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Merck

Y3125

Yohimbine hydrochloride

≥98% (HPLC), powder, α2-adrenergic receptor antagonist

Sinónimos:

17-Hydroxyyohimban-16-carboxylic acid methyl ester hydrochloride

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About This Item

Fórmula empírica (notación de Hill):
C21H26N2O3 · HCl
Número CAS:
Peso molecular:
390.90
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
EC Number:
200-600-4
MDL number:

Nombre del producto

Yohimbine hydrochloride, ≥98% (HPLC), powder

InChI key

PIPZGJSEDRMUAW-VJDCAHTMSA-N

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

SMILES string

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

assay

≥98% (HPLC)

form

powder

color

white to off-white

mp

288-290 °C (dec.) (lit.)

solubility

H2O: 10 mg/mL

Quality Level

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 featured on the α2-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Skull and crossbones

signalword

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Clase de almacenamiento

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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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
Yohimbine in erectile dysfunction: the facts
Morales, A
International Journal of Impotence Research, 12(S1), S70-S70 (2000)
MARTINDALE: Martindale?the Extra Pharmacopoeia
Lipman Arthur G
The International journal of pharmacy practice, 2(2), 124-124 (1993)
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)
L Pan et al.
Human & experimental toxicology, 39(3), 365-373 (2019-11-28)
Dexmedetomidine (DMED), an alpha-2 adrenoreceptor agonist, has been widely used in regional anesthesia procedures. However, the effect of DMED on local anesthetic cardiotoxicity has not been well delineated. This study consisted of two experiments. In experiment A, 42 Sprague-Dawley (SD)

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