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
Show more names
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
- Formal charge
- 0
- Complexity
- 555
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Hallucinogens
Pharmaceuticals -> Listed in ZINC15
LogP
2.73
2.01
Collision Cross Section
189.51 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
186.5 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
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
- solubility
- THF; DMSO; Chloroform;
- form
- Solid
- pka
- 14.39 · 14.39±0.40(Predicted)
- color
- Beige
- InChIKey
- BLGXFZZNTVWLAY-SCYLSFHTSA-N
- SMILES
- [C@@H]1(O)[C@H](C(OC)=O)[C@]2(C[C@@]3(N(C[C@@]2(CC1)[H])CCC1C2=C(NC3=1)C=CC=C2)[H])[H]
- LogP
- 2.73 · 2.730
- CAS DataBase Reference
- 146 · 146-48-5(CAS DataBase Reference)
- FDA UNII
- 2 Y49VWD90Q · 2Y49VWD90Q
- ATC code
- 4 BE04 · G04BE04
- NIST Chemistry Reference
- Yohimbine(146-48-5)
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 311 · H311-H301-H331
- Precautionary statements
- 264 · P264-P270-P301+P310-P321-P330-P405-P501-P280-P302+P352-P312-P322-P361-P363-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501
- Hazard Codes
- T
- Risk Statements
- 23 · 23/24/25-39
- Safety Statements
- 27 · 27-36/37/39-45
- RIDADR
- 1544 · 1544
- RTECS
- 1000000 · ZG1000000
- HazardClass
- 6.1 · 6.1(a)
- PackingGroup
- II
Safety & regulation
GHS classification
GHS Classification
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
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.
Toxicology
Hepatotoxicity
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
- safety_code
- 27-36/37/39-45
- hazard_class
- 6.1(a)
- packing_group
- II
- Hazard statements
- H311-H301-H331
- Precautionary statements
- P264-P270-P301+P310-P321-P330-P405-P501-P280-P302+P352-P312-P322-P361-P363-P405-P501-P261-P271-P304+P340-P311-P321-P403+P233-P405-P501
Chemistry & industry
Pharmacology
ATC Code
G04BE04
G - Genito urinary system and sex hormones
QG - Genito urinary system and sex hormones
QV - Various
Pharmacodynamics
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
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.
MeSH Pharmacological Classification
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
Applications
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.
Upstream & downstream products
Upstream raw materials
Suppliers50 total
Additional notes
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
Linked notes
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