Meconic acid, also known as acidum meconicum and poppy acid, is a

chemical substance A chemical substance is a form of matter having constant chemical composition and characteristic properties. Some references add that chemical substance cannot be separated into its constituent elements by physical separation methods, i.e., w ...

found in certain plants of the poppy family,

Papaveraceae The Papaveraceae are an economically important family of about 42 genera and approximately 775 known species of flowering plants in the order Ranunculales, informally known as the poppy family. The family is cosmopolitan, occurring in temperat ...

, such as ''

Papaver somniferum ''Papaver somniferum'', commonly known as the opium poppy or breadseed poppy, is a species of flowering plant in the family Papaveraceae. It is the species of plant from which both opium and poppy seeds are derived and is also a valuable orname ...

'' (opium poppy) and ''

Papaver bracteatum ''Papaver bracteatum'', also known as the Iranian poppy or Persian poppy and the great scarlet poppy (first described by Dr. N. Saharghi and l. Lalezari nature 213, 1244, 1967 doi:10.1038/2131244a0 ) is a sturdy hardy perennial poppy with large d ...

''. Meconic acid constitutes about 5% of opium and can be used as an analytical marker for the presence of opium. Meconic acid has erroneously been described as a mild narcotic, but it has little or no physiological activity, and is not used medicinally. Meconic acid forms

salts In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively c ...

with

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

s and

metal A metal (from Greek μέταλλον ''métallon'', "mine, quarry, metal") is a material that, when freshly prepared, polished, or fractured, shows a lustrous appearance, and conducts electricity and heat relatively well. Metals are typicall ...

s. These salts as well as meconic acid

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides a ...

s are called meconates. Meconic acid was first isolated by

Friedrich Sertürner Friedrich Wilhelm Adam Sertürner (19 June 1783 – 20 February 1841) was a German pharmacist and a pioneer of alkaloid chemistry. He is best known for his discovery of morphine in 1804. Biography Friedrich Wilhelm Adam Sertürner was born to J ...

in 1805.Friedrich Sertürner (1805
(Untitled letter to the editor)
''Journal der Pharmacie für Aerzte, Apotheker und Chemisten'' (Journal of Pharmacy for Physicians, Apothecaries, and Chemists), 13 : 229–243. See also: Sertuerner (1817
"Ueber das Morphium, eine neue salzfähige Grundlage, und die Mekonsäure, als Hauptbestandtheile des Opiums"
(On morphine, a new salifiable .e., precipitable fundamental substance, and meconic acid, as principal components of opium), ''Annalen der Physik'', 55 : 56–89.

Chemistry

Meconic acid is a dicarboxylic acid. Its structure contains two carboxylic acid

groups A group is a number of persons or things that are located, gathered, or classed together. Groups of people * Cultural group, a group whose members share the same cultural identity * Ethnic group, a group whose members share the same ethnic ide ...

(-COOH) and one

keto group In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bon ...

(=O) attached to a

pyran In chemistry, pyran, or oxine, is a six-membered heterocyclic, non-aromatic ring, consisting of five carbon atoms and one oxygen atom and containing two double bonds. The molecular formula is C5H6O. There are two isomers of pyran that differ ...

ring. Meconic acid gives a red color with

ferric chloride Iron(III) chloride is the inorganic compound with the formula . Also called ferric chloride, it is a common compound of iron in the +3 oxidation state. The anhydrous compound is a crystalline solid with a melting point of 307.6 °C. The col ...

. Meconic acid is colorless and is only slightly soluble in water but readily soluble in alcohol.

References

* {{Components of opium Dicarboxylic acids 4-Pyrones Enols