proliferation of murine thymus and spleen cells in vitro.

Several different methods have been developed to detect the presence of vinpocetine(CAS 42971-09-5) in a variety of matrices (e.g., plasma). These include high performance, thin layer, and gas chromatography(GC), and 1H nuclear magnetic resonance (NMR). Select methods have been described below. Additional methods may be reviewed in articles discussing absorption, distribution, metabolism, and excretion (ADME) of vinpocetine(CAS 42971-09-5) by humans and rodents.Furthermore, the U.S. Pharmacopeia describes a liquid chromatography method for analysis of formulations.

Uses of Vinpocetine(CAS 42971-09-5):
Vinpocetine(CAS 42971-09-5) has therapeutic use as a vasodilator. Since the late 1970s, it has been used in Japan, Hungary, Germany, Poland, and Russia  for the treatment of cerebrovascular-related diseases. Currently, it is reportedly used in the "management of psychic and neurological symptoms (memory disorder, aphasia, apraxia, motor disorders, dizziness and headache) and acute and chronic cerebral circulatory disorders of various origins (post-apoplectic, post-traumatic or sclerotic)".
In the United States, Vinpocetine(CAS 42971-09-5) is available as a dietary supplement to improve brain function.  In addition to the general population, athletes use Vinpocetine(CAS 42971-09-5) supplements and report significant enhancements in visual acuity, memory, and focus as well as rapid loss of body fat.Vinpocetine(CAS 42971-09-5)'s use in the body building community is also evident with its own guide on the website BodyBuilding.com, providing a list of vinpocetine(CAS 42971-09-5) products. The products include fat burning capsules and energy enhancing products (e.g., energy drinks). A dditional reported uses of vinpocetine(CAS 42971-09-5) are prevention of motion sickness and treatment of menopausal symptoms, chronic fatigue syndrome, and seizure disorders. V inpocetine has also been used to treat various forms of hearing disorders (e.g.,tinnitus and Meniere's disease) as well as eye disorders (e.g., macular degeneration, glaucoma,and visual loss secondary to arteriosclerosis).Patents claim additional applications of vinpocetine(CAS 42971-09-5), such as its use in a topical application to increase female sexual response and a primary ingredient in a nutritional supplement to improve "sleep and lucid dreaming".
The biological effects of vinpocetine(CAS 42971-09-5) include relaxing smooth muscle, dilating blood vessels, inhibiting ion channels, improving blood flow, and protecting nerve cells deprived of oxygen and nutrients and from oxidative stress when restoring blood flow. Its use in patients with chronic cerebral vascular ischemia has been reported in various studies, while evidence for potential use in treating acute ischemic stroke, dementia, urinary incontinence, and Alzheimer's disease is increasing. [ Note: O ne small study in Alzheimer's patients showed no improvements with vinpocetine(CAS 42971-09-5) supplementation]
Vinpocetine(CAS 42971-09-5) is a pharmaceutical agent in Europe, Japan, and Mexico used for the treatment of cerebrovascular and cognitive disorders. Furthermore, it is available as a prescription drug in Europe and Japan. Similar standards for identity and quality of vinpocetine(CAS 42971-09-5) products have been specified by the United States, British, and European Phamacopoeias.

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