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Key Documents

Y3125

Sigma-Aldrich

Yohimbine hydrochloride

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

Synonyme(s) :

17-Hydroxyyohimban-16-carboxylic acid methyl ester hydrochloride

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About This Item

Formule empirique (notation de Hill):
C21H26N2O3 · HCl
Numéro CAS:
Poids moléculaire :
390.90
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352200
ID de substance PubChem :
Nomenclature NACRES :
NA.77

product name

Yohimbine hydrochloride, ≥98% (HPLC), powder

Niveau de qualité

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Pf

288-290 °C (dec.) (lit.)

Solubilité

H2O: 10 mg/mL

Chaîne SMILES 

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

Clé InChI

PIPZGJSEDRMUAW-VJDCAHTMSA-N

Informations sur le gène

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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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Pictogrammes

Skull and crossbones

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

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


Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
MARTINDALE: Martindale?the Extra Pharmacopoeia
Lipman Arthur G
The International journal of pharmacy practice, 2(2), 124-124 (1993)
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
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

Articles

α2-Adrenoceptors

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