Substituted tropanes: Difference between revisions

(35 intermediate revisions by 8 users not shown)

Line 1:

[[File:tropane.png|thumb|~~255px~~|right|General tropane molecule.]]

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

'''~~Tropane alkaloids~~''' are a ~~class~~ of ~~chemicals~~ that include ~~compounds with 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==

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

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.

==Pharmacology==

Tropane alkaloids are mostly [[Acetylcholine#The ~~Cholinergic System~~|anti-cholinergics]] (antagonistic action on acetylcholine receptors) or ~~stimulants~~ (prevention of dopamine reuptake).

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, including psychoactive and anaesthetic compounds~~.

{| class="wikitable"

|-

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

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

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

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

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

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

|-

| [[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]]

|-

|}

~~'''Anticholinergic Drugs'''~~

==External links==

*[~~[Atropine]]~~

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

*[[Hyoscyamine]]

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

*[[~~Scopolamine~~]]

~~'''Stimulant Drugs'''~~

==References==

*[[~~Cocaine~~]]

[[Category:Chemical class]]

[[Category:Tropane|*]]

=~~=See Also==~~

*[[Deliriants]]

*[[Anti-histamines]]

@@ Line 1: / Line 1: @@
-[[File:tropane.png|thumb|255px|right|General tropane molecule.]]
+[[File:tropane.png|thumb|200px|right|General tropane molecule]]
-'''Tropane alkaloids''' are a class of chemicals that include compounds with psychoactive effects.
+{{Stub}}
+'''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==
-Tropane alkaloids are molecules that contain a tropane ring in their structure.
+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.
 ==Pharmacology==
-Tropane alkaloids are mostly [[Acetylcholine#The Cholinergic System|anti-cholinergics]] (antagonistic action on acetylcholine receptors) or stimulants (prevention of dopamine reuptake).
+{{pharmacology}}
+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, including psychoactive and anaesthetic compounds.
+{| class="wikitable"
+|-
+! scope="col" | '''Compound'''
+! scope="col" style="width: 50px;" | '''R<sub>2</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>3</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>6</sub>'''
+! scope="col" style="width: 50px;" | '''R<sub>7</sub>'''
+! scope="col" | '''Structure'''
+|-
+| [[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]]
+|-
+|}
-'''Anticholinergic Drugs'''
+==External links==
-*[[Atropine]]
+*[https://en.wikipedia.org/wiki/Tropane Tropane (Wikipedia)]
-*[[Hyoscyamine]]
+*[[wikipedia:Tropane alkaloid|Tropane alkaloid (Wikipedia)]]
-*[[Scopolamine]]
-'''Stimulant Drugs'''
+==References==
-*[[Cocaine]]
+{{references}}
+[[Category:Chemical class]]
+[[Category:Tropane|*]]
-==See Also==
+{{#set:Featured=true}}
-*[[Deliriants]]
-*[[Anti-histamines]]