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

COC(=O)[C@H]1[C@@H](O)CC[C@H]2CN3CCC4=C(NC5=C4C=CC=C5)[C@@H]3C[C@H]12

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-2 114 Target ID: CHEMBL2095158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10611634	Antagonist 2849
Serotonin 1 receptors; 5-HT1B & 5-HT1D 4 Target ID: CHEMBL2095230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10611634	Antagonist 2849
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10611634	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Erectile dysfunction 35 Sources: http://www.fatburner-1.com/fatburner/yohimbin-kaufen.html	Primary		Approved 8583	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
37.3 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/11744068/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
50.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	5.4 mg 3 times / day multiple, oral dose: 5.4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
78.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	5.4 mg 3 times / day multiple, oral dose: 5.4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
154 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	10.8 mg 3 times / day multiple, oral dose: 10.8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
131 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	10.8 mg 3 times / day multiple, oral dose: 10.8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
400 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	16.2 mg 3 times / day multiple, oral dose: 16.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
366 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	16.2 mg 3 times / day multiple, oral dose: 16.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
49.5 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	21.6 mg 3 times / day multiple, oral dose: 21.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
51.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	21.6 mg 3 times / day multiple, oral dose: 21.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
55.7 ng × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/11744068/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
30.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	5.4 mg 3 times / day multiple, oral dose: 5.4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
41.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	5.4 mg 3 times / day multiple, oral dose: 5.4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
119 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	10.8 mg 3 times / day multiple, oral dose: 10.8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
80.2 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	10.8 mg 3 times / day multiple, oral dose: 10.8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
476 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	16.2 mg 3 times / day multiple, oral dose: 16.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
319 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	16.2 mg 3 times / day multiple, oral dose: 16.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
72.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	21.6 mg 3 times / day multiple, oral dose: 21.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
75.1 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	21.6 mg 3 times / day multiple, oral dose: 21.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
1.3 h REVIEW https://pubmed.ncbi.nlm.nih.gov/11744068/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
0.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	5.4 mg 3 times / day multiple, oral dose: 5.4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.09 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	5.4 mg 3 times / day multiple, oral dose: 5.4 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.21 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	10.8 mg 3 times / day multiple, oral dose: 10.8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.32 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	10.8 mg 3 times / day multiple, oral dose: 10.8 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	16.2 mg 3 times / day multiple, oral dose: 16.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.39 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	16.2 mg 3 times / day multiple, oral dose: 16.2 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.16 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	21.6 mg 3 times / day multiple, oral dose: 21.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
0.24 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9234649/	21.6 mg 3 times / day multiple, oral dose: 21.6 mg route of administration: Oral experiment type: MULTIPLE co-administered:	YOHIMBINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
18% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8097957/			YOHIMBINE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
100 mg single, oral Highest studied dose Dose: 100 mg Route: oral Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9400452/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9400452/	Other AEs: Anxiety, Hypertension... Other AEs: Anxiety (18.2%) Hypertension (9%) Headache (13.6%) Urinary frequency aggravated (31.8%) Facial flushing (9%) Tachycardia (27.3%) Vertigo (13.6%) Urticaria (4.5%) Anorexia (4.5%) Flatulence (4.5%) Perspiration excessive (4.5%) Epigastralgia (4.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/9400452/
350 mg single, oral Overdose Dose: 350 mg Route: oral Route: single Dose: 350 mg Sources: https://pubmed.ncbi.nlm.nih.gov/11744068/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/11744068/	Other AEs: Drowsiness, Confused... Other AEs: Drowsiness Confused Retrosternal pain Hypertension Heart rate high Sources: https://pubmed.ncbi.nlm.nih.gov/11744068/

AEs

PubMed

Title	Date	PubMed
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
[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
Inhibition of field stimulation-induced contractions of rabbit vas deferens by muscarinic receptor agonists: selectivity of McN-A-343 for M1 receptors.	2001 Apr	11341365
Nitric oxide attenuates alpha(2)-adrenergic receptors by ADP-ribosylation of G(i)alpha in ciliary epithelium.	2001 Aug	11481272
Yohimbine for anxiety disorders.	2001 Aug	11481195
An isobolographic analysis of the adrenergic modulation of diclofenac antinociception.	2001 Aug	11473875
Insulin secretion and glucose kinetics during exercise with and without pharmacological alpha(1)- and alpha(2)-receptor blockade.	2001 Aug	11473046
High concentrations of adrenergic antagonists prolong sciatic nerve blockade by tetrodotoxin.	2001 Aug	11472294
Modulation of adipocyte lipoprotein lipase expression as a strategy for preventing or treating visceral obesity.	2001 Aug	11461172
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
Visceral antinociception produced by bee venom stimulation of the Zhongwan acupuncture point in mice: role of alpha(2) adrenoceptors.	2001 Aug 3	11457577
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
Presynaptic alpha2-adrenoceptor-mediated modulation of adenosine 5' triphosphate and noradrenaline corelease: differences in canine mesenteric artery and vein.	2001 Feb	11422578
The role of neurochemical mechanisms of ventromedial hypothalamus in various models of anxiety in rats.	2001 Jan	11329078
Alpha 2-adrenoceptor activity induces the antidepressant-like glycolipid in mouse forced swimming.	2001 Jan-Feb	11413859
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
Divergent effects of an alpha2-adrenergic antagonist on lipolysis and thermogenesis: interactions with a beta3-adrenergic agonist in rats.	2001 Jul	11408957
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
Agmatine potentiates the analgesic effect of morphine by an alpha(2)-adrenoceptor-mediated mechanism in mice.	2001 Jul	11377923
The effect of adrenergic compounds on neurogenic dural vasodilatation.	2001 Jul 13	11470260
The role of Kupffer cell alpha(2)-adrenoceptors in norepinephrine-induced TNF-alpha production.	2001 Jul 27	11476962
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	11440779
Alpha2-adrenoceptors inhibit antidiuretic hormone-stimulated Na+ absorption across tight epithelia (Rana esculenta).	2001 Jun	11484764
An obligatory role for spinal cholinergic neurons in the antiallodynic effects of clonidine after peripheral nerve injury.	2001 Jun	11465600
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
Immunoaffinity purification and reconstitution of human alpha(2)-adrenergic receptor subtype C2 into phospholipid vesicles.	2001 Jun	11388793
Comparison of the effect of intrathecal administration of clonidine and yohimbine on the locomotion of intact and spinal cats.	2001 Jun	11387398
Vascular actions of MDMA involve alpha1 and alpha2-adrenoceptors in the anaesthetized rat.	2001 Jun	11375260
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
Effect of electrical field stimulation on insulin and glucagon secretion from the pancreas of normal and diabetic rats.	2001 May	11440274
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
Oral drug therapy for erectile dysfunction.	2001 May	11402584
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
Pharmacological aids to locomotor training after spinal injury in the cat.	2001 May 15	11351014
Agmatine produces antinociception in tonic pain in mice.	2001 May-Jun	11420073
Neuropeptide Y in obese women during treatment with adrenergic modulation drugs.	2001 May-Jun	11386016
Effects of alpha(2)-adrenergic agonists on lipopolysaccharide-induced aqueous flare elevation in pigmented rabbits.	2001 May-Jun	11369369
Effects of adrenergic agonists and antagonists on tetrodotoxin-induced nerve block.	2001 May-Jun	11359223
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

YOHIMBINUM

Preferred 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

Classification Tree Code System Code

CFR

21 CFR 522.2670