Substituted tropanes: Difference between revisions

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[[File:tropane.png|thumb|200px|right|General tropane molecule]]

'''~~Tropane alkaloids~~''' are a ~~class~~ of ~~chemicals~~ that include ~~compounds with~~ [[~~subjective effects index|psychoactive effects~~]].

'''Substituted tropanes''' (or simply '''tropanes''') are a group of [[psychoactive compounds]] that include a tropane ring in their structure. Prominent examples include certain [[stimulants]] like [[cocaine]] and its derivatives as well as [[deliriants]] like [[atropine]] and [[scopolamine]].

==Chemistry==

~~{{chemistry}}~~

Tropanes are molecules which contain a substituted tropane ring in their structure. Tropane is a nitrogen-containing bicyclic organic molecule which consists of a [[piperidine]] and [[pyrrolidine]] ring fused at carbons R1 and R5 along with an additional methyl substitution at RN. It is mainly known for a group of [[alkaloids]] derived from it. Tropane alkaloids are commonly substituted at R3 with an ether bridge (as seen in [[scopolamine]], [[atropine]], [[hyoscyamine]], and [[cocaine]]). Synthetic analogs of tropane alkaloids also exist, such as the phenyltropanes. They are not considered to be alkaloids per definition.

~~Tropane alkaloids~~ are molecules ~~that~~ contain a tropane ring in their structure.

~~A tropane ring~~ is a nitrogen-containing bicyclic organic molecule, which consists of a piperidine and pyrrolidine ring fused at carbons R1 and R5~~. It has~~ additional methyl substitution at RN.

==Pharmacology==

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Tropane alkaloids are mostly [[Acetylcholine#The cholinergic system|anti-cholinergics]] (antagonistic action on acetylcholine [[receptors]]) or [[stimulant]]s (prevention of [[dopamine]] reuptake).

==~~Examples~~==

==List of substituted tropanes==

~~Tropane alkaloids are seen throughout organic chemistry and include psychoactive and anaesthetic compounds.~~

{| class="wikitable"

|-

'''~~Anticholinergic drugs~~:'''

! scope="col" | '''Compound'''

*[[Atropine]]

! scope="col" style="width: 50px;" | '''R2'''

*[[Hyoscyamine]]

! scope="col" style="width: 50px;" | '''R3'''

*[[Scopolamine]]

! scope="col" style="width: 50px;" | '''R6'''

! scope="col" style="width: 50px;" | '''R7'''

~~'''Stimulant drugs~~:~~'''~~

! scope="col" | '''Structure'''

*[[~~Cocaine~~]]

|-

| [[Atropine]] || H || OCOCH(CH2OH)C6H5 || H || H || [[File:Atropine.svg|170px]]

|-

| [[Hyoscyamine]] || H || OCOCH(CH2OH)C6H5 || H || H || [[File:Hyoscyamine.svg|170px]]

|-

| [[Scopolamine]] || H || OCOCH(CH2OH)C6H5 || O- || - || [[File:Scopolamine.svg|170px]]

|-

| [[Cocaine]] || CO2CH3 || OCOC6H5 || H || H || [[File:Cocaine.svg|170px]]

|-

| [[Troparil]] || CO2CH3 || C6H5 || H || H || [[File:Troparil.svg|170px]]

|-

| [[RTI-111]] || CO2CH3 || C6H3Cl2 || H || H || [[File:RTI-111.svg|170px]]

|-

|}

==~~See also~~==

==External links==

*[~~[Responsible use]]~~

*[https://en.wikipedia.org/wiki/Tropane Tropane (Wikipedia)]

*[[Deliriants]]

*[[wikipedia:Tropane alkaloid|Tropane alkaloid (Wikipedia)]]

*[[Anti-histamines]]

*[[Stimulants]]

*[[~~Datura~~]]

==References==

[[Category:Chemical class]]

[[Category:Tropane|*]]

@@ Line 1: / Line 1: @@
 [[File:tropane.png|thumb|200px|right|General tropane molecule]]
 {{Stub}}
-'''Tropane alkaloids''' are a class of chemicals that include compounds with [[subjective effects index|psychoactive effects]].
+'''Substituted tropanes''' (or simply '''tropanes''') are a group of [[psychoactive compounds]] that include a tropane ring in their structure. Prominent examples include certain [[stimulants]] like [[cocaine]] and its derivatives as well as [[deliriants]] like [[atropine]] and [[scopolamine]].
 ==Chemistry==
-{{chemistry}}
+Tropanes are molecules which contain a substituted tropane ring in their structure. Tropane is a nitrogen-containing bicyclic organic molecule which consists of a [[piperidine]] and [[pyrrolidine]] ring fused at carbons R<sub>1</sub> and R<sub>5</sub> along with an additional methyl substitution at R<sub>N</sub>. It is mainly known for a group of [[alkaloids]] derived from it. Tropane alkaloids are commonly substituted at R<sub>3</sub> with an ether bridge (as seen in [[scopolamine]], [[atropine]], [[hyoscyamine]], and [[cocaine]]). Synthetic analogs of tropane alkaloids also exist, such as the phenyltropanes. They are not considered to be alkaloids per definition.
-Tropane alkaloids are molecules that contain a tropane ring in their structure.
-A tropane ring is a nitrogen-containing bicyclic organic molecule, which consists of a piperidine and pyrrolidine ring fused at carbons R<sub>1</sub> and R<sub>5</sub>. It has additional methyl substitution at R<sub>N</sub>.
 ==Pharmacology==
@@ Line 13: / Line 10: @@
 Tropane alkaloids are mostly [[Acetylcholine#The cholinergic system|anti-cholinergics]] (antagonistic action on acetylcholine [[receptors]]) or [[stimulant]]s (prevention of [[dopamine]] reuptake).
-==Examples==
+==List of substituted tropanes==
-Tropane alkaloids are seen throughout organic chemistry and include psychoactive and anaesthetic compounds.
+{| class="wikitable"
+|-
-'''Anticholinergic drugs:'''
+! scope="col" | '''Compound'''
-*[[Atropine]]
+! scope="col" style="width: 50px;" | '''R<sub>2</sub>'''
-*[[Hyoscyamine]]
+! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
-*[[Scopolamine]]
+! scope="col" style="width: 50px;" | '''R<sub>6</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>7</sub>'''
-'''Stimulant drugs:'''
+! scope="col" | '''Structure'''
-*[[Cocaine]]
+|-
+| [[Atropine]] || H ||  OCOCH(CH<sub>2</sub>OH)C<sub>6</sub>H<sub>5</sub> || H || H || [[File:Atropine.svg|170px]]
+|-
+| [[Hyoscyamine]] || H ||  OCOCH(CH<sub>2</sub>OH)C<sub>6</sub>H<sub>5</sub> || H || H || [[File:Hyoscyamine.svg|170px]]
+|-
+| [[Scopolamine]] || H ||  OCOCH(CH<sub>2</sub>OH)C<sub>6</sub>H<sub>5</sub> || O- || - || [[File:Scopolamine.svg|170px]]
+|-
+| [[Cocaine]] || CO</sub>2</sub>CH</sub>3</sub> ||  OCOC<sub>6</sub>H<sub>5</sub> || H || H || [[File:Cocaine.svg|170px]]
+|-
+| [[Troparil]] || CO</sub>2</sub>CH</sub>3</sub> ||  C<sub>6</sub>H<sub>5</sub> || H || H || [[File:Troparil.svg|170px]]
+|-
+| [[RTI-111]] || CO</sub>2</sub>CH</sub>3</sub> ||  C<sub>6</sub>H<sub>3</sub>Cl<sub>2</sub> || H || H || [[File:RTI-111.svg|170px]]
+|-
+|}
-==See also==
+==External links==
-*[[Responsible use]]
+*[https://en.wikipedia.org/wiki/Tropane Tropane (Wikipedia)]
-*[[Deliriants]]
+*[[wikipedia:Tropane alkaloid|Tropane alkaloid (Wikipedia)]]
-*[[Anti-histamines]]
-*[[Stimulants]]
-*[[Datura]]
 ==References==
 {{references}}
+[[Category:Chemical class]]
+[[Category:Tropane|*]]
+{{#set:Featured=true}}