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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O3
Molecular Weight 354.4427
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of YOHIMBINE

SMILES

[H][C@@]12CC[C@H](O)[C@H](C(=O)OC)[C@@]1([H])C[C@]3([H])N(CCC4=C3NC5=C4C=CC=C5)C2

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 354.4427
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
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
Effect of alpha-adrenoceptor agents on imipramine-induced antinociception in nerve-ligated mice.
2001 Apr
Effect of vanilloid drugs on gastrointestinal transit in mice.
2001 Apr
Yohimbine for anxiety disorders.
2001 Aug
An isobolographic analysis of the adrenergic modulation of diclofenac antinociception.
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
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
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
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 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
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
Clonidine-induced antinociception and locomotor hypoactivity are reduced by dexamethasone in mice.
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
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
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
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 Wed Jul 05 22:55:16 UTC 2023
Edited
by admin
on Wed Jul 05 22:55:16 UTC 2023
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 Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
NCI_THESAURUS C29713
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
WHO-VATC QV03AB93
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
WHO-ATC G04BE04
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
CFR 21 CFR 310.528
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
WHO-VATC QG04BE04
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
DSLD 2366 (Number of products:175)
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID9040130
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
DRUG CENTRAL
3659
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
NCI_THESAURUS
C77304
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-672-0
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
MERCK INDEX
M11570
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY Merck Index
EVMPD
SUB15744MIG
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
FDA UNII
2Y49VWD90Q
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
DRUG BANK
DB01392
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
DAILYMED
2Y49VWD90Q
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
CAS
146-48-5
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
MESH
D015016
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
CHEBI
10093
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
WIKIPEDIA
YOHIMBINE
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
IUPHAR
102
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
PUBCHEM
8969
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
SMS_ID
100000076753
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY
RXCUI
220982
Created by admin on Wed Jul 05 22:55:16 UTC 2023 , Edited by admin on Wed Jul 05 22:55:16 UTC 2023
PRIMARY RxNorm
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Duration of Action PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC