Hygrine: Difference between revisions

Revision as of 20:46, 30 December 2024

Chemical compound

{{Infobox chemical | verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477239679 | image = Hygrine.png | image_size = 200px | IUPACName = (R)-1-[(2S)-1-Methylpyrrolidin-2-yl]propan-2-one | othernames = 1-(2-Pyrrolidinyl)-2-propanone | section1 = Template:Chembox Identifiers

| section2 = Template:Chembox Properties

Hygrine is a pyrrolidine alkaloid found in the leaves of the coca plant (Erythroxylum coca). It was first isolated by the German chemist Carl Liebermann in 1889. Hygrine is one of the many alkaloids present in coca leaves, although it is not the primary active compound responsible for the stimulant effects of cocaine.

Chemical Structure and Properties

Hygrine is a ketone with a pyrrolidine ring, which is a five-membered heterocyclic amine. The chemical formula of hygrine is C₈H₁₅NO, and it has a molar mass of 141.21 g/mol. The structure consists of a pyrrolidine ring attached to a propanone group.

Occurrence and Isolation

Hygrine is naturally occurring in the leaves of the coca plant, which is native to South America. The isolation of hygrine from coca leaves involves the extraction of the alkaloid fraction, followed by purification processes such as chromatography.

Biological Activity

While hygrine itself does not have significant pharmacological activity, it is often studied in conjunction with other alkaloids found in coca leaves. The primary interest in hygrine is due to its presence in the coca plant and its potential role in the biosynthesis of other alkaloids.

References

External Links

Hygrine on PubChem

@@ Line 1: / Line 1: @@
+{{Short description|Chemical compound}}
 {{Infobox chemical
-| name = Hygrine
+| verifiedfields = changed
-| image = Hygrine_structure.png
+| Watchedfields = changed
+| verifiedrevid = 477239679
+| image = Hygrine.png
 | image_size = 200px
-| image_alt = Skeletal formula of hygrine
+| IUPACName = (R)-1-[(2S)-1-Methylpyrrolidin-2-yl]propan-2-one
-| pin = 496-49-1
+| othernames = 1-(2-Pyrrolidinyl)-2-propanone
-| IUPAC_name = (R)-1-(1-Methylpyrrolidin-2-yl)-propan-2-one
+| section1 = {{Chembox Identifiers
-| other_names = 2-(1-Methyl-2-pyrrolidinyl)-propan-2-one
+| CASNo = 496-49-1
+| PubChem = 439302
+| ChemSpiderID = 388086
+| UNII = 0F3X4QK1QY
+| ChEMBL = 2105980
+| SMILES = CC(=O)C1CCCN1C
+| InChI = 1S/C8H15NO/c1-7(10)8-4-3-5-9(8)2/h8H,3-6H2,1-2H3
+| InChIKey = YKQUGTRCQXQGIM-UHFFFAOYSA-N
+}}
+| section2 = {{Chembox Properties
 | C = 8
 | H = 15
 | N = 1
 | O = 1
-| molar_mass = 141.21 g/mol
+| MolarMass = 141.21 g/mol
 }}
-'''Hygrine''' is a [[pyrrolidine]] alkaloid found in the leaves of the [[coca plant]] (''Erythroxylum coca''). It is a minor alkaloid in coca leaves, where it is present alongside other alkaloids such as [[cocaine]] and [[cinnamoylcocaine]].
+'''Hygrine''' is a [[pyrrolidine]] [[alkaloid]] found in the leaves of the [[coca plant]] (''[[Erythroxylum coca]]''). It was first isolated by the German chemist [[Carl Liebermann]] in 1889. Hygrine is one of the many [[alkaloids]] present in coca leaves, although it is not the primary active compound responsible for the [[stimulant]] effects of [[cocaine]].
-==Structure and Properties==
-Hygrine is a [[ketone]] with the chemical formula C₈H₁₅NO. It consists of a pyrrolidine ring, which is a five-membered nitrogen-containing ring, attached to a propan-2-one group. The presence of the ketone group makes hygrine a relatively polar compound compared to other alkaloids found in coca leaves.
-==Biosynthesis==
+== Chemical Structure and Properties ==
-Hygrine is biosynthesized in the coca plant through the [[polyketide]] pathway. The biosynthesis involves the condensation of [[acetyl-CoA]] and [[malonyl-CoA]] units, followed by cyclization to form the pyrrolidine ring. The specific enzymes involved in the biosynthesis of hygrine are not fully characterized, but it is known to share some pathways with the biosynthesis of other pyrrolidine alkaloids.
+Hygrine is a [[ketone]] with a [[pyrrolidine]] ring, which is a five-membered [[heterocyclic]] [[amine]]. The chemical formula of hygrine is C<sub>8</sub>H<sub>15</sub>NO, and it has a [[molar mass]] of 141.21 g/mol. The structure consists of a [[pyrrolidine]] ring attached to a [[propanone]] group.
-==Pharmacology==
+== Occurrence and Isolation ==
-Hygrine itself is not known to have significant pharmacological effects in humans. However, it is often studied in the context of its presence in coca leaves and its potential role in the overall pharmacological profile of coca leaf extracts. Unlike cocaine, hygrine does not have stimulant properties and is not considered addictive.
+Hygrine is naturally occurring in the leaves of the [[coca plant]], which is native to [[South America]]. The isolation of hygrine from coca leaves involves the extraction of the [[alkaloid]] fraction, followed by purification processes such as [[chromatography]].
-==Isolation and Analysis==
+== Biological Activity ==
-Hygrine can be isolated from coca leaves through extraction and chromatographic techniques. Analytical methods such as [[gas chromatography-mass spectrometry]] (GC-MS) and [[high-performance liquid chromatography]] (HPLC) are commonly used to identify and quantify hygrine in plant extracts.
+While hygrine itself does not have significant [[pharmacological]] activity, it is often studied in conjunction with other [[alkaloids]] found in coca leaves. The primary interest in hygrine is due to its presence in the [[coca plant]] and its potential role in the [[biosynthesis]] of other [[alkaloids]].
-==Applications==
+== See Also ==
-While hygrine itself does not have direct applications, its presence in coca leaves makes it of interest in the study of coca plant chemistry and the development of analytical methods for detecting coca alkaloids. It is also of interest in the study of plant alkaloid biosynthesis.
-==Also see==
 * [[Cocaine]]
-* [[Coca plant]]
 * [[Pyrrolidine]]
 * [[Alkaloid]]
-* [[Biosynthesis]]
+* [[Erythroxylum coca]]
+== References ==
+{{Reflist}}
-{{Alkaloids}}
+== External Links ==
-{{Coca}}
+* [https://pubchem.ncbi.nlm.nih.gov/compound/Hygrine Hygrine on PubChem]
 [[Category:Alkaloids]]
 [[Category:Pyrrolidines]]
+[[Category:Ketones]]
 [[Category:Coca plant]]