Yohimbine

Last updated
Yohimbine
Yohimbine structure.svg
Yohimbine-from-xtal-3D-bs-17.png
Clinical data
Pronunciation /joʊˈhɪmbiːn/ [1]
Other namesQuebrachine
Routes of
administration 		By mouth
Drug class α2-Adrenergic receptor antagonist
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 7-86% (mean 33%)
Elimination half-life 0.25–2.5 hours [2]
Excretion Urine (as metabolites)
Identifiers
  • 17α-hydroxyyohimban-16α-carboxylic acid methyl ester
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.005.157 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H26N2O3
Molar mass 354.450 g·mol−1
3D model (JSmol)
  • [H][C@@]15CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@@]4([H])c3[nH]c2ccccc2c3CCN4C5
  • 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 Yes check.svgY
  • Key:BLGXFZZNTVWLAY-SCYLSFHTSA-N Yes check.svgY
   (verify)

Yohimbine, also known as quebrachine, is an indole alkaloid derived from the bark of the African tree Pausinystalia johimbe (yohimbe) and from the bark of the unrelated South American tree Aspidosperma quebracho-blanco . [3] [4] It is a veterinary drug used to reverse xylazine.

Contents

Substances purported to be extracts from the yohimbe tree have been marketed as dietary supplements for various purposes, especially for erectile dysfunction, but they contain highly variable amounts of yohimbine, if any; no published clinical evidence supports their efficacy for treating sexual dysfunction or any disease. [3] [4] [5]

In the United States, it is illegal to market an over-the-counter (OTC) supplement product containing yohimbine as a treatment for any supposed health effect without having approval from the Food and Drug Administration (FDA). [3] [6] [7] In the United Kingdom, yohimbine is an unlicensed drug, rarely and specifically compounded as a "prescription-only medicine", while yohimbine herbal supplements are banned from manufacturing as dangerous substances. [8]

Uses

Poison warning and variable content in over-the-counter supplements

In 2022, the Tennessee Poison Center warned that use of yohimbine supplements may have fatal effects due to the possibility for high, unregulated amounts of yohimbine in over-the-counter (OTC) supplement products. [9] Due to inaccurate product labeling and the potential for serious adverse effects, yohimbine supplements have been banned in many countries. [3] Use of such products has been associated with cardiovascular problems and seizures. [3] [9]

The European Food Safety Authority Panel on Food Additives determined that it was not possible to conclude about the safety or to establish a health-based guidance value for yohimbine in supplement products. [5] : 38  They wrote:

Overall the missing information include[s] quantitative data on the composition and specifications of yohimbe bark and its preparations used in food and food supplements covering other alkaloids besides yohimbine, data on the bioavailability of active ingredients from the yohimbe bark extract and data on the toxicity of well specified individual preparations of yohimbe bark and the major yohimbe bark alkaloids, especially regarding subchronic toxicity, genotoxicity and reproductive toxicity.

One study found that samples of brands sold in American brick-and-mortar stores contained highly variable amounts of yohimbine, with some brands of "yohimbe" not containing yohimbine from the P. johimbe tree, and other products containing no yohimbine at all. [10] : 368  Labeling claims were often misleading. [10] : 368 

In analyses by other laboratories for products sold in the US, in other countries, and on the internet, highly variable content levels of yohimbine were revealed. [11] [12] [13] [14] [15]

Yohimbe sold in markets in West Africa where the tree grows may be adulterated with other species of the genus Pausinystalia, which contain little yohimbine. [16] The amounts of alkaloid found even in genuine P. johimbe bark vary considerably, depending on the source of the bark (roots, stem, branches, height). [17]

FDA warning letters

During the 21st century, the FDA issued multiple warning letters to American manufacturers of yohimbe supplements for making false health claims and interstate marketing of such products as misbranded, unapproved drugs. [7] [10]

Sexual dysfunction and aphrodisiac

There is no evidence that yohimbe herbal supplements are effective as an aphrodisiac or as an OTC replacement for sildenafil (Viagra) for erectile dysfunction. [3] [4] Prescriptions for it are rare, and most United States pharmaceutical manufacturers have discontinued production of prescription capsules and tablets. [10] : 357–8  In Canada during 2019, yohimbe products were removed from the market out of concern their use for sexual enhancement, weight loss, or as an exercise aid would pose serious health risks. [18]

It has been studied as a potential treatment for erectile dysfunction, but there is insufficient evidence to rate its effectiveness. [3] [19] [20] Nevertheless, the quantity of yohimbine in dietary supplements, often advertised as promoting sexual function, has been found to overlap with prescription doses of yohimbine. [6]

In the United Kingdom, supplement preparations of yohimbe are banned as introducing a considerable risk for adverse effects. [8] The drug form of yohimbine, called Yohimbine hydrochloride (yohimbine HCl) [21] – which is not licensed as a medicine for any condition – may rarely and specifically be compounded by a pharmacist ("chemist" in the UK) as a prescription-only medicine for treating delayed ejaculation [22] – a formulation that cannot be sold, supplied or advertised as a retail product. [23]

Yohimbine has been used to treat female sexual dysfunction, but there are few reported clinical trials and these do not show it to be better than placebo. [24] [25] [26]

In the United States, "yohimbe" preparations are sold as dietary supplements for enhancing libido, for weight loss and as aids for bodybuilding, but "there is virtually no published research on yohimbe which supports these or any other claims". [3] [25] : 861 

Other uses

Yohimbine has been used to increase peripheral blood flow and to dilate the pupil of the eye. [27]

Adverse effects

Adverse effects of yohimbine in humans at high doses include hypertension (high blood pressure), tachycardia (rapid heartbeat), agitation, hypervigilance, anxiety, tremors, nausea, and urinary frequency. [3] [4] [28] [29] [30] The drug is described as producing a psychoactive state of considerable anxiety along with tenseness, restlessness, and irritability and as being "extremely unpleasant", at least at the assessed doses. [31] In animals, yohimbine likewise produces effects suggestive of severe anxiety. [31] Yohimbine has been used in animals as a model of anxiety in the evaluation of novel anxiolytics. [31]

Drug interactions

Yohimbine has extensive interactions with prescription drugs, some with severe health consequences, including sudden hypotension, irregular heart rate, heart failure, and death. [3] [4] [27]

Barbiturates and benzodiazepines can reduce the anxiety produced by yohimbine. [31] Conversely, combination with imipramine, which is notably known to act as a norepinephrine reuptake inhibitor, has been reported to augment the restlessness and anxiety of yohimbine and to convert them into panic. [31]

Pharmacology

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 dopamine D2 receptors, and weak affinity for the 5-HT1E, 5-HT2A, 5-HT5A, 5-HT7, and dopamine D3 receptors. [32] [33] It behaves as an antagonist at α1-adrenergic, α2-adrenergic, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, and dopamine D2, and as a partial agonist at 5-HT1A. [32] [34] [35] [36] Yohimbine interacts with serotonin and dopamine receptors in high concentrations. [37]

Pharmacologic profile
Molecular target Binding affinity
(Ki in nanomolar) [33] 		Pharmacologic action
[32] [34] [35] [36] [38] [39] 		SpeciesSource
SERT 1,000InhibitorHumanFrontal cortex
5-HT1A 346Partial agonistHumanCloned
5-HT1B 19.9AntagonistHumanCloned
5-HT1D 44.3AntagonistHumanCloned
5-HT1E 1,264UnknownHumanCloned
5-HT1F 91.6UnknownHumanCloned
5-HT2A 1,822AntagonistHumanCloned
5-HT2B 43–143.7AntagonistHumanCloned
5-HT7 2,850UnknownHumanCloned
α1A 1,680AntagonistHumanCloned
α1B 1,280AntagonistHumanCloned
α1C 770AntagonistHumanCloned
α1D 557AntagonistHumanCloned
α2A 1.05AntagonistHumanCloned
α2B 1.19AntagonistHumanCloned
α2C 1.19AntagonistHumanCloned
D2 339AntagonistHumanCloned
D3 3,235AntagonistHumanCloned

Yohimbine selectively blocks the pre-synaptic α2-adrenergic receptors. Blockade of post-synaptic α2-adrenergic receptors causes only minor corpus cavernosum smooth muscle relaxation, due to the fact that the majority of adrenoceptors in the corpus cavernosum are of the α1 type. Blockade of pre-synaptic α2-adrenergic 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-adrenergic receptors on the corpus cavernosum smooth muscle. Under physiologic conditions, however, nitric oxide attenuates norepinephrine vasoconstriction. [40]

Yohimbine binds to the a2 adrenergic receptor at a ratio of 40:1 and is the only a2 adrenergic receptor antagonist with no imidazoline receptor activity. [41]

Chemistry

Yohimbine is a polycyclic cyclized tryptamine and yohimban derivative.

Other related compounds include ajmalicine, alstonine, corynanthine, deserpidine, mitragynine, rauwolscine, spegatrine, reserpine, and rescinnamine.

Natural occurrence

Pausinystalia johimbe

Yohimbine should not be confused with yohimbe [42] but often is. [43] Yohimbe is the common English name for the tree species P. johimbe (also called Corynanthe johimbe) and, by extension, the name of a medicinal preparation made from the bark of that tree, sold as an aphrodisiac. [44] In contrast, yohimbine is a pure alkaloid that can be isolated from yohimbe bark.

Yohimbine is just one of at least 55 indole alkaloids that have been isolated from the bark; [45] and, while it has been described as the most active of these, [10] it constitutes only 15% of the total alkaloid content. [25] Others include rauwolscine, corynanthine and ajmalicine; [25] the bark also contains non-alkaloids about which virtually nothing is known. [25]

Yohimbe, thus a complex mixture, has been studied far less thoroughly than yohimbine, the pure compound. [25] Pharmaceutical grade yohimbine is usually presented as the hydrochloride, [5] [25] which is more soluble.

The traditional source of yohimbine is the bark of the African tree P. johimbe. It has other uses, but the tree is sought out primarily for its bark; in practice, harvesting the bark kills the tree. Tree density is relatively low (average ≈ 4 harvestable trees/hectare). The high demand for medicines based on the bark has led to the tree's over-exploitation. The bark is traded in local markets and, because it is scarce, it is often adulterated with that of other species which contain little yohimbine. [16] The species is becoming endangered. [46]

Around the year 2000, Cameroon was shipping P. johimbe to Europe at the rate of about 100 tonnes annually. Most bark is collected illegally by local people who are paid 150 CFA francs per kilo (about US$0.10 per pound) for delivery of pre-dried bark at the roadside. In practice they confuse and mix it with P. macroceras ("false yohimbe"), a species that contains little yohimbine. [47]

Aspidosperma quebracho-blanco

Aspidosperma quebracho-blanco is an unrelated tree whose common name is quebracho blanco. [48] It is found in large areas of central South America, particularly the Gran Chaco, where it is often the dominant species in the canopy. [49] It is one of the most widely distributed Argentine arboreal species. [50] [51] Traditionally it was logged for fuel, timber and railway sleepers. [51] While in recent times cattle ranching and soya cultivation have led to considerable habitat loss, [52] and while there is still illegal logging, no shortage of the bark is reported. The tree has not been described as endangered: a few members of the genus Aspidosperma are on the IUCN Red List. but the quebracho blanco species is not one of them. [53]

In its bark an alkaloid is found which was given the name quebrachine. In 1914, two scientific papers claimed quebrachine was chemically identical to yohimbine. [54] This was disputed, [55] and the matter long remained in doubt. [56] However, in 1972, Effler and Effler using modern analytical techniques, including mass spectrometry, UV absorption, IR absorption, and NMR, established that quebrachine and yohimbine are one and the same thing. They wrote:

While it was almost unthinkable in 1914 ... that the same alkaloid was formed in [completely] different plants, recent studies have shown that this is certainly the case for indole alkaloids. [57]

The term 'quebrachine' may be used as a synonym for yohimbine. [58] [59] [60] [61] [62]

Strictly speaking, wrote George Barger, yohimbine should have been given the scientific name quebrachine, seeing that it was first isolated from the quebracho tree and first named in the scientific literature. However, the later work on P. yohimbe was better known. [54]

Other plants

Yohimbine has also been isolated from other plant genera in the family Apocynaceae including Lochnera (Catharanthus), [63] Rauvolfia , Amsonia , Vallesia and Vinca ; from the family Loganiaceae (genera Gelsemium and Strychnos ); and from the family Euphorbiaceae (genus Alchornea ). [25]

History

Yohimbe ( Pausinystalia johimbe ) is a tree that grows in western and central Africa; [64] yohimbine was named as originally extracted from the bark of yohimbe in 1896 by Adolph Spiegel [65] (but see § Aspidosperma quebracho-blanco below). Yohimbe is used in folk medicine as an aphrodisiac. In 1900, it attracted scientific interest in Germany, where an initial report claimed that yohimbe exerted a strong aphrodisiacal effect in animals and humans. [25] Attention soon shifted from the plant to its active constituents, particularly yohimbine. [25] In 1943 the correct constitution of yohimbine was proposed by Witkop. [66] Fifteen years later, a team led by Eugene van Tamelen used a 23-step synthesis to become the first persons to achieve the synthesis of yohimbine. [67] [68] [69]

Society and culture

Doping in sport

There was a case in the World Anti-Doping Agency practice in 2007, when an athlete, who reportedly consumed Yohimbine prior to a given athletic event, was later tested positive for 19-norandrosterone, which is a prohibited substance. [70] However, WADA did not yet list Yohimbine (which can come into a body via an energy drink, [71] also in a form of pre-workout supplement or fat burner [72] ) as a prohibited substance, nor did it confirm that its use can increase the endogenous level of anabolic steroids, in particular of 19-norandrostenedione and testosterone.

Research

Post-traumatic stress disorder

Yohimbine has been studied as a way to improve the effects of exposure therapy in people with post-traumatic stress disorder (PTSD). [73] [74] [75]

Veterinary use

Yohimbine has been used since the 1970s to reverse the effects of xylazine. [41] A 2011 preliminary study found that intravenous yohimbine has slow elimination and a large distribution in horses. [41] [76] Yohimbine is not commonly used in small animal medicine anymore but is still commonly used in large animal medicine to reverse α2 adrenergic receptor agonists such as xylazine. [41]

References

  1. ↑ "Yohimbine. (n.d.)". Collins English Dictionary – Complete and Unabridged. (1991, 1994, 1998, 2000, 2003). Retrieved 27 January 2015.
  2. ↑ 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): 651–6. doi:10.1007/BF02284967. PMID   1493849. S2CID   12346330.
  3. 1 2 3 4 5 6 7 8 9 10 "Yohimbe". National Center for Complementary and Integrative Health, US National Institutes of Health. April 2025. Retrieved 20 June 2025.
  4. 1 2 3 4 5 "Yohimbe". Drugs.com. 26 June 2024. Retrieved 20 June 2025.
  5. 1 2 3 EFSA Panel on Food Additives and Nutrient Sources Added to Food, European Food Safety Authority (2013). "Scientific Opinion on the evaluation of the safety in use of Yohimbe (Pausinystalia yohimbe (K. Schum.) Pierre ex Beille)". EFSA Journal . 7. 11 (7): 3302 (1–46). doi: 10.2903/j.efsa.2013.3302 .
  6. 1 2 Cohen PA, Wang YH, Maller G, DeSouza R, Khan IA (March 2016). "Pharmaceutical quantities of yohimbine found in dietary supplements in the USA". Drug Testing and Analysis. 8 (3–4): 357–69. doi: 10.1002/dta.1849 . PMID   26391406.
  7. 1 2 "FDA warning letter to TEK Naturals". Inspections, Compliance, Enforcement, and Criminal Investigations, US Food and Drug Administration. 5 February 2019. Retrieved 15 January 2026.
  8. 1 2 "Banned and restricted herbal ingredients". Medicines and Healthcare Products, UK Government. 18 December 2014. Retrieved 16 January 2026.
  9. 1 2 Seger, Donna (15 February 2022). "Yohimbine or NO-himbine? A Potentially Fatal Over-the-Counter Supplement". Tennessee Poison Center, Vanderbilt University Medical Center. Retrieved 15 January 2026.
  10. 1 2 3 4 5 Cohen PA, Wang YH, Maller G, DeSouza R, Khan IA (2015). "Pharmaceutical quantities of yohimbine found in dietary supplements in the USA". Drug Testing and Analysis. 8 (3–4): 357–69. doi: 10.1002/dta.1849 . PMID   26391406.
  11. ↑ Betz JM, White KD, der Marderosian AH (1995). "Gas chromatographic determination of yohimbine in commercial yohimbe products". Journal of AOAC International. 78 (5): 1189–94. doi: 10.1093/jaoac/78.5.1189 . PMID   7549534. Concentrations of yohimbine in the commercial products ranged from < 0.1 to 489 ppm, compared with 7089 ppm in the authentic bark.
  12. ↑ Zanolari B, Ndjoko K, Ioset JR, Marston A, Hostettmann K (2003). "Qualitative and quantitative determination of yohimbine in authentic yohimbe bark and in commercial aphrodisiacs by HPLC-UV-API/ MS methods". Phytochemical Analysis. 14 (4): 193–201. Bibcode:2003PChAn..14..193Z. doi:10.1002/pca.699. PMID   12892413. Twenty commercial aphrodisiac preparations were analysed and the amount of yohimbine measured and expressed as the maximal dose per day suggested on product labels ranged from 1.32 to 23.16 mg.
  13. ↑ Raman V, Avula B, Galal AM, Wang YH, Khan IA (January 2013). "Microscopic and UPLC-UV-MS analyses of authentic and commercial yohimbe (Pausinystalia johimbe) bark samples". Journal of Natural Medicines. 67 (1): 42–50. doi:10.1007/s11418-012-0642-2. PMID   22402817. S2CID   11977944. Of 12 commercial samples tested, yohimbine was not detected in one; its presence in other samples was found to be in the range 0.1–0.91%.
  14. ↑ Sun J, Chen P (March 2012). "Chromatographic fingerprint analysis of yohimbe bark and related dietary supplements using UHPLC/UV/MS". Journal of Pharmaceutical and Biomedical Analysis. 61: 142–9. doi:10.1016/j.jpba.2011.11.013. PMID   22221902. Wide variability was observed in fingerprints and yohimbine content among yohimbe dietary supplement samples. For most of the dietary supplements, the yohimbine content was not consistent with the label claims.
  15. ↑ Badr JM (January 2013). "A validated high performance thin layer chromatography method for determination of yohimbine hydrochloride in pharmaceutical preparations". Pharmacognosy Magazine. 9 (33): 4–8. doi: 10.4103/0973-1296.108124 . PMC   3647393 . PMID   23661986. Amount of yohimbine hydrochloride ranged from 2.3 to 5.2 mg/tablet or capsule in preparations containing the pure alkaloid, while it varied from zero to 1.5–1.8 mg/capsule in dietary supplements containing powdered yohimbe bark.
  16. 1 2 Jiofack Tafokou RB (2012). "Pausinystalia johimbe". In Lemmens RH, Louppe D, Oteng-Amoako AA (eds.). Timbers 2 of Plant Resources of Tropical Africa. Vol. 7. Wageningen, Ne: PROTA Foundation. pp. 516–519. ISBN   978-92-9081-495-5.
  17. ↑ Paris R, Letouzey R (1960). "Répartition des alcaloïdes dans le Yohimbe (Pausinystalia yohimbe) (K. Schum.) ex Pierre". Journal d'Agriculture Traditionnelle et de Botanique Appliquée (in French). 7 (4–5): 256–258. doi:10.3406/jatba.1960.2608.
  18. ↑ "Unauthorized products may pose serious health risks". Health Canada, Government of Canada. 17 May 2019. Retrieved 16 January 2026.
  19. ↑ Morales A (March 2000). "Yohimbine in erectile dysfunction: the facts". review. International Journal of Impotence Research. 12 (Suppl 1): S70–74. doi: 10.1038/sj.ijir.3900508 . PMID   10845767.
  20. ↑ Andersson KE (September 2001). "Pharmacology of penile erection". Pharmacological Reviews. 53 (3): 417–50. doi:10.1016/S0031-6997(24)01503-5. PMID   11546836.
  21. ↑ "Yohimbine hydrochloride". UK National Health Service. 10 April 2003. Retrieved 16 January 2026.
  22. ↑ "Ejaculation problems". UK National Health Service. 9 February 2023. Retrieved 2026-01-16.
  23. ↑ "Urgent Notices Issued in Accordance with Part 9, Regulation 165, of The Human Medicines Regulations" (PDF). Medicine and Healthcare Products, UK Government. March 2023. Retrieved 16 January 2026.
  24. ↑ Tam SW, Worcel M, Wyllie M (2001). "Yohimbine: a clinical review". Pharmacology and Therapeutics. 91 (3): 239. doi:10.1016/S0163-7258(01)00156-5. PMID   11744068.
  25. 1 2 3 4 5 6 7 8 9 10 Betz JM (2010). "Yohimbe". In Coates PM, Betz JM, Blackman MR, Cragg GM, Levine M, Moss J, White JD (eds.). Encyclopedia of Dietary Supplements (2nd ed.). New York and London: Informa Healthcare. pp.  861–3. ISBN   978-1-4398-1928-9.
  26. ↑ Andersson KE (December 2011). "Mechanisms of penile erection and basis for pharmacological treatment of erectile dysfunction". Pharmacological Reviews. 63 (4): 811–59. doi:10.1124/pr.111.004515. PMID   21880989. S2CID   6146853.
  27. 1 2 "Yohimbine (oral route) - Side effects & dosage". Mayo Clinic. Retrieved 11 September 2025.
  28. ↑ Tam SW, Worcel M, Wyllie M (September 2001). "Yohimbine: a clinical review". Pharmacol Ther. 91 (3): 215–243. doi:10.1016/s0163-7258(01)00156-5. PMID   11744068.
  29. ↑ Biaggioni I, Robertson RM, Robertson D (May 1994). "Manipulation of norepinephrine metabolism with yohimbine in the treatment of autonomic failure". J Clin Pharmacol. 34 (5): 418–423. doi:10.1002/j.1552-4604.1994.tb04981.x. PMID   8089252.
  30. ↑ Cimolai N, Cimolai T (December 2011). "Yohimbine use for physical enhancement and its potential toxicity". J Diet Suppl. 8 (4): 346–354. doi:10.3109/19390211.2011.615806. PMID   22432773.
  31. 1 2 3 4 5 Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144 (118–119). ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. Archived from the original on 2025-05-27. Retrieved 2025-06-14.
  32. 1 2 3 Millan MJ, Newman-Tancredi A, Audinot V, Cussac D, Lejeune F, Nicolas JP, 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. doi:10.1002/(SICI)1098-2396(200002)35:2<79::AID-SYN1>3.0.CO;2-X. PMID   10611634. S2CID   20221398.
  33. 1 2 "Yohimbine Test Ligand Search". PDSP Ki Database.
  34. 1 2 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. doi:10.1016/0006-2952(93)90208-E. PMID   8517875.
  35. 1 2 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. doi:10.1007/BF00634263. PMID   6136920. S2CID   23251900.
  36. 1 2 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. doi:10.1111/j.1476-5381.1994.tb13072.x. PMC   1910288 . PMID   8032658.
  37. ↑ "Yohimbine (PIM 567)". Inchem.org. Retrieved 2013-05-26.
  38. ↑ "Yohimbine". DrugBank. University of Alberta. Archived from the original on January 30, 2013. Retrieved 12 April 2014.
  39. ↑ Bender AM, Parr LC, Livingston WB, Lindsley CW, Merryman WD (August 2023). "2B Determined: The Future of the Serotonin Receptor 2B in Drug Discovery". J Med Chem. 66 (16): 11027–11039. doi:10.1021/acs.jmedchem.3c01178. PMC   11073569 . PMID   37584406.
  40. ↑ Saenz de Tejada I, Kim NN, Goldstein I, Traish AM (March 2000). "Regulation of pre-synaptic alpha adrenergic activity in the corpus cavernosum". Review. International Journal of Impotence Research. 12 (Suppl 1): S20–25. doi: 10.1038/sj.ijir.3900500 . PMID   10845761.
  41. 1 2 3 4 Lamont LA, Creighton CM (11 September 2024). "Sedatives and Tranquilizers". In Lamont L, Grimm K, Robertson S, Love L, Schroeder C (eds.). Veterinary Anesthesia and Analgesia, The 6th Edition of Lumb and Jones. Wiley Blackwell. pp. 338–344. ISBN   978-1-119-83027-6.
  42. ↑ Jeske AH, ed. (2013). Mosby's Dental Drug Reference - E-Book (11th ed.). Elsevier Health Sciences. ISBN   978-0-323-17226-4., Appendix H, e83;
  43. ↑ Holt S, Atkins RC, Krueger RJ, Sinatra ST, Taylor T (1999). The sexual revolution: natural and healthy alternatives to sex. ProMotion Pub. p. 105. ISBN   978-1-57901-040-9.
  44. ↑ Oxford English Dictionary Online, article "Yohimbe", senses 1 and 2, respectively; Merriam-Webster Online, article "Yohimbe", first and second senses, respectively.
  45. ↑ Sun J, Baker A, Chen P (September 2011). "Profiling the indole alkaloids in yohimbe bark with ultra-performance liquid chromatography coupled with ion mobility quadrupole time-of-flight mass spectrometry". Rapid Communications in Mass Spectrometry. 25 (18): 2591–602. Bibcode:2011RCMS...25.2591S. doi:10.1002/rcm.5158. PMID   23657953.
  46. ↑ Rao MR, Palada MC, Becker BN (2013). "Medicinal and aromatic plants in agroforestry systems". In Nain PK, Rao MR, Buck LE (eds.). New Vistas in Agroforestry: A Compendium for the 1st World Congress of Agroforestry, 2004. Vol. 1. Springer Science and Business Media. p. 109. ISBN   978-94-017-2424-1.
  47. ↑ Sunderland TC, Ngo-Mpeck M, Tchoundjeu Z, Laird SA (2002). "Yohimbe (Pausinstalia johimbe)". In Shanley P, Pierce AR, Laird SA, Guillén A (eds.). Tapping the Green Market: Certification & Management of Non-Timber Forest Products. Earthscan Publications Ltd. pp. 215–224. ISBN   978-1-85383-871-2.
  48. ↑ "Quebracho" is formed from the Spanish words for "axe breaker'.
  49. ↑ Bucher EH (2012). "Chaco and Caatinga — South American Arid Savannas, Woodlands and Thickets". In Huntley BJ, Walker BH (eds.). Ecology of Tropical Savannas. Ecological Studies. Vol. 42. Springer Science and Business. Media. pp. 54–57. ISBN   978-3-642-68786-0.
  50. ↑ "Nombre científico: Aspidosperma quebracho-blanco". Herbario Digital (in Spanish). CONICET. Retrieved 12 January 2019.[ dead link ]
  51. 1 2 Moglia JG, López CR (2001). "Variabilidad radial de algunos caracteres anatómicos de Aspidosperma quebracho blanco" [Radial variability of some anatomical characters of Aspidosperma white quebracho]. Bosque (in Spanish). 22 (2): 4. doi: 10.4206/bosque.2001.v22n2-01 . ISSN   0304-8799.
  52. ↑ Kent RB (2006). Latin America: Regions and People. Texts in regional geography. Guilford Press. p. 151. ISBN   978-1-57230-909-8.
  53. ↑ "The IUCN Red List of Threatened Species" . Retrieved 12 January 2019.
  54. 1 2 Barger G, Field E (1915). "Yohimbine (Quebrachine)". Journal of the Chemical Society, Transactions. 107: 1025. doi:10.1039/CT9150701025.
  55. ↑ Allen AH, Sadler SS, Lathrop EC, Mitchell CA (1929). Allen's Commercial Organic Analysis. Philadelphia: P. Blakiston's Son & Co. p. 217.
  56. ↑ Moyano Navarro B (1942). "Quebrachina y Yohimbina: Efectos Sobre la Corriente de Acción del Corazón". Revista de la Universidad Nacional de Córdoba (in Spanish): 369–403.. ('Quebrachine' and 'yohimbine' had different effects on the heart in the dog model; but the suppliers of those reagents were trusted to vouch for their authenticity.)
  57. ↑ Effler EH, Effler AH (1972). "Ûber die Identitat von Quebrachin und Yohimbin". Chemischer Informationsdienst (in German). 4 (14): 921–924.
  58. ↑ Abel G, Bos R, Bowen IH, Chandler RF, Corrigan D, Cubbin IJ, De Smet PA, Pras N, Scheffer JJ, Van Beek TT, Van Uden W, Woerdenbag HJ (2012). Adverse Effects of Herbal Drugs. Vol. 3. Springer Science & Business Media. ISBN   978-3-642-60367-9.
  59. ↑ Philippsborn H (2006). Elsevier's Dictionary of Vitamins and Pharmacochemistry. Elsevier. p. 599. ISBN   978-0-08-048879-0.
  60. ↑ Lewis RA, Hawley GG (2016). Larrañaga MD, Lewis RJ, Lewis R (eds.). Hawley's Condensed Chemical Dictionary. John Wiley & Sons. p. 1438. ISBN   978-1-118-13515-0.
  61. ↑ Jeske AH, ed. (2013). Mosby's Dental Drug Reference - E-Book (11th ed.). Elsevier Health Sciences. pp. Appendix H, e83. ISBN   978-0-323-17226-4.
  62. ↑ Riviere JE, Papich MG, eds. (2013). Veterinary Pharmacology and Therapeutics (9th ed.). John Wiley & Sons. p. 353. ISBN   978-1-118-68590-7.
  63. ↑ Hammouda Y, Janot MM, Le Men J (May 1956). "[Presence of yohimbine (quebrachin) in the roots of Madagascar periwinkle, Lochnera lancea]". Annales Pharmaceutiques Françaises (in French). 14 (5): 341–4. PMID   13373134.
  64. ↑ "Pausinystalia johimbe". Kew World Checklist of Selected Plant Families.
  65. ↑ Year Book of the American Pharmaceutical Association. American Pharmaceutical Association. 1914. p. 564. Retrieved 20 December 2024.
  66. ↑ Witkop B (1943). "Zur Konstitution des Yohimbins und seiner Abbauprodukte" [On the constitution of yohimbine and its breakdown products]. Justus Liebig's Annalen der Chemie (in German). 554 (1): 83–126. doi:10.1002/jlac.19435540108.
  67. ↑ The Alkaloids: Chemistry and Pharmacology. Vol. 32. Academic Press. 1988. p. 564. ISBN   978-0-12-469532-0.
  68. ↑ van Tamelen E, Shamma M, Burgstahler A, Tamm R, Aldrich P (1958). "The Total Synthesis of Yohimbine". J. Am. Chem. Soc. 80 (18): 5006–5007. Bibcode:1958JAChS..80.5006V. doi:10.1021/ja01551a062.
  69. ↑ Herlé B, Wanner MJ, van Maarseveen JH, Hiemstra H (November 2011). "Total synthesis of (+)-yohimbine via an enantioselective organocatalytic Pictet-Spengler reaction". The Journal of Organic Chemistry. 76 (21): 8907–12. doi:10.1021/jo201657n. PMID   21950549.
  70. ↑ See the Mohadanni case.
  71. ↑ U.S. Anti-Doping Agency Supplement Guide, p. 28.
  72. ↑ Doping substances in dietary supplements
  73. ↑ Singewald N, Schmuckermair C, Whittle N, Holmes A, Ressler KJ (May 2015). "Pharmacology of cognitive enhancers for exposure-based therapy of fear, anxiety and trauma-related disorders". Review. Pharmacology & Therapeutics. 149: 150–90. doi:10.1016/j.pharmthera.2014.12.004. PMC   4380664 . PMID   25550231.
  74. ↑ McGuire JF, Lewin AB, Storch EA (August 2014). "Enhancing exposure therapy for anxiety disorders, obsessive-compulsive disorder and post-traumatic stress disorder". Review. Expert Review of Neurotherapeutics. 14 (8): 893–910. doi:10.1586/14737175.2014.934677. PMC   4125602 . PMID   24972729.
  75. ↑ van der Kolk BA (1995). "The Treatment of Post Traumatic Stress Disorder". In Hobfoll SE, De Vries MW (eds.). Extreme stress and communities: impact and intervention. Boston: Kluwer Academic Publishers. pp. 421–44. ISBN   978-0-7923-3468-2.
  76. ↑ Dimaio Knych HK, Steffey EP, Stanley SD (August 2011). "Pharmacokinetics and pharmacodynamics of three intravenous doses of yohimbine in the horse". Journal of Veterinary Pharmacology and Therapeutics. 34 (4): 359–366. doi:10.1111/j.1365-2885.2010.01234.x. PMID   20950351.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.