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
Pricing and availability is not currently available.

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@H1C@@H(O)CCC2CN3CCc4c(nHc5ccccc45)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

human ... ADRA2A(150), ADRA2B(151), ADRA2C(152)

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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.
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.

Legal Information

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

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Hazard Codes

T

Risk Statement

23/24/25

Safety Statement

22-36/37/39-45

RIDADR

UN 1544PSN2 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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)
Claudio Biancalani et al.
Journal of medicinal chemistry, 52(23), 7397-7409 (2009-10-01)
A number of pyridazinone derivatives bearing an arylpiperazinylalkyl chain were synthesized and tested icv in a model of acute nociception induced by thermal stimuli in mice (tail flick). The most interesting and potent compound in this series was 6a, which...
D D Schwartz et al.
Journal of veterinary pharmacology and therapeutics, 21(5), 342-347 (1998-11-12)
The alpha2-adrenergic receptor antagonists, yohimbine, atipamezole and tolazoline, are used in veterinary medicine as reversal agents for the sedative/hypnotic effects of alpha2-agonists. Ruminants have increased sensitivity to the sedative/hypnotic effects of alpha2-agonists compared to other species. The receptors mediating the...
Articles

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