Apomorphine

January 31, 2022
I鈥檓 an opioid, but don鈥檛 take me for pain.
What molecule am I?
Image of Apomorphine 3D Image of Apomorphine

Apomorphine is a synthetic opioid that has been known since at least 1871, when German researcher E. L. Mayer treated the natural drug morphine with . About 70 years later, Lyndon Small*, Burt F. Faris, and James Mallonee at the University of Virginia (Charlottesville) of this reaction (without ZnCl2, which is apparently unnecessary).1

In 1973, John L. Neumeyer and colleagues at Arthur D. Little (Cambridge, MA) and Sterling-Winthrop Research Institute (New York) reported the and other morphine and codeine derivatives. Eight years later, Vishnu J. Ram and Neumeyer*, now at Northeastern University (Boston) from the natural opiates thebaine2 and bulbocapnine3.

Unlike, many opioids, apomorphine has several medical uses not related pain management. In humans, it has such diverse applications as a Parkinson鈥檚 disease drug, as an emetic, and most recently, as a treatment for erectile dysfunction. It has also been touted as a treatment for heroin addiction, but no clinical evidence has shown that it is effective for this purpose.

Apomorphine can be used as an emetic for dogs when they ingest poisonous substances such as antifreeze. It must, however, be injected because it travels too slowly through the blood鈥揵rain barrier when given orally.

Apomorphine is somewhat unstable; it decomposes and turns green when it is exposed to light and air. It is much more stable as its hydrochloride hemihydrate4, which is the preferred article of commerce.

1. More than 80 years ago, authorities were concerned about opiate addiction. The authors noted, 鈥淭he work reported in this paper is part of a unification of effort by a number of agencies having responsibility for the solution of the problem of drug addiction.鈥�
2. CAS Reg. No. 115-37-7.
3. CAS Reg. No. 298-45-3.
4. CAS Reg. No. 41372-20-7.

Apomorphine听hazard information*

Hazard class**GHS code and hazard statement
Acute toxicity, oral, category 4H302鈥擧armful if swallowedChemical Safety Warning
Acute toxicity, dermal, category 4H312鈥擧armful in contact with skinChemical Safety Warning

Skin sensitization, category 1

H317鈥擬ay cause an allergic skin reactionChemical Safety Warning
Acute toxicity, inhalation, category 4H332鈥擧armful if inhaledChemical Safety Warning
Sensitization, respiratory, category 1H334鈥擬ay cause allergy or asthma symptoms or breathing difficulties if inhaledChemical Safety Warning

*Information for the more common article of commerce, apomorphine hydrochloride hemihydrate.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.听

MOTW update

1,4-Benzoquinone1 (aka quinone) was the Molecule of the Week for November 23, 2009. It is a useful oxidizing agent and, along with its reduced form, hydroquinone2 (1,4-benzenediol), is the basis of many redox systems.

This month, Qinglei Meng, Buxing Han, and collaborators at the Chinese Academy of Sciences (Beijing) and East China Normal University (Shanghai) reported an for simultaneously producing benzoquinone and cyclohexanone3 from phenol and water. In the authors鈥� electrochemical system, the cathode consists of nickel and platinum supported on nitrogen-doped hierarchically porous carbon (NHPC), whereas the anode contains iron and ruthenium, also supported on NHPC. Benzophenone and cyclohexanone form at the cathode and anode, respectively, both with >99.9% selectivity.

1. CAS Reg. No. 106-51-4.
2. CAS Reg. No. 123-31-9.
3. CAS Reg. No. 108-94-1.

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Apomorphine fast facts

CAS Reg. No.58-00-4

nomenclature
4H-Dibenzo[de,g] quinoline-10,11-diol, 5,6,6a,7-tetrahydro-6-methyl-, (6aR)-
Empirical formulaC17H17NO2
Molar mass267.32听g/mol
AppearanceWhite crystals or powder
Melting point195 掳C (dec.)
Water solubility20 g/L
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