yohimbine
Yohimbine is a plant alkaloid with alpha-2-adrenergic blocking activity. Yohimbine has been used as a mydriatic and in the treatment of impotence. The exact mechanism for its use in impotence has not been fully elucidated. Yohimbine exerts antagonist actions at halpha(2A)-AR, h5-HT(1B), h5-HT(1D), and hD(2) sites, partial agonist actions at h5-HT(1A) sites. 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. 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. Side effect of Yohimbine include anxiety, tremor, palpitations, diarrhea, and supine hypertension. — NCATS
Clinical trial activity
27 trials · 25 clinical orgs · 0 marketing orgs
Earliest trial started Dec 1, 1996 (NCT00748059)
Timeline
Indications
Approved for
Studied for
- Alcoholism · Phase 2
- Autonomic Nervous System Diseases · Phase 1
- Blood Flow Velocity · Phase 4
- Borderline Personality Disorder · Phase 4
- Cannabis · Early Phase 1
- Cigarette Smoking · Phase 1
- Cocaine-Related Disorders · Phase 2
- Depression · Phase 2
- Diabetes Mellitus, Type 2 · Phase 2
- Dopamine beta-Hydroxylase · Phase 1
- Erectile Dysfunction · Phase 4
- Healthy Volunteers · Phase 2
- Heroin Dependence · Phase 1
- Homeostasis · Phase 4
- Hypertension · Early Phase 1
- Hypotension, Orthostatic · Phase 1
- Major Depressive Disorder · Phase 2
- Marijuana Abuse · Phase 1
- Ocular Physiological Phenomena · Phase 4
- Opioid-Related Disorders · Phase 2
- Orthostatic Intolerance · Phase 1
- Parkinson Disease · Early Phase 1
- Phobia, Social · Phase 3
- Psychological Distress · Phase 2
- Pure Autonomic Failure · Phase 1
- Stress Disorders, Post-Traumatic · Phase 2
Mechanism of action
- Alpha-2b adrenergic receptorINHIBITOR
ADRA2B inhibitor
Chemistry & pharmacology
SMILES
COC(=O)[C@@H]1[C@H]2C[C@H]3c4[nH]c5ccccc5c4CCN3C[C@@H]2CC[C@@H]1O- Mol. weight
- 354.45 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- ChEMBLCHEMBL15245 ↗
- WikipediaYohimbine ↗
- NCATS2Y49VWD90Q ↗
- ChEMBLCHEMBL537669 ↗
Also known as
- (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester
- (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester
- 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester
- 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester
- aphrodine
- aphrodine
- corynine
- corynine
- johimbin
- johimbin
- prowess plain
- quebrachin
- quebrachin
- quebrachin
- quebrachine
- quebrachine
- quebrachine
- yocon
- yocon
- yohimbic acid methyl ester
- yohimbic acid methyl ester
- yohimbin
- yohimbin
- yohimbin
- yohimbine
- yohimbine
- yohimbine
- yohimbine
- yohimbine
- yohimbine
- yohimbine
- yohimbine
- (+)-yohimbine
- (+)-yohimbine
- yohimbine hcl
- yohimbine hcl
- yohimbine hcl
- yohimbine hydrochloride
- yohimbine hydrochloride
- yohimbine hydrochloride
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06939608 | N/A | Apr 28, 2025 | University of Greifswald |
| NCT06430580 | Early Phase 1 (Phase 1) | Aug 15, 2024 | Auburn University, National Institute on Drug Abuse (NIDA), Wayne State University |
| NCT06018727 | Phase 4 | Mar 31, 2024 | University of North Carolina at Chapel Hill |
| NCT04181515 | Phase 2 | Jul 31, 2020 | Wayne State University |
| NCT04346394 | Early Phase 1 (Phase 1) | Apr 30, 2020 | Dartmouth University |
| NCT04231708 | Phase 2 | Mar 1, 2020 | Wayne State University |
| NCT04180969 | Phase 2 | Dec 1, 2019 | Wayne State University |
| NCT04359147 | N/A | Nov 1, 2019 | Humboldt University |
| NCT03520543 | Phase 1 | May 21, 2018 | University of Lyon |
| NCT02963181 | Early Phase 1 (Phase 1) | Sep 1, 2017 | University of Western Ontario |
| NCT03154567 | Phase 1 | May 1, 2017 | Wayne State University |
| NCT03015246 | Phase 1 | Dec 1, 2016 | Wayne State University |
| NCT03670212 | Phase 1 | Jan 7, 2016 | National Institute on Drug Abuse (NIDA), Wayne State University |
| NCT02470026 | N/A | Jun 1, 2014 | Humboldt University |
| NCT02541071 | N/A | Nov 1, 2013 | Humboldt University |
| NCT01621620 | N/A | Aug 1, 2012 | Tel Aviv University |
| NCT01593215 | Phase 2 | May 1, 2012 | Lund University, Region Skane |
| NCT01031979 | Phase 2 | Dec 1, 2010 | Department of Veteran Affairs |
| NCT00975325 | Phase 4 | Oct 1, 2009 | SocraTec R&D GmbH, Walter Ritter GmbH & Co |
| NCT00958880 | Phase 3 | Mar 1, 2009 | Boston University, Southern Methodist University |
Organizations
Research & Development (25)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Wayne State University | Academic/Hospital | 7 | 6 | 2 | 2016 |
| Humboldt University | Academic/Hospital | 3 | 3 | 1 | 2013 |
| National Institute on Drug Abuse (NIDA) | Government | 3 | 0 | 2 | 2007 |
| National Institutes of Health (NIH) | Government | 3 | 0 | 1 | 2004 |
| Vanderbilt University | Academic/Hospital | 2 | 2 | 1 | 1996 |
| Auburn University | Academic/Hospital | 1 | 1 | 1 | 2024 |
| Boston University | Academic/Hospital | 1 | 0 | 1 | 2009 |
| Dartmouth University | Academic/Hospital | 1 | 1 | 1 | 2020 |
| Department of Veteran Affairs | Government | 1 | 1 | 1 | 2010 |
| Lund University | Academic/Hospital | 1 | 0 | 1 | 2012 |
| Mayo Clinic | Academic/Hospital | 1 | 1 | 1 | 2005 |
| Medical University of South Carolina | Academic/Hospital | 1 | 0 | 1 | 2007 |
| National Institute of Mental Health (NIMH) | Government | 1 | 1 | 1 | 2004 |
| National Institute on Alcohol Abuse and Alcoholism (NIAAA) | Government | 1 | 1 | 1 | 2008 |
| Region Skane | Government | 1 | 1 | 1 | 2012 |
| SocraTec R&D GmbH | For profit | 1 | 0 | 1 | 2009 |
| Southern Methodist University | Academic/Hospital | 1 | 1 | 1 | 2009 |
| Tel Aviv University | Academic/Hospital | 1 | 1 | 1 | 2012 |
| University of Greifswald | Academic/Hospital | 1 | 1 | 1 | 2025 |
| University of Lyon | Academic/Hospital | 1 | 1 | 1 | 2018 |