Methylecgonidine

Methylecgonidine (anhydromethylecgonine; anhydroecgonine methyl ester; AEME) is a chemical intermediate derived from ecgonine or cocaine.wikipedia
35 Related Articles

Crack cocaine

crackcrack-cocainecrack pipe
Methylecgonidine is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite.
Many of these issues relate specifically to the release of methylecgonidine and its effect on the heart, lungs, and liver.

Cocaine

cokecocaine traffickingcrack
Methylecgonidine (anhydromethylecgonine; anhydroecgonine methyl ester; AEME) is a chemical intermediate derived from ecgonine or cocaine. Methylecgonidine could also theoretically be used to produce cocaine and so may be a controlled substance in some countries.
Smoking freebase cocaine has the additional effect of releasing methylecgonidine into the user's system due to the pyrolysis of the substance (a side effect which insufflating or injecting powder cocaine does not create).

Troparil

AEME is also used in scientific research for the manufacture of phenyltropane analogues such as troparil, dichloropane, iometopane, and CFT.
Troparil is a phenyltropane-based dopamine reuptake inhibitor (DRI) that is derived from methylecgonidine.

Ecgonidine

anhydroecgonine
Methylecgonidine has a relatively short half-life of 18–21 minutes, after which it is metabolised to ecgonidine, meaning that the relative concentrations of the two compounds can be used to estimate how recently crack cocaine has been smoked.
Methylecgonidine is produced by pyrolysis in the process of smoking crack cocaine, and then subsequently metabolised to ecgonidine, and so these two compounds can be tested for as a specific biomarker for crack cocaine use.

RTI-55

β-CITβ-CITCIT
AEME is also used in scientific research for the manufacture of phenyltropane analogues such as troparil, dichloropane, iometopane, and CFT.
RTI-55 is a non-selective dopamine reuptake inhibitor derived from methylecgonidine.

Ecgonine

ecogonine
Methylecgonidine (anhydromethylecgonine; anhydroecgonine methyl ester; AEME) is a chemical intermediate derived from ecgonine or cocaine.
Methylecgonidine

Dichloropane

AEME is also used in scientific research for the manufacture of phenyltropane analogues such as troparil, dichloropane, iometopane, and CFT.
Methylecgonidine is the direct precursor to this compound.

WIN-35428

CFT(-)-2β-Carbomethoxy-3β-(4-fluorophenyl)tropaneWIN 35,428
AEME is also used in scientific research for the manufacture of phenyltropane analogues such as troparil, dichloropane, iometopane, and CFT.
Another radioisotope-substituted analog [11C]WIN 35,428 (where the carbon atom of either the N-methyl group, or the methyl from the 2-carbomethoxy group of CFT, has been replaced with 11 C) is now more commonly used for this application, as it is quicker and easier in practice to make radiolabelled CFT by methylating nor-CFT or 2-desmethyl-CFT than by reacting methylecgonidine with parafluorophenylmagnesium bromide, and also avoids the requirement for a licence to work with the restricted precursor ecgonine.

Pyrolysis

pyrolyticpyrolyzedvacuum pyrolysis
Methylecgonidine is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite. Methylecgonidine can be synthesized non pyrolytically from cocaine via hydrolysis/dehydration followed by esterification with methanol.

Metabolite

metabolitesactive metabolitebreakdown product
Methylecgonidine is a pyrolysis product formed when crack cocaine is smoked, making this substance a useful biomarker to specifically test for use of crack cocaine, as opposed to powder cocaine which does not form methylecgonidine as a metabolite.

Partial agonist

partialpartial agonismpartially
The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis.

Muscarinic acetylcholine receptor M1

M 1 M1M 1 -Muscarinic receptors
The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis.

Muscarinic acetylcholine receptor M3

M 3 M3M3 muscarinic receptors
The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis.

DNA fragmentation

DNA cleavageFragmentationsheared
The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis.

Apoptosis

apoptoticprogrammed cell deathcell death
The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis.

Phenyltropane

AEME is also used in scientific research for the manufacture of phenyltropane analogues such as troparil, dichloropane, iometopane, and CFT.

Structural analog

analogueanaloganalogs
AEME is also used in scientific research for the manufacture of phenyltropane analogues such as troparil, dichloropane, iometopane, and CFT.

Controlled substance

controlled substancescontrolledillegal substance
Methylecgonidine could also theoretically be used to produce cocaine and so may be a controlled substance in some countries.

Hydrolysis

hydrolyzedhydrolysehydrolyze
Methylecgonidine can be synthesized non pyrolytically from cocaine via hydrolysis/dehydration followed by esterification with methanol.

Dehydration

dehydrateddehydratedehydrating
Methylecgonidine can be synthesized non pyrolytically from cocaine via hydrolysis/dehydration followed by esterification with methanol.

Ester

estersesterificationmonoester
Methylecgonidine can be synthesized non pyrolytically from cocaine via hydrolysis/dehydration followed by esterification with methanol.

Phenyllithium

aryllithiumphenyl lithiumPhLi
In the accompanying patent these same authors react their methylecgonidine with two equivalents of PhLi to form a tertiary alcohol by "hard" addition to the ester and not "soft" Michael addition.

Michael reaction

MichaelMichael additionMichael acceptor
In the accompanying patent these same authors react their methylecgonidine with two equivalents of PhLi to form a tertiary alcohol by "hard" addition to the ester and not "soft" Michael addition.

Atropine

atropine sulfateatropine eye dropsatropin
However, the product is only one tenth the potency of atropine.

Cope rearrangement

Copeanionic oxy-Copeoxy-Cope rearrangement
Davies et al. synthesized (R/S)-methylecgonidine by a tandem cyclopropanation/Cope rearrangement.