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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

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
37.3 ng/mL
8 mg single, oral
YOHIMBINE plasma
Homo sapiens
50.9 ng/mL
5.4 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
78.7 ng/mL
5.4 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
154 ng/mL
10.8 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
131 ng/mL
10.8 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
400 ng/mL
16.2 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
366 ng/mL
16.2 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
49.5 ng/mL
21.6 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
51.7 ng/mL
21.6 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
55.7 ng × h/mL
8 mg single, oral
YOHIMBINE plasma
Homo sapiens
30.8 ng × h/mL
5.4 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
41.8 ng × h/mL
5.4 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
119 ng × h/mL
10.8 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
80.2 ng × h/mL
10.8 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
476 ng × h/mL
16.2 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
319 ng × h/mL
16.2 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
72.4 ng × h/mL
21.6 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
75.1 ng × h/mL
21.6 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.3 h
8 mg single, oral
YOHIMBINE plasma
Homo sapiens
0.29 h
5.4 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
0.09 h
5.4 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
0.21 h
10.8 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
0.32 h
10.8 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
0.34 h
16.2 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
0.39 h
16.2 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
0.16 h
21.6 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens
0.24 h
21.6 mg 3 times / day multiple, oral
YOHIMBINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
18%
YOHIMBINE plasma
Homo sapiens

Doses

AEs

PubMed

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
Record UNII
2Y49VWD90Q
Record Status Validated (UNII)
Record Version