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References

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Economics

Properties

Spectra

Taxonomy

Yohimbine

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

Identification

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.

Structure

Similar Structures

Synonyms

(+)-yohimbine
(16α,17α)-17-hydroxyyohimban-16-carboxylic acid methyl ester
17α-hydroxyyohimban-16α-carboxylic acid methyl ester
Johimbin
Quebrachin
Yohimbic acid methyl ester
Yohimbin
Yohimbine
Yohimbinum

Product Ingredients

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

Prescription Products

Name	Dosage	Route	Labeller	Marketing Start	Marketing End
Unlock Additional Data
Yocon Tablet 5.4mg	Tablet	Oral	Palisades Pharmaceuticals Inc.	1988-12-31	2010-07-16
Yohimbine HCl 2mg	Tablet	Oral	Odan Laboratories Ltd	1992-12-31	2010-07-19
Yohimbine HCl 5.4mg	Tablet	Oral	Odan Laboratories Ltd	1996-09-09	2010-07-19
Yohimbine Hydrochloride Tab 2mg	Tablet	Oral	Odan Laboratories Ltd	1992-12-31	Not applicable
Yohimbine Hydrochloride Tablets 5.4mg	Tablet	Oral	Tanta Pharmaceuticals Inc	1994-12-31	2009-09-15
Yohimbine Tab 2mg	Tablet	Oral	Welcker Lyster Ltd., Division Of Technilab Inc.	1951-12-31	2005-08-05
Yohimbine Tab 5.4mg	Tablet	Oral	Odan Laboratories Ltd	1991-12-31	Not applicable
Yohimbine Tab 6mg	Tablet	Oral	Rougier Pharma Division Of Ratiopharm Inc	1990-12-31	2003-09-22
Yohimbine-odan 6mg	Tablet	Oral	Odan Laboratories Ltd	1992-12-31	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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International/Other Brands

Actibine / Aphrodine / Aphrodyne / Baron-X / Corynine / Dayto himbin / Thybine / Yocon / Yohimar / Yohimex / Yoman / Yovital

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][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]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.

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	antagonist	Humans
AAlpha-2B adrenergic receptor	antagonist	Humans
AAlpha-2C adrenergic receptor	antagonist	Humans
U5-hydroxytryptamine receptor 1A	partial agonist	Humans
U5-hydroxytryptamine receptor 1B	antagonist	Humans
U5-hydroxytryptamine receptor 1D	antagonist	Humans
UDopamine D2 receptor	antagonist	Humans
UDopamine D3 receptor	antagonist	Humans
U5-hydroxytryptamine receptor 2A	antagonist	Humans
U5-hydroxytryptamine receptor 2C	antagonist	Humans
UATP-sensitive potassium channel	inhibitor	Humans
U5-hydroxytryptamine receptor 2B	antagonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
Unlock Additional Data
(R)-warfarin	The risk or severity of adverse effects can be increased when Yohimbine is combined with (R)-warfarin.
(S)-Warfarin	The risk or severity of adverse effects can be increased when Yohimbine is combined with (S)-Warfarin.
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine	The metabolism of Yohimbine can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-benzylimidazole	The risk or severity of hypertension can be increased when Yohimbine is combined with 1-benzylimidazole.
2,5-Dimethoxy-4-ethylamphetamine	The therapeutic efficacy of Yohimbine can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamine	The therapeutic efficacy of Yohimbine can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The therapeutic efficacy of Yohimbine can be decreased when used in combination with 4-Bromo-2,5-dimethoxyamphetamine.
4-Bromo-2,5-dimethoxyphenethylamine	The therapeutic efficacy of 4-Bromo-2,5-dimethoxyphenethylamine can be decreased when used in combination with Yohimbine.
4-hydroxycoumarin	The risk or severity of adverse effects can be increased when Yohimbine is combined with 4-hydroxycoumarin.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Yohimbine is combined with 4-Methoxyamphetamine.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Take with or without food.

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: 50203564
RxNav: 220982
ChEBI: 10093
ChEMBL: CHEMBL15245
ZINC: ZINC000003860825
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

Phase	Status	Purpose	Conditions	Count
0	Not Yet Recruiting	Other	Parkinson's Disease (PD)	1
0	Terminated	Treatment	Autonomic Nervous System Diseases / High Blood Pressure (Hypertension) / Orthostatic Hypotension	1
1	Active Not Recruiting	Screening	Autonomic Nervous System Diseases / Dopamine Beta-Hydroxylase Deficiency / Orthostatic Hypotension / Orthostatic Intolerance	1
1	Completed	Not Available	Autonomic Failure / Orthostatic Hypotension	1
1	Completed	Basic Science	Healthy Controls	1
1	Completed	Basic Science	Smoking, Cigarette	1
1	Recruiting	Basic Science	Marijuana Abuse	1
1	Recruiting	Treatment	Heroin Dependence / Opioid Use Disorder (OUD)	1
1, 2	Completed	Treatment	Healthy Volunteers	1
2	Completed	Other	Depression, Involutional / Major Depresssion	1
2	Completed	Treatment	Alcohol Dependence	1
2	Completed	Treatment	Post Traumatic Stress Disorder (PTSD)	1
2	Completed	Treatment	Type 2 Diabetes Mellitus	1
2	Not Yet Recruiting	Basic Science	Healthy Volunteers / Stress	1
2	Not Yet Recruiting	Basic Science	Opioid Use Disorder (OUD)	1
2	Not Yet Recruiting	Basic Science	Opioid Use Disorder (OUD) / Opioid-use Disorder / Stress	1
3	Completed	Treatment	Social Anxiety Disorder (SAD)	1
4	Completed	Not Available	Erectile Dysfunction	1
4	Completed	Treatment	Autoregulation / Blood Flow Velocity / Physiology, Ocular	1
Not Available	Completed	Not Available	Cocaine Related Disorders / Cocaine-Related Disorders	1
Not Available	Completed	Not Available	Erectile Dysfunction	1
Not Available	Completed	Not Available	Healthy Volunteers	2
Not Available	Completed	Basic Science	Early Life Trauma / Major Depressive Disorder (MDD)	1
Not Available	Completed	Basic Science	Intrusive Memories	1
Not Available	Recruiting	Basic Science	Hydrocortisone / Placebo / Yohimbine / Yohimbine + Hydrocortisone	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

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	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

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	8.5	N/A	N/A	16562853
Ki (nM)	0.32	N/A	N/A	1353247
Ki (nM)	0.42	N/A	N/A	10762040
Ki (nM)	0.43	N/A	N/A	7908054
Ki (nM)	0.5	N/A	N/A	1353247
Ki (nM)	0.61	N/A	N/A	7908054
Ki (nM)	0.71	N/A	N/A	9400006
Ki (nM)	1.2	N/A	N/A	9605427
Ki (nM)	1.6	N/A	N/A	6149136 / 11408545
Ki (nM)	2.5	N/A	N/A	11132243
Ki (nM)	2.7	N/A	N/A	6149136
Ki (nM)	3.1	N/A	N/A	10602703
Ki (nM)	3.16	N/A	N/A	10611634
Ki (nM)	3.5	N/A	N/A	11408545
Ki (nM)	3.6	N/A	N/A	7855217
Ki (nM)	3.71	N/A	N/A	7996470
Ki (nM)	3.76	N/A	N/A	7996470
Ki (nM)	6.3	N/A	N/A	10611634
Ki (nM)	7.5	N/A	N/A	7562902
Ki (nM)	7.94	N/A	N/A	10611634

Details1. Alpha-2A adrenergic receptor

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.32	N/A	N/A	2172775
Ki (nM)	0.37	N/A	N/A	1353247
Ki (nM)	1.18	N/A	N/A	1353247
Ki (nM)	1.2	N/A	N/A	2172775 / 9605427
Ki (nM)	1.99	N/A	N/A	10611634
Ki (nM)	13.6	N/A	N/A	7996470
Ki (nM)	2.01	N/A	N/A	10762040
Ki (nM)	4.59	N/A	N/A	7996470
Ki (nM)	4.6	N/A	N/A	7562902
Ki (nM)	77	N/A	N/A	2172775

Details2. Alpha-2B adrenergic receptor

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	0.13	N/A	N/A	1353247
Ki (nM)	0.25	N/A	N/A	10611634
Ki (nM)	0.3	N/A	N/A	1353247
Ki (nM)	0.55	N/A	N/A	9605427
Ki (nM)	0.78	N/A	N/A	7996470
Ki (nM)	2.3	N/A	N/A	7562902
Ki (nM)	3.02	N/A	N/A	7996470

Details3. Alpha-2C adrenergic receptor

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1258.92	N/A	N/A	10611634
Ki (nM)	1500	N/A	N/A	8155646
Ki (nM)	50.11	N/A	N/A	10611634
Ki (nM)	642	N/A	N/A	9686407

Details4. 5-hydroxytryptamine receptor 1A

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	158.48	N/A	N/A	10611634
Ki (nM)	16	N/A	N/A	1565658
Ki (nM)	22	N/A	N/A	1565658
Ki (nM)	251.18	N/A	N/A	7984267
Ki (nM)	26.91	N/A	N/A	7984267
Ki (nM)	39.81	N/A	N/A	7984267
Ki (nM)	40.73	N/A	N/A	7984267
Ki (nM)	46.77	N/A	N/A	7984267
Ki (nM)	5	N/A	N/A	1315531
Ki (nM)	5.01	N/A	N/A	7984267

Details5. 5-hydroxytryptamine receptor 1B

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	15.84	N/A	N/A	7984267
Ki (nM)	19.95	N/A	N/A	10611634
Ki (nM)	21.87	N/A	N/A	7984267
Ki (nM)	25.11	N/A	N/A	10611634
Ki (nM)	27	N/A	N/A	1565658
Ki (nM)	40	N/A	N/A	1565658
Ki (nM)	47.86	N/A	N/A	7984267
Ki (nM)	51	N/A	N/A	1652050
Ki (nM)	58.88	N/A	N/A	7984267
Ki (nM)	59	N/A	N/A	1652050

Details6. 5-hydroxytryptamine receptor 1D

Kind: Protein
Organism: Humans
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]

Details7. Dopamine D2 receptor

Kind: Protein
Organism: Humans
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]

Details8. Dopamine D3 receptor

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	>10000	N/A	N/A	7582481
Ki (nM)	1000	N/A	N/A	7582481 / 10611634
Ki (nM)	252	N/A	N/A	8632342
Ki (nM)	288.4	N/A	N/A	9225287
Ki (nM)	3467.36	N/A	N/A	9225287

Details9. 5-hydroxytryptamine receptor 2A

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	>10000	N/A	N/A	7582481 / 9225287
Ki (nM)	1000	N/A	N/A	10611634
Ki (nM)	1690	N/A	N/A	8632342
Ki (nM)	645.65	N/A	N/A	9225287

Details10. 5-hydroxytryptamine receptor 2C

Kind: Protein
Organism: Humans
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]

Details11. ATP-sensitive potassium channel (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

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:

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

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]

Details12. 5-hydroxytryptamine receptor 2B

Kind: Protein
Organism: Humans
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

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	8.4	N/A	N/A	15481972
Ki (nM)	140	N/A	N/A	8487254
Ki (nM)	180	N/A	N/A	8487254 / 15481972
Ki (nM)	190	N/A	N/A	8487254
Ki (nM)	230	N/A	N/A	8487254
Ki (nM)	520	N/A	N/A	8487254

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

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

Le Corre P, Parmer RJ, Kailasam MT, Kennedy BP, Skaar TP, Ho H, Leverge R, Smith DW, Ziegler MG, Insel PA, Schork NJ, Flockhart DA, O'connor DT: Human sympathetic activation by alpha2-adrenergic blockade with yohimbine: Bimodal, epistatic influence of cytochrome P450-mediated drug metabolism. Clin Pharmacol Ther. 2004 Aug;76(2):139-53. doi: 10.1016/j.clpt.2004.04.010. [PubMed:15289791]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
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

Le Corre P, Parmer RJ, Kailasam MT, Kennedy BP, Skaar TP, Ho H, Leverge R, Smith DW, Ziegler MG, Insel PA, Schork NJ, Flockhart DA, O'connor DT: Human sympathetic activation by alpha2-adrenergic blockade with yohimbine: Bimodal, epistatic influence of cytochrome P450-mediated drug metabolism. Clin Pharmacol Ther. 2004 Aug;76(2):139-53. doi: 10.1016/j.clpt.2004.04.010. [PubMed:15289791]

Drug created on July 08, 2007 11:00 / Updated on May 25, 2020 23:44

Yohimbine

Identification

Structure for Yohimbine (DB01392)

Pharmacology

Interactions

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

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Components:

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Enzymes

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