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Yohimbin

Yohimbine Struktur
146-48-5
CAS-Nr.
146-48-5
Bezeichnung:
Yohimbin
Englisch Name:
Yohimbine
Synonyma:
Yohimbin;Yocon;Yohimex;Corynine;Aphrosol;RAUBASIN;Aphrodine;yohimbine;Aphrodyne;Quebrachin
CBNumber:
CB4129677
Summenformel:
C21H26N2O3
Molgewicht:
354.44
MOL-Datei:
146-48-5.mol

Yohimbin Eigenschaften

Schmelzpunkt:
231-233 °C(lit.)
alpha 
D20 +50.9 to +62.2° (ethanol); D20 +108° (pyridine); 20546 +129° (c = 0.5 in pyridine)
Siedepunkt:
487.66°C (rough estimate)
Dichte
1.1640 (rough estimate)
Brechungsindex
1.6500 (estimate)
storage temp. 
Sealed in dry,Room Temperature
L?slichkeit
THF; DMSO; Chloroform;
Aggregatzustand
Solid
pka
14.39±0.40(Predicted)
Farbe
Beige
InChIKey
BLGXFZZNTVWLAY-SCYLSFHTSA-N
SMILES
[C@@H]1(O)[C@H](C(OC)=O)[C@]2(C[C@@]3(N(C[C@@]2(CC1)[H])CCC1C2=C(NC3=1)C=CC=C2)[H])[H]
LogP
2.730
CAS Datenbank
146-48-5(CAS DataBase Reference)
NIST chemische Informationen
Yohimbine(146-48-5)
Sicherheit
  • Risiko- und Sicherheitserkl?rung
  • Gefahreninformationscode (GHS)
Kennzeichnung gef?hrlicher T
R-S?tze: 23/24/25-39
S-S?tze: 27-36/37/39-45
RIDADR  1544
RTECS-Nr. ZG1000000
HazardClass  6.1(a)
PackingGroup  II
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H301 Giftig bei Verschlucken. Akute Toxizit?t oral Kategorie 3 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P264, P270, P301+P310, P321, P330,P405, P501
H311 Giftig bei Hautkontakt. Akute Toxizit?t dermal Kategorie 3 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P280, P302+P352, P312, P322, P361,P363, P405, P501
H331 Giftig bei Einatmen. Akute Toxizit?t inhalativ Kategorie 3 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
Sicherheit
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P271 Nur im Freien oder in gut belüfteten R?umen verwenden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P302+P352 BEI BERüHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckm??ig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen.
P312 Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P321 Besondere Behandlung
P322 Gezielte Ma?nahmen
P330 Mund ausspülen.
P361 Alle kontaminierten Kleidungsstücke sofort ausziehen.
P363 Kontaminierte Kleidung vor erneutem Tragen waschen.
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Beh?lter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

Yohimbin Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R23/24/25:Giftig beim Einatmen, Verschlucken und Berührung mit der Haut.
R39:Ernste Gefahr irreversiblen Schadens.

S-S?tze Betriebsanweisung:

S27:Beschmutzte, getr?nkte Kleidung sofort ausziehen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn m?glich, dieses Etikett vorzeigen).

Beschreibung

Yohimbine is a natural alkaloid. It was first extracted from the barks of Corynanthe yohimbe, a species of Rubiaceae trees in West Africa. It was reported that, in the dried bark of Pausinystalia johimbe, the content of mixed alkaloids is higher than 6.1%, in which the main component is yohimbine, indicating a great prospect for development . Yohimbe bark has been used as an aphrodisiac in Africa since ancient times. In 1900, it was applied by Kowit and Muller to patients with impotence and paralytic insensitivity caused by neurasthenia and obtained curative effect. From then on, clinical application of yohimbine began. Currently, yohimbine is a pure plant preparation in the treatment of erectile dysfunction with more affirmation and more applications.

Chemische Eigenschaften

Glistening, needle-like alkaloid, soluble in alcohol and ether, very slightly soluble in water.

Physikalische Eigenschaften

Appearance: white powder. Solubility: soluble in ethanol, chloroform, and hot benzene; slightly soluble in water and ether, usually salified by hydrochloric acid to increase its solubility in water. Specific rotatory power (°): D22 +105° (in water). Melting point: 241–246?°C.

History

Yohimbine has been used as an aphrodisiac for many years. At first, pharmacologists attributed its aphrodisiac effects to psychological effects similar to placebo or increasement of peripheral vascular congestion, rather than real sexual stimulation. Physiologists at the Stanford University first conducted a study on the pharmacological effects of yohimbine and found that yohimbine could increase the mating ability of rats , which was then published on Science in 1984 . In addition, researchers in the Queensland University in Canada conducted experiments on 23 patients with sexual dysfunction. Six of them recovered after taking the drug for 10?weeks. In 1987, Canadian scientists confirmed that yohimbine treatment in psychogenic impotence was safe and effective and this drug could restore the patient’ssexual ability . Besides, they proved that this medicine showed good curative effects on organic impotence.

Verwenden

Yohimbine occurs in Corinanthe johimbeK. and Rubiaceae trees. It is also foundin the roots of Rauwolfia serpentina L.and Apocyanaceae. Its derivatives areused therapeutically as adrenergic blockingagents.

Definition

ChEBI: Yohimbine is an indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina. It has a role as an alpha-adrenergic antagonist, a serotonergic antagonist and a dopamine receptor D2 antagonist. It is functionally related to a yohimbic acid.

Indications

This product is listed in the 2017 edition of the British Pharmacopoeia, 40 editions of the American Pharmacopoeia, and 9.0 edition of the European Pharmacopoeia. The main clinical application of yohimbine includes tablets and injections. It is mainly used to treat various types of impotence and sexual dysfunction in men.

Allgemeine Beschreibung

Yohimbine (Yocon)is a competitive and selective 2-blocker. The compound isan indolealkylamine alkaloid and is found in the bark of thetree Pausinystalia yohimbe and in Rauwolfia root.

Health Hazard

Pharmacologically, yohimbine is an adrenergic blocking agent. It exhibits hypotensive and cardiostimulant activities. Poisoningfrom excessive doses may become severe,causing convulsions and respiratory failure
LD50 value, intraperitoneal (mice): 16 mg/kg
LD50 value, oral (mice): 37 mg/kg.

Biologische Aktivit?t

α 2 -adrenoceptor antagonist (pK i values are 8.52, 8.00 and 9.17 for human a 2A , a 2B and a 2C receptors respectively).

Pharmakologie

Studies have shown that yohimbine has extensive pharmacological effects and has been developed for the clinical treatment of arteriosclerosis, rheumatism, and other diseases. The most obvious pharmacological action is in the treatment of male sexual dysfunction. Yohimbine tablets have been approved by the FDA and circulate in international markets. Yohimbine can selectively block the presynaptic alpha 2 receptors and promote the release of norepinephrine . It stimulates more norepinephrine released by cavernous nerve endings and reduces reflux of phallic vein, which is conducive to congestive erection. A small amount of application can make the perineum swell and stimulate the erection center at the spinal cord, leading to sexual hyperfunction . Yohimbine hydrochloride also has a psychological stimulant effect and increases libido. Like other types of adrenergic blocking drugs, yohimbine’s resistance to adrenergic mediator in blood circulation is much stronger than to sympathetic nerve impulse. Again, like tolazoline, yohimbine shows slight effect in resisting adrenergic response in ocular smooth muscle. This drug does not block the frequency and inotropic effects of epinephrine on mammalian hearts. Yohimbine has minor direct effects on smooth muscle, and its effect on the central nervous system is far less than that of ergot alkaloids, because yohimbine performs an excited-to-paralyzed action. This drug produces diuretic effect, probably due to the stimulation of the hypothalamus, resulting in release of posterior pituitary hormone. In addition, yohimbine has a significant local anesthetic effect .

Clinical Use

Yohimbine increases heart rate and blood pressure as aresult of its blockade of 2-receptors in the CNS. It has beenused experimentally to treat male erectile impotence.

l?uterung methode

Crystallise the alkaloid from EtOH, and dry it in a vacuum to remove EtOH of crystallisation. [Van Tamelen et al. J Am Chem Soc 91 7315 1969, Stork

Mode of action

Yohimbine is a selective α2-adrenergic antagonist. It is chemically similar to the alkaloid reserpine. Being a derivative of indolylalkylamine, it selectively blocks α2-adrenergic receptors. It weakens the negative feedback mechanism of norepinephrine release in nerve endings. It has a sympathomimetic effect, and can also cause sympathomimetic action. Additional research is evidently needed to conclusively delineate its pharmacological action.

Yohimbin Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Yohimbin Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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146-48-5(Yohimbin)Verwandte Suche:


  • yohimbine
  • YOHIMBINE, C-
  • 17alpha-Hydroxyyohimban-16alpha-carboxylic acid
  • 17-alpha-hydroxy-yohimban-16-alpha-carboxylicacimethylester
  • 17-Hydroxyyohimban-16-carboxylic acid methyl ester
  • 17-hydroxyyohimban-16-carboxylicacidmethylester
  • Aphrodine
  • Aphrosol
  • Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.
  • Corynine
  • Methyl 17-hydroxyyohimban-16-carboxylate
  • Quebrachin
  • Quebrachine
  • Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester
  • Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-
  • Yohimbic acid methyl ester
  • yohimbicacidmethylester
  • D-YOHIMBINE
  • 17alpha-hydroxy-yohimban-16alpha-carboxylic acid methyl ester
  • ALPHA-YOHIMBIN
  • RAUBASIN
  • 17alpha-Hydroxyyohimban-16-carboxylic acid methyl ester
  • (+)-17α-Hydroxyyohimban-16α-carboxylic acid methyl
  • (16alpha,17alpha)-17-Hydroxy-yohimban-16-carboxylic acid methyl ester
  • 17-Hydroxy-yohimbane-16-carboxylic acid methyl ester
  • 2-Hydroxy-1,2,3,4,4A,5,7,8,13,13B,14,14A-dodecahydro-indolo[2',3':3,4]pyrido[1,2-B]isoquinoline-1-carboxylic acid methyl ester
  • Inchi=1/C21H26N2o3/C1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/H2-5,12,15,17-19,22,24H,6-11H2,1H3/T12,15,17,18-,19+/m0/s
  • Methyl (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylate
  • YOHIMBINE(P)
  • Yohimbine hydrochloride,17-Hydroxyyohimban-16-carboxylic acid methyl ester hydrochloride
  • Aphrodyne
  • Dayto himbin
  • Yocon
  • Yohimex
  • Yohimban-16-carboxylic acid, 17-hydroxy-,methyl ester, (16α,17α)-
  • Hydroergotocin
  • YohiMvetol
  • (16α,17α)-17-hydroxy-Yohimban-16-carboxylic acid methyl ester
  • YohiMban-16-carboxylicacid, 17-hydroxy-, Methyl ester, (16a,17a)-
  • Yohimbine hydrochloride CAS 146-48-5
  • 17α-Hydroxy-yohimban-16α-carboxylic Acid Methyl Ester
  • Yohimbine USP/EP/BP
  • YOHIMBE BARK EXTRACT POWDER
  • Yohimbin
  • 17alpha-Hydroxy-yohimban-16alpha-carboxylic acid methyl ester HCL
  • Yohimbine Monomer
  • 146-48-5
  • Adrenoceptor
  • Plant extracts
  • API
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