Yohimbine

HCID 8969CAS 146-48-5

Basic information

Standard SMILES
COC(=O)[C@@H]1[C@H]2C[C@H]3c4[nH]c5ccccc5c4CCN3C[C@@H]2CC[C@@H]1O
InChIKey
BLGXFZZNTVWLAY-SCYLSFHTSA-N
Molecular formula
C21H26N2O3
Average molar mass
354.4 g/mol
Monoisotopic mass
354.19434269

Overview

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

Names & identifiers

Preferred name
Yohimbine
IUPAC
methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
English name
Yohimbine
Molecular formula
C21H26N2O3
Molecular weight
354.44

Names & synonyms

Yohimbine146-48-5YohimbinQuebrachineCorynineQuebrachinAPHRODINEYohimbic acid methyl ester(+)-YohimbineYohimbinumDTXSID904013017alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester
Show more names
YoconYohimexAphrosolRAUBASINAphrodyne
2Y49VWD90Qmethyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate(16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl esterYohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-DTXCID7020130CHEBI:10093methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylatemethyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo(11.8.0.0^(2,10).0^(4,9).0^(15,20))henicosa-2(10),4,6,8-tetraene-19-carboxylate

Database identifiers

CAS
146-48-5、37247-87-3
PubChem CID
8969
DTXSID
DTXSID9040130
ChEMBL
CHEMBL15245
ChEBI
CHEBI:10093
UNII
2Y49VWD90Q
EC Number
205-672-0
Nikkaji
J9.366A

Properties

Computed structural properties

XLogP
2.9
Topological polar surface area
65.6 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
2
Heavy atoms
26

Experimental & physicochemical properties

Drugs · 2 items

DEA NFLIS-Drug Category -> Hallucinogens

Pharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesCrystal structure
LogP · 2 items

2.73

2.01

Solubility3.48e-01 g/L
Human DrugsPharmaceuticals
Melting Point241 °C

Physicochemical properties

Melting point
231 · 231-233 °C(lit.)
alpha
20 · D20 +50.9 to +62.2° (ethanol); D20 +108° (pyridine); 20546 +129° (c = 0.5 in pyridine)
Boiling point
487.66 °C · 487.66°C (rough estimate)
Density
1.164 · 1.1640 (rough estimate)
refractive index
1.65 · 1.6500 (estimate)
storage temp.
Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 27 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Regulation (EC) No 178/2002 (amended)

Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.alpha.,17.alpha.)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Other Safety InformationIMAP assessments - Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.alpha.,17.alpha.)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 3 (100%)

Toxicology

Hepatotoxicity · 1 item

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.

Safety data

rtecs
ZG1000000
ridadr
1544
risk_code
23/24/25-39
Signal word
Danger
Symbol(GHS)
GHS06
hazard_code
T

Chemistry & industry

Pharmacology

ATC Code · 4 items

G04BE04

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

QV - Various

Pharmacodynamics · 1 item

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.

Mechanism of Action · 1 item

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.

Biological Half-LifeElimination half-life is approximately 36 minutes.
Metabolism/MetabolitesYohimbine 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.
MeSH Pharmacological Classification · 3 items

Agents that dilate the pupil. They may be either sympathomimetics or parasympatholytics.

Drugs that bind to and block the activation of ADRENERGIC ALPHA-2 RECEPTORS.

Drugs used in the treatment of urological conditions and diseases such as URINARY INCONTINENCE and URINARY TRACT INFECTIONS.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >10
Use ClassificationPharmaceuticals
Applications · 5 items

DescriptionYohimbine 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.

HistoryYohimbine 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 10weeks. 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.

UsesObtained 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.

UsesYohimbine 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.

General DescriptionYohimbine (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.

Suppliers50 total

北京华美互利生物化工010-56205725 · [email protected]
浙江超慧医药科技有限公司021-34514716 18238002504 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
上海纯优生物科技有限公司18302135232 18302135232 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
Additional notes · 1 item

DefinitionChEBI: 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.

Related reactions

1 records

Linked notes

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