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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O3
Molecular Weight 354.4435
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of YOHIMBINE

SMILES

COC(=O)[C@]1([H])[C@@]2([H])C[C@@]3([H])c4c(CCN3C[C@]2([H])CC[C@]1([H])O)c5ccccc5[nH]4

InChI

InChIKey=BLGXFZZNTVWLAY-SCYLSFHTSA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/10611634

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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
Yohimbine use in a natural setting: effects on posttraumatic stress disorder.
1999 Aug 1
The use of oral vasopressors in the management of autonomic dysfunction and orthostatic hypotension.
1999 May
Hypertensive crisis from herbal treatment of impotence.
1999 May
Parkinson's disease: a preliminary study of yohimbine challenge in patients with anxiety.
1999 May-Jun
The alpha2-adrenergic receptor antagonist idazoxan reduces dyskinesia and enhances anti-parkinsonian actions of L-dopa in the MPTP-lesioned primate model of Parkinson's disease.
1999 Sep
Hypoxic-ischaemic brain damage in immature rats: effects of adrenoceptor modulation.
2001
Efficacy of 1.25% amitraz solution in the treatment of generalized demodicosis (eight cases) and sarcoptic mange (five cases) in dogs.
2001 Apr
Inhibition of field stimulation-induced contractions of rabbit vas deferens by muscarinic receptor agonists: selectivity of McN-A-343 for M1 receptors.
2001 Apr
Alpha2 adrenergic receptors and the central control of breathing in the cane toad, Bufo marinus.
2001 Apr
Hyperglycaemia: a morphine-like effect produced by naloxone.
2001 Apr
Nonnoradrenergic mechanism of reflex cutaneous vasoconstriction in men.
2001 Apr
Voltage-operated Ca(2+) channels involved in K(+)-evoked release of vasoactive intestinal polypeptide from the rat hypothalamus.
2001 Apr
Conformational analysis of indole alkaloids corynantheine and dihydrocorynantheine by dynamic 1H NMR spectroscopy and computational methods: steric effects of ethyl vs vinyl group.
2001 Apr 6
An isobolographic analysis of the adrenergic modulation of diclofenac antinociception.
2001 Aug
Phentolamine mesylate relaxes rabbit corpus cavernosum by a nonadrenergic, noncholinergic mechanism.
2001 Feb
Presynaptic alpha2-adrenoceptor-mediated modulation of adenosine 5' triphosphate and noradrenaline corelease: differences in canine mesenteric artery and vein.
2001 Feb
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.
2001 Feb
Determination of relative triplet sublevel populating rates during optical pumping using ODMR.
2001 Feb
Alpha2-adrenoceptors modulating neuronal serotonin release: a study in alpha2-adrenoceptor subtype-deficient mice.
2001 Feb
Immunomodulatory effect of xylazine, an alpha(2) adrenergic agonist, on rat spleen cells in culture.
2001 Feb 1
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors.
2001 Feb 16
Neural mechanisms involved in the delay of gastric emptying and gastrointestinal transit of liquid after thoracic spinal cord transection in awake rats.
2001 Feb 20
The role of neurochemical mechanisms of ventromedial hypothalamus in various models of anxiety in rats.
2001 Jan
Alpha2-adrenoceptor-mediated inhibition of cultured sympathetic neurons: changes in alpha2A/D-adrenoceptor-deficient mice.
2001 Jan
Catecholaminergic regulation of Na-K-Cl cotransport in pigmented ciliary epithelium: differences between PE and NPE.
2001 Jan
alpha(2)-Adrenoceptor agonists inhibit vitreal glutamate and aspartate accumulation and preserve retinal function after transient ischemia.
2001 Jan
In vivo demonstration of alpha(1A)-adrenoceptor subtype selectivity of KMD-3213 in rat tissues.
2001 Jan
Baclofen-impairment of memory retention in rats: possible interaction with adrenoceptor mechanism(s).
2001 Jan 12
Receptor reserve analysis of the human alpha(2C)-adrenoceptor using.
2001 Jan 12
Frequency dependent alpha(2)-adrenoceptor mediated modulation of excitatory junction potentials in guinea-pig mesenteric artery.
2001 Jan 5
Bradykinin and electrical stimulation increase prostaglandin production in the rat vas deferens.
2001 Jul
Disturbance of the prejunctional modulation of cholinergic neurotransmission during chronic granulomatous inflammation of the mouse ileum.
2001 Jul
Rabbit alpha2-adrenoceptors: both platelets and adipocytes have alpha2A-pharmacology.
2001 Jul
The role of Kupffer cell alpha(2)-adrenoceptors in norepinephrine-induced TNF-alpha production.
2001 Jul 27
The influence of chloroethylclonidine-induced contraction in isolated arteries of Wistar Kyoto rats: alpha1D- and alpha1A-adrenoceptors, protein kinase C, and calcium influx.
2001 Jul-Aug
The alpha 2 adrenoceptor antagonists RX 821002 and yohimbine delay-dependently impair choice accuracy in a delayed non-matching-to-position task in rats.
2001 Jun
Pharmacological identification of the major subtypes of adrenoceptors involved in the canine external carotid vasoconstrictor effects of adrenaline and noradrenaline.
2001 Jun 1
Discriminative stimulus properties of indorenate, a 5-HT1A, 5-HT1B and 5-HT2C agonist: a study in rats.
2001 Mar
Selective imidazoline I2 ligands do not show antidepressant-like activity in the forced swim test in mice.
2001 Mar
Ultrasonic vocalizations of preweanling rats: involvement of both alpha(2)-adrenoceptor and kappa-opioid receptor systems.
2001 Mar
Characterization of secretory and morphologic properties of primary cultured endocrine cells from porcine pancreata.
2001 Mar
Adenosine inhibits norepinephrine release in the postischemic rat heart: the mechanism of neuronal stunning.
2001 Mar
Agmatine produces antinociception in tonic pain in mice.
2001 May-Jun
Dopamine inhibits vasopressin action in the rat inner medullary collecting duct via alpha(2)-adrenoceptors.
2001 Sep
Patents

Sample Use Guides

2 single-dose administrations of 5 mg yohimbine hydrochloride at least one week i.e. 6 treatment free days between all administrations
Route of Administration: Oral
In Vitro Use Guide
In order to test the putative role of alpha 2 receptors in ethanol intoxication, it was studied the interaction between ethanol and yohimbine on the spontaneous firing rate of rat locus coeruleus (LC) in an in vitro slice model. If yohimbine (20 microM) was simultaneously perfused, the ethanol-induced inhibition was rapidly antagonized. This effect is reversible after long time washout of yohimbine.
Name Type Language
YOHIMBINE
MI   VANDF   WHO-DD  
Common Name English
YOHIMBINE [MI]
Common Name English
YOHIMBINE [WHO-DD]
Common Name English
17.ALPHA.-HYDROXY-20-.ALPHA.-YOHIMBAN-16-.BETA.-CARBOXYLIC ACID, METHYL ESTER
Common Name English
YOHIMBINE [VANDF]
Common Name English
YOHIMBINUM [HPUS]
Common Name English
YOHIMBINUM
HPUS  
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.2670
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
NCI_THESAURUS C29713
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
WHO-VATC QV03AB93
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
WHO-ATC G04BE04
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
CFR 21 CFR 310.528
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
WHO-VATC QG04BE04
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
DSLD 2366 (Number of products:175)
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
Code System Code Type Description
EPA CompTox
146-48-5
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
DRUG CENTRAL
3659
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
NCI_THESAURUS
C77304
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-672-0
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
MERCK INDEX
M11570
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY Merck Index
EVMPD
SUB15744MIG
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
FDA UNII
2Y49VWD90Q
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
DRUG BANK
DB01392
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
CAS
146-48-5
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
MESH
D015016
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
WIKIPEDIA
YOHIMBINE
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
IUPHAR
102
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
PUBCHEM
8969
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY
RXCUI
220982
Created by admin on Sat Jun 26 15:37:49 UTC 2021 , Edited by admin on Sat Jun 26 15:37:49 UTC 2021
PRIMARY RxNorm