Yohimbine
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Yohimbine
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CAS No:
146-48-5
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Formula:
C21H26N2O3
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Chemical Name:
Yohimbine
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Synonyms:
Yohimban-16-carboxylic acid,17-hydroxy-,methyl ester,(16α,17α)-;Yohimban-16α-carboxylic acid,17α-hydroxy-,methyl ester;Yohimbol-16α-carboxylic acid,methyl ester;Benz[g]indolo[2,3-a]quinolizine,yohimban-16-carboxylic acid deriv.;Aphrodine;Aphrosol;Corynine;Quebrachine;Yohimbic acid methyl ester;Yohimbine;Quebrachin;Yohimbin;(+)-Yohimbine;trans-Quinolizidine yohimbine;54725-25-6;80925-02-6
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CAS No:
Description
Yohimbine is a potent and relatively nonselective alpha 2-adrenergicreceptor (AR) antagonist, with IC50 of 0.6 μM. IC50 value: 0.6 uM [1]Target: alpha 2-adrenergic receptorin vitro: Yohimbine inhibits alpha2-receptor antagonist with Ki of 1.05 nM, 1.19 nM, and 1.19 nM for α2A, α2B, α2C, respectively. Yohimbine also inhibits 5-HT1B with Ki of 19.9 nM. Yohimbine acts to block the lowering of cAMP by alpha-2 adrenoceptor agonists. yohimbine actually causes a pronounced lowering of tyrosinas
Solid
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 derives from a yohimbic acid.|A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac.|Yohimbine is an indole alkaloid derived from the bark of the Central African yohimbe tree (Pausinystalia yohimbe) that is widely used as therapy for erectile dysfunction. Yohimbine use has been associated with occasional severe adverse events, but has not been linked to serum enzyme elevations or clinically apparent acute liver injury.|A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of ERECTILE DYSFUNCTION.
Yohimbine Basic Attributes
354.45
354.44
205-672-0
2Y49VWD90Q
DTXSID9040130
G04BE04|G - Genito urinary system and sex hormones
Characteristics
65.56000
2.20
Solid
1.3±0.1 g/cm3
241 °C
543.0±50.0 °C at 760 mmHg
282.2±30.1 °C
1.661
3.48e-01 g/L
Store at RT
1.27E-12mmHg at 25°C
D20 +50.9 to +62.2° (ethanol); D20 +108° (pyridine); 20546 +129° (c = 0.5 in pyridine)
186.5 Ų [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Safety Information
II
6.1(a)
1544
23/24/25-39
27-36/37/39-45
ZG1000000
T
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501
H301
Toxicity
In small clinical trials and case series, yohimbine therapy has not been linked to serum enzyme elevations or clinical liver disease. Although yohimbine is often found in weight loss and muscle building herbal combinations, it has not been associated with cases of clinically apparent acute liver injury.
Drug Information
Indicated as a sympatholytic and mydriatic. Impotence has been successfully treated with yohimbine in male patients with vascular or diabetic origins and psychogenic origins.
Yohimbine is an indole alkaloid derived from the bark of the Central African yohimbe tree (Pausinystalia yohimbe) that is widely used as therapy for erectile dysfunction. Yohimbine use has been associated with occasional severe adverse events, but has not been linked to serum enzyme elevations or clinically apparent acute liver injury.
Herbal and Dietary Supplements
Yohimbine is an indolalkylamine alkaloid with chemical similarity to reserpine. Yohimbine blocks presynaptic alpha-2 adrenergic receptors. Its action on peripheral blood vessels resembles that of reserpine, though it is weaker and of short duration. Yohimbine's peripheral autonomic nervous system effect is to increase parasympathetic (cholinergic) and decrease sympathetic (adrenergic) activity. It is to be noted that in male sexual performance, erection is linked to cholinergic activity and to alpha-2 adrenergic blockade which may theoretically result in increased penile inflow, decreased penile outflow or both. Yohimbine exerts a stimulating action on the mood and may increase anxiety. Such actions have not been adequately studied or related to dosage although they appear to require high doses of the drug. Yohimbine has a mild anti-diuretic action, probably via stimulation of hypothalmic center and release of posterior pituitary hormone. Reportedly Yohimbine exerts no significant influence on cardiac stimulation and other effects mediated by (beta)-adrenergic receptors. Its effect on blood pressure, if any, would be to lower it; however, no adequate studies are at hand to quantitate this effect in terms of Yohimbine dosage.
Drugs that bind to and block the activation of ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Antagonists.)|Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics. (See all compounds classified as Mydriatics.)|Drugs used in the treatment of urogenital conditions and diseases such as URINARY INCONTINENCE; PROSTATIC HYPERPLASIA; and ERECTILE DYSFUNCTION. (See all compounds classified as Urological Agents.)
Rapidly absorbed following oral administration. Bioavailability is highly variable, ranging from 7 to 87% (mean 33%).
Yohimbine appears to undergo extensive metabolism in an organ of high flow such as the liver or kidney, however, the precise metabolic fate of yohimbine has not been fully determined.
Elimination half-life is approximately 36 minutes.
Yohimbine is a pre-synaptic alpha 2-adrenergic blocking agent. The exact mechanism for its use in impotence has not been fully elucidated. However, yohimbine may exert its beneficial effect on erectile ability through blockade of central alpha 2-adrenergic receptors producing an increase in sympathetic drive secondary to an increase in norepinephrine release and in firing rate of cells in the brain noradrenergic nuclei. Yohimbine-mediated norepinephrine release at the level of the corporeal tissues may also be involved. In addition, beneficial effects may involve other neurotransmitters such as dopamine and serotonin and cholinergic receptors.
Aphrodine Hydrochloride
Computed Properties
Molecular Weight:354.4
XLogP3:2.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:354.19434270
Monoisotopic Mass:354.19434270
Topological Polar Surface Area:65.6
Heavy Atom Count:26
Complexity:555
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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