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65-19-0

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  • High Quality 99% Yohimban-16-carboxylicacid,17-hydroxy-,methyl ester, hydrochloride (1:1), (16a,17a)- 65-19-0 ISO Producer

    Cas No: 65-19-0

  • USD $ 0.1-0.1 / Gram

  • 1 Gram

  • 100 Metric Ton/Year

  • Xi'an Xszo Chem Co., Ltd.
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65-19-0 Usage

Overview

Yohimbine hydrochloride is an α2-adrenergic receptor antagonist and increases the firing rate of the locus coeruleus with a resultant increase in sympathetic outflow (Redmond, 1987). Oral and intravenous yohimbine causes an increase in MHPG and blood pressure in healthy human subjects (Charney et al., 1982d; Goldberg et al., 1986). Depressed patients demonstrate an increased cortisol and blood pressure response to intravenous yohimbine compared with healthy subjects, while plasma MHPG is not significantly different between the two groups of subjects (Heninger et al., 1988). The effects of acute or chronic antidepressant treatments on the neuroendocrine or behavioural responses to yohimbine in depressed patients have not been studied.

Side effects

Yohimbine hydrochloride has been associated with high blood pressure, increased heart rate, headache, anxiety, dizziness, nausea, vomiting, tremors, and sleeplessness. It can be dangerous if taken in large doses or for long periods of time. It should not be taken in combination with monoamine oxidase (MAO) inhibitors, as effects may be additive. Yohimbe should be used with caution when taken with medicines for high blood pressure, tricyclic antidepressants, or phenothiazines. People with kidney problems and people with psychiatric conditions should not use yohimbe. Women who are pregnant or breastfeeding should not take yohimbe. The Journal of Medical Toxicology reports an instance of refractory priapism associated with ingestion of yohimbe extract, and there are other scattered reports of adverse reactions. However, may studies report it to be generally well tolerated.

Mechanism of action

Yohimbine hydrochloride 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.

Pharmacokinetics

Yohimbine hydrochloride—an α2-adrenoceptor antagonist that is approved for treatment of erectile dysfunction—may increase BP.1,2,In normal volunteers and in patients with panic disorders, oral administration at doses used clinically may slightly increase BP.1 However, in hypertensive patients oral yohimbine was reported to induce a significant increase in mean arterial pressure.The magnitude of the pressor response was related to baseline norepinephrine levels and to the yohimbine-induced increment in plasma norepinephrine levels.Thus yohimbine increases BP by stimulation of the sympathetic nervous outflow, and the drug should be administered with caution to patients with evidence for increased basal sympathetic outflow or those undergoing concurrent treatment with tricyclic antidepressants or other drugs that interfere with neuronal uptake or metabolism of norepinephrine.

Chemical Properties

white to slightly yellow powder, slightly fragrant, slightly bitter taste, easily soluble in chloroform, soluble in methanol, ethanol, slightly soluble in water.

Uses

Different sources of media describe the Uses of 65-19-0 differently. You can refer to the following data:
1. Yohimbine hydrochloride is an Indole alkaloid with α2-adrenergic blocking activity. It is an alpha adrenergic blocker, mydriatic, antidepressant that used in the treatment of neurological disorders and erectile dysfunction.
2. Yohimbine hydrochloride is an α2-adrenergic receptor antagonist. It blocks the central α2-adrenegic receptors in the brain, thus preventing and reducing the effects of xylazine, an α2-adrenergic agonist. The sedative effects and respiratory depression that accompany xylazine administration are both antagonized and reversed by yohimbine. Yohimbine hydrochloride also produces an antidiuretic effect, and increases heart rate and blood pressure.

General Description

Yohimbine hydrochloride is an indole alkaloid derived from the tree bark. It is an antagonist of α2-adrenergic receptors in the brain, reducing the effects of xylazine, which is an α2-adrenergic agonis.?

Biochem/physiol Actions

Yohimbine is derived from the Coryanthe yohimbe tree cortex. It is an alkaloid. Yohimbine hydrochloride is an α2-adrenergic receptor antagonist. It blocks the central α2-adrenergic receptors in the brain, thus preventing and reducing the effects of xylazine, an α2-adrenergic agonist. The sedative effects and respiratory depression that accompany xylazine administration are both antagonized and reversed by yohimbine. Yohimbine hydrochloride also produces an antidiuretic effect, and increases heart rate and blood pressure. It is useful in treating erectile dysfunction and promotes sexual functioning.

Veterinary Drugs and Treatments

Yohimbine is indicated to reverse the effects of xylazine in dogs, but it is being used clinically in several other species as well. Yohimbine may be efficacious in reversing some of the toxic effects associated with other agents (e.g., amitraz) and can be used prophylactically before amitraz dips.

Check Digit Verification of cas no

The CAS Registry Mumber 65-19-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 5 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 65-19:
(4*6)+(3*5)+(2*1)+(1*9)=50
50 % 10 = 0
So 65-19-0 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/p+1/t12-,15-,17-,18-,19+/m0/s1

65-19-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Yohimbine hydrochloride

1.2 Other means of identification

Product number -
Other names Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, monohydrochloride, (16α,17α)-

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:65-19-0 SDS

65-19-0Synthetic route

yohimbine
65-19-0

yohimbine

2α,7α-dihydroyohimbine
142696-96-6

2α,7α-dihydroyohimbine

Conditions
ConditionsYield
With sodium cyanoborohydride In trifluoroacetic acid100%
With sodium cyanoborohydride In trifluoroacetic acid at 20℃; for 3h;100%
yohimbine
65-19-0

yohimbine

1-hydroxyyohimbine
366456-76-0

1-hydroxyyohimbine

Conditions
ConditionsYield
Stage #1: yohimbine With sodium cyanoborohydride In trifluoroacetic acid at 20℃; for 3h;
Stage #2: With sodium tungstate; dihydrogen peroxide In methanol; water at 0℃; for 1h; Further stages.;
86%
Multi-step reaction with 2 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
View Scheme
yohimbine
65-19-0

yohimbine

A

10-hydroxy-yohimbine
41928-02-3

10-hydroxy-yohimbine

B

11-hydroxy-yohimbine

11-hydroxy-yohimbine

C

9-Hydroxyyohimbine

9-Hydroxyyohimbine

D

12-Hydroxyyohimbine

12-Hydroxyyohimbine

Conditions
ConditionsYield
With sodium persulfate; hydrogen fluoride; antimony pentafluoride at -35℃; for 1h;A 32 % Chromat.
B 23 % Chromat.
C 11 % Chromat.
D 3 % Chromat.
yohimbine
65-19-0

yohimbine

1-propargyloxyyohimbine

1-propargyloxyyohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C
1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C
2.1: 99 percent / K2CO3 / dimethylformamide / 0.5 h / 20 °C
View Scheme
yohimbine
65-19-0

yohimbine

1-isopropyloxyyohimbine

1-isopropyloxyyohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C
1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C
2.1: Cs2CO3 / methanol / 0.33 h / 20 °C
2.2: 99 percent / dimethylformamide / 1 h / 20 °C
View Scheme
yohimbine
65-19-0

yohimbine

(dl)-1-(1-methoxycarbonyl)ethoxyyohimbine

(dl)-1-(1-methoxycarbonyl)ethoxyyohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C
1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C
2.1: Cs2CO3 / methanol / 0.33 h / 20 °C
2.2: 99 percent / dimethylformamide / 1 h / 20 °C
View Scheme
yohimbine
65-19-0

yohimbine

1-cyclohexyloxyyohimbine

1-cyclohexyloxyyohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C
1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C
2.1: Cs2CO3 / methanol / 0.33 h / 20 °C
2.2: 11 percent / dimethylformamide / 1 h / 20 °C
View Scheme
yohimbine
65-19-0

yohimbine

Na-methoxyyohimbine
142756-69-2

Na-methoxyyohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C
1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C
2.1: 77 percent / methanol; diethyl ether / 1 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 77 percent / methanol
View Scheme
yohimbine
65-19-0

yohimbine

1-allyloxyyohimbine

1-allyloxyyohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C
1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C
2.1: 99 percent / K2CO3 / dimethylformamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 93 percent / K2CO3 / dimethylformamide
View Scheme
yohimbine
65-19-0

yohimbine

1-n-butyloxyyohimbine

1-n-butyloxyyohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C
1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C
2.1: 93 percent / K2CO3 / dimethylformamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 99 percent / K2CO3 / dimethylformamide
View Scheme
yohimbine
65-19-0

yohimbine

1-(p-nitrobenzyloxy)yohimbine

1-(p-nitrobenzyloxy)yohimbine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaBH3CN / trifluoroacetic acid / 3 h / 20 °C
1.2: 86 percent / Na2WO4*2H2O; H2O2 / H2O; methanol / 1 h / 0 °C
2.1: 90 percent / K2CO3 / dimethylformamide / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 90 percent / K2CO3 / dimethylformamide
View Scheme
yohimbine
65-19-0

yohimbine

yohimbine pseudoindoxyl A

yohimbine pseudoindoxyl A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 71 percent / NaOAc / 1 h / 65 °C
4: KOH / methanol / 20 °C
5: aq. NaOH / methanol / Heating
View Scheme
Multi-step reaction with 5 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 9 percent / 48 h / 65 °C
4: KOH / methanol / 20 °C
5: aq. NaOH / methanol / Heating
View Scheme
yohimbine
65-19-0

yohimbine

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

(+)-7α-acetoxy-7H-yohimbine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 71 percent / NaOAc / 1 h / 65 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 9 percent / 48 h / 65 °C
View Scheme
yohimbine
65-19-0

yohimbine

(1R,2S,4aR,8aS,13bS,14aS)-2,8a-Dihydroxy-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
2288-52-0

(1R,2S,4aR,8aS,13bS,14aS)-2,8a-Dihydroxy-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
Multi-step reaction with 4 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 71 percent / NaOAc / 1 h / 65 °C
4: KOH / methanol / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 9 percent / 48 h / 65 °C
4: KOH / methanol / 20 °C
View Scheme
yohimbine
65-19-0

yohimbine

17-O-acetyl-7α-hydroxyyohimbine

17-O-acetyl-7α-hydroxyyohimbine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 71 percent / NaOAc / 1 h / 65 °C
4: 62 percent / 6 h / 65 °C
5: 96 percent / NaHCO3 / methanol / 13 h / 24 °C
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 8 percent / NaOAc / 1 h / 65 °C
4: 96 percent / NaHCO3 / methanol / 13 h / 24 °C
View Scheme
Multi-step reaction with 5 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 9 percent / 48 h / 65 °C
4: 62 percent / 6 h / 65 °C
5: 96 percent / NaHCO3 / methanol / 13 h / 24 °C
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 44 percent / 48 h / 65 °C
4: 96 percent / NaHCO3 / methanol / 13 h / 24 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 12 percent / NaOAc / 6 h / 65 °C
View Scheme
yohimbine
65-19-0

yohimbine

7α,17α-diacetoxy-7H-yohimbine
364777-89-9

7α,17α-diacetoxy-7H-yohimbine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 71 percent / NaOAc / 1 h / 65 °C
4: 62 percent / 6 h / 65 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 8 percent / NaOAc / 1 h / 65 °C
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 9 percent / 48 h / 65 °C
4: 62 percent / 6 h / 65 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 44 percent / 48 h / 65 °C
View Scheme
yohimbine
65-19-0

yohimbine

C25H30N2O6

C25H30N2O6

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 16 percent / 48 h / 65 °C
View Scheme
Multi-step reaction with 3 steps
1: 100 percent / NaBH3CN / trifluoroacetic acid
2: 86 percent / Na2WO4*2H2O; 30 percent H2O2
3: 12 percent / NaOAc / 6 h / 65 °C
View Scheme
yohimbine
65-19-0

yohimbine

yohimbohydrazide hydrate

yohimbohydrazide hydrate

Conditions
ConditionsYield
With hydrazine hydrate In ethanol
yohimbine
65-19-0

yohimbine

yohimbinic acid
522-87-2

yohimbinic acid

Conditions
ConditionsYield
With sodium hydroxide In methanol; water

65-19-0Upstream product

65-19-0Relevant articles and documents

NOVEL PROCESS FOR EXTRACTING ALPHA YOHIMBINE (RAUWOLSCINE) FROM RAUWOLFIA SPECIES

-

Page/Page column 16, (2018/05/27)

Present invention discloses a novel, commercially viable process for extraction of Alpha yohimbine from the bark, stem and leaves of Rauwolfia species. The extract is obtained by a precipitation method involving alternate steps of acidification and alkalization along with use of specific organic solvents. The extract gives higher yield of 7-8 fold as compared to other processes and without use of any column chromatography at all. Yield of alpha yohimbine from roots and leaves of Rauwolfia canescens by process of present invention was 0.017% and 0.4% respectively, indicating that leaves are a much better source. The HPLC analysis of the compound obtained indicated a purity of > 90%.

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