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

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
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
The use of oral vasopressors in the management of autonomic dysfunction and orthostatic hypotension.	1999 May	10369619
Parkinson's disease: a preliminary study of yohimbine challenge in patients with anxiety.	1999 May-Jun	10367182
Gastroprokinetic effect and mechanism of SK-896, a new motilin analogue, during the interdigestive period in conscious dogs.	2001	11490202
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
Voltage-operated Ca(2+) channels involved in K(+)-evoked release of vasoactive intestinal polypeptide from the rat hypothalamus.	2001 Apr	11137631
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	11281758
High concentrations of adrenergic antagonists prolong sciatic nerve blockade by tetrodotoxin.	2001 Aug	11472294
Differential role of adrenoceptors in control of plasma glucose and fatty acids in carp, Cyprinus carpio (L.).	2001 Aug	11448867
Microinjection of carbachol in the lateral hypothalamus produces opposing actions on nociception mediated by alpha(1)- and alpha(2)-adrenoceptors.	2001 Aug 17	11489441
Hydroxylation of yohimbine in superacidic media: one-step access to human metabolites 10 and 11-hydroxyyohimbine.	2001 Feb	11429998
Presynaptic alpha2-adrenoceptor-mediated modulation of adenosine 5' triphosphate and noradrenaline corelease: differences in canine mesenteric artery and vein.	2001 Feb	11422578
Oral alpha adrenoceptor blockade as a treatment of erectile dysfunction.	2001 Feb	11289574
Alpha2-adrenoceptors modulating neuronal serotonin release: a study in alpha2-adrenoceptor subtype-deficient mice.	2001 Feb	11181434
Role of NK2 receptors in gastric barosensitivity and in experimental ileus in rats.	2001 Feb	11169125
Immunomodulatory effect of xylazine, an alpha(2) adrenergic agonist, on rat spleen cells in culture.	2001 Feb 1	11137573
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors.	2001 Feb 16	11226401
Differences between the Lewis and Sprague-Dawley rats in chronic inflammation induced norepinephrine sensitivity of cutaneous C-fiber nociceptors.	2001 Feb 16	11166928
Noradrenaline modulates GABA-mediated synaptic transmission in neurones of the mediolateral part of the guinea pig lateral septum via local circuits.	2001 Jan	11164254
Baclofen-impairment of memory retention in rats: possible interaction with adrenoceptor mechanism(s).	2001 Jan 12	11164386
Receptor reserve analysis of the human alpha(2C)-adrenoceptor using.	2001 Jan 12	11164378
Frequency dependent alpha(2)-adrenoceptor mediated modulation of excitatory junction potentials in guinea-pig mesenteric artery.	2001 Jan 5	11137866
Bradykinin and electrical stimulation increase prostaglandin production in the rat vas deferens.	2001 Jul	11487302
Disturbance of the prejunctional modulation of cholinergic neurotransmission during chronic granulomatous inflammation of the mouse ileum.	2001 Jul	11429394
Rabbit alpha2-adrenoceptors: both platelets and adipocytes have alpha2A-pharmacology.	2001 Jul	11408545
Agmatine potentiates the analgesic effect of morphine by an alpha(2)-adrenoceptor-mediated mechanism in mice.	2001 Jul	11377923
The role of Kupffer cell alpha(2)-adrenoceptors in norepinephrine-induced TNF-alpha production.	2001 Jul 27	11476962
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
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
Neural circuits regulating pulsatile luteinizing hormone release in the female guinea-pig: opioid, adrenergic and serotonergic interactions.	2001 Mar	11207938
Inverse agonist activity at the alpha(2A)-adrenergic receptor.	2001 Mar	11179449
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
Increased responsiveness to the hyperglycemic, hyperglucagonemic and hyperinsulinemic effects of circulating norepinephrine in ob/ob mice.	2001 May	11360153
Interaction of formamidine pesticides with the presynaptic alpha(2)-adrenoceptor regulating.	2001 May 1	11312645
Agmatine produces antinociception in tonic pain in mice.	2001 May-Jun	11420073
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.

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

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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