Yohimbine

Identification

Summary

Yohimbine is an alpha-2-adrenergic blocker and sympatholytic found in supplements used to.

Generic Name
Yohimbine
DrugBank Accession Number
DB01392
Background

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.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Weight
Average: 354.4427
Monoisotopic: 354.194342708
Chemical Formula
C21H26N2O3
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

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.

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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
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
partial agonist
Humans
U5-hydroxytryptamine receptor 1D
partial agonist
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
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

Adverse Effects
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Toxicity

Not Available

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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Yohimbine is combined with 1,2-Benzodiazepine.
AbametapirThe serum concentration of Yohimbine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Yohimbine can be increased when combined with Abatacept.
AbirateroneThe metabolism of Yohimbine can be decreased when combined with Abiraterone.
AcebutololThe metabolism of Yohimbine can be decreased when combined with Acebutolol.
Food Interactions
  • Take with or without food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Yohimbine hydrochlorideNB2E1YP49F65-19-0PIPZGJSEDRMUAW-VJDCAHTMSA-N
International/Other Brands
Actibine / Aphrodine / Aphrodyne / Baron-X / Corynine / Dayto himbin / Thybine / Yocon / Yohimar / Yohimex / Yoman / Yovital
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Yocon Tablet 5.4mgTablet5.4 mgOralPalisades Pharmaceuticals Inc.1988-12-312010-07-16Canada flag
Yohimbine HCl 2mgTablet2 mgOralOdan Laboratories Ltd1992-12-312010-07-19Canada flag
Yohimbine HCl 5.4mgTablet5.4 mgOralOdan Laboratories Ltd1996-09-092010-07-19Canada flag
Yohimbine Hydrochloride Tab 2mgTablet2 mgOralOdan Laboratories Ltd1992-12-31Not applicableCanada flag
Yohimbine Hydrochloride Tablets 5.4mgTablet5.4 mgOralTanta Pharmaceuticals Inc1994-12-312009-09-15Canada flag

Categories

ATC Codes
G04BE04 — Yohimbine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
3-alkylindole / Alcohol / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Beta-carboline / 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)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
2Y49VWD90Q
CAS number
146-48-5
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[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]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

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
  1. Holmes A, Quirk GJ: Pharmacological facilitation of fear extinction and the search for adjunct treatments for anxiety disorders--the case of yohimbine. Trends Pharmacol Sci. 2010 Jan;31(1):2-7. doi: 10.1016/j.tips.2009.10.003. Epub 2009 Dec 28. [Article]
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
MSDS
Download (73.3 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailableErectile Dysfunction1
4CompletedTreatmentAutoregulation / Blood Flow Velocity / Physiology, Ocular1
4Not Yet RecruitingBasic ScienceBorderline Personality Disorder (BPD)1
3CompletedTreatmentSocial Anxiety Disorder (SAD)1
2CompletedOtherDepression, Involutional / Major Depressive Disorder (MDD)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
FormRouteStrength
TabletOral2 mg
TabletOral5.4 mg
TabletOral6 mg
Tablet, sugar coatedOral5 mg
TabletOral5 mg
Prices
Unit descriptionCostUnit
Yohimbine hcl powder22.8USD g
Yohimbine 5.4 mg tablet1.04USD tablet
Yocon 5.4 mg tablet0.96USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)241 °CPhysProp
logP2.73HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.348 mg/mLALOGPS
logP2.36ALOGPS
logP2.1Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)14.68Chemaxon
pKa (Strongest Basic)7.48Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area65.56 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity99.63 m3·mol-1Chemaxon
Polarizability40.24 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9782
Blood Brain Barrier-0.5738
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.8762
P-glycoprotein inhibitor IInhibitor0.6002
P-glycoprotein inhibitor IINon-inhibitor0.9318
Renal organic cation transporterInhibitor0.5738
CYP450 2C9 substrateNon-substrate0.8514
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.5677
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.9094
CYP450 3A4 inhibitorNon-inhibitor0.8333
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.8681
CarcinogenicityNon-carcinogens0.9696
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7324 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8104
hERG inhibition (predictor II)Non-inhibitor0.6141
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-008i-0396000000-43448cca1e1ad4343ac0
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-3921000000-e28dd8692e2b8dd63330
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-e24a26d68c84d464f55e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-6bba98c018bd13bfaf5c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-8e3105503b9f3af02c4d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufr-0059000000-f6ac08071a9a86cec985
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052b-0793000000-9b8c6564b1103d4d127e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufs-0091000000-2a81a6f6549d29b3952a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-196.1746023
predicted
DarkChem Lite v0.1.0
[M-H]-196.9527023
predicted
DarkChem Lite v0.1.0
[M-H]-197.6491023
predicted
DarkChem Lite v0.1.0
[M-H]-184.83653
predicted
DeepCCS 1.0 (2019)
[M+H]+197.2047023
predicted
DarkChem Lite v0.1.0
[M+H]+196.5547023
predicted
DarkChem Lite v0.1.0
[M+H]+197.2886023
predicted
DarkChem Lite v0.1.0
[M+H]+186.82262
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.4049023
predicted
DarkChem Lite v0.1.0
[M+Na]+195.7947023
predicted
DarkChem Lite v0.1.0
[M+Na]+192.73514
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. Kalkman HO, Loetscher E: alpha2C-Adrenoceptor blockade by clozapine and other antipsychotic drugs. Eur J Pharmacol. 2003 Feb 21;462(1-3):33-40. [Article]
  5. 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. [Article]
  6. 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. [Article]
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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]
  6. 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. [Article]
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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. Kalkman HO, Loetscher E: alpha2C-Adrenoceptor blockade by clozapine and other antipsychotic drugs. Eur J Pharmacol. 2003 Feb 21;462(1-3):33-40. [Article]
  5. 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. [Article]
  6. 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. [Article]
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
  1. 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. [Article]
  2. 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. [Article]
  3. Holmes A, Quirk GJ: Pharmacological facilitation of fear extinction and the search for adjunct treatments for anxiety disorders--the case of yohimbine. Trends Pharmacol Sci. 2010 Jan;31(1):2-7. doi: 10.1016/j.tips.2009.10.003. Epub 2009 Dec 28. [Article]
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 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
  1. 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. [Article]
  2. 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. [Article]
  3. Holmes A, Quirk GJ: Pharmacological facilitation of fear extinction and the search for adjunct treatments for anxiety disorders--the case of yohimbine. Trends Pharmacol Sci. 2010 Jan;31(1):2-7. doi: 10.1016/j.tips.2009.10.003. Epub 2009 Dec 28. [Article]
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 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
  1. 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. [Article]
  2. Holmes A, Quirk GJ: Pharmacological facilitation of fear extinction and the search for adjunct treatments for anxiety disorders--the case of yohimbine. Trends Pharmacol Sci. 2010 Jan;31(1):2-7. doi: 10.1016/j.tips.2009.10.003. Epub 2009 Dec 28. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
  2. 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. [Article]
  3. Holmes A, Quirk GJ: Pharmacological facilitation of fear extinction and the search for adjunct treatments for anxiety disorders--the case of yohimbine. Trends Pharmacol Sci. 2010 Jan;31(1):2-7. doi: 10.1016/j.tips.2009.10.003. Epub 2009 Dec 28. [Article]
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
  1. 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. [Article]
  2. 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. [Article]
  3. Holmes A, Quirk GJ: Pharmacological facilitation of fear extinction and the search for adjunct treatments for anxiety disorders--the case of yohimbine. Trends Pharmacol Sci. 2010 Jan;31(1):2-7. doi: 10.1016/j.tips.2009.10.003. Epub 2009 Dec 28. [Article]
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:
References
  1. 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. [Article]
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
  1. 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. [Article]
  2. 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. [Article]

Enzymes

Details
1. 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
  1. 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. [Article]
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
  1. 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. [Article]

Drug created at July 08, 2007 17:00 / Updated at March 18, 2024 16:48