Diphenyl-2-pyridylmethane is a
triaryl organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
that has been used to selectively extract specific metal ions (as their
thiocyanate
Thiocyanate (also known as rhodanide) is the anion . It is the conjugate base of thiocyanic acid. Common derivatives include the colourless salts potassium thiocyanate and sodium thiocyanate. Mercury(II) thiocyanate was formerly used in pyrot ...
complexes) into organic solvents. Its pharmacology is similar to the stimulant
desoxypipradrol
Desoxypipradrol, also known as 2-diphenylmethylpiperidine (2-DPMP), is a drug developed by Ciba in the 1950s which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI).
Chemistry
Desoxypipradrol is closely related on a structural lev ...
in which the
pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...
ring is
reduced to a
piperidine
Piperidine is an organic compound with the molecular formula (CH2)5NH. This heterocyclic compound, heterocyclic amine consists of a six-membered ring containing five methylene bridges (–CH2–) and one amine bridge (–NH–). It is a colorless ...
and for which it is a chemical precursor.
Preparation
Diphenyl-2-pyridylmethane was prepared by researchers at Ciba Pharmaceuticals (now
Novartis
Novartis AG is a Swiss-American multinational pharmaceutical corporation based in Basel, Switzerland and
Cambridge, Massachusetts, United States (global research).name="novartis.com">https://www.novartis.com/research-development/research-loc ...
) as the immediate precursor of desoxypipradrol, when they patented the latter as a
psychomotor stimulant or
narcoleptic
Narcolepsy is a long-term neurological disorder that involves a decreased ability to regulate sleep–wake cycles. Symptoms often include periods of excessive daytime sleepiness and brief involuntary sleep episodes. About 70% of those affec ...
.
Diphenyl acetonitrile was reacted with
2-bromopyridine, using
sodamide as base and the resulting diphenyl-2-pyridylacetonitrile was hydrolysed and decarboxylated using potassium hydroxide in methanol.
Uses
Diphenyl-2-pyridylmethane behaves in coordination complexes with metal
cations
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by con ...
in the same way as
pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a d ...
, with the aromatic nitrogen potentially forming a bond to the metal. In this case, the bulky and
lipophilic
Lipophilicity (from Greek λίπος "fat" and φίλος "friendly"), refers to the ability of a chemical compound to dissolve in fats, oils, lipids, and non-polar solvents such as hexane or toluene. Such non-polar solvents are themselves lipop ...
diphenylmethyl substituent means that the resulting complex may be appreciably soluble in organic solvents like
chloroform
Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
and
benzene
Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...
. This ability to transfer metal cations from water into non-miscible solvents has been exploited to extract thiocyanate complexes for example of silver, gold, cobalt and zinc; in some cases in the presence of other metals which were retained in the aqueous phase.
Pharmacology
Pipradol and desoxypipradrol are
norepinephrine-dopamine reuptake inhibitors that were not in practice widely used as drugs owing to their perceived potential for abuse. Although diphenyl-2-pyridylmethane is less potent than these molecules and its 4-pyridyl equivalent
it was nevertheless specifically included when the UK
ACMD
The Advisory Council on the Misuse of Drugs (ACMD) is a British statutory non-departmental public body, advisory non-departmental public body, which was established under the Misuse of Drugs Act 1971.
Mandate
Its terms of reference, according to ...
advised that this group of drugs be controlled as Class B.
See also
*
Bisacodyl
Bisacodyl (INN) is an organic compound that is used as a stimulant laxative drug. It works directly on the colon to produce a bowel movement. It is typically prescribed for relief of episodic and chronic constipation and for the management of ...
(the diacetoxy derivative that is used as a laxative)
*
Diphenyl-2-pyridylphosphine
Diphenyl-2-pyridylphosphine is an organophosphorus compound with the formula P(C6H5)2(2-C5H4N). It is the most widely used mono-pyridylphosphine ligand. Other mono-pyridylphosphines ligands (3-, 4-) are not common in chemical literature; however ...
(a phosphorus atom replaces the central carbon atom).
References
{{Dopaminergics
Dopamine reuptake inhibitors
Stimulants
2-Pyridyl compounds