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A4393

Sigma-Aldrich

R-(−)-Apomorphine hydrochloride hemihydrate

calcined, ≥98.5% (with NaOH, titration)

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About This Item

Linear Formula:
C17H17NO2 · HCl · 1/2H2O
CAS Number:
41372-20-7
Molecular Weight:
312.79
EC Number:
206-243-0
MDL number:
MFCD00150904
UNSPSC Code:
12352210
PubChem Substance ID:
24278821
NACRES:
NA.77

Quality Level

200

Assay

≥98.5% (with NaOH, titration)

form

calcined
 (Powder to Crystalline Powder)

storage condition

protect from light
under inert gas

color

white to gray

mp

285-287 °C (lit.)

solubility

H2O: ~10 mg/mL, clear, yellow-green

SMILES string

Cl[H].Cl[H].[H]O[H].[H][C@]12Cc3ccc(O)c(O)c3-c4cccc(CCN1C)c24.[H][C@]56Cc7ccc(O)c(O)c7-c8cccc(CCN5C)c68

InChI

1S/2C17H17NO2.2ClH.H2O/c2*1-18-8-7-10-3-2-4-12-15(10)13(18)9-11-5-6-14(19)17(20)16(11)12;;;/h2*2-6,13,19-20H,7-9H2,1H3;2*1H;1H2/t2*13-;;;/m11.../s1

InChI key

CXWQXGNFZLHLHQ-DPFCLETOSA-N

Gene Information

human ... DRD1(1812) , DRD2(1813) , DRD3(1814) , DRD4(1815) , DRD5(1816)

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Application

R-(-)-Apomorphine hydrochloride hemihydrate has been used as a dopamine receptor agonist to study its effects of rotational behavior in rat models of Parkinson′s disease.

Biochem/physiol Actions

R-(−)-Apomorphine acts as a non-selective D1 and D2 dopamine receptor agonist. It shows therapeutic effects against Parkinson′s disease and male erectile dysfunction. R-(−)-Apomorphine also shows neuroprotective, radical scavenging, and emetic effects. Apomorphine stimulates the brain chemoreceptor trigger zone. It stimulates the chemoreceptor trigger zone in the brain.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P310

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Kristina Malinovskaja et al.
European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V, 83(3), 477-484 (2012-12-05)
The objective of this study was to test a drug delivery system that combines iontophoresis and cation-exchange fibers as drug matrices for the controlled transdermal delivery of antiparkinsonian drug apomorphine. Positively charged apomorphine was bound to the ion-exchange groups of
Y H Dang et al.
Neuroscience, 169(4), 1872-1880 (2010-07-06)
The present study examined the role of dopamine and D(1)-and D(2)-like dopamine receptors in ventrolateral orbital cortex (VLO)-evoked anti-hypersensitivity in a rat model of neuropathic pain, as well as the possible underlying mechanisms. Results showed that microinjection of apomorphine [(R(-)-apomorphine
Fumitoshi Kodaka et al.
European journal of nuclear medicine and molecular imaging, 40(4), 574-579 (2012-12-15)
Dopamine D receptors (DRs) have two affinity states for endogenous dopamine, referred to as high-affinity state (D ), which has a high affinity for endogenous dopamine, and low-affinity state (D ). The density of D can be measured with (R)-2-CHO-N-n-propylnorapomorphine
Qian Li et al.
Neuron, 76(5), 1030-1041 (2012-12-12)
Much recent discussion about the origin of Parkinsonian symptoms has centered around the idea that they arise with the increase of beta frequency waves in the EEG. This activity may be closely related to an oscillation between subthalamic nucleus (STN)
Anthony C Vernon et al.
Methods in molecular biology (Clifton, N.J.), 711, 487-510 (2011-02-01)
Neurotoxin-based rodent models of Parkinson's disease (PD) are widely used for pre-clinical evaluation of novel therapeutics for PD and have provided insights into mechanisms underlying motor dysfunction and nigrostriatal degeneration in PD. Predominantly, magnetic resonance imaging (MRI) studies in such
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