41372-20-7

Basic information

• Product Name: R-(-)-Apomorphine
• Synonyms: (r)-5,6,6a,7-tetrahydro-6-methyl-4h-dibenzo[de,g]quinoline-10,11-diol;Apomorphine hydrochloride R-(-)-;(6Ar)-5,6,6A,7-tetrahydro-6-methyl-4H-dibenzo(de,G)chinolin-10,11-diol hydrochlorid;4H-Dibenzo(de,G)quinoline-10,11-diol, 5,6,6A,7-tetrahydro-6-methyl-, hydrochloride, hemihydrate, (R)-;Apokyn;Apomorphin hydrochlorid wasser (2/1);Apomorphine Hydrochloride (250 mg);(-)-10,11-Dihydroxy-aporphine Hydrochloride HeMihydrate
• CAS NO: 41372-20-7
• Molecular Formula: C17H17NO2
• Molecular Weight: 267.32
• EINECS: 206-243-0
• Product Categories: Dopamine receptor;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;APOKYN;Inhibitors;Erectile Dysfunction;Agonists;Dopaminergics;Neurotransmitters
• Mol File: 41372-20-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 285-287 °C(lit.)
• Boiling Point: 473.4 °C at 760 mmHg
• Flash Point: 268.8 °C
• Appearance: white to gray/calcined
• Vapor Pressure: 1.38E-09mmHg at 25°C
• Storage Temp.: Refrigerator
• Solubility: H2O: ~10 mg/mL, clear, yellow-green
• Stability: Stable for 1 year from date of purchase as supplied. Solutions in distilled water may be stored at -20°C for up to 1 week.
• Merck: 13,751
• CAS DataBase Reference: R-(-)-Apomorphine(CAS DataBase Reference)
• NIST Chemistry Reference: R-(-)-Apomorphine(41372-20-7)
• EPA Substance Registry System: R-(-)-Apomorphine(41372-20-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 41372-20-7(Hazardous Substances Data)

Usage

Description

R-(-)-Apomorphine, also known as Apomorphine, is an archetypal dopamine pan-receptor agonist derived from the plant Papaver somniferum. It is an off-white solid with a molecular formula of C17H17NO2 and a molecular weight of 267.32 g/mol. R-(-)-Apomorphine displays anti-Parkinson's activity in vivo and protects against MPTP-induced neurotoxicity in a mouse model. It is in clinical use for Parkinson's disease.

Uses

Used in Pharmaceutical Industry:
R-(-)-Apomorphine is used as an emetic for inducing vomiting in cases of poisoning or drug overdose. It acts as a dopamine receptor agonist, stimulating the chemoreceptor trigger zone in the brain, which leads to the sensation of nausea and vomiting.
Used in Parkinson's Disease Treatment:
R-(-)-Apomorphine is used as an antiparkinsonian agent for the treatment of Parkinson's disease. It acts as a nonselective dopamine agonist, helping to alleviate symptoms such as tremors, rigidity, and bradykinesia by increasing dopamine levels in the brain.
Used in Erectile Dysfunction Therapy:
R-(-)-Apomorphine is used as a treatment for erectile dysfunction. It works by increasing blood flow to the penis, allowing for a stronger and more sustained erection.
Used in Neuroprotection:
R-(-)-Apomorphine hydrochloride hemihydrate is used as a neuroprotective agent with anti-Parkinsonian effects in vivo. It provides protection against neurotoxicity induced by substances like MPTP, potentially slowing down the progression of neurodegenerative diseases.

Purification Methods

Crystallise the salt from H2O (hemihydrate) and from EtOH. Crystals turn green on exposure to light. (see previous entry). NARCOTIC.

References

1) Merck Index 14:746 2) Millan et al. (2002), Differential actions of antiparkinson agents at multiple classes of monoaminergic receptor. I. A multivariate analysis of the binding profiles of 14 drugs at 21 native and cloned human receptor subtypes; J. Pharmacol. Exp. Therap., 303 791 3) Grunblatt et al. (1999), Apomorphine protects against MPTP-induced neurotoxicity in mice.; Mov. Discord, 14 612 4) Auffret et al. (2017), Apomorphine pump in advanced Parkinson’s disease: Effects on motor and nonmotor symptoms with brain metabolism correlations; J. Neurol. Sci, 372 279 5) Jenner and Katzenschlager (2016), Apomorphine – pharmacological properties and clinical trials in Parkinson’s disease; Parkinsonism. Related. Disord., 33 Suppl. 1:S13

InChI:InChI=1/2C17H17NO2.2ClH.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