Y3125

Sigma-Aldrich

Yohimbine hydrochloride

≥98% (HPLC), powder

Synonym(s):
17-Hydroxyyohimban-16-carboxylic acid methyl ester hydrochloride
Empirical Formula (Hill Notation):
C21H26N2O3 · HCl
CAS Number:
Molecular Weight:
390.90
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to off-white

mp

288-290 °C (dec.) (lit.)

solubility

H2O: 10 mg/mL

SMILES string

Cl.COC(=O)[C@H]1[C@@H](O)CCC2CN3CCc4c([nH]c5ccccc45)C3CC12

InChI

1S/C21H26N2O3.ClH/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;1H/t12-,15-,17-,18-,19+;/m0./s1

InChI key

PIPZGJSEDRMUAW-VJDCAHTMSA-N

Gene Information

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Application

Yohimbine hydrochloride has been:
  • used to study its in vitro antiviral, antibacterial and antifungal activities and cytotoxicity
  • used as a tyramine receptor blocker to oppose the effects of increased tyramine in relation with flight initiation and maintenance deficits in experimental flies
  • used alone and as well as with brimonidine to study the neuroprotective effect of brimonidine in the presence of glutamate-induced neurotoxicity, oxidative stress and hypoxia on in vitro cultures of purified rat retinal ganglion cells

Biochem/physiol Actions

Yohimbine is derived from the Coryanthe yohimbe tree cortex. It is an alkaloid. Yohimbine hydrochloride is an α2-adrenergic receptor antagonist. It blocks the central α2-adrenergic receptors in the brain, thus preventing and reducing the effects of xylazine, an α2-adrenergic agonist. The sedative effects and respiratory depression that accompany xylazine administration are both antagonized and reversed by yohimbine. Yohimbine hydrochloride also produces an antidiuretic effect, and increases heart rate and blood pressure. It is useful in treating erectile dysfunction and promotes sexual functioning.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.
This compound is featured on the α2-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

hazcat

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

storage_class_code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Flight Initiation and Maintenance Deficits in Flies with Genetically Altered Biogenic Amine Levels
Brembs B, et al.
The Journal of Neuroscience, 27(41), 11122-11131 (2007)
Brimonidine is neuroprotective against glutamate-induced neurotoxicity, oxidative stress, and hypoxia in purified rat retinal ganglion cells
Lee KYC, et al.
Molecular Vision, 16, 246-246 (2010)
C Becker et al.
Neuropharmacology, 38(4), 525-532 (1999-04-30)
In line with the idea that cholecystokinin (CCK) is involved in anxiety-related behaviours, previous investigations showed that stressful conditions and an 'anxiogenic' drug, yohimbine, increased the cortical release of CCK like-material (CCKLM) in awake rats, and that this effect could...
Yohimbine in erectile dysfunction: the facts
Morales, A
International Journal of Impotence Research, 12(S1), S70-S70 (2000)
Susan X Jiang et al.
European journal of pharmacology, 629(1-3), 12-19 (2009-12-05)
Intracellular calcium ([Ca(2+)]i) influx through N-methyl-d-aspartic acid (NMDA) receptors in cortical neurons is central to NMDA receptor-mediated excitotoxicity. Drugs that uncompetitively modulate NMDA receptor-mediated [Ca(2+)]i influx are potential leads for development to treat NMDA receptor-mediated neuronal damage since these drugs...
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