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A9611

Sigma-Aldrich

Atipamezole

≥98% (HPLC)

Synonym(s):

4-(2-Ethyl-2,3-dihydro-1H-inden-2-yl)-1H-Imidazole, Antisedan, MPV 1248

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About This Item

Empirical Formula (Hill Notation):
C14H16N2
CAS Number:
104054-27-5
Molecular Weight:
212.29
MDL number:
MFCD00864502
UNSPSC Code:
12352200
PubChem Substance ID:
329771055
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to brown

solubility

DMSO: ≥30 mg/mL

storage temp.

room temp

SMILES string

CCC1(Cc2ccccc2C1)c3c[nH]cn3

InChI

1S/C14H16N2/c1-2-14(13-9-15-10-16-13)7-11-5-3-4-6-12(11)8-14/h3-6,9-10H,2,7-8H2,1H3,(H,15,16)

InChI key

HSWPZIDYAHLZDD-UHFFFAOYSA-N

General description

Atipamezole has an imidazole structure and gets localized in the central nervous system on administration.

application

Atipamezole has been used as a α2-adrenoceptor antagonist in mesencephalic trigeminal nucleus (MTN) neurons, CD4+ T-lymphocyte and human embryonic kidney (HEK293) membrane preparation.

Biochem/physiol Actions

Atipamezole elicits affinity towards adrenoreceptor subtypes namely α2A, α2B and α2C. High levels of atipamezole impairs cognitive functions. It also reverses the adrenoreceptor agonist functionalities. Atipamezole shows no affinity towards muscarinic and dopamine or neurotransmitter receptors. Atipamezole when used along with morphine elicits antinociceptive effects.
Atipamezole is a selective α2 adrenergic blocker. Atipamezole is more potent than yohimbine; it is very selective for α2 adrenergic vs α1 sites, but not selelctive for α2 subtypes.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Tuomas O Lilius et al.
Anesthesia and analgesia, 114(6), 1353-1358 (2012-05-05)
Opioid analgesics are effective in the treatment of chronic pain, but they have serious adverse effects such as development of tolerance and dependence. Adrenergic α(2) agonists and μ-opioid receptor agonists show synergistic potentiation and cross-tolerance in spinal analgesia, whereas α(2)-adrenergic
D Van Vynckt et al.
The Journal of small animal practice, 52(12), 638-644 (2011-10-25)
To assess the influence of two sedation protocols on the degree of lameness in dogs. Fifty lame dogs were allocated to one of two sedation protocols. Group ACPM (acepromazine + methadone; n=25) was sedated with acepromazine and methadone. Group MED
The C-terminal half of the alpha 2C-adrenoceptor determines the receptor's membrane expression level and drug selectivity
Jahnsen JA and Uhlen S
Naunyn-Schmiedeberg'S Archives of Pharmacology, 386(12), 1031-1040 (2013)
Brian Milne et al.
Anesthesia and analgesia, 112(6), 1500-1503 (2011-05-06)
Ultralow-dose opioid antagonists prolong opioid antinociception and block tolerance. In this study we determined whether low doses of the α-2 adrenergic receptor (A2-R) antagonist, atipamezole, similarly influenced A2-R-induced antinociception and tolerance. In rats, intrathecal norepinephrine (NE) or clonidine in combination
Antti Pertovaara et al.
CNS drug reviews, 11(3), 273-288 (2006-01-04)
Atipamezole is an alpha2-adrenoceptor antagonist with an imidazole structure. Receptor binding studies indicate that its affinity for alpha2-adrenoceptors and its alpha2/alpha1 selectivity ratio are considerably higher than those of yohimbine, the prototype alpha2-adrenoceptor antagonist. Atipamezole is not selective for subtypes
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