Methylecgonidine

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"AEME" redirects here. For the Australian Army corps, see Royal Australian Electrical and Mechanical Engineers.
Methylecgonidine
Names
IUPAC name
Methyl trop-2-ene-2β-carboxylate
Systematic IUPAC name
Methyl (1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylate
Other names
Anhydromethylecgonine
Anhydroecgonine methyl ester
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.164.719 Edit this at Wikidata
UNII
  • InChI=1S/C10H15NO2/c1-11-7-3-5-8(10(12)13-2)9(11)6-4-7/h5,7,9H,3-4,6H2,1-2H3/t7-,9+/m0/s1 checkY
    Key: MPSNEAHFGOEKBI-IONNQARKSA-N checkY
  • InChI=1/C10H15NO2/c1-11-7-3-5-8(10(12)13-2)9(11)6-4-7/h5,7,9H,3-4,6H2,1-2H3/t7-,9+/m0/s1
    Key: MPSNEAHFGOEKBI-IONNQARKBC
  • CN2[C@@H]/1CC[C@@H]2C\C=C\1C(=O)OC
Properties
C10H15NO2
Molar mass 181.235 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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

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.[1] 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 has been shown to be specifically more harmful to the body than other byproducts of cocaine; for example to the heart,[2] lungs[3] & liver.[4] The toxicity is due to a partial agonist effect at M1 and M3 muscarinic receptors, leading to DNA fragmentation and neuronal death by apoptosis.[5]

AEME is also used in scientific research for the manufacture of

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

Synthesis

Methylecgonidine synthesis from cocaine

Methylecgonidine can be synthesized non

esterification with methanol.[7][8]

Methylecgonidine synthesis by Kline

The scheme by Kline

Michael addition. However, the product is only one tenth the potency of atropine. The methyl 2,4,6-cycloheptatriene-1-carboxylate can be made synthetically.[10][11]

Enantioselective[12]

Davies et al. synthesized (R/S)-methylecgonidine by a tandem cyclopropanation/

TBAF and reductive methylation with formaldehyde and sodium cyanoborohydride
, (R/S)-5 was obtained in overall good yield.

See also

References

  1. S2CID 15619796
    .
  2. ^ Pharmacokinetics and Pharmacodynamics of Methylecgonidine, a Crack Cocaine Pyrolyzate - Scheidweiler et al. 307 (3): 1179 Figure IG6 - Journal of Pharmacology and Experimental Therapeutics
  3. PMID 11159694
    .
  4. PMID 12482236
    .
  5. PMID 26626425
    .
  6. PMID 8575031
    .
  7. doi:10.1002/recl.19370560215
    .
  8. doi:10.1021/ja01854a038
    .
  9. PMID 2362282
    .
  10. ^ "Methyl 2,4,6-cycloheptatriene-1-carboxylate - C9H10O2, density, melting point, boiling point, structural formula, synthesis".
  11. hdl:2268/237697
    .
  12. ISSN 0040-4039
    .
  13. doi:10.1021/jo00019a044
    .
  14. doi:10.1016/S0040-4039(01)80766-8
    .
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