Ecgonidine

Last updated
Ecgonidine
Ecgonidine.png
Names
IUPAC name
Trop-2-ene-2-carboxylic acid
Systematic IUPAC name
(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-ene-2-carboxylic acid
Other names
Anhydroecgonine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.919 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H11NO2/c10-8(11)6-3-1-5-2-4-7(6)9-5/h3,5,7,9H,1-2,4H2,(H,10,11)/t5-,7-/m1/s1 Yes check.svgY
    Key: ZAZOGAHQAWUCJK-IYSWYEEDSA-N Yes check.svgY
  • InChI=1/C8H11NO2/c10-8(11)6-3-1-5-2-4-7(6)9-5/h3,5,7,9H,1-2,4H2,(H,10,11)/t5-,7-/m1/s1
    Key: ZAZOGAHQAWUCJK-IYSWYEEDBT
  • CN1C2CCC1C(=CC2)C(=O)O
  • OC(=O)\C2=C\C[C@@H]1CC[C@H]2N1
Properties
C9H13NO2
Molar mass 167.205 g·mol1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ecgonidine (anhydroecgonine) is an alkaloid related to ecgonine and cocaine. It has a structure with a cycloheptene ring, with a nitrogen bridge, and a carboxylic acid side chain.

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. [1] Ecgonidine is formed as a metabolite of methylecgonidine, and so the relative concentrations of the two compounds can be used to gauge how recently crack cocaine was smoked. If levels of methylecgonidine are higher, then the drug was smoked recently; however after a longer time period mainly ecgonidine will be present. [2] Ecgonidine has a half-life in the body of around 94–137 minutes, and so can be used to detect use of crack cocaine up to 8–10 hours after the drug is consumed.

See also

Related Research Articles

<span class="mw-page-title-main">Alkaloid</span> Class of naturally occurring chemical compounds

Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.

<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 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.

<span class="mw-page-title-main">Recreational drug use</span> Use of drugs with the primary intention to alter the state of consciousness

Recreational drug use is the use of one or more psychoactive drugs to induce an altered state of consciousness, either for pleasure or for some other casual purpose or pastime. When a psychoactive drug enters the user's body, it induces an intoxicating effect. Generally, recreational drugs are divided into three categories: depressants, stimulants, and hallucinogens.

<span class="mw-page-title-main">Narcotic</span> Chemical substance with psycho-active properties

The term narcotic originally referred medically to any psychoactive compound with numbing or paralyzing properties. In the United States, it has since become associated with opiates and opioids, commonly morphine and heroin, as well as derivatives of many of the compounds found within raw opium latex. The primary three are morphine, codeine, and thebaine.

<span class="mw-page-title-main">Nicotine</span> Mild chemical stimulant produced by some plants

Nicotine is a naturally produced alkaloid in the nightshade family of plants and is widely used recreationally as a stimulant and anxiolytic. As a pharmaceutical drug, it is used for smoking cessation to relieve withdrawal symptoms. Nicotine acts as a receptor agonist at most nicotinic acetylcholine receptors (nAChRs), except at two nicotinic receptor subunits where it acts as a receptor antagonist.

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

Salvinorin A is the main active psychotropic molecule in Salvia divinorum. Salvinorin A is considered a dissociative hallucinogen.

<span class="mw-page-title-main">Effects of cannabis</span> Effects resulting from the use of cannabis

The effects of cannabis are caused by chemical compounds in the cannabis plant, including 113 different cannabinoids such as tetrahydrocannabinol (THC) and 120 terpenes, which allow its drug to have various psychological and physiological effects on the human body. Different plants of the genus Cannabis contain different and often unpredictable concentrations of THC and other cannabinoids and hundreds of other molecules that have a pharmacological effect, so the final net effect cannot reliably be foreseen.

<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.

Lacing or cutting, in drug culture, refer to the act of using a substance to adulterate substances independent of the reason. The resulting substance is laced or cut.

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

(–)-2-β-Carbomethoxy-3-β-(4-fluorophenyl)tropane 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.

Coca paste is a crude extract of the coca leaf which contains 40% to 91% cocaine freebase along with companion coca alkaloids and varying quantities of benzoic acid, methanol, and kerosene. In South America, coca paste, also known as cocaine base and, therefore, often confused with cocaine sulfate in North America, is relatively inexpensive and is widely used by low-income populations. The coca paste is smoked in tobacco or cannabis cigarettes and use has become widespread in several Latin American countries. Traditionally, coca paste has been relatively abundant in South American countries such as Colombia where it is processed into cocaine hydrochloride for distribution to the rest of the world. The caustic reactions associated with the local application of coca paste prevents its use by oral, intranasal, mucosal, intramuscular, intravenous or subcutaneous routes. Coca paste can only be smoked when combined with a combustible material such as tobacco or cannabis.

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

Methylecgonidine is a chemical intermediate derived from ecgonine or cocaine.

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

Lobeline is a piperidine alkaloid found in a variety of plants, particularly those in the genus Lobelia, including Indian tobacco, Devil's tobacco, great lobelia, Lobelia chinensis, and Hippobroma longiflora. In its pure form, it is a white amorphous powder which is freely soluble in water.

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

Troparil is a stimulant drug used in scientific research. Troparil is a phenyltropane-based dopamine reuptake inhibitor (DRI) that is derived from methylecgonidine. Troparil is a few times more potent than cocaine as a dopamine reuptake inhibitor, but is less potent as a serotonin reuptake inhibitor, and has a duration spanning a few times longer, since the phenyl ring is directly connected to the tropane ring through a non-hydrolyzable carbon-carbon bond. The lack of an ester linkage removes the local anesthetic action from the drug, so troparil is a pure stimulant. This change in activity also makes troparil slightly less cardiotoxic than cocaine. The most commonly used form of troparil is the tartrate salt, but the hydrochloride and naphthalenedisulfonate salts are also available, as well as the free base.

<span class="mw-page-title-main">Smoking</span> Practice of inhaling a burnt substance for psychoactive effects

Smoking is a practice in which a substance is combusted and the resulting smoke is typically inhaled to be tasted and absorbed into the bloodstream of a person. Most commonly, the substance used is the dried leaves of the tobacco plant, which have been rolled with a small rectangle of paper into an elongated cylinder called a cigarette. Other forms of smoking include the use of a smoking pipe or a bong.

Free base is the conjugate base (deprotonated) form of an amine, as opposed to its conjugate acid (protonated) form. The amine is often an alkaloid, such as nicotine, cocaine, morphine, and ephedrine, or derivatives thereof. Freebasing is a more efficient method of self-administering alkaloids via the smoking route.

<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">Crack cocaine</span> Form of the drug cocaine

Crack cocaine, commonly known simply as crack, and also known as rock, is a free base form of the stimulant cocaine that can be smoked. Crack offers a short, intense high to smokers. The Manual of Adolescent Substance Abuse Treatment calls it the most addictive form of cocaine.

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

Methylecgonine is a prominent tropane alkaloid found in coca leaves. It is metabolite of cocaine, 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 and Datura innoxia.

References

  1. Scheidweiler KB, Shojaie J, Plessinger MA, Wood RW, Kwong TC (November 2000). "Stability of methylecgonidine and ecgonidine in sheep plasma in vitro". Clinical Chemistry. 46 (11): 1787–95. doi: 10.1093/clinchem/46.11.1787 . PMID   11067814.
  2. Paul BD, McWhorter LK, Smith ML (June 1999). "Electron ionization mass fragmentometric detection of urinary ecgonidine, a hydrolytic product of methylecgonidine, as an indicator of smoking cocaine". Journal of Mass Spectrometry. 34 (6): 651–60. Bibcode:1999JMSp...34..651P. doi:10.1002/(SICI)1096-9888(199906)34:6<651::AID-JMS817>3.0.CO;2-M. PMID   10394630.