Alkaloids heroin

J. H. Knox and J. Jurand, Separation of morphine alkaloids heroin, methadone and other drugs by ion-exchange chromatography, J. Chromatogr., 52 398 (1973). 

R. S. Schwartz and K. O. David, Liquid chromatography of opium alkaloids heroin cocaine and related compounds using electrochemical detection, Anal. Chem., 57 (1985). 

Morphine is the principal alkaloid of opium. It acts both as a base and as a phenol and reacts to form methylmorphine (codeine ) and diacetylmorphine (diamorphine or heroin). 

Partial synthesis is relatively unimportant in the field of alkaloid synthesis, since only a few compounds are available at low price (see table 23). An exception is the derivatization of the morphine base, which leads to codeine, heroin, and other important compounds. These trivial reactions, however, are covered in elementary text books. 

An opium alkaloid Although it is an excellent analgesic its use is restricted because of the potential for addiction Heroin is the diacetate ester of morphine )... 

Fig. 1 Fluorescence scan of a mixture of alkaloids with ca. 50 ng substance per chromatogram zone morphine (1), 6-monoacetylmorphine (2) and heroin (3).

Fig. 1 Reflectance scan (A) and fluorescence scan (B) of a mixture of alkaloids with 725 ng (A) and 100 ng (B) substance per chromatogram zone. Morphine (1), codeine (2), 6-mono-acetylmorphine (3), heroin (4).

Alkaloids range from the belladonna alkaloids, such as atropine and scopalomine—which are used as poisons, cold remedies, and truth serums —to dextromethorphan, a cough suppressant (anti-tussive). But the most widely known alkaloids are the opiates, such as morphine, heroin, fentanyl, oxycodone, and methadone. These act on... 

Morphine (10) and codeine (11), constituents of opium, are the most interesting alkaloids found in nature. Morphine is also the oldest alkaloid isolated, in 1805, by the German pharmacist Sertiimer from opium, the sun dried latex of Papaver somniferum. The structure of morphine with its so-called morphinan skeleton, once called the acrobat under the alkaloids, was finally elucidated in 1952 by the first total synthesis performed by Gates and Tschudi. Many syntheses would follow [26], but all morphine used today, whether legal or illicit, originates in the natural source P. somniferum or its extract, opium. The latex may contain up to 20% morphine. Most legal morphine is converted into the anticough medicine codeine (Table 5.1) by treatment with trimethylanilinium methoxide, whereas almost all illicit morphine is acetylated to the diacetate heroin. 

The PE spectra of some other alkaloids like methadone and the opiate narcotics morphine, codeine and heroin have been investigated by Klasinc and coworkers95. Also in this study structure-activity relationships based on IPs were sought but not found. Since the interaction of the drug molecule with the receptor is highly specific, it is not unreasonable that the molecular rather than the electronic structure is more important for the physiological activity. 

More than 30 alkaloids have been identified in opium (Robbers et al. 1996). The most relevant are morphine (4-21%), codeine (0.8-2.5%), noscapine (4-8%), papaverine (0.5-2.5%), and thebaine (0.5-2%) (figure 8.4). Other opium alkaloids include narceine, protopine, laudanine, codamine, cytopine, lanthopine, and meconidine. Numerous other opioids have been synthesized from opium alkaloids. Among them is heroin, or diacetylmorphine. 

Opioids are administered in several ways. Opium was most commonly taken recreationally by smoking, but intravenous administration has become most common since the isolation of opium alkaloids and invention of the hypodermic needle. The development of heroin from morphine at the turn of the twentieth century led to more intense euphoric effects and greater risk for addiction. Heroin may also be snorted, or it can be smoked when added to a medium such as tobacco. Medically, opioids are commonly given through oral, subcutaneous, intravenous, transdermal, or rectal routes. 

Many pharmacologically active organic chemicals fonnd in natnre are alkaloids. In general, these componnds contain one or more nitrogen atoms, which in turn impart some basicity to the molecnle. Well-known alkaloid examples are caffeine, cocaine, codeine, ephedrine, morphine, nicotine, qninine, and scopolamine. Heroin is derived from morphine by a chemical modification that increases lipophilicity, making the heroin molecnle inherently more pharmacologically potent than morphine. The exhibition of its basic properties by an alkaloid (Aik) involves (by definition) the acceptance of a proton H+ according to ... 

The above mentioned reactions are widely used in alkaloid modification. A good example of alkaloid modifications for clinical curation purposes are opioides. Morphine and codeine are natural products of Papaver somniferum. However, the codeine is naturally produced in small amounts. This is one reason why it is produced synthetically from morphine by modification. As codeine is the 3-0-methyl ether of morphine, the mono-O-methylation occurs in the acidic phenolic hydroxyl. Pholcodine is obtained by modification of morphine through alkylation with A-(chloroethyl)morpholine. Moreover, dihydrocodeine, hydro-morphone and heroine are also obtained from morphine through modifications. 

The most known narcotics are the opium alkaloids such as morphine, codeine, thebaine, papaverine, noscapine and their derivatives and modified compounds such as nalmorphine, apomorphine, apomopholcodine, dihydrocodeine, hydro-morphone and heroine, also known as diamorphine. Synthetic narcotics share the structural skeleton of morphine and include dextromethorphan, pentazocine, phenazocine meperidine (pethidine), phentanyl, anfentaitil, remifentalin, methadone, dextropropoxyphene, levoproxyphene, dipipanone, dextromoramide, meptazinol and tramadol. Thebaine derivatives are also modified narcotics and include oxycodone, oxymorphone, etorphine, buprenorphine, nalbuphine, naloxone or naltrexone. Narcotics can be semi-synthesized or totally synthesized from the morphine and thebaine model. The compounds serve various purposes in clinical practise. 

Dams et al. [19] determined seven different opium alkaloids and derivatives in seized heroin using fast LC-MS analysis. Analytes were separated in 5 min on a monolithic silica column with a gradient elution system and an optimized flow of 5 mL/min. Detection was carried out using a sonic spray ion source [20] a modified ESI source were ionization is achieved using a nebulizer gas at sonic speed instead of applying an electrical field. 

An alkaloid is a complex organic chemical substance found in plants, which characteristically combines nitrogen with other elements, has a bitter taste, and typically has some toxic, stimulant, analgesic effects. There are many different alkaloids, 30 of which are found in the opium plant. While morphine is the most important alkaloid in opium—for its natural narcotic qualities as well as providing the chemical structure for heroin—another alkaloid, codeine, is also sought after for its medicinal attributes. Other alkaloids include papaverine, narcotine, nicotine, atropine, cocaine, and mescaline. While the concentration of morphine in opium varies depending on where and how the plant is cultivated, it typically ranges from 3 percent to 20 percent. 

But the question remains if OxyContin is such a great drug, why the concern It stems from the fact that OxyContin comes from the poppy plant, in the form of the alkaloid thebaine. While less powerful than raw opium, and certainly much less powerful than heroin, thebaine is still an opiate... 

Opioid refers to any compound that acts like morphine, the most abundant alkaloid compound in opium. The term opioid includes substances that are derived from plants (such as morphine and codeine), those that occur naturally in the body (such as endorphins and enkephalins), and synthesized compounds (such as heroin and fentanyl). [Endorphins and enkephalins are discussed in Chapters 2 and 3. Fen-tanyi is discussed in Chapter 3.]... 

The chromatographic problem which we investigated is difficult. The solutes are seven nitrogen containing alkaloids. These alkaloids were selected because they may accompany heroin in illegally sold street drugs. 

Therefore the influence of temperature and humidity on the robustness will be investigated. The maximum number of alkaloids to be separated in the paper of Coenegracht et al [3] was six in opium, and the separation of seven alkaloids in this paper is a severe test of the four solvent systems suitability for the separation of alkaloids. The alkaloids are strychnine, quinine, narceine, heroin, noscapine, caffeine and papaverine. 

A robust TLC separation of the seven alkaloids (strychnine, quinine, heroin, noscapine, caffeine, papaverine and narceine) is difficult to obtain. The solutes used have different properties and can therefore not be separated trustworthy for all possible values of relative humidity and temperature. 

Liquid chromatography is two decades more mature than capillary electrophoresis. As trained electropherographers become more common, more separations will be handled by electrophoresis. For example, electrophoresis displaced liquid chromatography as the preferred method for forensic analysis of alkaloids in opium and heroin.51 The enabling technology for this application was dynamic coating of the capillary between runs to eliminate adsorption of analytes on the silica surface and decrease variations in migration times to less than 0.5%. 

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