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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

Molecular Formula C21H26N2O3
Molecular Weight 354.4435
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Gastroprokinetic effect and mechanism of SK-896, a new motilin analogue, during the interdigestive period in conscious dogs.
2001
Orthostatic hypotension in patients with Parkinson's disease: pathophysiology and management.
2001
[Agmatine inhibits the afferent activity of carotid baroreceptor in rats].
2001 Apr
Role of the alpha(1)- and alpha(2)-adrenoceptors of the paraventricular nucleus on the water and salt intake, renal excretion, and arterial pressure induced by angiotensin II injection into the medial septal area.
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
Nitric oxide attenuates alpha(2)-adrenergic receptors by ADP-ribosylation of G(i)alpha in ciliary epithelium.
2001 Aug
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
Modulation of adipocyte lipoprotein lipase expression as a strategy for preventing or treating visceral obesity.
2001 Aug
Differential role of adrenoceptors in control of plasma glucose and fatty acids in carp, Cyprinus carpio (L.).
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
Visceral antinociception produced by bee venom stimulation of the Zhongwan acupuncture point in mice: role of alpha(2) adrenoceptors.
2001 Aug 3
Phentolamine mesylate relaxes rabbit corpus cavernosum by a nonadrenergic, noncholinergic mechanism.
2001 Feb
Hydroxylation of yohimbine in superacidic media: one-step access to human metabolites 10 and 11-hydroxyyohimbine.
2001 Feb
Presynaptic alpha2-adrenoceptor-mediated modulation of adenosine 5' triphosphate and noradrenaline corelease: differences in canine mesenteric artery and vein.
2001 Feb
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
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
Divergent effects of an alpha2-adrenergic antagonist on lipolysis and thermogenesis: interactions with a beta3-adrenergic agonist in rats.
2001 Jul
Rabbit alpha2-adrenoceptors: both platelets and adipocytes have alpha2A-pharmacology.
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 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
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 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
Pharmacological aids to locomotor training after spinal injury in the cat.
2001 May 15
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
Effects of adrenergic agonists and antagonists on tetrodotoxin-induced nerve block.
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:37:48 UTC 2021
Edited
by admin
on Sat Jun 26 15:37:48 UTC 2021
Record UNII
2Y49VWD90Q
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
LABELED -> NON-LABELED
TARGET -> INHIBITOR
IC50
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Duration of Action PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC