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In
chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...
, a free base (freebase, free-base) is a term for the neutral form of an
amine In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
or other Lewis base. The term is used in the pharmaceutical industry in contrast to
salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
-based formulations like hydrochlorides. The amine is often an
alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...
, such as
nicotine Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...
,
cocaine Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...
,
morphine Morphine, formerly also called morphia, is an opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (''Papaver somniferum''). It is mainly used as an analgesic (pain medication). There are ...
, and
ephedrine Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent hypotension, low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred ...
, or derivatives thereof. Colloquially, "free-basing" also means the treatment of salts or other formulations to convert them into the free base form, especially for
recreational drug 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 Sub ...
s.


Properties

Some alkaloids are more stable as ionic salts than as free base. The salts usually exhibit greater water solubility. Common counterions include
chloride The term chloride refers to a compound or molecule that contains either a chlorine anion (), which is a negatively charged chlorine atom, or a non-charged chlorine atom covalently bonded to the rest of the molecule by a single bond (). The pr ...
, bromide,
sulfate The sulfate or sulphate ion is a polyatomic anion with the empirical formula . Salts, acid derivatives, and peroxides of sulfate are widely used in industry. Sulfates occur widely in everyday life. Sulfates are salts of sulfuric acid and many ...
,
phosphate Phosphates are the naturally occurring form of the element phosphorus. In chemistry, a phosphate is an anion, salt, functional group or ester derived from a phosphoric acid. It most commonly means orthophosphate, a derivative of orthop ...
,
nitrate Nitrate is a polyatomic ion with the chemical formula . salt (chemistry), Salts containing this ion are called nitrates. Nitrates are common components of fertilizers and explosives. Almost all inorganic nitrates are solubility, soluble in wa ...
,
acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic, or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...
,
oxalate Oxalate (systematic IUPAC name: ethanedioate) is an anion with the chemical formula . This dianion is colorless. It occurs naturally, including in some foods. It forms a variety of salts, for example sodium oxalate (), and several esters such as ...
,
citrate Citric acid is an organic compound with the formula . It is a colorless weak organic acid. It occurs naturally in citrus fruits. In biochemistry Biochemistry, or biological chemistry, is the study of chemical processes within and relati ...
, and tartrate. Amine salts formed from the
acid–base reaction In chemistry, an acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms an ...
with
hydrochloric acid Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...
are known as hydrochlorides. For example, compare the free base hydroxylamine (NH2OH) with the
salt In common usage, salt is a mineral composed primarily of sodium chloride (NaCl). When used in food, especially in granulated form, it is more formally called table salt. In the form of a natural crystalline mineral, salt is also known as r ...
hydroxylamine hydrochloride (NH3OH+ Cl).


Freebasing

Cocaine hydrochloride ("powder cocaine") cannot be smoked; it decomposes at the high temperatures produced by smoking. Free base cocaine, on the other hand, has a melting point of 98°C and is volatile at temperatures above 90°C, and is therefore actively smokable. After inhalation the alkaloid is absorbed into the blood stream and rapidly transported throughout the body. However, since blood is buffered with carbonate at physiological pH (near 7.4), free-base amines will be rapidly converted back into their acid form. In fact, 94.19% of cocaine will exist as the acid form under equilibrium at pH=7.4, calculated using the Henderson–Hasselbalch equation assuming a pKa of 8.61. A small portion (5.81%) of cocaine will remain as free-base and pass through the blood-brain barrier; according to Le Chatelier's principle the acid form of cocaine will be continually converted to free-base as the base form is continually removed across the blood-brain barrier. Extraction kits for converting the hydrochloride to the base are commercially available. Freebasing also tends to remove water-soluble impurities and adulterants such as sugars (
lactose Lactose is a disaccharide composed of galactose and glucose and has the molecular formula C12H22O11. Lactose makes up around 2–8% of milk (by mass). The name comes from (Genitive case, gen. ), the Latin word for milk, plus the suffix ''-o ...
,
sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...
,
glucose Glucose is a sugar with the Chemical formula#Molecular formula, molecular formula , which is often abbreviated as Glc. It is overall the most abundant monosaccharide, a subcategory of carbohydrates. It is mainly made by plants and most algae d ...
,
mannitol Mannitol is a type of sugar alcohol used as a sweetener and medication. It is used as a low calorie sweetener as it is poorly absorbed by the intestines. As a medication, it is used to decrease pressure in the eyes, as in glaucoma, and to l ...
,
inositol In biochemistry, medicine, and related sciences, inositol generally refers to ''myo''-inositol (formerly ''meso''-inositol), the most important stereoisomer of the chemical compound cyclohexane-1,2,3,4,5,6-hexol. Its elemental formula, formula is ...
), which are often added to street cocaine. Cocaine freebase is only slightly soluble in water (1 in 600 of water) as compared to the high solubility of cocaine hydrochloride (1 in 0.5 of water).


Preparation

The free base form of cocaine is prepared from cocaine hydrochloride by extracting the cocaine with an alkaline solution (
sodium hydroxide Sodium hydroxide, also known as lye and caustic soda, is an inorganic compound with the formula . It is a white solid ionic compound consisting of sodium cations and hydroxide anions . Sodium hydroxide is a highly corrosive base (chemistry), ...
or
ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
) and adding a non-polar solvent such as
diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...
or
benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
. The mixture separates into two layers, the organic layer containing the dissolved cocaine, which is then separated and evaporated, leaving almost pure cocaine crystals that are white and crumbly. Alternatively, the free base can be obtained using an organic chemistry technique called trituration. Trituration of the free base from cocaine hydrochloride (or "cooking") is done by dissolving the cocaine hydrochloride in water over constant heat, while simultaneously adding a base (such as
baking soda Sodium bicarbonate (IUPAC name: sodium hydrogencarbonate), commonly known as baking soda or bicarbonate of soda (or simply “bicarb” especially in the UK) is a chemical compound with the formula NaHCO3. It is a salt (chemistry), salt compose ...
) to form the free base cocaine. The free base of cocaine forms a solid "rock", pieces of which can be smoked directly (
crack 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 Smoking, smoked. Crack offers a short, intense Euphoria (emotion), high to smokers. The ''Manual of Adolescent Sub ...
).


History

The smoking of cocaine base first appeared in the United States in 1974 and was mostly confined to the state of California. The first hospital admission for a problem related to free-basing was in 1975, the year in which extraction kits and smoking accessories became commercially available. In 1978, distribution of these accessories or paraphernalia spread from California throughout the United States. In 1979, only 1% of cocaine-related hospital admissions involved the use of free base, but by 1982 this figure had increased to 7%.


Other

In South America, coca leaves are traditionally chewed with a quantity of an alkaline lime substance ("llipta") typically derived from the ashes remaining after burning plants, shells or limestone. In South America, coca paste, also known as cocaine base or basuco and, therefore, often confused with cocaine freebase in North America, is relatively inexpensive and is widely used by low-income populations.


Betel nut

In a similar fashion to coca leaves, betel nuts are chewed with added limestone, turning the active ingredient
arecoline Arecoline is a cholinergic agent, stimulant, and natural product, naturally occurring alkaloid found in areca nut, areca (betel) nuts of the areca palm (''Areca catechu'') found in South Asia, South and Southeast Asia. Its effects, depending on ...
into the freebase form, allowing it to be absorbed sublingually.


References

{{Reflist Alkaloids Bases (chemistry) Drug culture