yohimbine

Small moleculeexperimental

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

Chemistry & pharmacology

Loading structure…

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

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 IDPhaseStart dateSponsor(s)
NCT06939608N/AApr 28, 2025University of Greifswald
NCT06430580Early Phase 1 (Phase 1)Aug 15, 2024Auburn University, National Institute on Drug Abuse (NIDA), Wayne State University
NCT06018727Phase 4Mar 31, 2024University of North Carolina at Chapel Hill
NCT04181515Phase 2Jul 31, 2020Wayne State University
NCT04346394Early Phase 1 (Phase 1)Apr 30, 2020Dartmouth University
NCT04231708Phase 2Mar 1, 2020Wayne State University
NCT04180969Phase 2Dec 1, 2019Wayne State University
NCT04359147N/ANov 1, 2019Humboldt University
NCT03520543Phase 1May 21, 2018University of Lyon
NCT02963181Early Phase 1 (Phase 1)Sep 1, 2017University of Western Ontario
NCT03154567Phase 1May 1, 2017Wayne State University
NCT03015246Phase 1Dec 1, 2016Wayne State University
NCT03670212Phase 1Jan 7, 2016National Institute on Drug Abuse (NIDA), Wayne State University
NCT02470026N/AJun 1, 2014Humboldt University
NCT02541071N/ANov 1, 2013Humboldt University
NCT01621620N/AAug 1, 2012Tel Aviv University
NCT01593215Phase 2May 1, 2012Lund University, Region Skane
NCT01031979Phase 2Dec 1, 2010Department of Veteran Affairs
NCT00975325Phase 4Oct 1, 2009SocraTec R&D GmbH, Walter Ritter GmbH & Co
NCT00958880Phase 3Mar 1, 2009Boston University, Southern Methodist University
Showing 20 of 27 trials
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Organizations

Research & Development (25)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Wayne State UniversityAcademic/Hospital7622016
Humboldt UniversityAcademic/Hospital3312013
National Institute on Drug Abuse (NIDA)Government3022007
National Institutes of Health (NIH)Government3012004
Vanderbilt UniversityAcademic/Hospital2211996
Auburn UniversityAcademic/Hospital1112024
Boston UniversityAcademic/Hospital1012009
Dartmouth UniversityAcademic/Hospital1112020
Department of Veteran AffairsGovernment1112010
Lund UniversityAcademic/Hospital1012012
Mayo ClinicAcademic/Hospital1112005
Medical University of South CarolinaAcademic/Hospital1012007
National Institute of Mental Health (NIMH)Government1112004
National Institute on Alcohol Abuse and Alcoholism (NIAAA)Government1112008
Region SkaneGovernment1112012
SocraTec R&D GmbHFor profit1012009
Southern Methodist UniversityAcademic/Hospital1112009
Tel Aviv UniversityAcademic/Hospital1112012
University of GreifswaldAcademic/Hospital1112025
University of LyonAcademic/Hospital1112018
25 organizations
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