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Alkaloids SUBJECT FORENSIC SCIENCE SUBJECT FORENSIC SCIENCE Paper No. and Title PAPER No. 9: Drugs of Abuse Module No. and Title MODULE No. 33: Alkaloids Module Tag FSC_P9_M33 FORENSIC SCIENCE PAPER No.9: Drugs of Abuse MODULE No.33: Alkaloids TABLE OF CONTENTS 1. Learning Outcomes 2. Introduction 3. Forensic Significance 4. Chemical Properties of Alkaloids 5. Classification of Alkaloids 6. Some Notable Alkaloids of Forensic Importance 7. Summary FORENSIC SCIENCE PAPER No.9: Drugs of Abuse MODULE No.33: Alkaloids 1. Learning Outcomes After studying this module, you shall be able to know about- The significance of Alkaloids Classification of Alkaloids and importance of some notable Alkaloids Forensic importance and examination of Alkaloids 2. Introduction Alkaloids are a group of molecules with a comparatively large occurrence in nature around the world. They are very diverse chemicals and biomolecules, but they are completely secondary compounds and they are derivative of amino acids. However, an exact definition of the word ‘alkaloid’ (alkali-like) is slightly difficult because there is no clear-cut borderline between alkaloids and naturally occurring complex amines. The term alkaloid was coined in 1819 by the pharmacist W. Meisner and meant simply, alkali like. Typical alkaloids are derived from plant sources, they are basic, they comprehend one or more nitrogen atoms, generally existing in a heterocyclic ring, and they habitually have a noticeable physiological action on human or other animals. The term ‘proto-alkaloid’ or ‘amino-alkaloid’ is occasionally applied to compounds such as hordenine, ephedrine and colchicine which lack one or more of the properties of typical alkaloids. Alkaloids are organic bases. A “True Alkaloid” can be regarded as by: The possession of a nitrogen atom as part of a heterocyclic system; A multifaceted molecular structure; Significant pharmacological properties; Its origin from the plant kingdom The majority of alkaloids fit this four part definition; however, a number of exceptions exist. The compounds Samandarine, Samandarone, and Cycloneosamandarine, secluded from the dermal glands of the European Fire Salamander displays the usual properties of an alkaloid substance, but do not fit the definition of a “true alkaloid” owing to their animal origin. True alkaloids are of rare occurrence in lower plants. In the fungi the lysergic acid derivatives and the sulphur-containing alkaloids, e.g. the gliotoxins, are the best known. Many alkaloids are poisonous, others are addictive (e.g. cocaine), and some are used clinically (e.g. morphine). More than 10,000 alkaloids are currently known, the first discovered being Narcotine, isolated from opium. FORENSIC SCIENCE PAPER No.9: Drugs of Abuse MODULE No.33: Alkaloids Alkaloids are constituents very well recognized for their biological action at the commencement of world evolution. They were used in traditional herbal medication for the treatment of ailments and in weapons as venoms in the course of tribal wars and during hunting. After the discovery of the first alkaloid, narcotine, other alkaloids were rapidly discovered like Morphine form opium, strychnine from Strychnos nux-vomica seeds, emetine from ipecacuanha root, quinine from Cinchona bark and coniine from hemlock. Alkaloids are used medicinally in their own right e.g. hyoscyamine and vinblastine and they have often provided lead compounds for the development of synthetic drugs. For example, cocaine was the first local anaesthetic, quinine the first antimalarial and tubocurarine the first neuromuscular blocking agent. Alkaloids frequently have powerful physiological effects. Most alkaloids are colourless, crystalline compounds: e.g. coniines, but some such as nicotine and hygrine, are liquids. Usually, many are optically active in nature and the various active forms are generally found but not in different plants. Alkaloids are produced by secondary metabolism of primary metabolites, usually amino acids. These pathways are long, intricate, stereochemically precise and energy consuming, and are assumed to be of evolutionary benefit. 3. Forensic Significance The poisonous and therapeutic effects of plants have been known since time immemorial, but the active constituents have been studied for only about 200 years. In most human history, alkaloids from plant extracts have been used as ingredients in potions (liquid medicine) and poisons. Ancient people used plant excerpts containing alkaloids for the treatment of a large number of diseases such as snakebite, fever and insanity. Habitually the bioactive compounds in the plants that intrigue the chemist are the nitrogen containing bases called alkaloids. Alkaloids have complex molecule structure and they have significant pharmacology activities. Alkaloids are time and again toxic to man and have many intense physiological actions, hence their wide used in medicine. For examples, cinchona alkaloids which, is existing in the bark of Cinchona species and Remijia species consisted of quinine as their main constituents which has been known as anti- malarial agent. Alkaloids have delivered a means of pharmacologically active compounds. Approximately 25% of the drugs used at present are of plant origin. These are administered either as pure compounds or as extracts and have often served as model structures for synthetic drugs. FORENSIC SCIENCE PAPER No.9: Drugs of Abuse MODULE No.33: Alkaloids 4. Chemical Properties of Alkaloids Maximum alkaloids are well-defined crystalline substances which bond with acids to form salts. In the plant they may exist in the free- state, as salts or as N -oxides. In addition to the elements carbon, hydrogen and nitrogen, most alkaloids contain oxygen. A small number of alkaloids, such as coniine from hemlock and nicotine from tobacco, are oxygen-free and are liquids. Even if coloured alkaloids are comparatively uncommon, they are not unknown; berberine, for example, is yellow and the salts of sanguinarine are copper-red. 5. Classification of Alkaloids 5.1 CLASSIFICATION BASED UPON THE BIOGENESIS: Alkaloids show great variety in their botanical and biochemical origin, in chemical structure and in pharmacological action. Consequently, many different systems of classification are possible and the classification mentioned hereinafter is not exhaustive. Alkaloids can be classified by their mutual molecular precursors, founded on the biological pathway used to build the molecule. From a structural perspective, alkaloids are separated according to their shapes and origins. There are three main types of alkaloids: (1) True alkaloids (2) Protoalkaloids (3) Pseudoalkaloids True alkaloids and Protoalkaloids are derived from amino acids, whereas pseudoalkaloids are not derived from these compounds. 5.1.1 True alkaloids True alkaloids are derived from amino acids and they share a heterocyclic ring with nitrogen. These alkaloids are extremely reactive substances with biological activity even in small doses. All true alkaloids have a bitter taste and appear as a white solid, with the exception of nicotine which is a brown liquid. True alkaloids form water-soluble salts. Furthermore, most of them are crystalline substances which bond with acids to form salts. FORENSIC SCIENCE PAPER No.9: Drugs of Abuse MODULE No.33: Alkaloids True alkaloids may occur in plants in the Free State, as salts and as N-oxides. These alkaloids befall in a narrow sum of species and families, and are those compounds in which decarboxylated amino acids are condensed with a non-nitrogenous structural moiety. They are typically found as salts in plant such as liriodenine and morphine. 5.1.2 Protoalkaloids Protoalkaloids are compounds, in which the N atom derived from an amino acid is not a fragment of the heterocyclic ring. Such kinds of alkaloid include compounds derived from l- tyrosine and l-tryptophan. Protoalkaloids are of a closed ring, being impeccable but structurally simple alkaloids. They are not restricted to any specific class of alkaloids and are often classified according to the amino acids from which they are derived. They form a minority of all alkaloids. Hordenine, mescaline and yohimbine are good examples of these kinds of alkaloid. 5.1.3 Pseudoalkaloids Pseudoalkaloids are compounds of elementary carbon skeletons of which are not derived from amino acids. They can also result from the amination and transamination reactions of the different pathways coupled with precursors or post-cursors of amino acids. These alkaloids can also be derived from non-amino acid precursors. The N atom is introduced into the molecule at a relatively late stage, for example, in the case of steroidal or terpenoid skeletons. Pseudoalkaloids can be acetate and phenylalanine derived or terpenoid, as well as steroidal alkaloids. Examples of pseudoalkaloids include such compounds as coniine, capsaicin, ephedrine, solanidine, caffeine, theobromine and pinidine. 5.2 CLASSIFICATION BASED UPON THE RING SYSTEM It is perhaps the most extensively established and mutual approach of classification of alkaloids for which the principal condition is the presence of the basic heterocyclic nucleus. According to this concept, the alkaloids are classified on the basis of the ring system present in them. FORENSIC SCIENCE PAPER No.9: Drugs of Abuse MODULE No.33: Alkaloids 5.2.1 PYRROLIDINE ALKALOIDS Pyrrolidine alkaloids have a pyrrolidine (C4N skeleton) nucleus. The structural α of these alkaloids is l-ornithine (in plants) and l-arginine (in animals). e.g., Hygrine Pyrrolidine Ring System 5.2.2 PIPERIDINE ALKALOIDS
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