Ecgonine: Difference between revisions

| verifiedrevid = 443718052

| Name = Ecgonine

| ImageFile = Ecgonin - Ecgonine.svg

<!-- | ImageSize = 200px -->

| ImageName = Semi-skeletal formula of ecgonine

| ImageFile1 = Ecgonine-3D-balls.png

<!-- | ImageSize1 = 200px -->

| ImageName1 = Ball-and-stick model of the ecgonine molecule

| IUPACName = (1''R'',2''R'',3''S'',5''S'')-3-hydroxy-8-methyl-8-azabicyclo

[3.2.1]octane-2-carboxylic acid

| Section1 = {{Chembox Identifiers

| CASNo = 481-37-8

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| SMILES = CN2C1CCC2CC(O)C1C(O)=O

}}

| Section2 = {{Chembox Properties

| Formula = C₉H₁₅NO₃

| MolarMass = 185.2203&nbsp;g&middot;mol^&minus;1

| Density = 1.293&nbsp;±&nbsp;0.06&nbsp;g&middot;cm^&minus;3

| MeltingPt = 198&ndash;199&nbsp;°C

| BoilingPt =

| legal_status = Schedule II (US), Class A (UK)

'''Ecgonine''' is an [[organic chemical]] and [[tropane alkaloid]] found naturally in [[coca]] leaves. It has a close structural relation to [[cocaine]]: it is both a [[metabolite]] and a [[wiktionary:Precursor|precursor]], and as such, it is a [[controlled substance]], as are all known substances which can be used as precursors to ecgonine itself.

Structurally, ecgonine is a [[cycloheptane]] derivative with a [[nitrogen bridge]]. It is obtained by [[hydrolysis]] of [[cocaine]] with acids or [[alkali]]s, and crystallizes with one molecule of water, the crystals melting at 198&ndash;199&nbsp;°C. It is [[levorotary]], and on warming with alkalis gives iso-ecgonine, which is [[dextrorotary]].

It is a tertiary [[Lewis base|base]], and has the properties of an acid and an alcohol. It is the [[carboxylic acid]] corresponding to [[tropine]], for it yields the same products on oxidation, and by treatment with [[phosphorus pentachloride]] is converted into [[anhydroecgonine]], C₉H₁₃NO₂, which, when heated to 280&nbsp;°C with [[hydrochloric acid]], eliminates [[carbon dioxide]] and yields [[tropidine]], C₈H₁₃N.

==See also==

*[[Anhydroecgonine]]

*[[Benzoylecgonine]]

*[[Cocaethylene]]

*[[Cocaine]]

*[[Cuscohygrine]]

*[[Dihydrocuscohygrine]]

*[[Hydroxytropacocaine]]

*[[Hygrine]]

*[[Methylecgonidine]]

*[[Salicylmethylecgonine]]

*[[Tropinone]]

*[[Truxilline]]

*[[Tropacocaine]]

*[[Troparil]]

==References==

{{Citation style|date=September 2007}}

*{{1911}}

[[Category:Alcohols]]

[[Category:Carboxylic acids]]

[[Category:Natural tropane alkaloids]]

[[de:Ecgonin]]

[[es:Ecgonina]]

[[fr:Ecgonine]]

[[it:Ecgonina]]

[[ru:Экгонин]]

[[fi:Ekgoniini]]

[[sv:Ekgonin]]