{"ATC Code":["G04BE04","G - Genito urinary system and sex hormones","G04 - Urologicals","G04B - Urologicals","G04BE - Drugs used in erectile dysfunction","G04BE04 - Yohimbine","QG - Genito urinary system and sex hormones","QG04 - Urologicals","QG04B - Urologicals","QG04BE - Drugs used in erectile dysfunction","QG04BE04 - Yohimbine","QV - Various","QV03 - All other therapeutic products","QV03A - All other therapeutic products","QV03AB - Antidotes","QV03AB93 - Yohimbine"],"Absorption, Distribution and Excretion":"Rapidly absorbed following oral administration. Bioavailability is highly variable, ranging from 7 to 87% (mean 33%).","Aliases":["Yohimbine","Yohimbin","Quebrachine","Corynine","Quebrachin","APHRODINE","Yohimbic acid methyl ester","Yohimbinum","17α-hydroxyyohimban-16α-carboxylic acid methyl ester","Dtxsid9040130","Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16α,17α)-","(16α,17α)-17-hydroxyyohimban-16-carboxylic acid methyl ester","Dtxcid7020130","Chebi:10093","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","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","Tartrate, Corynanthine","205-672-0","Aphrosol","Johimbin","Mfcd00005093","17-Hydroxyyohimban-16-carboxylic acid methyl ester","methyl 17α-hydroxyyohimban-16α-carboxylate","Chembl15245","Actibine","Yohimbine chloride","17α-hydroxy-yohimban-16α-carboxylic acid methyl ester","Chembl537669","Cas-146-48-5","methyl hydroxy[?]carboxylate","Einecs 205-672-0","17?-Hydroxy-yohimban-16?-carboxylic Acid Methyl Ester","Brn 0097276","trans-Quinolizidine yohimbine","Unii-2y49vwd90q","CCRIS 9415","Sr-01000075297","Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.","NSC19509","Prestwick0_000584","Prestwick1_000584","Prestwick2_000584","Prestwick3_000584","Yohimban-16-α-carboxylic acid, 17-α-hydroxy-, methyl ester","cid_6169","cid_8969","Yohimbe hydrochloride","Lopac0_001210","Schembl33954","BSPBio_000428","BSPBio_001236","GTPL102","KBioGR_000576","KBioSS_000576","4-25-00-01237","Mls000728591","SPBio_002647","BPBio1_000472","orb1685173","Yohimbol-16α-carboxylic acid, methyl ester","Schembl29385789","BCBcMAP01_000032","KBio2_000576","KBio2_003144","KBio2_005712","KBio3_001031","KBio3_001032","Bio1_000455","Bio1_000944","Bio1_001433","Bio2_000458","Bio2_000938","HMS1362N17","HMS1792N17","HMS1990N17","HMS2089G19","HMS2234C18","Tox21_110019","Bdbm50013515","Bdbm50203564","EBC-26708","Akos015902024","Tox21_110019_1","Yohimban-16α-carboxylic acid, 17α-hydroxy-, methyl ester","CCG-205284","CS-5173","DB01392","FY01219","GS-5751","Sdccgsbi-0051177.p002","Idi1_002213","Mrf-0000020","Smp1_000320","Ncgc00013260-01","Ncgc00025018-05","Ncgc00025018-06","Ncgc00025018-07","Ncgc00025018-10","Ncgc00025018-11","Ncgc00025018-16","Ncgc00025018-17","Ncgc00025018-24","Ncgc00025018-29","HY-12715","Smr000470778","17a-hydroxy-16a-methoxycarbonyl-yohimbane","NS00003970","C09256","D08685","H10057","En300-19731915","Sr-01000075297-5","Brd-k35586044-001-02-6","Brd-k35586044-003-03-0","Brd-k35586044-003-11-3","Brd-k35586044-003-14-7","Brd-k35586044-003-15-4","Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16|A,17|A)-","17α-Hydroxy-20-α-yohimban-16-β-carboxylic acid, methyl ester","(1R,2S,4aR,13bS,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2'',3'':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester hydrochloride","103834-06-6","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(9),5,7-tetraene-19-carboxylate"],"Biological Half-Life":"Elimination half-life is approximately 36 minutes.","CAS":"146-48-5","Chemical Classes":"Alkaloids","ChemicalClasses":["β-carboline"],"Chirality":"absolute","Drug Classes":"Herbal and Dietary Supplements","Drug 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.","EliminationHalfLife":"0.25 – 2.5 hours\u003ca href='#cite_note-3'\u003e\u003csup\u003e[3]\u003c/sup\u003e\u003c/a\u003e","Esters":[],"European Community (EC) Number":"205-672-0","Formating":[],"HMDB ID":"HMDB0015464","HeavyAtomCount":26,"Human Drugs":"Pharmaceuticals","IUPACName":"methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate","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","InChIKey":"BLGXFZZNTVWLAY-SCYLSFHTSA-N","KEGG Entries":[{"Id":"D06671","Interactions":[],"Synonyms":["Yohimbine hydrochloride"]},{"Id":"D08685","Interactions":[],"Synonyms":["Yohimbine"]},{"Id":"D06671","Interactions":[],"Synonyms":["Yohimbine hydrochloride"]},{"Id":"D08685","Interactions":[],"Synonyms":["Yohimbine"]},{"Id":"D06671","Interactions":[],"Synonyms":["Yohimbine hydrochloride"]},{"Id":"D08685","Interactions":[],"Synonyms":["Yohimbine"]}],"MeSH Headers":[{"Id":"M0023104","Link":"https://id.nlm.nih.gov/mesh/M0023104.html","Name":"Yohimbine","Ref":105},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":107},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":131},{"Id":"M0014317","Link":"https://id.nlm.nih.gov/mesh/M0014317.html","Name":"Mydriatics","Ref":132},{"Id":"M0543997","Link":"https://id.nlm.nih.gov/mesh/M0543997.html","Name":"Adrenergic alpha-2 Receptor Antagonists","Ref":133},{"Id":"M0584314","Link":"https://id.nlm.nih.gov/mesh/M0584314.html","Name":"Urological Agents","Ref":134}],"MeSH Pharmacological Classification":[{"Id":"M0014317","Link":"https://id.nlm.nih.gov/mesh/M0014317.html","Name":"Mydriatic","Ref":132},{"Id":"M0543997","Link":"https://id.nlm.nih.gov/mesh/M0543997.html","Name":"Adrenergic alpha-2 Receptor Antagonist","Ref":133},{"Id":"M0584314","Link":"https://id.nlm.nih.gov/mesh/M0584314.html","Name":"Urological Agent","Ref":134}],"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.","Melting Point":"241 °C","Metabolism/Metabolites":"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.","MolecularFormula":"C\u003csub\u003e21\u003c/sub\u003eH\u003csub\u003e26\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e3\u003c/sub\u003e","MolecularWeight":"354.4 g/mol","Opticalactivity":"UNSPECIFIED","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.","Physical Description":"Solid","PubChemId":8969,"Records":{"UNII":{"Impurities":[]}},"RefChem":"56477","RefCount":4,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Yohimbine","Name":"Yohimbine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q412226","Name":"Yohimbine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB01392","Name":"Yohimbine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/8969","Name":"Yohimbine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=146-48-5","Name":"Yohimbine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0015464","Name":"Yohimbine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C09256","Name":"Yohimbine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/2Y49VWD90Q","Name":"Yohimbine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID9040130","Name":"Yohimbine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 8969, Yohimbine. Accessed April 20, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/8969\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/8969\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Yohimbine. UNII: 2Y49VWD90Q. Global Substance Registration System. Accessed April 20, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/2Y49VWD90Q\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/2Y49VWD90Q\u003c/a\u003e","Hedner T, Edgar B, Edvinsson L, Hedner J, Persson B, Pettersson A. Yohimbine pharmacokinetics and interaction with the sympathetic nervous system in normal volunteers. European Journal of Clinical Pharmacology. 43(6):651–6."],"SMILES":"COC(=O)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O","SaltData":[{"AcidCount":1,"Amine":"Yohimbine","AmineCount":1,"Formula":"Cl","Name":"hydrochloride","RName":"hydrochloride","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 141.376 91.063\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h142v92H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m101.452 90.095-11.347-2.113M85.138 83.534l-3.744-10.599\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m81.394 72.935-11.346-2.113M79.564 75.074l-9.963-1.855\"/\u003e\u003cpath 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