Open Access Articles- Top Results for Yohimbine


File:Yohimbine structure.svg
Systematic (IUPAC) name
carboxylic acid methyl ester
Clinical data
Pharmacokinetic data
Bioavailability 7-87% (mean 33%)
Half-life 0.25-2.5 hours[1]
Excretion Urine (as metabolites)
146-48-5 7pxY
G04BE04 QV03AB93
PubChem CID 8969
IUPHAR ligand 102
DrugBank DB01392 7pxY
ChemSpider 8622 7pxY
UNII 2Y49VWD90Q 7pxY
ChEBI CHEBI:10093 7pxY
Chemical data
Formula C21H26N2O3
354.44 g/mol (base)
390.90 g/mol (hydrochloride)
 14pxY (what is this?)  (verify)

Yohimbine (/jˈhɪmbn/)[2] is an indole alkaloid derived from the bark of the Pausinystalia yohimbe tree in Central Africa. It is a veterinary drug used to reverse sedation in dogs and deer. Yohimbine has been studied as a potential treatment for erectile dysfunction but there is insufficient evidence to rate its effectiveness.[3][4] Extracts from yohimbe containing yohimbine have been used in traditional medicine in West Africa as an aphrodisiac and have been marketed as dietary supplements[5]

Veterinary uses

Yohimbine is a drug used in veterinary medicine to reverse the effects of xylazine in dogs and deer.[6]


Depending on dosage, yohimbine can either increase or decrease systemic blood pressure (through vasoconstriction or vasodilation, respectively); small amounts of yohimbine can increase blood pressure, while large amounts can dangerously lower blood pressure.[3]

The therapeutic index of yohimbine is quite low; the range between an effective dose and a dangerous dose is very narrow.[7]

Hallucinations or paralysis may occur with doses greater than 40 mg.[8] Higher doses of oral yohimbine may create numerous side effects, such as rapid heart rate, overstimulation, anomalous blood pressure, cold sweating, and insomnia. In rare cases panic attacks, hallucinations, headaches, dizziness, and skin flushing have occurred.[7] Large doses of yohimbe have caused priapism.[9]

Serious adverse effects of overdose may include seizures and kidney failure. Yohimbine should not be consumed by anyone with liver, kidney, or heart disease, or a psychological disorder.[7]


Yohimbine was first isolated from the yohimbe extract in 1896 by Adolph Spiegel.[10] In 1943 the correct constitution of yohimbine was proposed by Witkop.[11] Fifteen years later, Van Tamelen used a 23-step synthesis to become the first person to achieve the synthesis of yohimbine.[12][13][14]


Yohimbine has high affinity for the α2-adrenergic receptor, moderate affinity for the α1 receptor, 5-HT1A, 5-HT1B, 5-HT1D, 5-HT1F, 5-HT2B, and D2 receptors, and weak affinity for the 5-HT1E, 5-HT2A, 5-HT5A, 5-HT7, and D3 receptors.[15][16] It behaves as an antagonist at α1-adrenergic, α2-adrenergic, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, and D2, and as a partial agonist at 5-HT1A.[15][17][18][19] Yohimbine interacts with serotonin and dopamine receptors in high concentrations.[20]

Pharmacologic profile
Molecular Target Binding Affinity
(Ki in nanomoles)[21]
Pharmacologic Action
Species Source
SERT 1,000 Inhibitor Human Frontal Cortex
5-HT1A 346 Partial Agonist Human Cloned
5-HT1B 19.9 Antagonist Human Cloned
5-HT1D 44.3 Antagonist Human Cloned
5-HT1E 1,264 Unknown Human Cloned
5-HT1F 91.6 Unknown Human Cloned
5-HT2A 1,822 Antagonist Human Cloned
5-HT2B 143.7 Antagonist Human Cloned
5-HT7 2,850 Unknown Human Cloned
α1A 1,680 Antagonist Human Cloned
α1B 1,280 Antagonist Human Cloned
α1C 770 Antagonist Human Cloned
α1D 557 Antagonist Human Cloned
α2A 1.05 Antagonist Human Cloned
α2B 1.19 Antagonist Human Cloned
α2C 1.19 Antagonist Human Cloned
D2 339 Antagonist Human Cloned
D3 3,235 Antagonist Human Cloned


Sexual dysfunction

Main article: Sexual dysfunction

Yohimbine has been studied as a potential treatment for erectile dysfunction but there is insufficient evidence to rate its effectiveness.[3][4] It is illegal in the United States to market an over the counter product containing yohimbine as a treatment for erectile dysfunction without getting FDA approval to do so.[23]

Yohimbine blocks the pre- and post-synaptic α2 receptors. Blockade of post-synaptic α2 receptors causes minor corpus cavernosum smooth muscle relaxation. In fact, the majority of adrenoceptors in the corpus cavernosum are of the α1 type. Blockade of pre-synaptic α2 receptors facilitates the release of several neurotransmitters in the central and peripheral nervous system — thus in the corpus cavernosum — such as nitric oxide and norepinephrine. Whereas nitric oxide released in the corpus cavernosum is the major vasodilator contributing to the erectile process, norepinephrine is the major vasoconstrictor through stimulation of α1 receptors on the corpus cavernosum smooth muscle. Under physiologic conditions, nitric oxide attenuates norepinephrine vasoconstriction.[24]

Natural sources

Yohimbine was originally extracted from the bark of Pausinystalia johimbe, commonly known as yohimbe, a tree that grows in western and central Africa.[25] Yohimbe extracts from have been used in traditional medicine in West Africa as an aphrodisiac and have been marketed as dietary supplements.[5]

See also


  1. ^ Hedner, T; Edgar, B; Edvinsson, L; Hedner, J; Persson, B; Pettersson, A (1992). "Yohimbine pharmacokinetics and interaction with the sympathetic nervous system in normal volunteers". European Journal of Clinical Pharmacology 43 (6): 651–656. PMID 1493849. doi:10.1007/BF02284967. 
  2. ^ yohimbine. (n.d.) Collins English Dictionary – Complete and Unabridged. (1991, 1994, 1998, 2000, 2003). Retrieved January 27, 2015 from
  3. ^ a b c "Yohimbe: MedlinePlus Supplements". Medline. Retrieved 2013-05-26. 
  4. ^ a b Andersson KE (September 2001). "Pharmacology of penile erection". Pharmacological Reviews 53 (3): 417–50. PMID 11546836. 
  5. ^ a b Beille, P. E. (2013). "Scientific Opinion on the evaluation of the safety in use of Yohimbe (Pausinystalia yohimbe)". EFSA Journal 11. doi:10.2903/j.efsa.2013.3302. 
  6. ^ 21 CFR Sec. 522.2670 Yohimbine
  7. ^ a b c Prescription for Nutritional Healing, fourth edition Phyllis A. Balch, CNC.
  8. ^ "Yohimbine Dangers". Livestrong.Com. Retrieved 2013-05-26. 
  9. ^ Myers, A.; Barrueto, F. (2009). "Refractory priapism associated with ingestion of yohimbe extract". Journal of medical toxicology : official journal of the American College of Medical Toxicology 5 (4): 223–225. PMC 3550410. PMID 19876857. doi:10.1007/BF03178272.  edit
  10. ^ Year Book of the American Pharmaceutical Association. American Pharmaceutical Association. 1914. p. 564. Retrieved 2015-05-04. 
  11. ^ Witkop, B. (1943), Annalen 83: 554  Missing or empty |title= (help)
  12. ^ The Alkaloids: Chemistry and Pharmacology. Academic Press. 1988. p. 564. ISBN 0-12-469532-9. 
  13. ^ van Tamelen, E. E. (1958). "The Total Synthesis of Yohimbine". J. Am. Chem. Soc. 80: 5006–5007. doi:10.1021/ja01551a062. 
  14. ^ Herle, B. (2011). "Total Synthesis of (+)-Yohimbine via an Enantioselective Organocatalytic Pictet–Spengler Reaction". J. Org. Chem. 76: 8907–8912. doi:10.1021/jo201657n. 
  15. ^ a b c Millan MJ; Newman-Tancredi A; Audinot V et al. (February 2000). "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 35 (2): 79–95. PMID 10611634. doi:10.1002/(SICI)1098-2396(200002)35:2<79::AID-SYN1>3.0.CO;2-X. 
  16. ^ "PDSP Ki Database". 
  17. ^ a b Arthur JM, Casañas SJ, Raymond JR (June 1993). "Partial agonist properties of rauwolscine and yohimbine for the inhibition of adenylyl cyclase by recombinant human 5-HT1A receptors". Biochemical Pharmacology 45 (11): 2337–41. PMID 8517875. doi:10.1016/0006-2952(93)90208-E. 
  18. ^ a b Kaumann AJ (June 1983). "Yohimbine and rauwolscine inhibit 5-hydroxytryptamine-induced contraction of large coronary arteries of calf through blockade of 5 HT2 receptors". Naunyn-Schmiedeberg's Archives of Pharmacology 323 (2): 149–54. PMID 6136920. doi:10.1007/BF00634263. 
  19. ^ a b Baxter GS, Murphy OE, Blackburn TP (May 1994). "Further characterization of 5-hydroxytryptamine receptors (putative 5-HT2B) in rat stomach fundus longitudinal muscle". British Journal of Pharmacology 112 (1): 323–31. PMC 1910288. PMID 8032658. doi:10.1111/j.1476-5381.1994.tb13072.x. 
  20. ^ "Yohimbine (PIM 567)". Retrieved 2013-05-26. 
  21. ^ National Institute of Mental Health. "PDSP Ki Database". University of North Carolina. Retrieved 5 July 2013. 
  22. ^ "Yohimbine". DrugBank. University of Alberta. Retrieved 12 April 2014. 
  23. ^ FDA regulations on OTC products
  24. ^ Saenz De Tejada, I; Kim, NN; Goldstein, I; Traish, AM (2000). "Regulation of pre-synaptic alpha adrenergic activity in the corpus cavernosum". International Journal of Impotence Research. 12 Suppl 1: S20–25. PMID 10845761. doi:10.1038/sj.ijir.3900500. 
  25. ^ Kew World Checklist of Selected Plant Families, Pausinystalia johimbe