Cocaine reverse ester, (also known as Reverse ester cocaine or REC) is a
tropane
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae (including coca) an ...
derivative drug which is a reverse
ester
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ...
of
cocaine
Cocaine (from , from , ultimately from Quechua: ''kúka'') is a central nervous system (CNS) stimulant mainly used recreationally for its euphoric effects. It is primarily obtained from the leaves of two Coca species native to South Am ...
, with the 2-COOCH
3 methoxycarbonyl group swapped to an isomeric OCOCH
3 acetoxy group. It was synthesised because of the observation that the reverse ester pairs of several structurally related substances show similar activity to each other (see e.g.
methylphenidate
Methylphenidate, sold under the brand names Ritalin and Concerta among others, is the most widely prescribed central nervous system (CNS) stimulant medication used to treat attention deficit hyperactivity disorder (ADHD) and, to a lesser extent ...
vs
phacetoperane,
pethidine
Pethidine, also known as meperidine and sold under the brand name Demerol among others, is a synthetic opioid pain medication of the phenylpiperidine class. Synthesized in 1938 as a potential anticholinergic agent by the German chemist Otto Ei ...
vs
desmethylprodine
Desmethylprodine or 1-methyl-4-phenyl-4-propionoxypiperidine (MPPP, Ro 2-0718) is an opioid analgesic drug developed in the 1940s by researchers at Hoffmann-La Roche. Desmethylprodine has been labeled by the DEA as a Schedule I drug in the Un ...
). Cocaine reverse ester however did not produce cocaine-like
stimulant
Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
effects in animal studies,
and is also illegal in many jurisdictions as a
structural isomer
In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term met ...
of cocaine; nevertheless it has attracted attention from vendors of quasi-legal
designer drug
A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Des ...
s as a potential alternative to cocaine.
See also
*
3-(p-Fluorobenzoyloxy)tropane
*
4′-Fluorococaine
*
Benzoylecgonine
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.
Pharmacokinetics
Chemically, benzoylecgonine is the benzoate ester of ecgonine. It ...
*
Methylecgonine cinnamate
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,Merck Chemical Index, 1985 but some s ...
*
Salicylmethylecgonine
Salicylmethylecgonine, (2′-Hydroxycocaine) is a tropane derivative drug which is both a synthetic analogue and a possible active metabolite of cocaine. Its potency ''in vitro'' is around 10x that of cocaine, although it is only around three t ...
References
{{reflist
Tropanes
Acetate esters