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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Yohimbine
- Accession Number
- DB01392
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Description
A plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. [PubChem]
- Structure
Structure for DB01392 (Yohimbine)
- Synonyms
- (+)-yohimbine
- (16alpha,17alpha)-17-Hydroxyyohimban-16-carboxylic acid methyl ester
- 17alpha-Hydroxyyohimban-16alpha-carboxylic acid methyl ester
- Aphrodine
- Corynine
- Johimbin
- Quebrachin
- Quebrachine
- Yohimbic acid methyl ester
- Yohimbin
- Yohimbine
- Product Ingredients
Ingredient UNII CAS InChI Key Yohimbine hydrochloride NB2E1YP49F 65-19-0 PIPZGJSEDRMUAW-VJDCAHTMSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Yocon Tablet 5.4mg Tablet 5.4 mg Oral Palisades Pharmaceuticals Inc. 1988-12-31 2010-07-16 Canada 
Yohimbine HCl 2mg Tablet 2 mg Oral Odan Laboratories Ltd 1992-12-31 2010-07-19 Canada Yohimbine HCl 5.4mg Tablet 5.4 mg Oral Odan Laboratories Ltd 1996-09-09 2010-07-19 Canada Yohimbine Hydrochloride Tab 2mg Tablet 2 mg Oral Odan Laboratories Ltd 1992-12-31 Not applicable Canada Yohimbine Hydrochloride Tablets 5.4mg Tablet 5.4 mg Oral Tanta Pharmaceuticals Inc 1994-12-31 2009-09-15 Canada Yohimbine Tab 2mg Tablet 2 mg Oral Welcker Lyster Ltd., Division Of Technilab Inc. 1951-12-31 2005-08-05 Canada Yohimbine Tab 5.4mg Tablet 5.4 mg Oral Odan Laboratories Ltd 1991-12-31 Not applicable Canada Yohimbine Tab 6mg Tablet 6 mg Oral Rougier Pharma Division Of Ratiopharm Inc 1990-12-31 2003-09-22 Canada Yohimbine-odan 6mg Tablet 6 mg Oral Odan Laboratories Ltd 1992-12-31 Not applicable Canada - International/Other Brands
- Actibine / Aphrodyne / Baron-X / Dayto himbin / Thybine / Yocon / Yohimar / Yohimex / Yoman / Yovital
- Categories
- Adrenergic Agents
- Adrenergic alpha-2 Receptor Antagonists
- Adrenergic alpha-Antagonists
- Adrenergic Antagonists
- Alkaloids
- Autonomic Agents
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Drugs Used in Erectile Dysfunction
- Genito Urinary System and Sex Hormones
- Indole Alkaloids
- Indoles
- Mydriatics
- Neurotransmitter Agents
- Other Miscellaneous Therapeutic Agents
- Peripheral Nervous System Agents
- Secologanin Tryptamine Alkaloids
- Urological Agents
- Urologicals
- UNII
- 2Y49VWD90Q
- CAS number
- 146-48-5
- Weight
- Average: 354.4427
Monoisotopic: 354.194342708 - Chemical Formula
- C21H26N2O3
- InChI Key
- BLGXFZZNTVWLAY-SCYLSFHTSA-N
- 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+/m0/s1
- IUPAC Name
- methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate
- SMILES
- [H][[email protected]@]12CC[[email protected]](O)[[email protected]](C(=O)OC)[[email protected]@]1([H])C[[email protected]]1([H])N(CCC3=C1NC1=CC=CC=C31)C2
Pharmacology
- Indication
Indicated as a sympatholytic and mydriatic. Impotence has been successfully treated with yohimbine in male patients with vascular or diabetic origins and psychogenic origins.
- Structured Indications
- Not Available
- 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.
Target Actions Organism AAlpha-2A adrenergic receptor antagonistHuman AAlpha-2B adrenergic receptor antagonistHuman AAlpha-2C adrenergic receptor antagonistHuman U5-hydroxytryptamine receptor 1A partial agonistHuman U5-hydroxytryptamine receptor 1B antagonistHuman U5-hydroxytryptamine receptor 1D antagonistHuman UD(2) dopamine receptor antagonistHuman UD(3) dopamine receptor antagonistHuman U5-hydroxytryptamine receptor 2A antagonistHuman U5-hydroxytryptamine receptor 2C antagonistHuman UATP-sensitive potassium channel Not Available Human U5-hydroxytryptamine receptor 2B antagonistHuman - Absorption
Rapidly absorbed following oral administration. Bioavailability is highly variable, ranging from 7 to 87% (mean 33%).
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Yohimbine 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.
- Route of elimination
- Not Available
- Half life
Elimination half-life is approximately 36 minutes.
- Clearance
- Not Available
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group 7-Nitroindazole The therapeutic efficacy of 7-Nitroindazole can be decreased when used in combination with Yohimbine. Experimental Abiraterone The serum concentration of Yohimbine can be increased when it is combined with Abiraterone. Approved Acebutolol Yohimbine may decrease the antihypertensive activities of Acebutolol. Approved, Investigational Adinazolam The therapeutic efficacy of Adinazolam can be decreased when used in combination with Yohimbine. Approved Adipiplon The therapeutic efficacy of Adipiplon can be decreased when used in combination with Yohimbine. Investigational Aliskiren Yohimbine may decrease the antihypertensive activities of Aliskiren. Approved, Investigational Alprazolam The therapeutic efficacy of Alprazolam can be decreased when used in combination with Yohimbine. Approved, Illicit, Investigational Alprenolol Yohimbine may decrease the antihypertensive activities of Alprenolol. Approved, Withdrawn Ambrisentan Yohimbine may decrease the antihypertensive activities of Ambrisentan. Approved, Investigational Amineptine The serum concentration of Yohimbine can be increased when it is combined with Amineptine. Illicit, Withdrawn Amiodarone The metabolism of Yohimbine can be decreased when combined with Amiodarone. Approved, Investigational Amitriptyline The serum concentration of Yohimbine can be increased when it is combined with Amitriptyline. Approved Amlodipine Yohimbine may decrease the antihypertensive activities of Amlodipine. Approved Amoxapine The serum concentration of Yohimbine can be increased when it is combined with Amoxapine. Approved Apalutamide The serum concentration of Yohimbine can be decreased when it is combined with Apalutamide. Approved, Investigational Aprepitant The serum concentration of Yohimbine can be increased when it is combined with Aprepitant. Approved, Investigational Artemether The metabolism of Yohimbine can be decreased when combined with Artemether. Approved Atazanavir The metabolism of Yohimbine can be decreased when combined with Atazanavir. Approved, Investigational Atenolol Yohimbine may decrease the antihypertensive activities of Atenolol. Approved Atomoxetine The metabolism of Yohimbine can be decreased when combined with Atomoxetine. Approved Benazepril Yohimbine may decrease the antihypertensive activities of Benazepril. Approved, Investigational Bendroflumethiazide Yohimbine may decrease the antihypertensive activities of Bendroflumethiazide. Approved Benzoctamine The therapeutic efficacy of Benzoctamine can be decreased when used in combination with Yohimbine. Approved Bepridil Yohimbine may decrease the antihypertensive activities of Bepridil. Approved, Withdrawn Betaxolol Yohimbine may decrease the antihypertensive activities of Betaxolol. Approved, Investigational Bethanidine Yohimbine may decrease the antihypertensive activities of Bethanidine. Approved Bietaserpine Yohimbine may decrease the antihypertensive activities of Bietaserpine. Experimental Bimatoprost Yohimbine may decrease the antihypertensive activities of Bimatoprost. Approved, Investigational Bisoprolol Yohimbine may decrease the antihypertensive activities of Bisoprolol. Approved Boceprevir The metabolism of Yohimbine can be decreased when combined with Boceprevir. Approved, Withdrawn Bortezomib The metabolism of Yohimbine can be decreased when combined with Bortezomib. Approved, Investigational Bosentan The serum concentration of Yohimbine can be decreased when it is combined with Bosentan. Approved, Investigational BQ-123 Yohimbine may decrease the antihypertensive activities of BQ-123. Investigational Bretylium Yohimbine may decrease the antihypertensive activities of Bretylium. Approved Brimonidine Yohimbine may decrease the antihypertensive activities of Brimonidine. Approved Bromazepam The therapeutic efficacy of Bromazepam can be decreased when used in combination with Yohimbine. Approved, Illicit, Investigational Bupranolol Yohimbine may decrease the antihypertensive activities of Bupranolol. Approved Bupropion The metabolism of Yohimbine can be decreased when combined with Bupropion. Approved Buspirone The therapeutic efficacy of Buspirone can be decreased when used in combination with Yohimbine. Approved, Investigational Cadralazine Yohimbine may decrease the antihypertensive activities of Cadralazine. Experimental Cafedrine Yohimbine may decrease the antihypertensive activities of Cafedrine. Investigational Camazepam The therapeutic efficacy of Camazepam can be decreased when used in combination with Yohimbine. Approved, Illicit Candesartan Yohimbine may decrease the antihypertensive activities of Candesartan. Experimental Candesartan cilexetil Yohimbine may decrease the antihypertensive activities of Candesartan cilexetil. Approved Candoxatril Yohimbine may decrease the antihypertensive activities of Candoxatril. Experimental Captodiame The therapeutic efficacy of Captodiame can be decreased when used in combination with Yohimbine. Approved, Investigational Captopril Yohimbine may decrease the antihypertensive activities of Captopril. Approved Carbamazepine The metabolism of Yohimbine can be increased when combined with Carbamazepine. Approved, Investigational Carteolol Yohimbine may decrease the antihypertensive activities of Carteolol. Approved Carvedilol Yohimbine may decrease the antihypertensive activities of Carvedilol. Approved, Investigational Celecoxib The metabolism of Yohimbine can be decreased when combined with Celecoxib. Approved, Investigational Celiprolol Yohimbine may decrease the antihypertensive activities of Celiprolol. Approved, Investigational Ceritinib The serum concentration of Yohimbine can be increased when it is combined with Ceritinib. Approved Chlordiazepoxide The therapeutic efficacy of Chlordiazepoxide can be decreased when used in combination with Yohimbine. Approved, Illicit, Investigational Chlormezanone The therapeutic efficacy of Chlormezanone can be decreased when used in combination with Yohimbine. Approved, Investigational, Withdrawn Chloroquine The metabolism of Yohimbine can be decreased when combined with Chloroquine. Approved, Investigational, Vet Approved Chlorothiazide Yohimbine may decrease the antihypertensive activities of Chlorothiazide. Approved, Vet Approved Chlorpromazine The metabolism of Yohimbine can be decreased when combined with Chlorpromazine. Approved, Investigational, Vet Approved Chlorthalidone Yohimbine may decrease the antihypertensive activities of Chlorthalidone. Approved Cholecalciferol The metabolism of Yohimbine can be decreased when combined with Cholecalciferol. Approved, Nutraceutical Cicletanine Yohimbine may decrease the antihypertensive activities of Cicletanine. Investigational Cilazapril Yohimbine may decrease the antihypertensive activities of Cilazapril. Approved Cimetidine The metabolism of Yohimbine can be decreased when combined with Cimetidine. Approved, Investigational Cinacalcet The metabolism of Yohimbine can be decreased when combined with Cinacalcet. Approved Citalopram The metabolism of Yohimbine can be decreased when combined with Citalopram. Approved Clarithromycin The metabolism of Yohimbine can be decreased when combined with Clarithromycin. Approved Clemastine The metabolism of Yohimbine can be decreased when combined with Clemastine. Approved, Investigational Clobazam The therapeutic efficacy of Clobazam can be decreased when used in combination with Yohimbine. Approved, Illicit Clomipramine The serum concentration of Yohimbine can be increased when it is combined with Clomipramine. Approved, Investigational, Vet Approved Clonidine Yohimbine may decrease the antihypertensive activities of Clonidine. Approved Cloranolol Yohimbine may decrease the antihypertensive activities of Cloranolol. Experimental Clorazepate The therapeutic efficacy of Clorazepate can be decreased when used in combination with Yohimbine. Approved, Illicit Clotiazepam The therapeutic efficacy of Clotiazepam can be decreased when used in combination with Yohimbine. Approved, Illicit Clotrimazole The metabolism of Yohimbine can be decreased when combined with Clotrimazole. Approved, Vet Approved Cloxazolam The therapeutic efficacy of Cloxazolam can be decreased when used in combination with Yohimbine. Approved, Investigational Clozapine The metabolism of Yohimbine can be decreased when combined with Clozapine. Approved Cobicistat The serum concentration of Yohimbine can be increased when it is combined with Cobicistat. Approved Cocaine The metabolism of Yohimbine can be decreased when combined with Cocaine. Approved, Illicit Conivaptan The serum concentration of Conivaptan can be increased when it is combined with Yohimbine. Approved, Investigational Crizotinib The metabolism of Yohimbine can be decreased when combined with Crizotinib. Approved Cryptenamine Yohimbine may decrease the antihypertensive activities of Cryptenamine. Approved Cyamemazine The therapeutic efficacy of Cyamemazine can be decreased when used in combination with Yohimbine. Approved Cyclobenzaprine The serum concentration of Yohimbine can be increased when it is combined with Cyclobenzaprine. Approved Cyclopenthiazide Yohimbine may decrease the antihypertensive activities of Cyclopenthiazide. Experimental Cyclosporine The metabolism of Yohimbine can be decreased when combined with Cyclosporine. Approved, Investigational, Vet Approved Cyclothiazide Yohimbine may decrease the antihypertensive activities of Cyclothiazide. Approved Dabrafenib The serum concentration of Yohimbine can be decreased when it is combined with Dabrafenib. Approved, Investigational Darifenacin The metabolism of Yohimbine can be decreased when combined with Darifenacin. Approved, Investigational Darunavir The serum concentration of Yohimbine can be increased when it is combined with Darunavir. Approved Dasatinib The serum concentration of Yohimbine can be increased when it is combined with Dasatinib. Approved, Investigational Debrisoquin Yohimbine may decrease the antihypertensive activities of Debrisoquin. Approved, Investigational Deferasirox The serum concentration of Yohimbine can be decreased when it is combined with Deferasirox. Approved, Investigational Delapril Yohimbine may decrease the antihypertensive activities of Delapril. Experimental Delavirdine The metabolism of Yohimbine can be decreased when combined with Delavirdine. Approved Deramciclane The therapeutic efficacy of Deramciclane can be decreased when used in combination with Yohimbine. Investigational Deserpidine Yohimbine may decrease the antihypertensive activities of Deserpidine. Approved Desipramine The serum concentration of Yohimbine can be increased when it is combined with Desipramine. Approved, Investigational Diazepam The therapeutic efficacy of Diazepam can be decreased when used in combination with Yohimbine. Approved, Illicit, Investigational, Vet Approved Diazoxide Yohimbine may decrease the antihypertensive activities of Diazoxide. Approved Dibenzepin The serum concentration of Yohimbine can be increased when it is combined with Dibenzepin. Experimental Diethylnorspermine Yohimbine may decrease the antihypertensive activities of Diethylnorspermine. Investigational Dihydralazine Yohimbine may decrease the antihypertensive activities of Dihydralazine. Approved, Investigational Dihydroergotamine The metabolism of Yohimbine can be decreased when combined with Dihydroergotamine. Approved, Investigational Diltiazem Yohimbine may decrease the antihypertensive activities of Diltiazem. Approved, Investigational Diphenhydramine The metabolism of Yohimbine can be decreased when combined with Diphenhydramine. Approved, Investigational Doramectin The therapeutic efficacy of Doramectin can be decreased when used in combination with Yohimbine. Vet Approved Dorzolamide Yohimbine may decrease the antihypertensive activities of Dorzolamide. Approved Dosulepin The serum concentration of Yohimbine can be increased when it is combined with Dosulepin. Approved Doxazosin Yohimbine may decrease the antihypertensive activities of Doxazosin. Approved Doxepin The serum concentration of Yohimbine can be increased when it is combined with Doxepin. Approved, Investigational Doxycycline The metabolism of Yohimbine can be decreased when combined with Doxycycline. Approved, Investigational, Vet Approved Dronedarone The metabolism of Yohimbine can be decreased when combined with Dronedarone. Approved Duloxetine The metabolism of Yohimbine can be decreased when combined with Duloxetine. Approved Efonidipine Yohimbine may decrease the antihypertensive activities of Efonidipine. Approved, Investigational Eliglustat The metabolism of Yohimbine can be decreased when combined with Eliglustat. Approved Emylcamate The therapeutic efficacy of Emylcamate can be decreased when used in combination with Yohimbine. Experimental Enalapril Yohimbine may decrease the antihypertensive activities of Enalapril. Approved, Vet Approved Enalaprilat Yohimbine may decrease the antihypertensive activities of Enalaprilat. Approved Endralazine Yohimbine may decrease the antihypertensive activities of Endralazine. Experimental Enzalutamide The serum concentration of Yohimbine can be decreased when it is combined with Enzalutamide. Approved Epanolol Yohimbine may decrease the antihypertensive activities of Epanolol. Experimental Epoprostenol Yohimbine may decrease the antihypertensive activities of Epoprostenol. Approved Eprosartan Yohimbine may decrease the antihypertensive activities of Eprosartan. Approved Erythromycin The metabolism of Yohimbine can be decreased when combined with Erythromycin. Approved, Investigational, Vet Approved Esmirtazapine The serum concentration of Yohimbine can be increased when it is combined with Esmirtazapine. Investigational Estazolam The therapeutic efficacy of Estazolam can be decreased when used in combination with Yohimbine. Approved, Illicit Ethyl loflazepate The therapeutic efficacy of Ethyl loflazepate can be decreased when used in combination with Yohimbine. Approved, Illicit Etifoxine The therapeutic efficacy of Etifoxine can be decreased when used in combination with Yohimbine. Investigational, Withdrawn Etizolam The therapeutic efficacy of Etizolam can be decreased when used in combination with Yohimbine. Approved Fabomotizole The therapeutic efficacy of Fabomotizole can be decreased when used in combination with Yohimbine. Experimental Felodipine Yohimbine may decrease the antihypertensive activities of Felodipine. Approved, Investigational Fenoldopam Yohimbine may decrease the antihypertensive activities of Fenoldopam. Approved Ferulic acid Yohimbine may decrease the antihypertensive activities of Ferulic acid. Experimental Fesoterodine The serum concentration of the active metabolites of Fesoterodine can be increased when Fesoterodine is used in combination with Yohimbine. Approved Fluconazole The metabolism of Yohimbine can be decreased when combined with Fluconazole. Approved, Investigational Fludiazepam The therapeutic efficacy of Fludiazepam can be decreased when used in combination with Yohimbine. Approved, Illicit Flunitrazepam The therapeutic efficacy of Flunitrazepam can be decreased when used in combination with Yohimbine. Approved, Illicit Fluoxetine The metabolism of Yohimbine can be decreased when combined with Fluoxetine. Approved, Vet Approved Flurazepam The therapeutic efficacy of Flurazepam can be decreased when used in combination with Yohimbine. Approved, Illicit, Investigational Fluvoxamine The therapeutic efficacy of Fluvoxamine can be decreased when used in combination with Yohimbine. Approved, Investigational Fosamprenavir The metabolism of Yohimbine can be decreased when combined with Fosamprenavir. Approved Fosaprepitant The serum concentration of Yohimbine can be increased when it is combined with Fosaprepitant. Approved Fosinopril Yohimbine may decrease the antihypertensive activities of Fosinopril. Approved Fosphenytoin The metabolism of Yohimbine can be increased when combined with Fosphenytoin. Approved, Investigational Fusidic Acid The serum concentration of Yohimbine can be increased when it is combined with Fusidic Acid. Approved, Investigational Gabapentin The therapeutic efficacy of Gabapentin can be decreased when used in combination with Yohimbine. Approved, Investigational Gedocarnil The therapeutic efficacy of Gedocarnil can be decreased when used in combination with Yohimbine. Experimental Gepirone The therapeutic efficacy of Gepirone can be decreased when used in combination with Yohimbine. Investigational Guanabenz Yohimbine may decrease the antihypertensive activities of Guanabenz. Approved, Investigational Guanadrel Yohimbine may decrease the antihypertensive activities of Guanadrel. Approved Guanazodine Yohimbine may decrease the antihypertensive activities of Guanazodine. Experimental Guanethidine Yohimbine may decrease the antihypertensive activities of Guanethidine. Approved Guanfacine Yohimbine may decrease the antihypertensive activities of Guanfacine. Approved, Investigational Guanoclor Yohimbine may decrease the antihypertensive activities of Guanoclor. Experimental Guanoxabenz Yohimbine may decrease the antihypertensive activities of Guanoxabenz. Experimental Guanoxan Yohimbine may decrease the antihypertensive activities of Guanoxan. Experimental Halazepam The therapeutic efficacy of Halazepam can be decreased when used in combination with Yohimbine. Approved, Illicit, Withdrawn Haloperidol The metabolism of Yohimbine can be decreased when combined with Haloperidol. Approved Hexamethonium Yohimbine may decrease the antihypertensive activities of Hexamethonium. Experimental Hydralazine Yohimbine may decrease the antihypertensive activities of Hydralazine. Approved Hydrochlorothiazide Yohimbine may decrease the antihypertensive activities of Hydrochlorothiazide. Approved, Vet Approved Hydroflumethiazide Yohimbine may decrease the antihypertensive activities of Hydroflumethiazide. Approved, Investigational Hydroxyzine The therapeutic efficacy of Hydroxyzine can be decreased when used in combination with Yohimbine. Approved Idelalisib The metabolism of Yohimbine can be decreased when combined with Idelalisib. Approved Imagabalin The therapeutic efficacy of Imagabalin can be decreased when used in combination with Yohimbine. Investigational Imatinib The metabolism of Yohimbine can be decreased when combined with Imatinib. Approved Imidapril Yohimbine may decrease the antihypertensive activities of Imidapril. Investigational Imipramine The serum concentration of Yohimbine can be increased when it is combined with Imipramine. Approved Indapamide Yohimbine may decrease the antihypertensive activities of Indapamide. Approved Indenolol Yohimbine may decrease the antihypertensive activities of Indenolol. Withdrawn Indinavir The metabolism of Yohimbine can be decreased when combined with Indinavir. Approved Indoramin Yohimbine may decrease the antihypertensive activities of Indoramin. Withdrawn Iprindole The serum concentration of Yohimbine can be increased when it is combined with Iprindole. Experimental Irbesartan Yohimbine may decrease the antihypertensive activities of Irbesartan. Approved, Investigational Isavuconazole The serum concentration of Yohimbine can be increased when it is combined with Isavuconazole. Approved, Investigational Isavuconazonium The metabolism of Yohimbine can be decreased when combined with Isavuconazonium. Approved, Investigational Isoniazid The metabolism of Yohimbine can be decreased when combined with Isoniazid. Approved, Investigational Isradipine Yohimbine may decrease the antihypertensive activities of Isradipine. Approved, Investigational Itraconazole The metabolism of Yohimbine can be decreased when combined with Itraconazole. Approved, Investigational Ivacaftor The serum concentration of Yohimbine can be increased when it is combined with Ivacaftor. Approved Ketanserin Yohimbine may decrease the antihypertensive activities of Ketanserin. Investigational Ketazolam The therapeutic efficacy of Ketazolam can be decreased when used in combination with Yohimbine. Approved Ketoconazole The metabolism of Yohimbine can be decreased when combined with Ketoconazole. Approved, Investigational Labetalol Yohimbine may decrease the antihypertensive activities of Labetalol. Approved Lacidipine Yohimbine may decrease the antihypertensive activities of Lacidipine. Approved, Investigational Latanoprost Yohimbine may decrease the antihypertensive activities of Latanoprost. Approved, Investigational Lercanidipine Yohimbine may decrease the antihypertensive activities of Lercanidipine. Approved, Investigational Linsidomine Yohimbine may decrease the antihypertensive activities of Linsidomine. Experimental Lisinopril Yohimbine may decrease the antihypertensive activities of Lisinopril. Approved, Investigational Lofepramine The serum concentration of Yohimbine can be increased when it is combined with Lofepramine. Experimental Lofexidine Yohimbine may decrease the antihypertensive activities of Lofexidine. Approved, Investigational Lopinavir The metabolism of Yohimbine can be decreased when combined with Lopinavir. Approved Loprazolam The therapeutic efficacy of Loprazolam can be decreased when used in combination with Yohimbine. Experimental Lorazepam The therapeutic efficacy of Lorazepam can be decreased when used in combination with Yohimbine. Approved Lorcaserin The metabolism of Yohimbine can be decreased when combined with Lorcaserin. Approved Lorpiprazole The serum concentration of Yohimbine can be increased when it is combined with Lorpiprazole. Approved Losartan Yohimbine may decrease the antihypertensive activities of Losartan. Approved Lovastatin The metabolism of Yohimbine can be decreased when combined with Lovastatin. Approved, Investigational Luliconazole The serum concentration of Yohimbine can be increased when it is combined with Luliconazole. Approved Lumacaftor The metabolism of Yohimbine can be increased when combined with Lumacaftor. Approved Lumefantrine The metabolism of Yohimbine can be decreased when combined with Lumefantrine. Approved Macitentan Yohimbine may decrease the antihypertensive activities of Macitentan. Approved Manidipine Yohimbine may decrease the antihypertensive activities of Manidipine. Approved, Investigational Mebicar The therapeutic efficacy of Mebicar can be decreased when used in combination with Yohimbine. Experimental Mebutamate The therapeutic efficacy of Mebutamate can be decreased when used in combination with Yohimbine. Approved Mecamylamine Yohimbine may decrease the antihypertensive activities of Mecamylamine. Approved, Investigational Medazepam The therapeutic efficacy of Medazepam can be decreased when used in combination with Yohimbine. Experimental Mephenoxalone The therapeutic efficacy of Mephenoxalone can be decreased when used in combination with Yohimbine. Experimental Meprobamate The therapeutic efficacy of Meprobamate can be decreased when used in combination with Yohimbine. Approved, Illicit Methadone The metabolism of Yohimbine can be decreased when combined with Methadone. Approved Methoserpidine Yohimbine may decrease the antihypertensive activities of Methoserpidine. Experimental Methotrimeprazine The metabolism of Yohimbine can be decreased when combined with Methotrimeprazine. Approved, Investigational Methyldopa Yohimbine may decrease the antihypertensive activities of Methyldopa. Approved Metipranolol Yohimbine may decrease the antihypertensive activities of Metipranolol. Approved Metolazone Yohimbine may decrease the antihypertensive activities of Metolazone. Approved Metoprolol The serum concentration of Metoprolol can be increased when it is combined with Yohimbine. Approved, Investigational Metyrosine Yohimbine may decrease the antihypertensive activities of Metyrosine. Approved Mibefradil Yohimbine may decrease the antihypertensive activities of Mibefradil. Investigational, Withdrawn Midazolam The therapeutic efficacy of Midazolam can be decreased when used in combination with Yohimbine. Approved, Illicit Midostaurin The metabolism of Yohimbine can be decreased when combined with Midostaurin. Approved, Investigational Mifepristone The serum concentration of Yohimbine can be increased when it is combined with Mifepristone. Approved, Investigational Minoxidil Yohimbine may decrease the antihypertensive activities of Minoxidil. Approved, Investigational Mirabegron The metabolism of Yohimbine can be decreased when combined with Mirabegron. Approved Mirtazapine The serum concentration of Yohimbine can be increased when it is combined with Mirtazapine. Approved Mitotane The serum concentration of Yohimbine can be decreased when it is combined with Mitotane. Approved Moexipril Yohimbine may decrease the antihypertensive activities of Moexipril. Approved Moxonidine Yohimbine may decrease the antihypertensive activities of Moxonidine. Approved, Investigational MRK-409 The therapeutic efficacy of MRK-409 can be decreased when used in combination with Yohimbine. Experimental Muzolimine Yohimbine may decrease the antihypertensive activities of Muzolimine. Experimental Nabilone The therapeutic efficacy of Nabilone can be decreased when used in combination with Yohimbine. Approved, Investigational Nadolol Yohimbine may decrease the antihypertensive activities of Nadolol. Approved Naftopidil Yohimbine may decrease the antihypertensive activities of Naftopidil. Investigational Nebivolol Yohimbine may decrease the antihypertensive activities of Nebivolol. Approved, Investigational Nefazodone The metabolism of Yohimbine can be decreased when combined with Nefazodone. Approved, Withdrawn Nelfinavir The metabolism of Yohimbine can be decreased when combined with Nelfinavir. Approved Netupitant The serum concentration of Yohimbine can be increased when it is combined with Netupitant. Approved, Investigational Nevirapine The metabolism of Yohimbine can be increased when combined with Nevirapine. Approved Nicardipine Yohimbine may decrease the antihypertensive activities of Nicardipine. Approved, Investigational Nicorandil Yohimbine may decrease the antihypertensive activities of Nicorandil. Approved, Investigational Niguldipine Yohimbine may decrease the antihypertensive activities of Niguldipine. Experimental Nilotinib The metabolism of Yohimbine can be decreased when combined with Nilotinib. Approved, Investigational Nilvadipine Yohimbine may decrease the antihypertensive activities of Nilvadipine. Approved, Investigational Nimodipine Yohimbine may decrease the antihypertensive activities of Nimodipine. Approved, Investigational Nisoldipine Yohimbine may decrease the antihypertensive activities of Nisoldipine. Approved Nitrazepam The therapeutic efficacy of Nitrazepam can be decreased when used in combination with Yohimbine. Approved Nitrendipine Yohimbine may decrease the antihypertensive activities of Nitrendipine. Approved, Investigational Nitroprusside Yohimbine may decrease the antihypertensive activities of Nitroprusside. Approved, Investigational Nortriptyline The serum concentration of Yohimbine can be increased when it is combined with Nortriptyline. Approved Olaparib The metabolism of Yohimbine can be decreased when combined with Olaparib. Approved Olmesartan Yohimbine may decrease the antihypertensive activities of Olmesartan. Approved, Investigational Omapatrilat Yohimbine may decrease the antihypertensive activities of Omapatrilat. Investigational Ondansetron The therapeutic efficacy of Ondansetron can be decreased when used in combination with Yohimbine. Approved Opipramol The serum concentration of Yohimbine can be increased when it is combined with Opipramol. Investigational Osimertinib The serum concentration of Yohimbine can be increased when it is combined with Osimertinib. Approved Oxazepam The therapeutic efficacy of Oxazepam can be decreased when used in combination with Yohimbine. Approved Oxprenolol The therapeutic efficacy of Oxprenolol can be decreased when used in combination with Yohimbine. Approved Palbociclib The serum concentration of Yohimbine can be increased when it is combined with Palbociclib. Approved, Investigational Panobinostat The serum concentration of Yohimbine can be increased when it is combined with Panobinostat. Approved, Investigational Pargyline Yohimbine may decrease the antihypertensive activities of Pargyline. Approved Paroxetine The metabolism of Yohimbine can be decreased when combined with Paroxetine. Approved, Investigational Peginterferon alfa-2b The serum concentration of Yohimbine can be decreased when it is combined with Peginterferon alfa-2b. Approved Penbutolol Yohimbine may decrease the antihypertensive activities of Penbutolol. Approved, Investigational Pentobarbital The metabolism of Yohimbine can be increased when combined with Pentobarbital. Approved, Investigational, Vet Approved Pentolinium Yohimbine may decrease the antihypertensive activities of Pentolinium. Approved Perindopril Yohimbine may decrease the antihypertensive activities of Perindopril. Approved Phenobarbital The metabolism of Yohimbine can be increased when combined with Phenobarbital. Approved, Investigational Phenoxybenzamine Yohimbine may decrease the antihypertensive activities of Phenoxybenzamine. Approved Phentolamine Yohimbine may decrease the antihypertensive activities of Phentolamine. Approved Phenytoin The metabolism of Yohimbine can be increased when combined with Phenytoin. Approved, Vet Approved Pinacidil Yohimbine may decrease the antihypertensive activities of Pinacidil. Approved Pinazepam The therapeutic efficacy of Pinazepam can be decreased when used in combination with Yohimbine. Experimental Pindolol Yohimbine may decrease the antihypertensive activities of Pindolol. Approved, Investigational Pitolisant The serum concentration of Pitolisant can be increased when it is combined with Yohimbine. Approved, Investigational Platelet Activating Factor Yohimbine may decrease the antihypertensive activities of Platelet Activating Factor. Experimental Polythiazide Yohimbine may decrease the antihypertensive activities of Polythiazide. Approved Posaconazole The metabolism of Yohimbine can be decreased when combined with Posaconazole. Approved, Investigational, Vet Approved Prazepam The therapeutic efficacy of Prazepam can be decreased when used in combination with Yohimbine. Approved, Illicit Prazosin Yohimbine may decrease the antihypertensive activities of Prazosin. Approved Pregabalin The therapeutic efficacy of Pregabalin can be decreased when used in combination with Yohimbine. Approved, Illicit, Investigational Primidone The metabolism of Yohimbine can be increased when combined with Primidone. Approved, Vet Approved Promazine The metabolism of Yohimbine can be decreased when combined with Promazine. Approved, Vet Approved Propranolol Yohimbine may decrease the antihypertensive activities of Propranolol. Approved, Investigational Protriptyline The serum concentration of Yohimbine can be increased when it is combined with Protriptyline. Approved Quinapril Yohimbine may decrease the antihypertensive activities of Quinapril. Approved, Investigational Quinidine The metabolism of Yohimbine can be decreased when combined with Quinidine. Approved, Investigational Quinine The metabolism of Yohimbine can be decreased when combined with Quinine. Approved Ramipril Yohimbine may decrease the antihypertensive activities of Ramipril. Approved Ranolazine The metabolism of Yohimbine can be decreased when combined with Ranolazine. Approved, Investigational Remikiren Yohimbine may decrease the antihypertensive activities of Remikiren. Approved Rescinnamine Yohimbine may decrease the antihypertensive activities of Rescinnamine. Approved Reserpine Yohimbine may decrease the antihypertensive activities of Reserpine. Approved, Investigational Rifabutin The metabolism of Yohimbine can be increased when combined with Rifabutin. Approved, Investigational Rifampicin The metabolism of Yohimbine can be increased when combined with Rifampicin. Approved Rifapentine The metabolism of Yohimbine can be increased when combined with Rifapentine. Approved, Investigational Rilmenidine Yohimbine may decrease the antihypertensive activities of Rilmenidine. Approved, Investigational Riociguat Yohimbine may decrease the antihypertensive activities of Riociguat. Approved Ritanserin The therapeutic efficacy of Ritanserin can be decreased when used in combination with Yohimbine. Investigational Ritonavir The metabolism of Yohimbine can be decreased when combined with Ritonavir. Approved, Investigational Rolapitant The metabolism of Yohimbine can be decreased when combined with Rolapitant. Approved, Investigational Ropinirole The metabolism of Yohimbine can be decreased when combined with Ropinirole. Approved, Investigational Rucaparib The metabolism of Yohimbine can be decreased when combined with Rucaparib. Approved, Investigational Saprisartan Yohimbine may decrease the antihypertensive activities of Saprisartan. Experimental Saquinavir The metabolism of Yohimbine can be decreased when combined with Saquinavir. Approved, Investigational Sarilumab The therapeutic efficacy of Yohimbine can be decreased when used in combination with Sarilumab. Approved, Investigational Selexipag Yohimbine may decrease the antihypertensive activities of Selexipag. Approved Sertraline The metabolism of Yohimbine can be decreased when combined with Sertraline. Approved Sildenafil The metabolism of Yohimbine can be decreased when combined with Sildenafil. Approved, Investigational Siltuximab The serum concentration of Yohimbine can be decreased when it is combined with Siltuximab. Approved, Investigational Simeprevir The serum concentration of Yohimbine can be increased when it is combined with Simeprevir. Approved Sitaxentan Yohimbine may decrease the antihypertensive activities of Sitaxentan. Approved, Investigational, Withdrawn Spirapril Yohimbine may decrease the antihypertensive activities of Spirapril. Approved St. John's Wort The serum concentration of Yohimbine can be decreased when it is combined with St. John's Wort. Approved, Investigational, Nutraceutical Stiripentol The serum concentration of Yohimbine can be increased when it is combined with Stiripentol. Approved Sulfisoxazole The metabolism of Yohimbine can be decreased when combined with Sulfisoxazole. Approved, Vet Approved Talinolol Yohimbine may decrease the antihypertensive activities of Talinolol. Investigational Tandospirone The therapeutic efficacy of Tandospirone can be decreased when used in combination with Yohimbine. Investigational Telaprevir The metabolism of Yohimbine can be decreased when combined with Telaprevir. Approved, Withdrawn Telithromycin The metabolism of Yohimbine can be decreased when combined with Telithromycin. Approved Telmisartan Yohimbine may decrease the antihypertensive activities of Telmisartan. Approved, Investigational Temazepam The therapeutic efficacy of Temazepam can be decreased when used in combination with Yohimbine. Approved, Investigational Temocapril Yohimbine may decrease the antihypertensive activities of Temocapril. Experimental, Investigational Terbinafine The metabolism of Yohimbine can be decreased when combined with Terbinafine. Approved, Investigational, Vet Approved Terlipressin Yohimbine may decrease the antihypertensive activities of Terlipressin. Approved, Investigational Tetrahydropalmatine Yohimbine may decrease the antihypertensive activities of Tetrahydropalmatine. Investigational Theodrenaline Yohimbine may decrease the antihypertensive activities of Theodrenaline. Investigational Thioridazine The serum concentration of Thioridazine can be increased when it is combined with Yohimbine. Approved, Withdrawn Tianeptine The serum concentration of Yohimbine can be increased when it is combined with Tianeptine. Approved, Investigational Tibolone Yohimbine may decrease the antihypertensive activities of Tibolone. Approved, Investigational Ticlopidine The metabolism of Yohimbine can be decreased when combined with Ticlopidine. Approved Ticrynafen Yohimbine may decrease the antihypertensive activities of Ticrynafen. Withdrawn Timolol Yohimbine may decrease the antihypertensive activities of Timolol. Approved Tipranavir The metabolism of Yohimbine can be decreased when combined with Tipranavir. Approved, Investigational Tocilizumab The serum concentration of Yohimbine can be decreased when it is combined with Tocilizumab. Approved Tofisopam The therapeutic efficacy of Tofisopam can be decreased when used in combination with Yohimbine. Approved Tolazoline Yohimbine may decrease the antihypertensive activities of Tolazoline. Approved, Vet Approved Tolonidine Yohimbine may decrease the antihypertensive activities of Tolonidine. Experimental Torasemide Yohimbine may decrease the antihypertensive activities of Torasemide. Approved Trandolapril Yohimbine may decrease the antihypertensive activities of Trandolapril. Approved Tranylcypromine The therapeutic efficacy of Tranylcypromine can be decreased when used in combination with Yohimbine. Approved, Investigational Travoprost Yohimbine may decrease the antihypertensive activities of Travoprost. Approved Trazodone The therapeutic efficacy of Trazodone can be decreased when used in combination with Yohimbine. Approved, Investigational Treprostinil Yohimbine may decrease the antihypertensive activities of Treprostinil. Approved, Investigational Triazolam The therapeutic efficacy of Triazolam can be decreased when used in combination with Yohimbine. Approved, Investigational Trichlormethiazide Yohimbine may decrease the antihypertensive activities of Trichlormethiazide. Approved, Vet Approved Trimazosin Yohimbine may decrease the antihypertensive activities of Trimazosin. Experimental Trimethaphan Yohimbine may decrease the antihypertensive activities of Trimethaphan. Approved, Investigational Trimipramine The serum concentration of Yohimbine can be increased when it is combined with Trimipramine. Approved Unoprostone Yohimbine may decrease the antihypertensive activities of Unoprostone. Approved, Investigational Urapidil Yohimbine may decrease the antihypertensive activities of Urapidil. Investigational Valsartan Yohimbine may decrease the antihypertensive activities of Valsartan. Approved, Investigational Vemurafenib The serum concentration of Yohimbine can be decreased when it is combined with Vemurafenib. Approved Venlafaxine The metabolism of Yohimbine can be decreased when combined with Venlafaxine. Approved Verapamil The metabolism of Yohimbine can be decreased when combined with Verapamil. Approved Vincamine Yohimbine may decrease the antihypertensive activities of Vincamine. Experimental Vinpocetine Yohimbine may decrease the antihypertensive activities of Vinpocetine. Investigational Voriconazole The metabolism of Yohimbine can be decreased when combined with Voriconazole. Approved, Investigational Vortioxetine The therapeutic efficacy of Vortioxetine can be decreased when used in combination with Yohimbine. Approved, Investigational Xipamide Yohimbine may decrease the antihypertensive activities of Xipamide. Experimental Xylometazoline Yohimbine may decrease the antihypertensive activities of Xylometazoline. Approved, Investigational Ziprasidone The metabolism of Yohimbine can be decreased when combined with Ziprasidone. Approved Zofenopril Yohimbine may decrease the antihypertensive activities of Zofenopril. Experimental Zolazepam The therapeutic efficacy of Zolazepam can be decreased when used in combination with Yohimbine. Vet Approved - Food Interactions
- Not Available
References
- Synthesis Reference
Germain Saint-Ruf, Pham Huu Chanh, Buu Hoi, "Yohimbine derivatives, process for their preparation and their applications." U.S. Patent US3940387, issued April, 1960.
US3940387- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015464
- KEGG Compound
- C09256
- PubChem Compound
- 8969
- PubChem Substance
- 46504602
- ChemSpider
- 8622
- BindingDB
- 50013515
- ChEBI
- 10093
- ChEMBL
- CHEMBL15245
- Therapeutic Targets Database
- DAP000087
- PharmGKB
- PA451946
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Yohimbine
- ATC Codes
- G04BE04 — Yohimbine
- AHFS Codes
- 92:92.00 — Other Miscellaneous Therapeutic Agents
- MSDS
- Download (73.3 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Amerisource Health Services Corp.
- Baroli
- Carlisle Laboratories Inc.
- Concord Labs
- Contract Pharm
- Eon Labs
- Glenwood Laboratories
- Iopharm Laboratories Inc.
- Major Pharmaceuticals
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmedix
- Physicians Total Care Inc.
- Professional Co.
- Southwood Pharmaceuticals
- Star Pharmaceuticals Inc.
- West-Ward Pharmaceuticals
- Dosage forms
Form Route Strength Tablet Oral 2 mg Tablet Oral 5.4 mg Tablet Oral 6 mg - Prices
Unit description Cost Unit Yohimbine hcl powder 22.8USD g Yohimbine 5.4 mg tablet 1.04USD tablet Yocon 5.4 mg tablet 0.96USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 241 °C PhysProp logP 2.73 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.348 mg/mL ALOGPS logP 2.36 ALOGPS logP 2.1 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 14.68 ChemAxon pKa (Strongest Basic) 7.65 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 65.56 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 99.63 m3·mol-1 ChemAxon Polarizability 40.22 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9782 Blood Brain Barrier - 0.5738 Caco-2 permeable + 0.8866 P-glycoprotein substrate Substrate 0.8762 P-glycoprotein inhibitor I Inhibitor 0.6002 P-glycoprotein inhibitor II Non-inhibitor 0.9318 Renal organic cation transporter Inhibitor 0.5738 CYP450 2C9 substrate Non-substrate 0.8514 CYP450 2D6 substrate Substrate 0.8919 CYP450 3A4 substrate Substrate 0.5677 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9094 CYP450 3A4 inhibitor Non-inhibitor 0.8333 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.8681 Carcinogenicity Non-carcinogens 0.9696 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7324 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8104 hERG inhibition (predictor II) Non-inhibitor 0.6141
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0006-3921000000-e28dd8692e2b8dd63330
Taxonomy
- Description
- This compound belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Yohimbine alkaloids
- Sub Class
- Not Available
- Direct Parent
- Yohimbine alkaloids
- Alternative Parents
- Corynanthean-type alkaloids / Beta carbolines / 3-alkylindoles / Aralkylamines / Beta hydroxy acids and derivatives / Benzenoids / Piperidines / Pyrroles / Heteroaromatic compounds / Methyl esters show 10 more
- Substituents
- Yohimbine / Corynanthean skeleton / Yohimbine alkaloid / Beta-carboline / Pyridoindole / 3-alkylindole / Indole / Indole or derivatives / Aralkylamine / Beta-hydroxy acid show 27 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- methyl 17-hydroxy-20xi-yohimban-16-carboxylate (CHEBI:10093) / Indole alkaloids (C09256)
Targets
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Laurila JM, Xhaard H, Ruuskanen JO, Rantanen MJ, Karlsson HK, Johnson MS, Scheinin M: The second extracellular loop of alpha2A-adrenoceptors contributes to the binding of yohimbine analogues. Br J Pharmacol. 2007 Aug;151(8):1293-304. Epub 2007 Jun 11. [PubMed:17558432]
- Zadori ZS, Shujaa N, Fulop K, Dunkel P, Gyires K: Pre- and postsynaptic mechanisms in the clonidine- and oxymetazoline-induced inhibition of gastric motility in the rat. Neurochem Int. 2007 Oct;51(5):297-305. Epub 2007 Jun 30. [PubMed:17664022]
- Paul BZ, Jin J, Kunapuli SP: Molecular mechanism of thromboxane A(2)-induced platelet aggregation. Essential role for p2t(ac) and alpha(2a) receptors. J Biol Chem. 1999 Oct 8;274(41):29108-14. [PubMed:10506165]
- Kalkman HO, Loetscher E: alpha2C-Adrenoceptor blockade by clozapine and other antipsychotic drugs. Eur J Pharmacol. 2003 Feb 21;462(1-3):33-40. [PubMed:12591093]
- Ozdogan UK, Lahdesmaki J, Scheinin M: The analgesic efficacy of partial opioid agonists is increased in mice with targeted inactivation of the alpha2A-adrenoceptor gene. Eur J Pharmacol. 2006 Jan 4;529(1-3):105-13. Epub 2005 Dec 2. [PubMed:16325800]
- Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Epinephrine binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
- Gene Name
- ADRA2B
- Uniprot ID
- P18089
- Uniprot Name
- Alpha-2B adrenergic receptor
- Molecular Weight
- 49565.8 Da
References
- Freitag A, Wessler I, Racke K: Adrenoceptor- and cholinoceptor-mediated mechanisms in the regulation of 5-hydroxytryptamine release from isolated tracheae of newborn rabbits. Br J Pharmacol. 1996 Sep;119(1):91-8. [PubMed:8872361]
- Cleary L, Vandeputte C, Docherty JR: Investigation of neurotransmission in vas deferens from alpha(2A/D)-adrenoceptor knockout mice. Br J Pharmacol. 2002 Jul;136(6):857-64. [PubMed:12110610]
- Gyires K, Mullner K, Ronai AZ: Functional evidence that gastroprotection can be induced by activation of central alpha(2B)-adrenoceptor subtypes in the rat. Eur J Pharmacol. 2000 May 19;396(2-3):131-5. [PubMed:10822066]
- Takada K, Clark DJ, Davies MF, Tonner PH, Krause TK, Bertaccini E, Maze M: Meperidine exerts agonist activity at the alpha(2B)-adrenoceptor subtype. Anesthesiology. 2002 Jun;96(6):1420-6. [PubMed:12170055]
- Alonso E, Garrido E, Diez-Fernandez C, Perez-Garcia C, Herradon G, Ezquerra L, Deuel TF, Alguacil LF: Yohimbine prevents morphine-induced changes of glial fibrillary acidic protein in brainstem and alpha2-adrenoceptor gene expression in hippocampus. Neurosci Lett. 2007 Jan 29;412(2):163-7. Epub 2006 Nov 22. [PubMed:17123717]
- Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Protein homodimerization activity
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
- Gene Name
- ADRA2C
- Uniprot ID
- P18825
- Uniprot Name
- Alpha-2C adrenergic receptor
- Molecular Weight
- 49521.585 Da
References
- Lalchandani SG, Lei L, Zheng W, Suni MM, Moore BM, Liggett SB, Miller DD, Feller DR: Yohimbine dimers exhibiting selectivity for the human alpha 2C-adrenoceptor subtype. J Pharmacol Exp Ther. 2002 Dec;303(3):979-84. [PubMed:12438517]
- Rizzo CA, Ruck LM, Corboz MR, Umland SP, Wan Y, Shah H, Jakway J, Cheng L, McCormick K, Egan RW, Hey JA: Postjunctional alpha(2C)-adrenoceptor contractility in human saphenous vein. Eur J Pharmacol. 2001 Feb 16;413(2-3):263-9. [PubMed:11226402]
- Cleary L, Murad K, Bexis S, Docherty JR: The alpha (1D)-adrenoceptor antagonist BMY 7378 is also an alpha (2C)-adrenoceptor antagonist. Auton Autacoid Pharmacol. 2005 Oct;25(4):135-41. [PubMed:16176444]
- Kalkman HO, Loetscher E: alpha2C-Adrenoceptor blockade by clozapine and other antipsychotic drugs. Eur J Pharmacol. 2003 Feb 21;462(1-3):33-40. [PubMed:12591093]
- Cleary L, Vandeputte C, Docherty JR: Investigation of neurotransmission in vas deferens from alpha(2A/D)-adrenoceptor knockout mice. Br J Pharmacol. 2002 Jul;136(6):857-64. [PubMed:12110610]
- Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
- Gene Name
- HTR1A
- Uniprot ID
- P08908
- Uniprot Name
- 5-hydroxytryptamine receptor 1A
- Molecular Weight
- 46106.335 Da
References
- Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
- Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
- Gene Name
- HTR1B
- Uniprot ID
- P28222
- Uniprot Name
- 5-hydroxytryptamine receptor 1B
- Molecular Weight
- 43567.535 Da
References
- Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
- Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
- Gene Name
- HTR1D
- Uniprot ID
- P28221
- Uniprot Name
- 5-hydroxytryptamine receptor 1D
- Molecular Weight
- 41906.38 Da
References
- Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Potassium channel regulator activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase.
- Gene Name
- DRD2
- Uniprot ID
- P14416
- Uniprot Name
- D(2) dopamine receptor
- Molecular Weight
- 50618.91 Da
References
- Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- G-protein coupled amine receptor activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which inhibit adenylyl cyclase. Promotes cell proliferation.
- Gene Name
- DRD3
- Uniprot ID
- P35462
- Uniprot Name
- D(3) dopamine receptor
- Molecular Weight
- 44224.335 Da
References
- Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, Coge F, Galizzi JP, Boutin JA, Rivet JM, Dekeyne A, Gobert A: Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states. Synapse. 2000 Feb;35(2):79-95. [PubMed:10611634]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Virus receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
- Gene Name
- HTR2A
- Uniprot ID
- P28223
- Uniprot Name
- 5-hydroxytryptamine receptor 2A
- Molecular Weight
- 52602.58 Da
References
- Baxter GS, Murphy OE, Blackburn TP: Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle. Br J Pharmacol. 1994 May;112(1):323-31. [PubMed:8032658]
- Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
- Gene Name
- HTR2C
- Uniprot ID
- P28335
- Uniprot Name
- 5-hydroxytryptamine receptor 2C
- Molecular Weight
- 51820.705 Da
References
- Baxter GS, Murphy OE, Blackburn TP: Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle. Br J Pharmacol. 1994 May;112(1):323-31. [PubMed:8032658]
- Kaumann AJ: Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors. Naunyn Schmiedebergs Arch Pharmacol. 1983 Jun;323(2):149-54. [PubMed:6136920]
- Kind
- Protein group
- Organism
- Human
- Pharmacological action
- Unknown
- General Function
- Phosphatidylinositol-4,5-bisphosphate binding
- Specific Function
- In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than...
Components:
References
- Plant TD, Henquin JC: Phentolamine and yohimbine inhibit ATP-sensitive K+ channels in mouse pancreatic beta-cells. Br J Pharmacol. 1990 Sep;101(1):115-20. [PubMed:2282453]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Serotonin receptor activity
- Specific Function
- G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various ergot alkaloid derivatives and psychoactive substances. Ligand binding causes a conformation...
- Gene Name
- HTR2B
- Uniprot ID
- P41595
- Uniprot Name
- 5-hydroxytryptamine receptor 2B
- Molecular Weight
- 54297.41 Da
References
- Baxter GS, Murphy OE, Blackburn TP: Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle. Br J Pharmacol. 1994 May;112(1):323-31. [PubMed:8032658]
- Bonhaus DW, Weinhardt KK, Taylor M, DeSouza A, McNeeley PM, Szczepanski K, Fontana DJ, Trinh J, Rocha CL, Dawson MW, Flippin LA, Eglen RM: RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist. Neuropharmacology. 1997 Apr-May;36(4-5):621-9. [PubMed:9225287]
Enzymes
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Drug created on July 08, 2007 11:00 / Updated on April 17, 2018 01:06