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Yohimbine information


Yohimbine
Clinical data
Routes of
administration
By mouth
ATC code
  • G04BE04 (WHO) QV03AB93 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • US: Not FDA approved; unscheduled
Pharmacokinetic data
Bioavailability7-86% (mean 33%)
Elimination half-life0.25-2.5 hours[1]
ExcretionUrine (as metabolites)
Identifiers
IUPAC name
  • 17α-hydroxyyohimban-16α-carboxylic acid methyl ester
CAS Number
  • 146-48-5 checkY
PubChem CID
  • 8969
IUPHAR/BPS
  • 102
DrugBank
  • DB01392 checkY
ChemSpider
  • 8622 checkY
UNII
  • 2Y49VWD90Q
KEGG
  • D08685 checkY
ChEBI
  • CHEBI:10093 checkY
ChEMBL
  • ChEMBL15245 checkY
CompTox Dashboard (EPA)
  • DTXSID9040130 Edit this at Wikidata
ECHA InfoCard100.005.157 Edit this at Wikidata
Chemical and physical data
FormulaC21H26N2O3
Molar mass354.450 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • [H][C@@]15CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@@]4([H])c3[nH]c2ccccc2c3CCN4C5
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 checkY
  • Key:BLGXFZZNTVWLAY-SCYLSFHTSA-N checkY
  (verify)

Yohimbine (/jˈhɪmbn/),[2] also known as quebrachine, is an indole alkaloid derived from the bark of the African tree Pausinystalia johimbe; also from the bark of the unrelated South American tree Aspidosperma quebracho-blanco. Yohimbine is an α2-adrenergic receptor antagonist, and has been used in a variety of research projects. It is a veterinary drug used to reverse sedation in dogs and deer.

While yohimbine behaves as an aphrodisiac in some mammals, it does not do so in humans. It has been prescribed as a treatment for erectile dysfunction, although its reported clinical benefits were modest and it has largely been superseded by the PDE5 inhibitor class of drugs. Substances that have purported to be extracts from the yohimbe tree have been marketed as dietary supplements for various purposes, but they contain highly variable amounts of yohimbine, if any; no published scientific evidence supports their efficacy.

  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): 651–6. doi:10.1007/BF02284967. PMID 1493849. S2CID 12346330.
  2. ^ "Yohimbine. (n.d.)". Collins English Dictionary – Complete and Unabridged. (1991, 1994, 1998, 2000, 2003). Retrieved 27 January 2015.

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Yohimbine

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Yohimbine (/joʊˈhɪmbiːn/), also known as quebrachine, is an indole alkaloid derived from the bark of the African tree Pausinystalia johimbe; also from...

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Corynanthe johimbe

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main phytochemical in the extract is the indoloquinolizidine alkaloid yohimbine. It also contains other alkaloids, such as corynanthine and raubasine...

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during surgical procedures. Alpha-2 antagonists such as atipamezole and yohimbine may be used to reverse the effects of xylazine in animals. Side-effects...

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α2-adrenergic receptor antagonists include: Atipamezole Idazoxan Mirtazapine Yohimbine Finally, the agents carvedilol and labetalol are both α and β-blockers...

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Food and Drug administration only for use in men. The NIH states that yohimbine hydrochloride has been shown in human studies to be possibly effective...

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Corynanthine

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Pausinystalia) genera of plants. It is one of the two diastereoisomers of yohimbine, the other being rauwolscine. It is also related to ajmalicine. Corynanthine...

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Ajmalicine

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Ajmalicine, also known as δ-yohimbine or raubasine, is an antihypertensive drug used in the treatment of high blood pressure. It has been marketed under...

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For example, one of the common reported side effects of the intake of yohimbine is piloerection. Piloerection is one of the signs of opioid withdrawal...

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been isolated from Vinca major. Akuammine is structurally related to yohimbine, mitragynine and more distantly Voacangine, all of which are alkaloid...

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Norepinephrine

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best-known drug in that class is yohimbine, which is extracted from the bark of the African yohimbe tree. Yohimbine acts as a male potency enhancer, but...

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Substituted tryptamine

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some more complex compounds, for example: LSD, ibogaine, mitragynine and yohimbine. A thorough investigation of dozens of tryptamine compounds was published...

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Alkaloid

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(with a solubility of ≥1g/L), whereas others, including morphine and yohimbine are very slightly water-soluble (0.1–1 g/L). Alkaloids and acids form...

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Adderall

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Mirtazapine

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Spegatrine Spiroxatrine Sunepitron Terguride Tolazoline Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine) Yohimbine...

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MDMA

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reports from a FOIA request that, "the spy agency purchased two pounds of Yohimbine hydrochloride... by Dr. Robert V. Lashbrook, the chief aide to Dr. Sidney...

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includes harmala alkaloids as well. Yohimbine, harmine, harmaline and ajmalicine occurs in descending order, yohimbine being highest. The tobacco plant readily...

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