Methylecgonine

Last updated
Methylecgonine
Methyl ecgonine.svg
Names
IUPAC name
methyl 3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
Other names
  • Ecgonine methyl ester
  • EME
  • Methyl ecgonine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3/t6-,7+,8-,9+/m0/s1
  • Key: QIQNNBXHAYSQRY-UYXSQOIJSA-N
  • unspecified sterocentres:InChI=1S/C10H17NO3/c1-11-6-3-4-7(11)9(8(12)5-6)10(13)14-2/h6-9,12H,3-5H2,1-2H3
    Key: QIQNNBXHAYSQRY-UHFFFAOYSA-N
  • CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)O)C(=O)OC
  • unspecified sterocentres:CN1C2CCC1C(C(C2)O)C(=O)OC
Properties
C10H17NO3
Molar mass 199.250 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methylecgonine, also known as ecgonine methylester is a prominent tropane alkaloid found in coca leaves. [1] It is metabolite of cocaine, [2] and may be used as a precursor for it. It also occurs as minor alkaloid in roots of many Datura species such as Datura stramonium [3] and Datura innoxia . [4]

Contents

Biosynthesis

It is the last step before cocaine is biosynthesized in coca plants with the help of BAHD acyltransferase. [5]

Animal study

Animals study suggest that it has beneficial effect on cognition and protects against cocaine lethality. [6] [7] It showed inhibition of sodium channels only at very high dosages. [8]

See also

Related Research Articles

<span class="mw-page-title-main">Cocaine</span> Tropane alkaloid and stimulant drug

Cocaine is a tropane alkaloid that acts as a central nervous system (CNS) stimulant. As an extract, it is mainly used recreationally and often illegally for its euphoric and rewarding effects. It is also used in medicine by Indigenous South Americans for various purposes and rarely, but more formally, as a local anaesthetic or diagnostic tool by medical practitioners in more developed countries. It is primarily obtained from the leaves of two Coca species native to South America: Erythroxylum coca and E. novogranatense. After extraction from the plant, and further processing into cocaine hydrochloride, the drug is administered by being either snorted, applied topically to the mouth, or dissolved and injected into a vein. It can also then be turned into free base form, in which it can be heated until sublimated and then the vapours can be inhaled.

<i>Datura</i> Genus of poisonous, potentially psychoactive plants

Datura is a genus of nine species of highly poisonous, vespertine-flowering plants belonging to the nightshade family (Solanaceae). They are commonly known as thornapples or jimsonweeds, but are also known as devil's trumpets or mad apple. Other English common names include moonflower, devil's weed, and hell's bells. All species of Datura are extremely poisonous and psychoactive, especially their seeds and flowers, which can cause respiratory depression, arrhythmias, fever, delirium, hallucinations, anticholinergic syndrome, psychosis, and death if taken internally.

<i>Datura stramonium</i> Species of flowering plant in the nightshade family Solanaceae

Datura stramonium, known by the common names thornapple, jimsonweed, or devil's trumpet, is a poisonous flowering plant in the Daturae tribe of the nightshade family Solanaceae. Its likely origin was in Central America, and it has been introduced in many world regions. It is an aggressive invasive weed in temperate climates and tropical climates across the world. D. stramonium has frequently been employed in traditional medicine to treat a variety of ailments. It has also been used as a hallucinogen, taken entheogenically to cause intense, sacred or occult visions. It is unlikely ever to become a major drug of abuse owing to effects upon both mind and body frequently perceived as being highly unpleasant, giving rise to a state of profound and long-lasting disorientation or delirium with a potentially fatal outcome. It contains tropane alkaloids which are responsible for the psychoactive effects, and may be severely toxic.

<span class="mw-page-title-main">Methylecgonine cinnamate</span> Chemical compound

Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is pharmacologically inactive, but some studies funded by anti-drug agencies imply that it is active when smoked. Furthermore, the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing agencies to postulate that illicit manufacturers have changed their oxidation procedures when refining cocaine from a crude form. Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline. It is notable that methylecgonine cinnamate is given in patents of active cocaine analogue structures.

<span class="mw-page-title-main">Benzoylecgonine</span> Chemical compound

Benzoylecgonine is the main metabolite of cocaine, formed by the liver and excreted in the urine. It is the compound tested for in most cocaine urine drug screens and in wastewater screenings for cocaine use.

<span class="mw-page-title-main">Cocaethylene</span> Chemical compound

Cocaethylene (ethylbenzoylecgonine) is the ethyl ester of benzoylecgonine. It is structurally similar to cocaine, which is the methyl ester of benzoylecgonine. Cocaethylene is formed by the liver when cocaine and ethanol coexist in the blood. In 1885, cocaethylene was first synthesized, and in 1979, cocaethylene's side effects were discovered.

<span class="mw-page-title-main">Tropinone</span> Chemical compound

Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone.

<span class="mw-page-title-main">WIN-35428</span> Chemical compound

WIN 35,428 is a stimulant drug used in scientific research. CFT is a phenyltropane based dopamine reuptake inhibitor and is structurally derived from cocaine. It is around 3-10x more potent than cocaine and lasts around 7 times longer based on animal studies. While the naphthalenedisulfonate salt is the most commonly used form in scientific research due to its high solubility in water, the free base and hydrochloride salts are known compounds and can also be produced. The tartrate is another salt form that is reported.

<span class="mw-page-title-main">Methylecgonidine</span> Chemical compound

Methylecgonidine is a chemical intermediate derived from ecgonine or cocaine.

Tropine is a derivative of tropane containing a hydroxyl group at the third carbon. It is also called 3-tropanol. It is a poisonous white hygroscopic crystalline powder. It is a heterocyclic alcohol and an amine.

<span class="mw-page-title-main">Tropane alkaloid</span> Class of chemical compounds

Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.

<span class="mw-page-title-main">Biosynthesis of cocaine</span>

The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N-methylpyrrolinium ring, which is preserved in the final product. The second phase incorporates a C4 unit with formation of the bicyclic tropane core.

<span class="mw-page-title-main">Littorine</span> Chemical compound

Littorine is a tropane alkaloid found in a variety of plants including Datura and Atropa belladonna. It is closely related in chemical structure to atropine, hyoscyamine, and scopolamine, which all share a common biosynthetic pathway.

Methylecgonone reductase (EC 1.1.1.334, MecgoR (gene name)) is an enzyme with systematic name ecgonine methyl ester:NADP+ oxidoreductase. This enzyme catalyses the following chemical reaction

Tropine acyltransferase is an enzyme with systematic name acyl-CoA:tropine O-acyltransferase. This enzyme catalyses the following chemical reaction

Pseudotropine acyltransferase is an enzyme with systematic name acyl-CoA:pseudotropine O-acyltransferase. This enzyme catalyses the following chemical reaction

Coca alkaloids are the alkaloids found in the coca plant, Erythroxylum coca. They are predominantly of either the pyrrolidine or the tropane types.

<span class="mw-page-title-main">Meteloidine</span> Chemical compound

Meteloidine is an alkaloid found in some Brugmansia and Datura species. Its also found in Erythroxylum australe and is said to be cocaine-like alkaloid.

<i>O</i>-Acylpseudotropine Class of chemical compounds

An O-acylpseudotropine is any derivative of pseudotropine in which the alcohol group is substituted with an acyl group.

References

  1. ↑ Johnson, Emanuel L.; Emche, Stephen D. (1994). "Variation of Alkaloid Content in Erythroxylum coca Leaves from Leaf Bud to Leaf Drop". Annals of Botany. 73 (6): 645–650. doi:10.1006/anbo.1994.1081. JSTOR   42759059.
  2. ↑ Ambre JJ, Ruo TI, Smith GL, Backes D, Smith CM (1982). "Ecgonine methyl ester, a major metabolite of cocaine". Journal of Analytical Toxicology . 6 (1): 26–9. doi:10.1093/jat/6.1.26. PMID   7078101.
  3. ↑ El Bazaoui A, Bellimam MA, Soulaymani A (March 2011). "Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS". Fitoterapia . 82 (2): 193–7. doi:10.1016/j.fitote.2010.09.010. PMID   20858536.
  4. ↑ El Bazaoui, Ahmed; Bellimam, My Ahmed; Soulaymani, Abdelmajid (2012). "Tropane Alkaloids of Datura innoxia from Morocco". Zeitschrift für Naturforschung C. 67 (1–2): 8–14. doi: 10.1515/znc-2012-1-202 . ISSN   1865-7125. PMID   22486036. S2CID   21953079.
  5. ↑ Schmidt GW, Jirschitzka J, Porta T, Reichelt M, Luck K, Torre JC, Dolke F, Varesio E, Hopfgartner G, Gershenzon J, D'Auria JC (January 2015). "The last step in cocaine biosynthesis is catalyzed by a BAHD acyltransferase". Plant Physiology . 167 (1): 89–101. doi:10.1104/pp.114.248187. PMC   4281001 . PMID   25406120.
  6. ↑ Curry SH, Marler M (May 2020). "Effects of ecgonine methyl ester on cognition in scopolamine-impaired and aged rats". Psychopharmacology . 237 (5): 1331–1342. doi:10.1007/s00213-020-05460-9. PMID   32034448. S2CID   211054455.
  7. ↑ Hoffman RS, Kaplan JL, Hung OL, Goldfrank LR (2004). "Ecgonine methyl ester protects against cocaine lethality in mice". Journal of Toxicology. Clinical Toxicology . 42 (4): 349–54. doi:10.1081/clt-120039540. PMID   15461242. S2CID   34545574.
  8. ↑ Matthews JC, Collins A (February 1983). "Interactions of cocaine and cocaine congeners with sodium channels". Biochemical Pharmacology . 32 (3): 455–60. doi:10.1016/0006-2952(83)90523-3. PMID   6303347.
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