U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
RS-127445: a selective, high affinity, orally bioavailable 5-HT2B receptor antagonist.
1999 Jul
Hypertensive crisis from herbal treatment of impotence.
1999 May
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
Agonist and antagonist actions of yohimbine as compared to fluparoxan at alpha(2)-adrenergic receptors (AR)s, serotonin (5-HT)(1A), 5-HT(1B), 5-HT(1D) and dopamine D(2) and D(3) receptors. Significance for the modulation of frontocortical monoaminergic transmission and depressive states.
2000 Feb
Hypoxic-ischaemic brain damage in immature rats: effects of adrenoceptor modulation.
2001
[Agmatine inhibits the afferent activity of carotid baroreceptor in rats].
2001 Apr
Alpha2 adrenergic receptors and the central control of breathing in the cane toad, Bufo marinus.
2001 Apr
Agonist trafficking of G(i/o)-mediated alpha(2A)-adrenoceptor responses in HEL 92.1.7 cells.
2001 Apr
Effect of vanilloid drugs on gastrointestinal transit in mice.
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
Nitric oxide attenuates alpha(2)-adrenergic receptors by ADP-ribosylation of G(i)alpha in ciliary epithelium.
2001 Aug
An isobolographic analysis of the adrenergic modulation of diclofenac antinociception.
2001 Aug
Modulation of adipocyte lipoprotein lipase expression as a strategy for preventing or treating visceral obesity.
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
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.
2001 Feb
Immunomodulatory effect of xylazine, an alpha(2) adrenergic agonist, on rat spleen cells in culture.
2001 Feb 1
Catecholaminergic regulation of Na-K-Cl cotransport in pigmented ciliary epithelium: differences between PE and NPE.
2001 Jan
Baclofen-impairment of memory retention in rats: possible interaction with adrenoceptor mechanism(s).
2001 Jan 12
Frequency dependent alpha(2)-adrenoceptor mediated modulation of excitatory junction potentials in guinea-pig mesenteric artery.
2001 Jan 5
Divergent effects of an alpha2-adrenergic antagonist on lipolysis and thermogenesis: interactions with a beta3-adrenergic agonist in rats.
2001 Jul
Alpha2-adrenoceptors inhibit antidiuretic hormone-stimulated Na+ absorption across tight epithelia (Rana esculenta).
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
Comparison of the effect of intrathecal administration of clonidine and yohimbine on the locomotion of intact and spinal cats.
2001 Jun
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
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
Neuropeptide Y in obese women during treatment with adrenergic modulation drugs.
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:24:57 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:57 GMT 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 Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
NCI_THESAURUS C29713
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
WHO-VATC QV03AB93
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WHO-ATC G04BE04
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
CFR 21 CFR 310.528
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
WHO-VATC QG04BE04
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
DSLD 2366 (Number of products:175)
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID9040130
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PRIMARY
DRUG CENTRAL
3659
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PRIMARY
NCI_THESAURUS
C77304
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PRIMARY
ECHA (EC/EINECS)
205-672-0
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PRIMARY
MERCK INDEX
m11570
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PRIMARY Merck Index
EVMPD
SUB15744MIG
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PRIMARY
FDA UNII
2Y49VWD90Q
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PRIMARY
DRUG BANK
DB01392
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PRIMARY
DAILYMED
2Y49VWD90Q
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
PRIMARY
CAS
146-48-5
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PRIMARY
MESH
D015016
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PRIMARY
CHEBI
10093
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
PRIMARY
WIKIPEDIA
YOHIMBINE
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
PRIMARY
IUPHAR
102
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PRIMARY
PUBCHEM
8969
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PRIMARY
SMS_ID
100000076753
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PRIMARY
RXCUI
220982
Created by admin on Fri Dec 15 15:24:57 GMT 2023 , Edited by admin on Fri Dec 15 15:24:57 GMT 2023
PRIMARY RxNorm
Related Record Type Details
LABELED -> NON-LABELED
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SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
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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