Yohimbine - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (12)Enzymes (2)

Targets (12)Enzymes (2)Biointeractions (14)

Identification

Name

Yohimbine

Accession Number

DB01392

Type

Small Molecule

Groups

Approved, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

External IDs

Not Available

Product Ingredients

Ingredient	UNII	CAS	InChI Key	Details
Yohimbine hydrochloride	NB2E1YP49F	65-19-0	PIPZGJSEDRMUAW-VJDCAHTMSA-N	Details

Approved 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

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Name	Company
Actibine	Not Available
Aphrodyne	Not Available
Baron-X	Not Available
Dayto himbin	Not Available
Thybine	Not Available
Yocon	Not Available
Yohimar	Not Available
Yohimex	Not Available
Yoman	Not Available
Yovital	Not Available

Brand mixtures

Not Available

Categories

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	Kind	Pharmacological action	Actions	Organism	UniProt ID
Alpha-2A adrenergic receptor	Protein	yes	antagonist	Human	P08913	details
Alpha-2B adrenergic receptor	Protein	yes	antagonist	Human	P18089	details
Alpha-2C adrenergic receptor	Protein	yes	antagonist	Human	P18825	details
5-hydroxytryptamine receptor 1A	Protein	unknown	partial agonist	Human	P08908	details
5-hydroxytryptamine receptor 1B	Protein	unknown	antagonist	Human	P28222	details
5-hydroxytryptamine receptor 1D	Protein	unknown	antagonist	Human	P28221	details
D(2) dopamine receptor	Protein	unknown	antagonist	Human	P14416	details
D(3) dopamine receptor	Protein	unknown	antagonist	Human	P35462	details
5-hydroxytryptamine receptor 2A	Protein	unknown	antagonist	Human	P28223	details
5-hydroxytryptamine receptor 2C	Protein	unknown	antagonist	Human	P28335	details
ATP-sensitive potassium channel	Protein group	unknown	Not Available	Human	not applicable	details
5-hydroxytryptamine receptor 2B	Protein	unknown	antagonist	Human	P41595	details

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
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
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
Bethanidine	Yohimbine may decrease the antihypertensive activities of Bethanidine.	Approved
Bexarotene	The serum concentration of Yohimbine can be decreased when it is combined with Bexarotene.	Approved, Investigational
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.	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
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
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
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.	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
Chlormezanone	The therapeutic efficacy of Chlormezanone can be decreased when used in combination with Yohimbine.	Approved, Withdrawn
Chloroquine	The metabolism of Yohimbine can be decreased when combined with Chloroquine.	Approved, 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, 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
Cilazapril	Yohimbine may decrease the antihypertensive activities of Cilazapril.	Approved
Cimetidine	The metabolism of Yohimbine can be decreased when combined with Cimetidine.	Approved
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
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, Vet Approved
Clonidine	Yohimbine may decrease the antihypertensive activities of Clonidine.	Approved
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 Yohimbine can be increased when it is combined with Conivaptan.	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
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
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
Deferasirox	The serum concentration of Yohimbine can be decreased when it is combined with Deferasirox.	Approved, Investigational
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
Dexamethasone	The serum concentration of Yohimbine can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Diazepam	The therapeutic efficacy of Diazepam can be decreased when used in combination with Yohimbine.	Approved, Illicit, Vet Approved
Diazoxide	Yohimbine may decrease the antihypertensive activities of Diazoxide.	Approved
Dihydralazine	Yohimbine may decrease the antihypertensive activities of Dihydralazine.	Investigational
Dihydroergotamine	The metabolism of Yohimbine can be decreased when combined with Dihydroergotamine.	Approved
Diltiazem	Yohimbine may decrease the antihypertensive activities of Diltiazem.	Approved
Diphenhydramine	The metabolism of Yohimbine can be decreased when combined with Diphenhydramine.	Approved
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
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
Efavirenz	The serum concentration of Yohimbine can be decreased when it is combined with Efavirenz.	Approved, Investigational
Efonidipine	Yohimbine may decrease the antihypertensive activities of Efonidipine.	Approved
Eliglustat	The metabolism of Yohimbine can be decreased when combined with Eliglustat.	Approved
Enalapril	Yohimbine may decrease the antihypertensive activities of Enalapril.	Approved, Vet Approved
Enalaprilat	Yohimbine may decrease the antihypertensive activities of Enalaprilat.	Approved
Enzalutamide	The serum concentration of Yohimbine can be decreased when it is combined with Enzalutamide.	Approved
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, Vet Approved
Eslicarbazepine acetate	The serum concentration of Yohimbine can be decreased when it is combined with Eslicarbazepine acetate.	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.	Withdrawn
Etizolam	The therapeutic efficacy of Etizolam can be decreased when used in combination with Yohimbine.	Approved
Etravirine	The serum concentration of Yohimbine can be decreased when it is combined with Etravirine.	Approved
Felodipine	Yohimbine may decrease the antihypertensive activities of Felodipine.	Approved, Investigational
Fenoldopam	Yohimbine may decrease the antihypertensive activities of Fenoldopam.	Approved
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
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
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
Fusidic Acid	The serum concentration of Yohimbine can be increased when it is combined with Fusidic Acid.	Approved
Gabapentin	The therapeutic efficacy of Gabapentin can be decreased when used in combination with Yohimbine.	Approved, Investigational
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
Guanadrel	Yohimbine may decrease the antihypertensive activities of Guanadrel.	Approved
Guanethidine	Yohimbine may decrease the antihypertensive activities of Guanethidine.	Approved
Guanfacine	Yohimbine may decrease the antihypertensive activities of Guanfacine.	Approved, Investigational
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
Hydroxyzine	The therapeutic efficacy of Hydroxyzine can be decreased when used in combination with Yohimbine.	Approved
Idelalisib	The serum concentration of Yohimbine can be increased when it is combined with Idelalisib.	Approved
Imagabalin	The therapeutic efficacy of Pd 0332334 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
Irbesartan	Yohimbine may decrease the antihypertensive activities of Irbesartan.	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
Isradipine	Yohimbine may decrease the antihypertensive activities of Isradipine.	Approved
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
Latanoprost	Yohimbine may decrease the antihypertensive activities of Latanoprost.	Approved, Investigational
Lercanidipine	Yohimbine may decrease the antihypertensive activities of Lercanidipine.	Approved, Investigational
Lisinopril	Yohimbine may decrease the antihypertensive activities of Lisinopril.	Approved, Investigational
Lofexidine	Yohimbine may decrease the antihypertensive activities of Lofexidine.	Approved, Investigational
Lopinavir	The metabolism of Yohimbine can be decreased when combined with Lopinavir.	Approved
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
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
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
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
Methotrimeprazine	The metabolism of Yohimbine can be decreased when combined with Methotrimeprazine.	Approved
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.	Withdrawn
Midazolam	The therapeutic efficacy of Midazolam can be decreased when used in combination with Yohimbine.	Approved, Illicit
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
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
Modafinil	The serum concentration of Yohimbine can be decreased when it is combined with Modafinil.	Approved, Investigational
Moexipril	Yohimbine may decrease the antihypertensive activities of Moexipril.	Approved
Moxonidine	Yohimbine may decrease the antihypertensive activities of Moxonidine.	Approved
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
Nafcillin	The serum concentration of Yohimbine can be decreased when it is combined with Nafcillin.	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
Nevirapine	The metabolism of Yohimbine can be increased when combined with Nevirapine.	Approved
Nicardipine	Yohimbine may decrease the antihypertensive activities of Nicardipine.	Approved
Nicorandil	Yohimbine may decrease the antihypertensive activities of Nicorandil.	Approved
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
Nimodipine	Yohimbine may decrease the antihypertensive activities of Nimodipine.	Approved
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
Nitroprusside	Yohimbine may decrease the antihypertensive activities of Nitroprusside.	Approved
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
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, 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
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.	Withdrawn
Pindolol	Yohimbine may decrease the antihypertensive activities of Pindolol.	Approved
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
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
Rifabutin	The metabolism of Yohimbine can be increased when combined with Rifabutin.	Approved
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
Rilmenidine	Yohimbine may decrease the antihypertensive activities of Rilmenidine.	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
Ropinirole	The metabolism of Yohimbine can be decreased when combined with Ropinirole.	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
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
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.	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
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.	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
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
Thioridazine	The serum concentration of Thioridazine can be increased when it is combined with Yohimbine.	Withdrawn
Tianeptine	The serum concentration of Yohimbine can be increased when it is combined with Tianeptine.	Approved
Tibolone	Yohimbine may decrease the antihypertensive activities of Tibolone.	Approved
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
Torasemide	Yohimbine may decrease the antihypertensive activities of Torasemide.	Approved
Trandolapril	Yohimbine may decrease the antihypertensive activities of Trandolapril.	Approved
Trans-2-Phenylcyclopropylamine	The therapeutic efficacy of Trans-2-Phenylcyclopropylamine can be decreased when used in combination with Yohimbine.	Experimental
Tranylcypromine	The therapeutic efficacy of Tranylcypromine can be decreased when used in combination with Yohimbine.	Approved
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
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
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
Valsartan	Yohimbine may decrease the antihypertensive activities of Valsartan.	Approved, Investigational
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
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
Xylometazoline	Yohimbine may decrease the antihypertensive activities of Xylometazoline.	Approved
Ziprasidone	The metabolism of Yohimbine can be decreased when combined with Ziprasidone.	Approved
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

Resource	Link
Human Metabolome Database (HMDB)	HMDB15464
KEGG Compound	C09256
PubChem Compound	8969
PubChem Substance	46504602
ChemSpider	8622
BindingDB	50013515
ChEBI	10093
ChEMBL	CHEMBL15245
Therapeutic Targets Database	DAP000087
PharmGKB	PA451946
Drug Product Database	20371
RxList	http://www.rxlist.com/cgi/generic/yohimbine.htm
Drugs.com	http://www.drugs.com/cdi/yohimbine.html
PDRhealth	http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/yoc1492.shtml
Wikipedia	Yohimbine

ATC Codes

G04BE04 — Yohimbine

AHFS Codes

92:00.00

PDB Entries

Not Available

FDA label

Not Available

MSDS

Download (73.3 KB)

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Not Yet Recruiting	Treatment	Autonomic Nervous System Diseases / Hypertensive / Idiopathic orthostatic hypotension	1
1	Completed	Not Available	Autonomic Failure / Idiopathic orthostatic hypotension	1
1	Recruiting	Treatment	Heroin Dependence / Opioid Use Disorders	1
1, 2	Completed	Treatment	Healthy Volunteers	1
2	Completed	Not Available	Depression, Involutional / Major Depresssion	1
2	Completed	Treatment	Alcoholism	1
2	Completed	Treatment	Post-Traumatic Stress Disorder (PTSD)	1
2	Completed	Treatment	Type 2 Diabetes Mellitus	1
3	Completed	Treatment	Social Anxiety Disorder (SAD)	1
4	Completed	Not Available	Erectile Dysfunction (ED)	1
4	Completed	Treatment	Autoregulation / Blood Flow Velocity / Physiology, Ocular	1
Not Available	Completed	Not Available	Cocaine Related Disorders	1
Not Available	Completed	Not Available	Healthy Volunteers	2
Not Available	Completed	Basic Science	Intrusive Memories	1
Not Available	Recruiting	Basic Science	Early Life Trauma / Major Depressive Disorder (MDD)	1
Not Available	Unknown Status	Basic Science	Pain	1

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0006-3921000000-e28dd8692e2b8dd63330	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

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

Substituents

Yohimbine / Corynanthean skeleton / Yohimbine alkaloid / Beta-carboline / Pyridoindole / 3-alkylindole / Indole / Indole or derivatives / Aralkylamine / Beta-hydroxy acid

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl 17-hydroxy-20xi-yohimban-16-carboxylate (CHEBI:10093 ) / Indole alkaloids (C09256 )

Targets

Details

1. Alpha-2A adrenergic receptor

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 oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianser...
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 ]

Details

2. Alpha-2B adrenergic receptor

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 > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phent...
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 ]

Details

3. Alpha-2C adrenergic receptor

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 ]

Details

4. 5-hydroxytryptamine receptor 1A

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 signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate cyclase. Beta-arrestin family members inhibit signaling via G pro...
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 ]

Details

5. 5-hydroxytryptamine receptor 1B

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 substances, such as lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of ...
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 ]

Details

6. 5-hydroxytryptamine receptor 1D

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 substances. Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors, such as adenylate c...
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 ]

Details

7. D(2) dopamine receptor

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 ]

Details

8. D(3) dopamine receptor

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 ]

Details

9. 5-hydroxytryptamine receptor 2A

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-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates...
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 ]

Details

10. 5-hydroxytryptamine receptor 2C

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-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modul...
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 ]

Details

11. ATP-sensitive potassium channel (Protein Group)

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 out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium.

Components:

Name	UniProt ID	Details
ATP-sensitive inward rectifier potassium channel 1	P48048	Details
ATP-sensitive inward rectifier potassium channel 10	P78508	Details
ATP-sensitive inward rectifier potassium channel 11	Q14654	Details
ATP-sensitive inward rectifier potassium channel 12	Q14500	Details
ATP-sensitive inward rectifier potassium channel 14	Q9UNX9	Details
ATP-sensitive inward rectifier potassium channel 15	Q99712	Details
ATP-sensitive inward rectifier potassium channel 8	Q15842	Details

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 ]

Details

12. 5-hydroxytryptamine receptor 2B

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 change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins ...
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

Details

1. Cytochrome P450 2D6

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 antidepressants.
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 ]

Details

2. Cytochrome P450 3A4

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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
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 September 01, 2017 10:39

Structure for DB01392 (Yohimbine)

Targets

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Components:

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Enzymes

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