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alpha-Yohimbine

CAS# 131-03-3

alpha-Yohimbine

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Chemical structure

alpha-Yohimbine

3D structure

Chemical Properties of alpha-Yohimbine

Cas No. 131-03-3 SDF Download SDF
PubChem ID 120635 Appearance Powder
Formula C21H26N2O3 M.Wt 354.5
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name methyl (1S,15S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
SMILES COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
Standard InChIKey BLGXFZZNTVWLAY-LSJCQCDQSA-N
Standard InChI InChI=1S/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+/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of alpha-Yohimbine

The barks of Pausinystalia yohimbe

Biological Activity of alpha-Yohimbine

Description1. Alpha-Yohimbine is strong selective 2-adrenoceptor antagonist. 2. Alpha-Yohimbine possess aphrodisiac effect. 3. Alpha-Yohimbine is a 5-HT1A receptor agonist.
Targets5-HT Receptor

alpha-Yohimbine Dilution Calculator

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Preparing Stock Solutions of alpha-Yohimbine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8209 mL 14.1044 mL 28.2087 mL 56.4175 mL 70.5219 mL
5 mM 0.5642 mL 2.8209 mL 5.6417 mL 11.2835 mL 14.1044 mL
10 mM 0.2821 mL 1.4104 mL 2.8209 mL 5.6417 mL 7.0522 mL
50 mM 0.0564 mL 0.2821 mL 0.5642 mL 1.1283 mL 1.4104 mL
100 mM 0.0282 mL 0.141 mL 0.2821 mL 0.5642 mL 0.7052 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on alpha-Yohimbine

A comparison of the binding characteristics of the alpha 2-adrenoceptor antagonists 3H-yohimbine and 3H-rauwolscine in bovine teat muscles.[Pubmed:2870688]

Arch Int Pharmacodyn Ther. 1986 Feb;279(2):212-22.

3H-Yohimbine and 3H-rauwolscine, both potent and selective alpha 2-adrenergic antagonists, were used to identify alpha 2-adrenoceptors in smooth muscles of the cistern wall of teats of lactating cows. Binding of these radioligands was rapid and readily reversed by 10 microM phentolamine. Saturation experiments in the presence of 3H-yohimbine showed an equilibrium KD value of 6.23 +/- 0.74 nM and a maximum number of sites of 81 +/- 7 fmol/mg of membrane protein. In the presence of 3H-rauwolscine, however, a higher density of alpha 2-receptors (164 +/- 12 fmol/mg protein) with a KD of 6.16 +/- 0.64 nM was found. No cooperative interactions among both binding sites were observed. Both 3H-yohimbine and 3H-rauwolscine binding sites showed alpha 2-adrenergic specificity. On the basis of its higher affinity to the alpha 2-adrenoceptor sites, better ratio of specific to non-specific binding and for other reasons, 3H-rauwolscine appears to be the ligand of choice.

[3H]rauwolscine behaves as an agonist for the 5-HT1A receptors in human frontal cortex membranes.[Pubmed:1680719]

Eur J Pharmacol. 1991 May 25;207(1):1-8.

The alpha 2 adrenergic antagonist [3H]rauwolscine binds with comparable nanomolar affinity to alpha 2 adrenoceptors and the nonadrenergic 5-HT1A receptors sites in human frontal cortex membranes. Addition of 0.5 mM GTP into the incubation medium produces a significant decrease in the amount of [3H]rauwolscine binding sites (Bmax = 230 +/- 16 and 115 +/- 11 fmol/mg protein in the absence and presence of GTP, respectively). The affinity for [3H]rauwolscine remains unchanged (i.e. KD = 40 +/- 0.9 nM and 4.1 +/- 1 nM). This effect of GTP can be attributed to decreased binding of the radioligand to the 5-HT1A receptors. GTP decreases binding of [3H]rauwolscine to nearly the same level as the one corresponding to the alpha 2 adrenoceptors in membranes from both the human frontal cortex and hippocampus. The venom of the marine cone snail, Conus tessulatus, preferentially inhibits [3H]rauwolscine binding to 5-HT1A receptors as compared with the alpha 2 adrenoceptors. Following complete masking of the 5-HT1A receptors by this venom. GTP no longer affects the saturation binding characteristics of [3H]rauwolscine for the remaining alpha 2 adrenoceptors. Nucleotides decrease the binding of [3H]rauwolscine to the 5-HT1A receptors with an order of potencies (i.e. GTP gamma S greater than GPP(NH)P much greater than GDP greater than GTP much greater than ATP) that is typical for nucleotide-mediated receptor-G protein dissociation. This suggests that [3H]rauwolscine is a 5-HT1A receptor agonist and this conclusion is compatible with earlier functional studies, indicating that rauwolscine (as well as yohimbine) has agonistic properties at the level of 5-HT autoreceptors.(ABSTRACT TRUNCATED AT 250 WORDS)

[3H]rauwolscine (alpha-yohimbine): a specific antagonist radioligand for brain alpha 2-adrenergic receptors.[Pubmed:6276200]

Eur J Pharmacol. 1981 Dec 17;76(4):461-4.

[3H]Rauwolscine, a specific and potent alpha 2-antagonist radioligand, was used to characterize alpha 2-receptor binding in bovine cerebral cortex. [3H]Rauwolscine binding was reversible, stereospecific, and saturable. Association, dissociation, and saturation studies revealed one site interactions (k -1/k+1 = 1.2 nM, KD = 2.5 nM, Bmax = 160 fmol/mg protein) and competition studies indicated that [3H]rauwolscine labeled the alpha 2-receptor. Agonists inhibited [3H]rauwolscine binding in a shallow, GTP-sensitive manner. These results suggest that [3H]rauwolscine specifically labels both the high and low affinity states of the alpha 2-receptor in brain membranes.

[3H]Rauwolscine: an antagonist radioligand for the cloned human 5-hydroxytryptamine2b (5-HT2B) receptor.[Pubmed:9459568]

Naunyn Schmiedebergs Arch Pharmacol. 1998 Jan;357(1):17-24.

In previous reports, [3H]5-HT has been used to characterize the pharmacology of the rat and human 5-HT2B receptors. 5-HT, the native agonist for the 5-HT2B receptor, has a limitation in its usefulness as a radioligand since it is difficult to study the agonist low-affinity state of a G protein-coupled receptor using an agonist radioligand. When using [3H]5-HT as a radioligand, rauwolscine was determined to have relatively high affinity for the human receptor (Ki human = 14.3+/-1.2 nM, compared to Ki rat = 35.8+/-3.8 nM). Since no known high affinity antagonist was available as a radioligand, these studies were performed to characterize [3H]rauwolscine as a radioligand for the cloned human 5-HT2B receptor expressed in AV12 cells. When [3H]rauwolscine was initially tested for its usefulness as a radioligand, complex competition curves were obtained. After testing several alpha2-adrenergic ligands, it was determined that there was a component of [3H]rauwolscine binding in the AV12 cell that was due to the presence of an endogenous alpha2-adrenergic receptor. The alpha2-adrenergic ligand efaroxan was found to block [3H]rauwolscine binding to the alpha2-adrenergic receptor without significantly affecting binding to the 5-HT2B receptor and was therefore included in all subsequent studies. In saturation studies at 37 degrees C, [3H]rauwolscine labeled a single population of binding sites, Kd = 3.75+/-0.23 nM. In simultaneous experiments using identical tissue samples, [3H]rauwolscine labeled 783+/-10 fmol of 5-HT2B receptors/mg of protein, as compared to 733+/-14 fmol of 5-HT2B receptors/mg of protein for [3H]5-HT binding. At 0 degrees C, where the conditions for [3H]5-HT binding should label mostly the agonist high affinity state of the human 5-HT2B receptor, [3H]rauwolscine (Bmax = 951+/-136 fmol/mg), again labeled significantly more receptors than [3H]5-HT (Bmax = 615+/-34 fmol/mg). The affinity of [3H]rauwolscine for the human 5-HT2B receptor at 0 degrees C did not change, Kd = 4.93+/-1.27 nM, while that for [3H]5-HT increased greatly (Kd at 37 degrees C = 7.76+/-1.06 nM; Kd at 0 degrees C = 0.0735+/-0.0081 nM). When using [3H]rauwolscine as the radioligand, competition curves for antagonist structures modeled to a single binding site, while agonist competition typically resulted in curves that best fit a two site binding model. In addition, many of the compounds with antagonist structures displayed higher affinity for the 5-HT2B receptor when [3H]rauwolscine was the radioligand. Typically, approximately 85% of [3H]rauwolscine binding was specific binding. These studies display the usefulness of [3H]rauwolscine as an antagonist radioligand for the cloned human 5-HT2B receptor. This should provide a good tool for the study of both the agonist high- and low-affinity states of the human cloned 5-HT2B receptor.

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