YOHIMBINE

US Previously Marketed

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 Search

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

Description
Sources: https://www.drugs.com/cdi/yohimbine.html
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.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor alpha-2 113 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10611634	Antagonist 2778
Serotonin 1 receptors; 5-HT1B & 5-HT1D 4 Target ID: CHEMBL2095230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10611634	Antagonist 2778
Serotonin 1a (5-HT1a) receptor 172 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10611634	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Erectile dysfunction 35 Sources: http://www.fatburner-1.com/fatburner/yohimbin-kaufen.html	Primary		Approved 8429	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Parkinson's disease: a preliminary study of yohimbine challenge in patients with anxiety.	1999 May-Jun	10367182
Characterization of human recombinant alpha(2A)-adrenoceptors expressed in Chinese hamster lung cells using intracellular Ca(2+) changes: evidence for cross-talk between recombinant alpha(2A)- and native alpha(1)-adrenoceptors.	2000 Apr	10742289
Gastroprokinetic effect and mechanism of SK-896, a new motilin analogue, during the interdigestive period in conscious dogs.	2001	11490202
Orthostatic hypotension in patients with Parkinson's disease: pathophysiology and management.	2001	11482743
Hypoxic-ischaemic brain damage in immature rats: effects of adrenoceptor modulation.	2001	11277361
[Agmatine inhibits the afferent activity of carotid baroreceptor in rats].	2001 Apr	11471214
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	11403985
Efficacy of 1.25% amitraz solution in the treatment of generalized demodicosis (eight cases) and sarcoptic mange (five cases) in dogs.	2001 Apr	11360342
Agonist trafficking of G(i/o)-mediated alpha(2A)-adrenoceptor responses in HEL 92.1.7 cells.	2001 Apr	11264241
Effect of vanilloid drugs on gastrointestinal transit in mice.	2001 Apr	11264233
Antinociceptive and respiratory effects of intrathecal H-Tyr-D-Arg-Phe-Lys-NH2 (DALDA) and [Dmt1] DALDA.	2001 Apr	11259564
Nonnoradrenergic mechanism of reflex cutaneous vasoconstriction in men.	2001 Apr	11247759
An isobolographic analysis of the adrenergic modulation of diclofenac antinociception.	2001 Aug	11473875
Microinjection of carbachol in the lateral hypothalamus produces opposing actions on nociception mediated by alpha(1)- and alpha(2)-adrenoceptors.	2001 Aug 17	11489441
Phentolamine mesylate relaxes rabbit corpus cavernosum by a nonadrenergic, noncholinergic mechanism.	2001 Feb	11468007
Hydroxylation of yohimbine in superacidic media: one-step access to human metabolites 10 and 11-hydroxyyohimbine.	2001 Feb	11429998
Release of intermediate reactive hydrogen peroxide by macrophage cells activated by natural products.	2001 Feb	11217094
Alpha2-adrenoceptors modulating neuronal serotonin release: a study in alpha2-adrenoceptor subtype-deficient mice.	2001 Feb	11181434
Postjunctional alpha(2C)-adrenoceptor contractility in human saphenous vein.	2001 Feb 16	11226402
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors.	2001 Feb 16	11226401
The role of neurochemical mechanisms of ventromedial hypothalamus in various models of anxiety in rats.	2001 Jan	11329078
Alpha2-adrenoceptor-mediated inhibition of cultured sympathetic neurons: changes in alpha2A/D-adrenoceptor-deficient mice.	2001 Jan	11191829
alpha(2)-Adrenoceptor agonists inhibit vitreal glutamate and aspartate accumulation and preserve retinal function after transient ischemia.	2001 Jan	11123383
Rabbit alpha2-adrenoceptors: both platelets and adipocytes have alpha2A-pharmacology.	2001 Jul	11408545
Activation of alpha(2)-receptors in the rostral ventrolateral medulla evokes natriuresis by a renal nerve mechanism.	2001 Jul	11404283
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	11441427
Pharmacological identification of the major subtypes of adrenoceptors involved in the canine external carotid vasoconstrictor effects of adrenaline and noradrenaline.	2001 Jun 1	11441904
Methadone patients exhibit increased startle and cortisol response after intravenous yohimbine.	2001 Mar	11351934
Selective imidazoline I2 ligands do not show antidepressant-like activity in the forced swim test in mice.	2001 Mar	11277603
Characterization of secretory and morphologic properties of primary cultured endocrine cells from porcine pancreata.	2001 Mar	11249067
Inverse agonist activity at the alpha(2A)-adrenergic receptor.	2001 Mar	11179449
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	11314679
In vivo assessment of the regulatory mechanism of cholinergic neuronal activity associated with motility in dog small intestine.	2001 May	11430475
Brimonidine and inhibition of nitrite production in isolated porcine ciliary processes.	2001 May	11417333
The nitric oxide synthase inhibitor L-NMMA potentiates noradrenaline-induced vasoconstriction: effects of the alpha2-receptor antagonist yohimbine.	2001 May	11393674
Increased responsiveness to the hyperglycemic, hyperglucagonemic and hyperinsulinemic effects of circulating norepinephrine in ob/ob mice.	2001 May	11360153
Alpha-2 and beta-adrenergic receptors mediate NE's biphasic effects on rat thick ascending limb chloride flux.	2001 Sep	11507016
Dopamine inhibits vasopressin action in the rat inner medullary collecting duct via alpha(2)-adrenoceptors.	2001 Sep	11504796

Patents

Sample Use Guides

In Vivo Use Guide

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

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

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 522.2670