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

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-2 114 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
The use of oral vasopressors in the management of autonomic dysfunction and orthostatic hypotension.	1999 May	10369619
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
Effect of alpha-adrenoceptor agents on imipramine-induced antinociception in nerve-ligated mice.	2001 Apr	11313154
Alpha2 adrenergic receptors and the central control of breathing in the cane toad, Bufo marinus.	2001 Apr	11282388
Effect of vanilloid drugs on gastrointestinal transit in mice.	2001 Apr	11264233
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
Yohimbine for anxiety disorders.	2001 Aug	11481195
Insulin secretion and glucose kinetics during exercise with and without pharmacological alpha(1)- and alpha(2)-receptor blockade.	2001 Aug	11473046
Modulation of adipocyte lipoprotein lipase expression as a strategy for preventing or treating visceral obesity.	2001 Aug	11461172
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
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
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
Neural mechanisms involved in the delay of gastric emptying and gastrointestinal transit of liquid after thoracic spinal cord transection in awake rats.	2001 Feb 20	11280307
Alpha2-adrenoceptor-mediated inhibition of cultured sympathetic neurons: changes in alpha2A/D-adrenoceptor-deficient mice.	2001 Jan	11191829
Frequency dependent alpha(2)-adrenoceptor mediated modulation of excitatory junction potentials in guinea-pig mesenteric artery.	2001 Jan 5	11137866
Alpha 2-adrenoceptor activity induces the antidepressant-like glycolipid in mouse forced swimming.	2001 Jan-Feb	11413859
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
The role of Kupffer cell alpha(2)-adrenoceptors in norepinephrine-induced TNF-alpha production.	2001 Jul 27	11476962
Comparison of the effect of intrathecal administration of clonidine and yohimbine on the locomotion of intact and spinal cats.	2001 Jun	11387398
Effect of methanolic extract of Cassia nigricans leaves on rat gastrointestinal tract.	2001 Mar	11295295
Clonidine-induced antinociception and locomotor hypoactivity are reduced by dexamethasone in mice.	2001 Mar	11291750
Inverse agonist activity at the alpha(2A)-adrenergic receptor.	2001 Mar	11179449
Interaction of formamidine pesticides with the presynaptic alpha(2)-adrenoceptor regulating.	2001 May 1	11312645
Effects of alpha(2)-adrenergic agonists on lipopolysaccharide-induced aqueous flare elevation in pigmented rabbits.	2001 May-Jun	11369369

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 `Mon Mar 31 17:56:57 GMT 2025` Edited by `admin` on `Mon Mar 31 17:56:57 GMT 2025`
Record UNII	2Y49VWD90Q
Record Status	`Validated (UNII)`
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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