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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:: description was created based on several sources, including http://www.fatburner-1.com/fatburner/yohimbin-kaufen.html 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
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Agmatine inhibits the afferent activity of carotid baroreceptor in rats].
2001 Apr
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
Effect of alpha-adrenoceptor agents on imipramine-induced antinociception in nerve-ligated mice.
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
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
Yohimbine for anxiety disorders.
2001 Aug
An isobolographic analysis of the adrenergic modulation of diclofenac antinociception.
2001 Aug
Insulin secretion and glucose kinetics during exercise with and without pharmacological alpha(1)- and alpha(2)-receptor blockade.
2001 Aug
High concentrations of adrenergic antagonists prolong sciatic nerve blockade by tetrodotoxin.
2001 Aug
Microinjection of carbachol in the lateral hypothalamus produces opposing actions on nociception mediated by alpha(1)- and alpha(2)-adrenoceptors.
2001 Aug 17
Phentolamine mesylate relaxes rabbit corpus cavernosum by a nonadrenergic, noncholinergic mechanism.
2001 Feb
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.
2001 Feb
Imidazolines inhibit secretory responses of rat colonic mucosa to calcium-dependent but not cyclic AMP-dependent secretagogues.
2001 Feb
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
Alpha 2-adrenoceptor activity induces the antidepressant-like glycolipid in mouse forced swimming.
2001 Jan-Feb
Disturbance of the prejunctional modulation of cholinergic neurotransmission during chronic granulomatous inflammation of the mouse ileum.
2001 Jul
Activation of alpha(2)-receptors in the rostral ventrolateral medulla evokes natriuresis by a renal nerve mechanism.
2001 Jul
Agmatine potentiates the analgesic effect of morphine by an alpha(2)-adrenoceptor-mediated mechanism in mice.
2001 Jul
The effect of adrenergic compounds on neurogenic dural vasodilatation.
2001 Jul 13
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
Alpha2-adrenoceptors inhibit antidiuretic hormone-stimulated Na+ absorption across tight epithelia (Rana esculenta).
2001 Jun
An obligatory role for spinal cholinergic neurons in the antiallodynic effects of clonidine after peripheral nerve injury.
2001 Jun
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
Immunoaffinity purification and reconstitution of human alpha(2)-adrenergic receptor subtype C2 into phospholipid vesicles.
2001 Jun
Comparison of the effect of intrathecal administration of clonidine and yohimbine on the locomotion of intact and spinal cats.
2001 Jun
Vascular actions of MDMA involve alpha1 and alpha2-adrenoceptors in the anaesthetized rat.
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
Methadone patients exhibit increased startle and cortisol response after intravenous yohimbine.
2001 Mar
Effect of methanolic extract of Cassia nigricans leaves on rat gastrointestinal tract.
2001 Mar
Clonidine-induced antinociception and locomotor hypoactivity are reduced by dexamethasone in mice.
2001 Mar
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
Modulation of MK-801-induced behaviour by noradrenergic agents in mice.
2001 Mar 1
The differential effects of prenatal stress in rats on the acoustic startle reflex under baseline conditions and in response to anxiogenic drugs.
2001 Mar 1
Effect of electrical field stimulation on insulin and glucagon secretion from the pancreas of normal and diabetic rats.
2001 May
In vivo assessment of the regulatory mechanism of cholinergic neuronal activity associated with motility in dog small intestine.
2001 May
Brimonidine and inhibition of nitrite production in isolated porcine ciliary processes.
2001 May
Oral drug therapy for erectile dysfunction.
2001 May
The nitric oxide synthase inhibitor L-NMMA potentiates noradrenaline-induced vasoconstriction: effects of the alpha2-receptor antagonist yohimbine.
2001 May
Increased responsiveness to the hyperglycemic, hyperglucagonemic and hyperinsulinemic effects of circulating norepinephrine in ob/ob mice.
2001 May
Effects of yohimbine on the antinociceptive and place conditioning effects of opioid agonists in rodents.
2001 May
Interaction of formamidine pesticides with the presynaptic alpha(2)-adrenoceptor regulating.
2001 May 1
Agmatine produces antinociception in tonic pain in mice.
2001 May-Jun
Neuropeptide Y in obese women during treatment with adrenergic modulation drugs.
2001 May-Jun
Effects of alpha(2)-adrenergic agonists on lipopolysaccharide-induced aqueous flare elevation in pigmented rabbits.
2001 May-Jun
Alpha-2 and beta-adrenergic receptors mediate NE's biphasic effects on rat thick ascending limb chloride flux.
2001 Sep
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