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146-48-5 Usage

Overview Information

Yohimbe is the name of an evergreen tree found in parts of central and western Africa. The bark of yohimbe contains a chemical called yohimbine, which is used to make medicine. Yohimbine hydrochloride (Aphrodyne, Yocon) is a form of yohimbine that is a prescription drug in the US. Yohimbe supplements often list yohimbe bark extract or yohimbine as the active ingredient. However, some of these products might not provide accurate information about the amount of yohimbine in the supplement. Also, some yohimbe supplements list yohimbine hydrochloride as an active ingredient. Yohimbe products containing man-made yohimbine hydrochloride as an ingredient are not legal to sell as a dietary supplement in the US. Yohimbe is taken by mouth arouse sexual excitement, for erectile dysfunction (ED), sexual problems caused by medications for depression called selective-serotonin reuptake inhibitors (SSRIs), and general sexual problems in both men and women. It is also used for athletic performance, weight loss, exhaustion, chest pain, high blood pressure, low blood pressure that occurs when standing up, diabetic nerve pain, and for depression along with certain other medications.

Effectiveness

Anxiety. There is mixed evidence about the effectiveness of yohimbine, the active ingredient in yohimbe, for treating anxiety related to phobias. Some research suggests that it does not improve anxiety when combined with therapy. However, other research suggests that it reduces fear related to certain phobias. Depression. Early research suggests that taking yohimbine, the active ingredient of yohimbe, daily for 10 days does not improve depression symptoms. Erectile dysfunction (ED). There is evidence that yohimbine, the active ingredient of yohimbe, can be helpful for ED. Some herbalists suggest that the yohimbe bark actually works better than the yohimbine ingredient alone. However, so far yohimbe bark has not been evaluated in research studies. Exercise performance. Early research suggests that taking yohimbine, the active ingredient in yohimbe, daily for 21 days does not improve exercise performance or build muscle mass in soccer players. Head rush (orthostatic hypotension). Early research suggests that taking a single dose of yohimbine, the active ingredient in yohimbe, increases blood pressure in people with a head rush due to low blood pressure. However, other early research suggests that it does not improve blood pressure. Sexual problems caused by selective-serotonin reuptake inhibitors (SSRIs). There is evidence from many studies that yohimbine, the active ingredient of yohimbe, can improve sexual problems associated with this class of medications used for depression. However, this benefit has not been described specifically for the yohimbe bark. Dry mouth. Early research suggests that taking yohimbine, the active ingredient in yohimbe, improves symptoms of dry mouth in people taking antidepressants. The effect of the yohimbe bark on dry mouth is not clear.

Side Effects

Yohimbe, taken by mouth, is POSSIBLY UNSAFE. Yohimbe has been linked to reports of severe side effects including irregular or rapid heart beat, kidney failure, seizure, heart attack, and others. The primary active ingredient in yohimbe is a drug called yohimbine. This is considered a prescription drug in North America. This drug can be safely used short-term when monitored by a health professional. However, it is not appropriate for unsupervised use due to potentially serious side effects that it can cause. Children should not take yohimbe. It is POSSIBLY UNSAFE for children because children appear to be extra sensitive to the harmful effects of yohimbe. When taken by mouth in typical doses, yohimbe and the ingredient yohimbine can cause stomach upset, excitation, tremor, sleep problems, anxiety or agitation, high blood pressure, a racing heartbeat, dizziness, stomach problems, drooling, sinus pain, irritability, headache, frequent urination, bloating, rash, nausea, and vomiting. Taking high doses can also cause other severe problems, including difficulty breathing, paralysis, very low blood pressure, heart problems, and death. After taking a one-day dose of yohimbine, one person reported an allergic reaction involving fever; chills; listlessness; itchy, scaly skin; progressive kidney failure; and symptoms that looked like the auto-immune disease called lupus.

Description

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.

Chemical Properties

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

Physical properties

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.

Uses

Different sources of media describe the Uses of 146-48-5 differently. You can refer to the following data:
1. 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.
2. sexual dysfunction
3. Obtained from leaves and bark of Corynanthe johimbe. Formerly used as an aphrodisiac in veterinary medicine, yohimbine works primarily by acting as an antagonist at α2-adrenergic receptors.

Definition

ChEBI: An indole alkaloid with alpha2-adrenoceptor antagonist activity. It is produced by Corynanthe johimbe and Rauwolfia serpentina.

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.

General Description

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 failureLD50 value, intraperitoneal (mice): 16 mg/kgLD50 value, oral (mice): 37 mg/kg.

Biological Activity

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).

Pharmacology

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.

Purification Methods

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

Check Digit Verification of cas no

The CAS Registry Mumber 146-48-5 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 6 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 146-48:
(5*1)+(4*4)+(3*6)+(2*4)+(1*8)=55
55 % 10 = 5
So 146-48-5 is a valid CAS Registry Number.
InChI: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/s1

146-48-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Yohimbine

1.2 Other means of identification

Product number -
Other names Quebrachin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:146-48-5 SDS

146-48-5Synthetic route

(1R,2S,4aR,13bS,14aS)-methyl-2-hydroxy-1,2,4a,5,7,8,13,13b,14,14a-decahydroindolo[2',3':3,4]pyrido-[1,2-b]isoquinoline-1-carboxylate
1011533-78-0

(1R,2S,4aR,13bS,14aS)-methyl-2-hydroxy-1,2,4a,5,7,8,13,13b,14,14a-decahydroindolo[2',3':3,4]pyrido-[1,2-b]isoquinoline-1-carboxylate

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With 10% Pd/C; hydrogen In ethyl acetate for 14h;100%
With palladium 10% on activated carbon; hydrogen In ethyl acetate under 760.051 Torr; for 15h;100%
(+)-yohimbinone
2671-57-0

(+)-yohimbinone

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With L-Selectride In tetrahydrofuran at -78℃; for 0.5h;86%
With sodium tetrahydroborate In isopropyl alcohol Product distribution; Reduction;
C23H29N3O4

C23H29N3O4

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With acetic acid at 160℃; for 0.0166667h; Reagent/catalyst; Temperature; Microwave irradiation; stereospecific reaction;74%
C25H33N3O4

C25H33N3O4

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With acetic acid at 160℃; for 0.0833333h; Microwave irradiation; stereospecific reaction;62%
C28H31N3O4

C28H31N3O4

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With acetic acid at 160℃; for 0.0166667h; Microwave irradiation; stereospecific reaction;59%
4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester
23943-82-0, 25181-38-8

4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With acetic acid at 160℃; for 0.0166667h; Time; Microwave irradiation; stereospecific reaction;50%
C28H31N3O4

C28H31N3O4

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With acetic acid at 160℃; for 0.0166667h; Microwave irradiation; stereospecific reaction;32%
C25H33N3O4

C25H33N3O4

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With acetic acid at 160℃; for 0.0833333h; Microwave irradiation; stereospecific reaction;17%
17α-hydroxy-16α-methoxycarbonyl-yohimba-3,5-dienium; perchlorate

17α-hydroxy-16α-methoxycarbonyl-yohimba-3,5-dienium; perchlorate

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate
17α-hydroxy-16α-methoxycarbonyl-yohimb-3-enium; perchlorate

17α-hydroxy-16α-methoxycarbonyl-yohimb-3-enium; perchlorate

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With acetic acid; zinc
yohimbinic acid
522-87-2

yohimbinic acid

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With hydrogenchloride; methanol
corynanthine
483-10-3

corynanthine

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With potassium hydroxide Behandeln des Reaktionsprodukts mit methanol.HCl;
(+)-3,14-didehydroyohimbine
90362-85-9

(+)-3,14-didehydroyohimbine

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

A

14α-benzoyloxypseudoyohimbine
90362-87-1, 90410-87-0

14α-benzoyloxypseudoyohimbine

B

14β-benzoyloxyyohimbine
90362-87-1, 90410-87-0

14β-benzoyloxyyohimbine

C

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With sodium tetrahydroborate Yield given. Multistep reaction. Yields of byproduct given;
(-)-Δ15,16-didehydroyohimbinone
51598-49-3

(-)-Δ15,16-didehydroyohimbinone

A

β-yohimbine
549-84-8

β-yohimbine

B

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride In methanol at 10 - 15℃;A 47 mg
B 25 mg
(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
94992-42-4

(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

A

(+)-3,14-didehydroyohimbine
90362-85-9

(+)-3,14-didehydroyohimbine

B

17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester
71748-23-7

17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester

C

17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester
36193-50-7

17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester

D

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With sodium methylate In methanol for 0.666667h; Heating; Further byproducts given. Title compound not separated from byproducts;A 16 % Spectr.
B 27 % Spectr.
C 22 % Spectr.
D 18 % Spectr.
(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
94992-42-4

(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

A

3,4,5,6-tetradehydroyohimbine

3,4,5,6-tetradehydroyohimbine

B

(+)-3,14-didehydroyohimbine
90362-85-9

(+)-3,14-didehydroyohimbine

C

17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester
71748-23-7

17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester

D

17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester
36193-50-7

17-hydroxy-2-methoxy-17,18-cyclo-corynox-1-ene-16-carboxylic acid methyl ester

E

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With sodium methylate In methanol for 0.666667h; Product distribution; Equilibrium constant; Mechanism; Heating; solvolysis by KOH, MeOH, NaOMe;A 17 % Spectr.
B 16 % Spectr.
C 27 % Spectr.
D 22 % Spectr.
E 18 % Spectr.
(+)-pseudoyohimbin

(+)-pseudoyohimbin

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With hydrogen bromide; acetic acid Behandeln des Reaktionsprodukts mit Diazomethan in Methanol und Aether;
water
7732-18-5

water

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

acetic acid
64-19-7

acetic acid

pseudoyohimbine
84-37-7

pseudoyohimbine

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Behandeln des Reaktionsprodukts mit Diazomethan in Methanol und Aether;
ethanol
64-17-5

ethanol

corynanthine
483-10-3

corynanthine

KOH

KOH

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Behandeln des Reaktionsprodukts mit methanol.HCl;
pseudoyohimbine
84-37-7

pseudoyohimbine

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
With acetic acid for 96h; Isomerization; epimerisation; Heating;
With acetic acid for 48h; Heating;
diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

yohimbinic acid
522-87-2

yohimbinic acid

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
In methanol1.8 mg
secologanin
19351-63-4

secologanin

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: pyridine / 12 h
2: TFA / tetrahydrofuran / 1 h / Heating
3: NaOMe / methanol / 12 h
4: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0
5: 85 percent / NaCNBH3 / methanol / 48 h
6: 75 percent / aq. HCl / acetone / 2 h / Heating
7: 100 percent / H2 / Pd/C / methanol
8: DMSO; Ac2O / 16 h
9: NaBH4 / propan-2-ol / 20 h
10: glacial acetic acid / 48 h / Heating
View Scheme
Multi-step reaction with 9 steps
1.1: pyridine / 12 h
2.1: TFA / 1 h / 13 °C / Heating
3.1: NaOMe / methanol / 12 h
4.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
5.1: methanol
5.2: 85 percent / NaCNBH3 / methanol
6.1: 75 percent / HCl (10 percent) / 2 h / Heating
7.1: hydrogen / PtO2 / ethanol / 24 h
8.1: DMSO; Ac2O
9.1: NaBH4 / propan-2-ol
View Scheme
Multi-step reaction with 10 steps
1.1: pyridine / 12 h
2.1: TFA / 1 h / 13 °C / Heating
3.1: NaOMe / methanol / 12 h
4.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
5.1: methanol
5.2: 85 percent / NaCNBH3 / methanol
6.1: 75 percent / HCl (10 percent) / 2 h / Heating
7.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
8.1: DMSO; Ac2O / 16 h
9.1: NaBH4 / propan-2-ol / 20 h
10.1: AcOH / 96 h / Heating
View Scheme
Multi-step reaction with 10 steps
1.1: pyridine / 12 h
2.1: TFA / 1 h / 13 °C / Heating
3.1: NaOMe / methanol / 12 h
4.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
5.1: methanol
5.2: 85 percent / NaCNBH3 / methanol
6.1: 75 percent / HCl (10 percent) / 2 h / Heating
7.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
8.1: AcOH / 96 h / Heating
9.1: DMSO; Ac2O
10.1: NaBH4 / propan-2-ol
View Scheme
O,O,O,O-tetraacetylsecologaninn
27856-66-2

O,O,O,O-tetraacetylsecologaninn

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: TFA / tetrahydrofuran / 1 h / Heating
2: NaOMe / methanol / 12 h
3: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0
4: 85 percent / NaCNBH3 / methanol / 48 h
5: 75 percent / aq. HCl / acetone / 2 h / Heating
6: 100 percent / H2 / Pd/C / methanol
7: DMSO; Ac2O / 16 h
8: NaBH4 / propan-2-ol / 20 h
9: glacial acetic acid / 48 h / Heating
View Scheme
Multi-step reaction with 8 steps
1.1: TFA / 1 h / 13 °C / Heating
2.1: NaOMe / methanol / 12 h
3.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
4.1: methanol
4.2: 85 percent / NaCNBH3 / methanol
5.1: 75 percent / HCl (10 percent) / 2 h / Heating
6.1: hydrogen / PtO2 / ethanol / 24 h
7.1: DMSO; Ac2O
8.1: NaBH4 / propan-2-ol
View Scheme
Multi-step reaction with 9 steps
1.1: TFA / 1 h / 13 °C / Heating
2.1: NaOMe / methanol / 12 h
3.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
4.1: methanol
4.2: 85 percent / NaCNBH3 / methanol
5.1: 75 percent / HCl (10 percent) / 2 h / Heating
6.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
7.1: DMSO; Ac2O / 16 h
8.1: NaBH4 / propan-2-ol / 20 h
9.1: AcOH / 96 h / Heating
View Scheme
Multi-step reaction with 9 steps
1.1: TFA / 1 h / 13 °C / Heating
2.1: NaOMe / methanol / 12 h
3.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
4.1: methanol
4.2: 85 percent / NaCNBH3 / methanol
5.1: 75 percent / HCl (10 percent) / 2 h / Heating
6.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
7.1: AcOH / 96 h / Heating
8.1: DMSO; Ac2O
9.1: NaBH4 / propan-2-ol
View Scheme
Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate
79409-45-3

Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-2-(β-D-glucopyranosyloxy)-3,4-dihydro-3-vinyl-2H-pyran-5-carboxylate

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0
2: 85 percent / NaCNBH3 / methanol / 48 h
3: 75 percent / aq. HCl / acetone / 2 h / Heating
4: 100 percent / H2 / Pd/C / methanol
5: DMSO; Ac2O / 16 h
6: NaBH4 / propan-2-ol / 20 h
7: glacial acetic acid / 48 h / Heating
View Scheme
Multi-step reaction with 6 steps
1.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
2.1: methanol
2.2: 85 percent / NaCNBH3 / methanol
3.1: 75 percent / HCl (10 percent) / 2 h / Heating
4.1: hydrogen / PtO2 / ethanol / 24 h
5.1: DMSO; Ac2O
6.1: NaBH4 / propan-2-ol
View Scheme
Multi-step reaction with 7 steps
1.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
2.1: methanol
2.2: 85 percent / NaCNBH3 / methanol
3.1: 75 percent / HCl (10 percent) / 2 h / Heating
4.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
5.1: DMSO; Ac2O / 16 h
6.1: NaBH4 / propan-2-ol / 20 h
7.1: AcOH / 96 h / Heating
View Scheme
Multi-step reaction with 7 steps
1.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
2.1: methanol
2.2: 85 percent / NaCNBH3 / methanol
3.1: 75 percent / HCl (10 percent) / 2 h / Heating
4.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
5.1: AcOH / 96 h / Heating
6.1: DMSO; Ac2O
7.1: NaBH4 / propan-2-ol
View Scheme
Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate
79409-46-4

Methyl (2S,3R,4S)-4-(1,3-Dioxolan-2-ylmethyl)-3,4-dihydro-2-(2,3,4,6-tetraacetyl-β-D-glucopyranosyloxy)-3-vinyl-2H-pyran-5-carboxylate

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: NaOMe / methanol / 12 h
2: 70 percent / β-glucosidase / H2O / 96 h / 37 °C / pH 7.0
3: 85 percent / NaCNBH3 / methanol / 48 h
4: 75 percent / aq. HCl / acetone / 2 h / Heating
5: 100 percent / H2 / Pd/C / methanol
6: DMSO; Ac2O / 16 h
7: NaBH4 / propan-2-ol / 20 h
8: glacial acetic acid / 48 h / Heating
View Scheme
Multi-step reaction with 7 steps
1.1: NaOMe / methanol / 12 h
2.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
3.1: methanol
3.2: 85 percent / NaCNBH3 / methanol
4.1: 75 percent / HCl (10 percent) / 2 h / Heating
5.1: hydrogen / PtO2 / ethanol / 24 h
6.1: DMSO; Ac2O
7.1: NaBH4 / propan-2-ol
View Scheme
Multi-step reaction with 8 steps
1.1: NaOMe / methanol / 12 h
2.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
3.1: methanol
3.2: 85 percent / NaCNBH3 / methanol
4.1: 75 percent / HCl (10 percent) / 2 h / Heating
5.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
6.1: DMSO; Ac2O / 16 h
7.1: NaBH4 / propan-2-ol / 20 h
8.1: AcOH / 96 h / Heating
View Scheme
Multi-step reaction with 8 steps
1.1: NaOMe / methanol / 12 h
2.1: 70 percent / β-glucosidase / 96 h / 37 °C / pH 7.0
3.1: methanol
3.2: 85 percent / NaCNBH3 / methanol
4.1: 75 percent / HCl (10 percent) / 2 h / Heating
5.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
6.1: AcOH / 96 h / Heating
7.1: DMSO; Ac2O
8.1: NaBH4 / propan-2-ol
View Scheme
17-oxo-yohimbane-16-carboxylic acid methyl ester
114030-03-4

17-oxo-yohimbane-16-carboxylic acid methyl ester

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaBH4 / propan-2-ol / 20 h
2: glacial acetic acid / 48 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: NaBH4 / propan-2-ol / 20 h
2: AcOH / 96 h / Heating
View Scheme
(1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-3-formyl-6-hydroxy-cyclohex-3-enecarboxylic acid methyl ester
120132-02-7

(1R,2R,6R)-2-[1,3]Dioxolan-2-ylmethyl-3-formyl-6-hydroxy-cyclohex-3-enecarboxylic acid methyl ester

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 85 percent / NaCNBH3 / methanol / 48 h
2: 75 percent / aq. HCl / acetone / 2 h / Heating
3: 100 percent / H2 / Pd/C / methanol
4: DMSO; Ac2O / 16 h
5: NaBH4 / propan-2-ol / 20 h
6: glacial acetic acid / 48 h / Heating
View Scheme
Multi-step reaction with 5 steps
1.1: methanol
1.2: 85 percent / NaCNBH3 / methanol
2.1: 75 percent / HCl (10 percent) / 2 h / Heating
3.1: hydrogen / PtO2 / ethanol / 24 h
4.1: DMSO; Ac2O
5.1: NaBH4 / propan-2-ol
View Scheme
Multi-step reaction with 6 steps
1.1: methanol
1.2: 85 percent / NaCNBH3 / methanol
2.1: 75 percent / HCl (10 percent) / 2 h / Heating
3.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
4.1: DMSO; Ac2O / 16 h
5.1: NaBH4 / propan-2-ol / 20 h
6.1: AcOH / 96 h / Heating
View Scheme
Multi-step reaction with 6 steps
1.1: methanol
1.2: 85 percent / NaCNBH3 / methanol
2.1: 75 percent / HCl (10 percent) / 2 h / Heating
3.1: 100 percent / hydrogen / Pd/C / methanol / 12 h
4.1: AcOH / 96 h / Heating
5.1: DMSO; Ac2O
6.1: NaBH4 / propan-2-ol
View Scheme
(-)-3-iso-19,20-dehydro-β-yohimbine
295790-93-1

(-)-3-iso-19,20-dehydro-β-yohimbine

Yohimbine
146-48-5

Yohimbine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / H2 / Pd/C / methanol
2: DMSO; Ac2O / 16 h
3: NaBH4 / propan-2-ol / 20 h
4: glacial acetic acid / 48 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: hydrogen / PtO2 / ethanol / 24 h
2: DMSO; Ac2O
3: NaBH4 / propan-2-ol
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / hydrogen / Pd/C / methanol / 12 h
2: DMSO; Ac2O / 16 h
3: NaBH4 / propan-2-ol / 20 h
4: AcOH / 96 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / hydrogen / Pd/C / methanol / 12 h
2: AcOH / 96 h / Heating
3: DMSO; Ac2O
4: NaBH4 / propan-2-ol
View Scheme
Yohimbine
146-48-5

Yohimbine

Yohimbyl alcohol
6784-29-8

Yohimbyl alcohol

Conditions
ConditionsYield
With lithium aluminium tetrahydride94%
Yohimbine
146-48-5

Yohimbine

yohimban-17-amide

yohimban-17-amide

Conditions
ConditionsYield
With sodium amide for 5 - 6h; Heating / reflux;90%
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride
2: sulfur trioxide pyridine complex; triethylamine / dimethyl sulfoxide
View Scheme
Yohimbine
146-48-5

Yohimbine

C21H23(2)H3N2O3

C21H23(2)H3N2O3

Conditions
ConditionsYield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; deuterium In tetrahydrofuran at 55℃; under 750.075 Torr; for 22h; Inert atmosphere;90%
Yohimbine
146-48-5

Yohimbine

A

2α,7α-dihydroyohimbine
142696-96-6

2α,7α-dihydroyohimbine

B

2β,7β-dihydroyohimbine
364777-85-5

2β,7β-dihydroyohimbine

Conditions
ConditionsYield
With sodium cyanoborohydride In trifluoroacetic acidA 89%
B 9%
With sodium cyanoborohydride In trifluoroacetic acid at 20℃; for 3h;A 79%
B 18%
With sodium tetrahydroborate; trifluoroacetic acidA 68%
B 1%
acetic acid
64-19-7

acetic acid

Yohimbine
146-48-5

Yohimbine

Acetate(1R,2S,4aR,14aS)-2-hydroxy-1-methoxycarbonyl-2,3,4,4a,5,7,8,13,14,14a-decahydro-1H-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-6-ylium;

Acetate(1R,2S,4aR,14aS)-2-hydroxy-1-methoxycarbonyl-2,3,4,4a,5,7,8,13,14,14a-decahydro-1H-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-6-ylium;

Conditions
ConditionsYield
With mercury(II) diacetate at 60℃;85%
ethylene glycol
107-21-1

ethylene glycol

Yohimbine
146-48-5

Yohimbine

C23H30N2O5

C23H30N2O5

Conditions
ConditionsYield
With ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 40℃; for 3h;83%
With ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 40℃; for 3h;83%
ethylene glycol
107-21-1

ethylene glycol

Yohimbine
146-48-5

Yohimbine

C23H30N2O5

C23H30N2O5

Conditions
ConditionsYield
With ammonium chloride; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 20 - 40℃; Inert atmosphere;83%
Yohimbine
146-48-5

Yohimbine

(+)-yohimbinone
2671-57-0

(+)-yohimbinone

Conditions
ConditionsYield
With phosphoric acid; dicyclohexyl-carbodiimide In dimethyl sulfoxide81%
allyl methyl carbonate
35466-83-2

allyl methyl carbonate

Yohimbine
146-48-5

Yohimbine

(7R)-allylyohimbine
1029578-58-2

(7R)-allylyohimbine

Conditions
ConditionsYield
Stage #1: allyl methyl carbonate With tris(dibenzylideneacetone)dipalladium (0); trifuran-2-yl-phosphane In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: Yohimbine In dichloromethane at 20℃; Inert atmosphere; diastereoselective reaction;
79%
6CO*2Co*C12H21BrF2Si

6CO*2Co*C12H21BrF2Si

Yohimbine
146-48-5

Yohimbine

6CO*2Co*C33H46F2N2O3Si

6CO*2Co*C33H46F2N2O3Si

Conditions
ConditionsYield
Stage #1: dicobalt octacarbonyl; 6CO*2Co*C12H21BrF2Si In dichloromethane; toluene at 20℃; for 3h; Inert atmosphere;
Stage #2: Yohimbine With silver trifluoromethanesulfonate; triethylamine In dichloromethane; toluene for 0.5h; Inert atmosphere; chemoselective reaction;
74%
Yohimbine
146-48-5

Yohimbine

(1R,2S,4aR,13bS,14aS)-2-Hydroxy-6-oxy-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

(1R,2S,4aR,13bS,14aS)-2-Hydroxy-6-oxy-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

Conditions
ConditionsYield
With dihydrogen peroxide In methanol at 60℃; for 6h;70%
lead(IV) tetraacetate
546-67-8

lead(IV) tetraacetate

Yohimbine
146-48-5

Yohimbine

(+)-7α-acetoxy-7H-yohimbine
94992-43-5

(+)-7α-acetoxy-7H-yohimbine

Conditions
ConditionsYield
In dichloromethane for 0.25h; Ambient temperature;67%
Yohimbine
146-48-5

Yohimbine

A

(1R,2S,4aR,8aS,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
94992-41-3

(1R,2S,4aR,8aS,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

B

(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester
94992-42-4

(1R,2S,4aR,8aR,13bS,14aS)-8a-Chloro-2-hydroxy-1,2,3,4,4a,5,7,8,8a,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With tert-butylhypochlorite; triethylamine In dichloromethaneA 67%
B 28%
With tert-butylhypochlorite In tetrachloromethane; dichloromethane at -17℃; for 0.5h;A 55%
B 32%
Yohimbine
146-48-5

Yohimbine

3,4-Didehydroyohimbin

3,4-Didehydroyohimbin

Conditions
ConditionsYield
With mercury(II) diacetate; edetate disodium In acetic acid for 1.5h; Heating;66%
With mercury(II) diacetate; edetate disodium In acetic acid for 1.5h; Heating; Yield given;
bromocyane
506-68-3

bromocyane

Yohimbine
146-48-5

Yohimbine

A

4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester
23943-82-0, 25181-38-8

4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

B

4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester
23943-82-0, 25181-38-8

4-cyano-3,17-dihydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran; dichloromethane; water at 20℃; for 23h; Inert atmosphere;A n/a
B 63%
With water In tetrahydrofuran; dichloromethane at 20℃; for 23h; Inert atmosphere; Overall yield = 63 %; Overall yield = 208 mg;A n/a
B n/a
bromocyane
506-68-3

bromocyane

Yohimbine
146-48-5

Yohimbine

C22H26BrN3O3

C22H26BrN3O3

Conditions
ConditionsYield
In dichloromethane; N,N-dimethyl-formamide at 100℃; for 0.000763889h; Microwave irradiation; Sealed tube;56%
In dichloromethane; N,N-dimethyl-formamide at 100℃; for 0.0458333h; Microwave irradiation; Inert atmosphere;56%
methanol
67-56-1

methanol

bromocyane
506-68-3

bromocyane

Yohimbine
146-48-5

Yohimbine

C23H29N3O4

C23H29N3O4

Conditions
ConditionsYield
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere;55%
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere;36%
formic acid
64-18-6

formic acid

2,3-Dihydroxybenzoic acid
303-38-8

2,3-Dihydroxybenzoic acid

Yohimbine
146-48-5

Yohimbine

A

C28H30N2O7

C28H30N2O7

B

C29H30N2O8

C29H30N2O8

Conditions
ConditionsYield
With silver(l) oxide at 20℃; for 8h; stereoselective reaction;A 55%
B 20%
bromocyane
506-68-3

bromocyane

ethanol
64-17-5

ethanol

Yohimbine
146-48-5

Yohimbine

A

C24H31N3O4

C24H31N3O4

B

4-cyano-3-ethoxy-17-hydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester
23943-81-9, 23943-84-2, 23944-14-1, 38739-02-5

4-cyano-3-ethoxy-17-hydroxy-3,4-seco-yohimbane-16-carboxylic acid methyl ester

Conditions
ConditionsYield
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere;A n/a
B 47%
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere; Overall yield = 47 %; Overall yield = 171 mg;A n/a
B n/a
bromocyane
506-68-3

bromocyane

isopropyl alcohol
67-63-0

isopropyl alcohol

Yohimbine
146-48-5

Yohimbine

A

C25H33N3O4

C25H33N3O4

B

C25H33N3O4

C25H33N3O4

Conditions
ConditionsYield
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere;A 39%
B 9%
3-cyanocarbonyl-3'-methoxycarbonyl-2,2'-binaphthalene

3-cyanocarbonyl-3'-methoxycarbonyl-2,2'-binaphthalene

Yohimbine
146-48-5

Yohimbine

[2,2']binaphthalenyl-1,3'-dicarboxylic acid 1-(1-methoxycarbonyl-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-2-yl) ester 3'-methyl ester

[2,2']binaphthalenyl-1,3'-dicarboxylic acid 1-(1-methoxycarbonyl-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinolin-2-yl) ester 3'-methyl ester

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃;37%
bromocyane
506-68-3

bromocyane

benzyl alcohol
100-51-6

benzyl alcohol

Yohimbine
146-48-5

Yohimbine

A

C29H33N3O4

C29H33N3O4

B

C29H33N3O4

C29H33N3O4

Conditions
ConditionsYield
In dichloromethane; chloroform at 20℃; for 6.5h; Inert atmosphere;A 37%
B 8%
In dichloromethane; chloroform for 4h; Reflux; Inert atmosphere;A 37%
B 8%
ethylene glycol
107-21-1

ethylene glycol

Yohimbine
146-48-5

Yohimbine

C23H30N2O5
1016560-15-8

C23H30N2O5

Conditions
ConditionsYield
With bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile at 40℃; for 3h;35%
2,3-Dihydroxybenzoic acid
303-38-8

2,3-Dihydroxybenzoic acid

Yohimbine
146-48-5

Yohimbine

C28H30N2O7

C28H30N2O7

Conditions
ConditionsYield
With formic acid; silver(l) oxide In acetonitrile at 40℃; for 12h; stereoselective reaction;35%

146-48-5Relevant articles and documents

Indole alkaloids and other constituents of Rauwolfia serpentina

Itoh, Atsuko,Kumashiro, Tomoko,Yamaguchi, Machiko,Nagakura, Naotaka,Mizushina, Yoshiyuki,Nishi, Toyoyuki,Tanahashi, Takao

, p. 848 - 852 (2005)

From the dried roots of Rauwolfia serpentina were isolated five new indole alkaloids, Nb-methylajmaline (1), Nb-methylisoajmaline (2), 3-hydroxysarpagine (3), yohimbinic acid (4), isorauhimbinic acid (5), a new iridoid glucoside, 7-epiloganin (6), and a new sucrose derivative, 6′-O-(3,4,5-trimethoxybenzoyl)glomeratose A (7), together with 20 known compounds. The structures of the new compounds were determined by spectroscopic and chemical means. The inhibitory activities of the selected alkaloids on topoisomerase I and II and their cytotoxicity against the human promyelocytic leukemia (HL-60) cell lines were assessed.

-

Ziegler,Sweeny

, p. 3545,3547 (1969)

-

-

Raymond-Hamet

, p. 1658 (1934)

-

Compounds and compositions for treating infection

-

, (2009/04/24)

Compounds from 14 Kenyan plants, including from the root of Dovyalis abyssinica and Clutia robusta have been characterized and isolated, and their uses are disclosed.

ANTIHYPERTENSIVE THERAPY

-

, (2009/09/08)

A new use of darusentan is provided in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy with one or more drugs. The composition comprises darusentan in an amount providing a therapeutically effective daily dose; wherein (a) the composition is orally deliverable and/or (b) the daily dose of darusentan is effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, trough sitting diastolic, 24-hour ambulatory systolic, 24-hour ambulatory diastolic, maximum diurnal systolic and maximum diurnal diastolic blood pressures. Further provided is a new use of darusentan in preparation of a pharmaceutical composition for lowering blood pressure in a patient exhibiting resistance to a baseline antihypertensive therapy, wherein the composition is administered adjunctively with at least one diuretic and at least one antihypertensive drug selected from ACE inhibitors, angiotensin II receptor blockers, beta-adrenergic receptor blockers and calcium channel blockers.

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