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Contents 1 Stim Temp Ed 1.1 phenethylamine 1.2 Substituted phenethylamine 1.2.1 Amphetamine 1.2.2 Dextroamphetamine 1.2.3 Phenyl 1.2.4 Propan-1-ol 1.3 General 1.4 Chemical properties 1.5 Preparation 1.5.1 Amine 1.6 Description 1.7 Introduction 1.7.1 Aliphatic Amines 1.7.2 Aromatic amines 1.8 Naming conventions 1.9 Physical properties 1.9.1 General properties 1.9.2 Chirality 1.9.3 Properties as bases 1.10 Biological activity 1.10.1 Dextroamphetamine 1.10.2 Dextroamphetamine 1.10.3 L-Lysine 1.10.4 Other Information 1.10.5 Extra 1.11 Properties 1.11.1 Lisdexamfetamine 1.11.2 Amphetamine 1.11.3 Methamphetamine 1.11.4 Levmetamfetamine 1.11.5 Aspartate 1.11.6 L-Lysine 1.12 Properties 2 Dextroamphetamine 2.1 Overview 2.2 History 2.3 Clinical uses 2.4 Other uses 2.5 Side effects 2.5.1 Chronic use 2.6 Time course and elimination 2.7 Notable users 2.8 See also 2.9 Images 2.10 Sulfate 2.11 Chemical properties 2.12 Uses 2.12.1 Oxoanion sulfides 2.13 Ampehtamine 2.14 Chemistry 2.15 Pharmacology 2.16 Aspartate 2.17 Aspartic Acid 2.18 Adderall 2.19 Use 2.19.1 Effects 2.20 Ephedrine 2.20.1 Neurotoxicity of Ephedrine 2.21 Desoxyn 2.22 Medical use 2.23 Methamphetamine 2.23.1 l-Methamphetamine 2.24 L-Methamphetamine 2.25 Pharmacology 2.25.1 Tolerance 2.26 Side effects 2.26.1 Immediate and Chronic Effects 2.26.2 Meth Mouth 2.27 Routes of administration 2.28 Hydrochloride 2.29 Uses

[edit] Stim Temp Ed

I made this user page to help understand ADHD medications better

Understanding Dextroamphetamine

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[edit] phenethylamine [edit] Substituted phenethylamine General structure of phenethylamines and amphetamines (see the table below). Substituted phenethylamines carry additional chemical modifications at the phenyl ring, the sidechain, or the amino group: Amphetamines are homologues of phenethylamines carrying an alpha-methyl (α-CH3) group at the sidechain carbon atom next to the amino group. Catecholamines are phenethylamines carrying two hydroxy groups in positions 3 and 4 of the phenyl ring. Examples are the hormones and neurotransmitters dopamine, epinephrine (adrenaline), and norepinephrine (noradrenaline). The aromatic amino acids phenylalanine and tyrosine are phenethylamines carrying a carboxyl group (COOH) in alpha position. 2C's are phenethylamines with methoxy groups attached to the 2 and 5 carbons and no alpha-methyl group.

[edit] Amphetamine Edward Bower/temp Systematic (IUPAC) name 1-phenylpropan-2-amine or l-amphetamine Identifiers CAS number 300-62-9 ATC code N06BA01 PubChem 3007 DrugBank APRD00480 Chemical data Formula C9H13N  Mol. mass 135.2084 Pharmacokinetic data Bioavailability 4L/kg; low binding to plasma proteins (20%) Metabolism Hepatic Half life 10–13 hours Excretion Renal; significant portion unaltered Therapeutic considerations Pregnancy cat. ? Legal status Routes Oral, Intravenous, Vaporized, Insufflated, Suppository

[edit] Dextroamphetamine Edward Bower/temp Systematic (IUPAC) name (2S)-1-phenylpropan-2-amine or d-amphetamine Identifiers CAS number 300-62-9 ATC code N06BA01 PubChem 5826 DrugBank APRD00480 Chemical data Formula C9H13N  Mol. mass 135.206 g/mol Pharmacokinetic data Bioavailability >75% Metabolism Hepatic Half life 10–28 hours (Average ~12 hours) Excretion Renal: ~45% Therapeutic considerations Pregnancy cat. ? Legal status Routes Oral

Understanding Phenethylamines

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[edit] Phenyl The structure of the phenyl group In chemistry, the phenyl group or phenyl ring (often abbreviated as -Ph) is the functional group with the formula -C6H5 where the six carbon atoms are arranged in a cyclic ring structure. It is highly stable, and is also a member of the aromatic family of compounds. This hydrophobic and aromatic hydrocarbon unit can be found in many organic compounds. It can be thought of as being derived from benzene (C6H6). In fact in chemical literature benzene itself is sometimes denoted as Ph. One of the simplest phenyl containing compounds is phenol, C6H5OH. Presence of a phenyl group typically results in an 1H-NMR shift around 7.7ppm. The phenyl group differs from the benzyl functional group in that benzyls have an extra CH2.

[edit] Propan-1-ol General Systematic name propan-1-ol Other names 1-propanol propyl alcohol n-propanol n-propyl alcohol propanol Molecular formula C3H8O SMILES CCCO Molar mass 60.09 g/mol Appearance Clear, colourless liquid CAS number [71-23-8] Properties Density and phase 0.8034 g/cm3, liquid Solubility in water Fully miscible All common solvents: Fully miscible Melting point −126.5 °C (146.7 K) Boiling point 97.1 °C (370.3 K) Acidity (pKa) (~16) Viscosity 2.26 cP at ?°C Dipole moment 1.68 D Hazards MSDS External MSDS EU classification Flammable (F) Irritant (Xi) NFPA 704 3 1 0   R-phrases R11, R41, R67 S-phrases (S2), S7, S16, S24, S26, S39 Flash point 15 °C RTECS number UH8225000 Supplementary data page Structure and properties n, εr, etc. Thermodynamic data Phase behaviour Solid, liquid, gas Spectral data UV, IR, NMR, MS Related compounds Related alcohols Ethanol Propan-2-ol Butan-1-ol Related compounds Propionaldehyde Propionic acid 1-Chloropropane Propyl acetate Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references [edit] General Propan-1-ol is a primary alcohol with the formula CH3CH2CH2OH. It is also known as 1-propanol, 1-propyl alcohol, n-propyl alcohol, or simply propanol. It is an isomer of propan-2-ol. It is used as a solvent in the pharmaceutical industry, and for resins and cellulose esters. It is formed naturally in small amounts during many fermentation processes. [edit] Chemical properties 1-Propanol shows the normal reactions of a primary alcohol. Thus it can be converted to alkyl halides; for example red phosphorus and iodine produce 1-iodopropane in 90% yield, while PCl3 with catalytic ZnCl2 gives 1-chloropropane. Reaction with acetic acid in the presence of an H2SO4 catalyst under Fischer esterification conditions gives propyl acetate, while refluxing propanol overnight with formic acid alone can produce propyl formate in 65% yield. Oxidation of 1-propanol with Na2Cr2O7 and H2SO4 gives only a 36% yield of propionaldehyde, and therefore for this type of reaction higher yielding methods using PCC or the Swern oxidation are recommended. Oxidation with chromic acid yields propionic acid [edit] Preparation 1-Propanol is a major constituent of fusel oil, a by-product formed from certain amino acids when potatoes or grains are fermented to produce ethanol. This is no longer a significant source of the material. 1-Propanol is manufactured by catalytic hydrogenation of propionaldehyde. The propionaldehyde is itself produced via the oxo process, by hydroformylation of ethylene using carbon monoxide and hydrogen in the presence of a catalyst such as cobalt octacarbonyl or a rhodium complex. (1) H2C=CH2 + CO + H2 → CH3CH2CH=O (2) CH3CH2CH=O + H2 → CH3CH2CH2OH A traditional laboratory preparation of 1-propanol involves treating 1-iodopropane with moist Ag2O.

[edit] Amine The general structure of an amine [edit] Description Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. Structurally amines resemble ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups. An important exception to this rule is that compounds of the type RC(O)NR2, where the C(O) refers to a carbonyl group, are called amides rather than amines. Amides and amines have different structures and properties, so the distinction is chemically important. Somewhat confusing is the fact that amines in which an N-H group has been replaced by an N-M group (M = metal) are also called amides. Thus (CH3)2NLi is lithium dimethylamide. See the Category:Amines for a list of types of amine and some real examples of this class of chemical. [edit] Introduction [edit] Aliphatic Amines As displayed in the images below, primary amines arise when one of three hydrogen atoms in ammonia is replaced by an organic substituent. Secondary amines have two organic substituents bound to N together with one H. In tertiary amines all three hydrogen atoms are replaced by organic substituents. Note: the subscripts on the R groups are simply used to differentiate the organic substituents . However, the number subscripts on the H atoms show how many H atoms there are in that group. It is also possible to have four alkyl substituents on the nitrogen. These compounds have a charged nitrogen center, and necessarily come with a negative counterion, so they are called quaternary ammonium salts. Primary amine Secondary amine Tertiary amine Similarly, an organic compound with multiple amino groups is called a diamine, triamine, tetraamine and so forth. [edit] Aromatic amines Main article: Aromatic amines Aromatic amines have the nitrogen atom connected to an aromatic ring as in anilines. The aromatic ring strongly decreases the basicity of the amine, depending on its substituents. Interestingly, the presence of an amine group strongly increases the reactivity of the aromatic ring, due to an electron-donating affect. One organic reaction involving aromatic amines is the Goldberg reaction. [edit] Naming conventions the prefix "N-" shows substitution on the nitrogen atom as prefix: "amino-" as suffix: "-amine" remember that chemical compounds are not proper nouns, so lower case is indicated throughout. Systematic names for some common amines: Primary amines: methylamine ethanolamine or 2-aminoethanol trisamine (or more commonly tris) (Its HCl salt is used as a pH buffering agent in biochemistry) Secondary amines: dimethylamine methylethanolamine or 2-(methylamino)ethanol Cyclic amines: aziridine (3-member ring), azetidine (4-member ring), pyrrolidine (5-member ring) and piperidine (6-member ring) Tertiary amines: trimethylamine dimethylethanolamine or 2-(dimethylamino)ethanol bis-tris (It is used as a pH buffering agent in biochemistry) [edit] Physical properties [edit] General properties Hydrogen bonding significantly influences the properties of primary and secondary amines as well as the protonated derivatives of all amines. Thus the boiling point of amines is higher than those for the corresponding phosphines, but generally lower than the corresponding alcohols. Alcohols, or alkanols, resemble amines but feature an -OH group in place of NR2. Since oxygen is more electronegative than nitrogen, RO-H is typically more acidic than the related R2N-H compound. Methyl-, dimethyl-, trimethyl-, and ethylamine are gases under standard conditions, while diethylamine and triethylamine are liquids. Most other common alkyl amines are liquids; high molecular weight amines are, of course, solids. Gaseous amines possess a characteristic ammonia smell, liquid amines have a distinctive "fishy" smell. Most aliphatic amines display some solubility in water, reflecting their ability to form hydrogen bonds. Solubility decreases with the increase in the number of carbon atoms, especially when the carbon atom number is greater than 6. Aliphatic amines display significant solubility in organic solvents, especially polar organic solvents. Primary amines react with ketones such as acetone, and most amines are incompatible with chloroform and carbon tetrachloride. The aromatic amines, such as aniline, have their lone pair electrons conjugated into the benzene ring, thus their tendency to engage in hydrogen bonding is diminished. Otherwise they display the following properties: Their boiling points are usually still high due to their larger size. Diminished solubility in water, although they retain their solubility in suitable organic solvents only. They are toxic and are easily absorbed through the skin: thus hazardous. [edit] Chirality Tertiary amines of the type NHRR' and NRR'R" are chiral: the nitrogen atom bears four distinct substituents counting the lone pair. The energy barrier for the inversion of the stereocenter is relatively low, e.g. ~7 kcal/mol for a trialkylamine. The interconversion of the stereoisomers has been compared to the inversion of an open umbrella in to a strong wind. Because of this low barrier, amines such as NHRR' cannot be resolved optically and NRR'R" can only be resolved when the R, R', and R" groups are constrained in cyclic structures. [edit] Properties as bases Like ammonia, amines act as bases and are reasonably strong (see table for examples of conjugate acid Ka values). The basicity of amines depends on: The availability of the lone pair of electrons on the Nitrogen atom. The electronic properties of the substituents (alkyl groups enhance the basicity, aryl groups diminish it). The degree of solvation of the protonated amine. The nitrogen atom features a lone electron pair that can bind H+ to form an ammonium ion R3NH+. The lone electron pair is represented in this article by a two dots above or next to the N. The water solubility of simple amines is largely due to hydrogen bonding between protons on the water molecules and these lone electron pairs. Inductive effect of alkyl groups Ions of compound Kb Ammonia NH3 1.8·10-5 M Methylamine CH3NH2 4.4·10-4 M propylamine CH3CH2CH2NH2 4.7·10-4 M 2-propylamine (CH3)2CHNH2 5.3·10-4 M diethylamine (CH3)2NH 9.6·10-4 M +I effect of alkyl groups raises the energy of the lone pair of electrons, thus elevating the basicity. Mesomeric effect of aromatic systems Ions of compound Kb Ammonia NH3 1.8·10-5 M Aniline C6H5NH2 3.8·10-10 M 4-methylphenylamine 4-CH3C6H4NH2 1.2·10-9 M +M effect of aromatic ring delocalise the lone pair electron into the ring, resulting in decreased basicity. The degree of protonation of protonated amines: Ions of compound Maximum number of H-bond NH4+ 4 Very Soluble in H2O RNH3+ 3 R2NH2+ 2 R3NH+ 1 Least Soluble in H2O [edit] Biological activity Amines have strong, characteristic, disagreeable odors, and are toxic. The smells of ammonia, fish, urine, rotting flesh and sperm are all mainly composed of amines. Many kinds of biological activity produce amines by breakdown of amino acids.

[edit] Dextroamphetamine Edward Bower/temp Systematic (IUPAC) name (2S)-1-phenylpropan-2-amine or d-amphetamine Identifiers CAS number 300-62-9 ATC code N06BA01 PubChem 5826 DrugBank APRD00480 Chemical data Formula C9H13N  Mol. mass 135.206 g/mol Pharmacokinetic data Bioavailability >75% Metabolism Hepatic Half life 10–28 hours (Average ~12 hours) Excretion Renal: ~45% Therapeutic considerations Pregnancy cat. ? Legal status Routes Oral

Comparisons

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[edit] Dextroamphetamine Edward Bower/temp Systematic (IUPAC) name (2S)-1-phenylpropan-2-amine or d-amphetamine Identifiers CAS number 300-62-9 ATC code N06BA01 PubChem 5826 DrugBank APRD00480 Chemical data Formula C9H13N  Mol. mass 135.206 g/mol Pharmacokinetic data Bioavailability >75% Metabolism Hepatic Half life 10–28 hours (Average ~12 hours) Excretion Renal: ~45% Therapeutic considerations Pregnancy cat. ? Legal status Routes Oral	[edit] L-Lysine Chemical structure of L-Lysine Acid Edward Bower/temp Systematic (IUPAC) name (S)-2,6-Diaminohexanoic acid Identifiers PubChem         876 Chemical data Formula C6H14N2O2  Molar mass 146.19 g/mol Complete data [edit] Other Information Abbreviations Lys,K Melting point 224 °C Specific rotation +14.6° Isoelectric point 9.74 pKa 2.15, 9.16, 10.67 CAS number [56-87-1] EINECS number 200-294-2 SMILES NCCCCC(N)C(=O)O [edit] Extra Lysine is one of the 20 amino acids normally found in proteins. With its 4-aminobutyl (primary amine) side-chain, it is classified as a basic amino acid, along with arginine and histidine. It is an essential amino acid, and the human nutritional requirement is 1–1.5 g daily. As a dietary supplement, it is claimed that lysine may be useful for those with herpes simplex infections; however, the evidence regarding these benefits is mixed. [edit] Properties L-Lysine is a necessary building block for all protein in the body. L-Lysine plays a major role in calcium absorption; building muscle protein; recovering from surgery or sports injuries; and the body's production of hormones, enzymes, and antibodies. Lysine Formula Lysine can undergo posttranslational modification in protein molecules, often by methylation or acetylation. Collagen contains hydroxylysine which is derived from lysine. O-Glycosylation of lysine residues in the endoplasmic reticulum or Golgi apparatus is used to mark certain proteins for secretion from the cell. Lysine is metabolised in mammals to give Acetyl-CoA, via an initial transamination with α-ketoglutarate. The bacterial degradation of lysine yields cadaverine by decarboxylation. It has been suggested that lysine may be beneficial for those with herpes simplex infections.[citation needed] However, more research is needed to fully substantiate this claim. For more information, refer to Herpes simplex - Lysine.	[edit] Lisdexamfetamine Edward Bower/temp Systematic (IUPAC) name (S)-2,6-diamino-N-[(S)-1-phenylpropan-2-yl]hexanamide Dimesylate Identifiers CAS number  ? ATC code  ? PubChem  ? Chemical data Formula C15H25N3O  Mol. mass 263.38 Pharmacokinetic data Bioavailability  ? Metabolism  ? Half life  ? Excretion  ? Therapeutic considerations Pregnancy cat. ? Legal status Routes  ? Lisdexamfetamine (L-lysine-d-amphetamine), marketed under the name Vyvanse, is a stimulant indicated for treatment of attention-deficit hyperactivity disorder. It was developed by Shire and New River Pharmaceuticals and received approval from the U.S. Food and Drug Administration on February 23, 2007. Lisdexafetamine is intended to provide an option of lower abuse potential, and the results of clinical trials seem to indicate that it is successful. 50mg of lisdexamfetamine contains 20mg of d-amphetamine, the well-known abusable Schedule II option; because of its being bound to L-Lysine, this amphetamine is released and activated more slowly as the molecule is hydrolyzed in the digestive system. This delayed release produced less "likeability", less euphoric effect and a later peak time than amphetamine alone in clinical trials, suggesting that lisdexamfetamine may be appropriate for use with patients with history of stimulant abuse. Nevertheless, it is currently up for designation as Schedule II as well.	[edit] Amphetamine Edward Bower/temp Systematic (IUPAC) name 1-phenylpropan-2-amine or l-amphetamine Identifiers CAS number 300-62-9 ATC code N06BA01 PubChem 3007 DrugBank APRD00480 Chemical data Formula C9H13N  Mol. mass 135.2084 Pharmacokinetic data Bioavailability 4L/kg; low binding to plasma proteins (20%) Metabolism Hepatic Half life 10–13 hours Excretion Renal; significant portion unaltered Therapeutic considerations Pregnancy cat. ? Legal status Routes Oral, Intravenous, Vaporized, Insufflated, Suppository	[edit] Methamphetamine Edward Bower/temp Systematic (IUPAC) name N-methyl-1-phenyl-propan-2-amine or d-Methamphetamine Identifiers CAS number 537-46-2 ATC code N06BA03 PubChem 1206 Chemical data Formula C10H15N  Mol. mass 149.233 g/mol SMILES eMolecules & PubChem Synonyms Deoxyephedrine Pervertin Anadrex Metamfetamine Methylamphetamine Pharmacokinetic data Bioavailability Depends on route of administration Metabolism Hepatic Half life 9-15 hours[1] Excretion Renal Therapeutic considerations Pregnancy cat. ? Legal status Routes Medical: Oral Recreational: Oral, I.V., I.M., Insufflation, Inhalation, Suppository	[edit] Levmetamfetamine Edward Bower/temp Systematic (IUPAC) name (R)-N-methyl-1-phenyl-propan-2-amine or l-methamphetamine Identifiers CAS number 537-46-2 ATC code N06BA03 PubChem 1206 Chemical data Formula C10H15N Mol. mass 149.2 Pharmacokinetic data Bioavailability  ? Metabolism Hepatic Half life  ? Excretion Renal Therapeutic considerations Pregnancy cat. ? Legal status Routes Nasal Inhalation
[edit] Aspartate Chemical structure of L-aspartic acid Edward Bower/temp Systematic (IUPAC) name (2S)-2-aminobutanedioic acid Identifiers PubChem         5960 Chemical data Formula C4H7NO4  Molar mass 133.10 Complete data	[edit] L-Lysine Lysine [2] Systematic name (S)-2,6-Diaminohexanoic acid Abbreviations Lys K Chemical formula C6H14N2O2 Molecular mass 146.19 g/mol PubChem 876 Melting point 224 °C Specific rotation +14.6° Isoelectric point 9.74 pKa 2.15 9.16 10.67 CAS number [56-87-1] EINECS number 200-294-2 SMILES NCCCCC(N)C(=O)O Disclaimer and references Lysine is one of the 20 amino acids normally found in proteins. With its 4-aminobutyl (primary amine) side-chain, it is classified as a basic amino acid, along with arginine and histidine. It is an essential amino acid, and the human nutritional requirement is 1–1.5 g daily. As a dietary supplement, it is claimed that lysine may be useful for those with herpes simplex infections; however, the evidence regarding these benefits is mixed. [edit] Properties L-Lysine is a necessary building block for all protein in the body. L-Lysine plays a major role in calcium absorption; building muscle protein; recovering from surgery or sports injuries; and the body's production of hormones, enzymes, and antibodies. Lysine Formula Lysine can undergo posttranslational modification in protein molecules, often by methylation or acetylation. Collagen contains hydroxylysine which is derived from lysine. O-Glycosylation of lysine residues in the endoplasmic reticulum or Golgi apparatus is used to mark certain proteins for secretion from the cell. Lysine is metabolised in mammals to give Acetyl-CoA, via an initial transamination with α-ketoglutarate. The bacterial degradation of lysine yields cadaverine by decarboxylation. It has been suggested that lysine may be beneficial for those with herpes simplex infections.[citation needed] However, more research is needed to fully substantiate this claim. For more information, refer to Herpes simplex - Lysine.

[edit] Dextroamphetamine

dextroamphetamine Dextroamphetamine is a powerful psychostimulant which produces increased wakefulness, energy and self-confidence in association with decreased fatigue and appetite. It works primarily by inducing the release of the neurotransmitters dopamine and norepinephrine from their storage areas in nerve terminals. Other common names for dextroamphetamine include d-amphetamine, dexamphetamine, (S)-(+)-amphetamine, and brand names such as Dexedrine and Dextrostat.

[edit] Overview

Dextroamphetamine, commonly abbreviated as d-amphetamine, is the dextrorotary stereoisomer of the amphetamine molecule, which can take two different forms. Its stimulant properties are similar to those of Ritalin and methamphetamine, though with a slower onset of action and a duration that lies somewhere between the two. It is perhaps the archetypal euphoric stimulant, and drugs with similar psychoactive properties are often referred to as "amphetamine analogues", or described as having "amphetamine-like" effects.

Both dopamine and norepinephrine are significant in dextroamphetamine's mechanism of action. In broad terms, dopamine is responsible for boosting mental focus and mood, while norepinephrine causes the typical fight-or-flight effects of appetite-suppression, reduced sense of fatigue, dry mouth and increased blood pressure.^[3]

Dextroamphetamine is most often prescribed as dextroamphetamine sulfate, available as 5 mg and 10 mg tablets, as well as 5 mg, 10 mg, and 15 mg time-release capsules. Other forms of the drug include the popular ADHD medication Adderall and its generic derivatives which contain equal proportions, by weight, of dextroamphetamine sulfate, dextroamphetamine saccharate and the sulfate and Aspartate Monohydrate salts of racemic d,l-amphetamine). The aspartate, saccharate and sulfate forms differ pharmacokinetically in the rate at which they are metabolized by the body.

[edit] History

Amphetamine was first synthesized under the chemical name "phenylisopropylamine" in 1887 by the Romanian chemist Lazar Edeleanu. It was not widely marketed until 1932, when the pharmaceutical company Smith, Kline, and French (currently known as GlaxoSmithKline) introduced it in the form of the "Benzedrine Inhaler," for combating cold symptoms. Notably, the chemical form of Benzedrine in the inhaler was the purely basic form (i.e., it was not a chloride or sulfate salt). In free-base form, amphetamine is a volatile oil, hence the efficacy of the inhalers.

Three years later, in 1935, the medical community became aware of the stimulant properties of amphetamine, specifically dextroamphetamine, and in 1937 Smith, Kline, and French introduced Dexedrine tablets, which consisted of pure dextroamphetamine sulfate (a salt of the basic form of D-amphetamine), under the tradename Dexedrine. In the United States, Dexedrine tablets were approved to treat narcolepsy, attention disorders, depression, and obesity. Dextroamphetamine was marketed in various other forms in the following decades, primarily by Smith, Kline, and French, such as several combination medications including a mixture of dextroamphetamine and amobarbital (a barbiturate) sold under the tradename Dexamyl and, in the 1950s, an extended release capsule (the "Spansule").

It quickly became apparent that Dexedrine and other amphetamines had a high potential for abuse, although they were not heavily controlled until 1970, when the Comprehensive Drug Abuse Prevention and Control Act was passed by the United States Congress. Dexedrine, along with other sympathomimetics, was eventually classified as schedule II, the most restrictive category possible for a drug with recognized medical uses.

[edit] Clinical uses

Dextroamphetamine is commonly used for treatment of attention deficit hyperactivity disorder (ADHD) or well-established narcolepsy, generally where non-pharmacological measures have proved insufficient. In some localities it has replaced methylphenidate as the first-choice medication for ADHD, a role in which it is considered highly effective. It is occasionally prescribed for weight-loss in cases of extreme obesity. Dextroamphetamine is contraindicated for patients with a history of substance abuse.

Though such use remains out of the mainstream, dextroamphetamine has been successfully applied in the treatment of certain categories of depression as well as other psychiatric syndromes.^[4] Such alternate uses include reduction of fatigue in cancer patients, antidepressant treatment for HIV patients with depression and debilitating fatigue,^[5] early stage physiotherapy for severe stroke victims,^[6] and replacement therapy for those with methamphetamine addiction.

[edit] Other uses

The U.S. Air Force uses dextroamphetamine as its "go-pill," given to pilots on long missions to help them remain focused and alert. Other branches of the U.S. military (as well as the armed forces of other nations) commonly use or have dispensed dextroamphetamine to troops to prevent or treat fatigue in combat situations. Because of the propensity of dextroamphetamine to cause behavioral side effects, this use is viewed as controversial; newer stimulant medications with fewer side effects, like modafinil are being investigated for this reason. NASA has also used dextroamphetamine to combat fatigue in astronauts near the end of a mission.

[edit] Side effects

Possible adverse effects of dextroamphetamine include sleeplessness, reduced appetite, dependence, nervousness, restlessness, irritability, diarrhea and euphoria that may be followed by fatigue and depression. There may be dryness of mouth, abdominal cramps, headache, dizziness, tremor, sweating, palpitations, increased or sometimes decreased blood pressure and altered libido.

[edit] Chronic use

While continuous dosing with amphetamine causes tolerance, intermittent dosing produces "reverse tolerance" or sensitization to its psychological effects.^[7][8] As a result, regular users commonly experience a quick decrease of unwanted side effects, without an equivalent loss of its stimulant properties. Notably, the sensitization is induced more quickly, and persists far longer than withdrawal-related effects, suggesting a phenomenon more complex than a simple tolerance-induced withdrawal syndrome.

There have also been reports of growth retardation of children with long-term use, although this effect can be reduced by periods of abstinence, referred to as "drug holidays".

[edit] Time course and elimination

On average, about one half of a given dose is eliminated unchanged in the urine, while the other half is broken down into various metabolites (mostly benzoic acid).^[9] However, the drug's half-life is highly variable because the rate of excretion is very sensitive to urinary pH. Under alkaline conditions, direct excretion is negligible and 95%+ of the dose is metabolized. The main metabolic pathway is d-amphetamine phenylacetone benzoic acid hippuric acid. Another pathway, mediated by enzyme CYP2D6, is d-amphetamine p-hydroxyamphetamine p-hydroxynorephedrine. Although p-hydroxyamphetamine is a minor metabolite (~5% of the dose), it may may have significant physiological effects as a norepinephrine analogue.^[10]

Subjective effects are increased by larger doses, however, over the course of a given dose there is a noticeable divergence between such effects and drug concentration in the blood.^[11] In particular, mental effects peak before maximal blood levels are reached, and decline as blood levels remain stable or even continue to increase.^[12][13][14] This indicates a mechanism for development of acute tolerance, perhaps distinct from that seen in chronic use. Its slower onset of action as compared to methamphetamine and methylphenidate is presumably due to a somewhat lower effectiveness in crossing the blood-brain barrier.^[15]

[edit] Notable users

• Mathematician Paul Erdős was a heavy user of amphetamines in his later life. When a friend bet him he could not abstain for a month, Erdős won the bet but complained that the progress of mathematics had been delayed by a month.

[edit] See also

• ADHD
• Amphetamine
• Dextroamphetamine formulations:
  • Adderall
  • Benzedrine
• Related drugs:
  • Methamphetamine (Desoxyn)
  • Methylphenidate (Ritalin)
  • Dexmethylphenidate (Focalin)

[edit] Images

 *Sustained-Release 15mg Spansules:

sulfate

In inorganic chemistry, a sulfate (IUPAC-recommended spelling; also sulphate in British English) is a salt of sulfuric acid.

[edit] Sulfate

sulfate

[edit] Chemical properties

The sulfate ion is a polyatomic anion with the empirical formula SO₄²⁻ and a molecular mass of 96.06 daltons; it consists of one central sulfur atom surrounded by four equivalent oxygen atoms in a tetrahedral arrangement. The sulfate ion carries a negative two charge and is the conjugate base of the hydrogen sulfate ion, HSO₄⁻, which is the conjugate base of H₂SO₄, sulfuric acid.

Sulfate compounds arise when cations combine with the anion SO₄²⁻. Often this combination results in an ionic compound, although sulfates can engage in covalent bonding with most elements. The metal complex PtSO₄P(C₆H₅)₃₂ is clearly covalent Pt-O bonding. Dialkylsulfates, such as dimethylsulfate are covalent, distillable species. Many sulfate salts are highly soluble in water. Exceptions include calcium sulfate, strontium sulfate, and barium sulfate, which are poorly soluble. The barium derivative is useful in the gravimetric analysis of sulfate: one adds a solution of, perhaps, barium chloride to a solution containing sulfate ions. The appearance of a white precipitate, which is barium sulfate, indicates that sulfate anions are present.

[edit] Uses

Sulfates are important in both the chemical industry and biological systems:

• The lead-acid battery typically uses sulfuric acid.
• Some anaerobic microorganisms, such as those living near deep sea thermal vents utilize sulfates as electron acceptors.
• Copper sulfate is a common algaecide.
• Magnesium sulfate, commonly known as Epsom salts, is used in therapeutic baths.
• Gypsum, the natural mineral form of hydrated calcium sulfate, is used to produce plaster.
• The sulfate ion is used as counter ion for some cationic drugs.

[edit] Oxoanion sulfides

• SO₅²⁻ persulfate ion
• SO₄²⁻ sulfate ion
• SO₃²⁻ sulfite ion
• SO₂²⁻ hyposulfite ion
• S₂O₈²⁻ peroxydisulfate ion

[edit] Ampehtamine

amphetamine

[edit] Chemistry

Amphetamine was first synthesized in 1887 by the Romanian chemist Lazăr Edeleanu at the University of Berlin, who called it "phenylisopropylamine". Amphetamine is a chiral compound. The racemic mixture can be divided into its optical antipodes: levo- and dextro-amphetamine. Amphetamine is the parent compound of its own structural class, comprising a broad range of psychoactive derivatives, e.g., MDMA (Ecstasy) and the N-methylated form, methamphetamine. Amphetamine is a homologue of phenethylamine.

Traditionally the medical drug came in the racemic salt d, l-amphetamine sulfate (racemic amphetamine contains levo- and dextro-form in equal amounts). Today, dextroamphetamine sulphate is the predominant form of the drug used; it consists entirely of the d-isomer. Attention disorders are often treated using Adderall and (Ritalin) or generic-equivalent formulations of mixed amphetamine salts that contain both d/l-amphetamine and d-amphetamine in the sulfate and saccharate forms mixed to a final ratio of 3 parts d-amphetamine to 1 part l-amphetamine.

[edit] Pharmacology

Amphetamine, both as d-amphetamine (dextroamphetamine) and l-amphetamine (or a racemic mixture of the two isomers), is believed to exert its effects by binding to the monoamine transporters and increasing extracellular levels of the biogenic amines dopamine, norepinephrine and serotonin. It is hypothesized that d-amphetamine acts primarily on the dopaminergic systems, while l-amphetamine is comparatively norepinephrinergic. The primary reinforcing and behavioral-stimulant effects of amphetamine, however, are linked to enhanced dopaminergic activity, primarily in the mesolimbic DA system. Amphetamine binds to the dopamine transporter (DAT) and blocks the transporters ability to clear DA from the synaptic space. In addition, amphetamine is transported into the cell which leads to dopamine efflux (DA is transported out of the cell and into the synaptic space via reverse transport of the DAT).

[edit] Aspartate

[edit] Aspartic Acid

aspartic acid Aspartic acid (Asp, D), also known as aspartate, the name of its anion, is one of the 20 natural proteinogenic amino acids which are the building blocks of proteins.

As with each of the 20 natural amino acids, there are two abbreviations commonly used to designate aspartic acid: Asp (three letter) and D (one letter). The abbreviations signifying a choice of either aspartic acid or asparagine are Asx (three-letter) and B (one letter).^[1]

As its name indicates, aspartic acid is the carboxylic acid analog of asparagine. It is non-essential in mammals, and might serve as an excitatory neurotransmitter in the brain and is an excitotoxin. It is also a metabolite in the urea cycle, and participates in gluconeogenesis.

As a neurotransmitter, aspartic acid may provide resistance to fatigue and thus lead to endurance, although the evidence to support this idea is not strong.

[edit] Adderall

adderall

[edit] Use

Adderall was introduced in 1996 as instant-release tablets, which has since become available as the generic formulation "mixed amphetamine salts." The active ingredients of Adderall include a combination of dextroamphetamine and racemic amphetamine salts. Shire later introduced a gradual-release preparation of these ingredients, Adderall XR (extended release), and retains patent rights on Adderall XR that will expire in 2009.[1]

In particular, Adderall XR is comprised of the following proportions of active ingredients:

• 1/4 Dextroamphetamine Saccharate
• 1/4 Dextroamphetamine Sulfate
• 1/4 dl-amphetamine Aspartate (racemic amphetamine)
• 1/4 dl-amphetamine Sulfate (racemic amphetamine)

The four component salts are claimed to be metabolized at different rates, thereby imparting a more gradual and "smoother" build-up and decline in effect compared to amphetamine preparations comprising only a single salt.

The average elimination half-life for dextroamphetamine is 10 hours in adults, and for levoamphetamine, 13 hours. Its effects are otherwise similar to other central nervous system stimulants (see amphetamine for details.).

The manufacturer claims that the mixture of salts makes Adderall's effects smoother, with softer highs and lows, than those of other treatments for the same disorders.

There is little evidence, however, to support this claim for immediate-release. A recent patent application for Adderall (USP #6,384,020) was a pharmaceutical composition patent listing a rapid immediate release oral dosage form. No claim of increased or smooth drug delivery was made. A recent double-blind, placebo-controlled crossover study, conducted among children, indicated that patients behaved similarly to other immediate release amphetamines. The authors found that sustained-release dexamphetamine (the main isomeric-amphetamine component of Adderall) had a longer duration of action, and cost less than Adderall, though dexamphetamine was less effective in the first few hours.[2]

Adderall is now sold in either an immediate-release tablet or an extended-release capsule, marketed as Adderall XR (for "eXtended Release"). Doses for both immediate-release and extended-release form come in 5, 10, 15, 20, 25 and 30 mg increments.

Adderall XR utilizes the Microtrol® delivery system to achieve the extended-release mechanism. This delivery system incorporates two beads: the first type of bead dissolves immediately and the second type releases four hours later. Maximum plasma concentration is achieved in seven hours, compared to regular Adderall IR (immediate-release) which reaches maximum plasma concentration within three hours. As a result of its high bioavailability, Adderall XR's effectiveness is not altered by food absorption in the gastrointestinal tract. However, tmax (mean plasma concentration) is prolonged by 2.5 hours (using a standard high-fat meal as the control). Acidic beverages should not be ingested with Adderall XR as they alter the pH balance of the stomach.[3]

[edit] Effects

While the exact mechanism is unknown, it is believed that Adderall works by blocking the reuptake of dopamine and norepinephrine into the presynaptic neuron and increasing their release from the presynaptic neuron into the extraneuronal space. In other words, Adderall reverses the reuptake mechanism, turning it into a pump instead of a vacuum. Sources note that amphetamine and related compounds (ephedrine, etc.) displace noradrenaline from the presynaptic neuron and do not act as reuptake inhibitors as referenced above. ^{[citation needed]}

The increased flow of dopamine and norepinephrine into the extraneuronal space causes the patients' brain, as one psychiatrist explains,^{[citation needed]} to experience a more intense level of concentration, causing an increased ability to focus for extended periods of time, and a heightened interest in performing focus based tasks.

Some patients feel they are less creative while taking Adderall, while others report that it can aid in creative work.Paul Erdős was noted for habitual use of prescription amphetamine throughout the final decades of his life;

Double-blind, placebo-controlled studies of dextroamphetamine in normal subjects have shown significant performance increases on cognitive tasks and decreased reaction time. http://www.sciencemag.org/cgi/content/abstract/199/4328/560

[edit] Ephedrine

Ephedrine

[edit] Neurotoxicity of Ephedrine

This section does not cite any references or sources. (December 2006) Please help improve this section by adding citations to reliable sources. Unverifiable material may be challenged and removed.

As a sympathomimetic agent similar in structure and activity to amphetamines, there has been a dispute over whether ephedrine produces some of the same neurodegenerative effects. It has been shown clinically that certain amphetamines (namely (d)-amphetamine and (d)-methamphetamine) can cause varying levels of long-term dopamine depletion in dopamine-rich brain and nervous centers such as the putamen and the basal ganglia.

Several studies have recently compared the quantities of such neurotransmitters as serotonin, dopamine, glutamate, and epinephrine after concurrent administration of ephedrine and various amphetamine-like agents. The results showed that ephedrine has a reduced neurotoxic effect on dopamine than its amphetamine counterparts.

Ephedrine increases serum dopamine levels minimally in comparison with an equivalent dose of dextroamphetamine (Adderall®). Dextromethamphetamine (Desoxyn®) raises dopamine levels dramatically (more than two times that of an equivalent dose of dextroamphetamine). This supports the general consensus that ephedrine has more of a peripheral action on the sympathetic nervous system, whereas amphetamines appear to cross the blood brain barrier more freely and tend to have a stronger central action. The fact that dopamine is believed to play a major role in the addiction response has been used in recent years as justification for controlling the distribution of dextroamphetamine and dextromethamphetamine, along with various other amphetamines.^[16]

[edit] Desoxyn

desoxyn

[edit] Medical use

Main article: Desoxyn

d-Methamphetamine is used medically under the brand name Desoxyn for the following conditions:

• Attention deficit hyperactivity disorder
• Extreme obesity
• Narcolepsy
• Decongestant

Because of its social stigma, Desoxyn is not generally prescribed for ADHD unless other stimulants, such as methylphenidate (Ritalin®), dextroamphetamine (Dexedrine®) or mixed amphetamines (Adderall®) have failed.

[edit] Methamphetamine

Methamphetamine (dextro-N-α-dimethyl-phenethylamine or desoxyephedrine and popularly shortened to crystal meth or ice ^[17] or simply meth) is an N-methylated analog of amphetamine hydrochloride. It is a psychostimulant drug prescribed for attention-deficit hyperactivity disorder and narcolepsy under the brand name Desoxyn.

Popular for its recreational use, methamphetamine acts as a dopamine and adrenergic reuptake inhibitor and sympathomimetic. Since it stimulates the mesolimbic reward pathway, causing euphoria and excitement, it is thus prone to abuse and addiction. Methamphetamine rapidly enters the brain and triggers a cascading release of norepinephrine, dopamine, and to a lesser extent, serotonin. Users may become obsessed or perform repetitive tasks such as cleaning, hand-washing, or assembling and disassembling objects. Withdrawal is characterized by hypersomnia, polyphagia, and depression-like symptoms, often accompanied by anxiety and drug-craving.^[18] Users of the drug often use one or more benzodiazepines as a means of "coming down".

[edit] l-Methamphetamine

Main article: Levmetamfetamine

l-Methamphetamine is available over the counter as Vicks inhaler as a nasal decongestant. l-Methamphetamine alone can raise blood pressure and cause the heart to beat rapidly due to its effects mimicking the sympathetic nervous system, but is not thought to be nearly as addictive or centrally active as the d- isomer of methamphetamine. Its common side effects include muscle tremors and stomach cramps.

[edit] L-Methamphetamine

Levmetamfetamine Levmetamfetamine (other names: l-desoxyephedrine, l-methamphetamine, levo-methamphetamine) is the l- stereoisomer of methamphetamine, a sympathomimetic vasoconstrictor which may be used in over-the-counter nasal decongestants. The common brand-name for levmetamfetamine in the U.S. is the Vicks Inhaler.

L-methamphetamine alone can raise blood pressure and cause the heart to beat rapidly due to its effects mimicking the sympathetic nervous system, but is not thought to be nearly as addictive or centrally active as the d- isomer of methamphetamine. Its common side effects include muscle tremors and stomach cramps.

[edit] Pharmacology

Methamphetamine is a potent central nervous system stimulant which affects neurochemical mechanisms responsible for regulating heart rate, body temperature, blood pressure, appetite, attention, mood and responses associated with alertness or alarm conditions. The methyl group is responsible for the potentiation of effects as compared to the related compound amphetamine, rendering the substance more lipid soluble and easing transport across the blood brain barrier.

Methamphetamine causes the norepinephrine and dopamine transporters to reverse their direction of flow. This inversion leads to a release of these transmitters from the vesicles to the cytoplasm and from the cytoplasm to the synapse, causing increased stimulation of post-synaptic receptors. Methamphetamine also indirectly prevents the reuptake of these neurotransmitters, causing them to remain in the synaptic cleft for a prolonged period. Serotonin levels are only weakly affected (ratio NE: DA = 2:1, NE:5HT = 60:1).^[19] It is a potent neurotoxin, shown to cause dopaminergic degeneration.^[20][21]

The acute effects of the drug closely resemble the physiological and psychological effects of an epinephrine-provoked fight-or-flight response, including increased heart rate and blood pressure, vasoconstriction (constriction of the arterial walls), bronchodilation, and hyperglycemia (increased blood sugar). Users experience an increase in focus, increased mental alertness, and the elimination of fatigue, as well as a decrease in appetite.

[edit] Tolerance

As with other amphetamines, tolerance to methamphetamine is not completely understood, but known to be sufficiently complex that it cannot be explained by any single mechanism. The extent of tolerance and the rate at which it develops varies widely between individuals, and even within one individual it is highly dependent on dosage, duration of use and frequency of administration. Many cases of narcolepsy are treated with methamphetamine for years without escalating doses or any apparent loss of effect.

Short term tolerance can be caused by depleted levels of neurotransmitters within the vesicles available for release into the synaptic cleft following subsequent reuse (tachyphylaxis). Short term tolerance typically lasts 2-3 days, until neurotransmitter levels are fully replenished. Prolonged overstimulation of dopamine receptors caused by methamphetamine may eventually cause the receptors to downregulate in order to compensate for increased levels of dopamine within the synaptic cleft.^[22] To compensate, larger quantities of the drug are needed in order to achieve the same level of effects.

[edit] Side effects

[edit] Immediate and Chronic Effects

Common immediate side effects:^[23]

• Euphoria
• Increased energy and attentiveness
• Diarrhea, nausea
• Loss of appetite, insomnia, tremor, jaw-clenching (Bruxism)
• Agitation, compulsive fascination with repetitive tasks (Punding)
• Talkativeness, irritability, panic attacks
• Increased libido
• Dilated pupils

Side effects associated with chronic use:

• Drug craving
• Weight loss
• Withdrawal-related depression and anhedonia
• Rapid tooth decay ("meth mouth")
• Amphetamine psychosis

Side effects associated with overdose:

• Brain damage (Neurotoxicity)
• Formication (sensation of flesh crawling with bugs, with possible associated compulsive picking and infecting sores)
• Paranoia, delusions, hallucinations
• Kidney damage (from Hyperkalemia)

Death from overdose is usually due to stroke or heart failure, but can also be caused by hyperthermia or kidney failure.

[edit] Meth Mouth

Main article: Meth mouth

Methamphetamine addicts may lose their teeth abnormally quickly, a condition known as "meth mouth". This effect is not caused by "corrosive" effects that meth itself has on teeth as per commonly repeated myth. According to the American Dental Association, meth mouth "is probably caused by a combination of drug-induced psychological and physiological changes resulting in xerostomia (dry mouth), extended periods of poor oral hygiene, frequent consumption of high calorie, carbonated beverages and tooth grinding and clenching."^[24] Similar, though far less severe symptoms have been reported in clinical use of other amphetamines, where effects are not exacerbated by a lack of oral hygiene for extended periods.^[25] Like other substances which stimulate the sympathetic nervous system, methamphetamine causes decreased production of acid-fighting saliva and increased thirst, resulting in increased risk for tooth decay, especially when thirst is quenched by high-sugar drinks.^[26]

[edit] Routes of administration

The usual route for medical use is oral administration. In recreational use, it can be swallowed, snorted, smoked, dissolved in water and injected (or even without water, in what is called a dry shot), inserted anally (with or without dissolution in water; also known as a booty bump), or into the urethra.^[27] The potential for addiction is greater when it is delivered by methods that cause the concentration in the blood to rise quickly, principally because the effects desired by the user are felt more quickly and with a higher intensity than through a moderated delivery mechanism. Studies have shown that the subjective pleasure of drug use (the reinforcing component of addiction) is proportional to the rate that the blood level of the drug increases.^{[citation needed]} In general, smoking is the fastest mechanism (i.e., it causes the blood concentration to rise the most quickly in the shortest period of time as it allows the substance to travel to the brain through a more direct route than intravenous injection), followed by injecting, anal insertion, insufflation and swallowing.

"Smoking" methamphetamine actually refers to vaporizing it to produce fumes, rather than burning and inhaling the resulting smoke, as with tobacco. It is commonly smoked in glass pipes, or in aluminum foil heated by a flame underneath. This method is also known as "chasing the white dragon" (as derived from the method of smoking heroin known as "chasing the dragon"). There is little evidence that methamphetamine inhalation results in greater toxicity than any other route of administration. Lung damage has been reported with long-term use, but manifests in forms independent of route (pulmonary hypertension and associated complications), or limited to injection users (pulmonary emboli).

[edit] Hydrochloride

Hydrochloride In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines).

For example, reaction of pyridine (C₅H₅N) with hydrochloric acid (HCl) yields pyridine hydrochloride (C₅H₅N·HCl). Even though this style of formulas is often used for denoting the hydrochlorides, the dot incorrectly implies that the two molecules are weakly bonded together. It is the salt C₅H₅NH⁺ Cl^- with correct chemical name pyridinium chloride.

[edit] Uses

Converting otherwise insoluble amines into their hydrochlorides is a common way to make them water and acid-soluble. This is particularly desirable for substances used in medications. Many pharmaceutical substances used are prepared as hydrochlorides so that they may be quickly absorbed in the gastrointestinal tract. The typical breadth of time needed for a hydrochloride to be absorbed thusly is 15-30 minutes.

Examples of hydrochlorides in medical uses are any, ranging from over-the-counter sinus relief to antinausea medication used mainly in the treatment of chemotherapy-induced nausea and vomiting (Zofran, Ondansetron hydrochloride).

v • d • e Stimulants Alkylamines Cyclopentamine • Geranamine • Isometheptene • Octodrine • Propylhexedrine • Tuamine Alphapyrrolidinylalkiophenones α-PPP • MDPPP • MDPV • MPHP • MPPP • MOPPP • Pyrovalerone Cholinergics ABT-089 • ABT-418 • Anabasine • Arecoline • Cotinine • Cytisine • Dianicline • Epibatidine • Epiboxidine • GTS-21 • Ispronicline • Nicotine • Rivanicline • Tebanicline • Varenicline Convulsants Bicuculline • DMCM • Gabazine • Pentetrazol • Picrotoxin • Strychnine • Thujone Eugeroics Adrafinil • Armodafinil • Carphedon • Modafinil Phenethylamines 4-Bromomethcathinone • 4-Fluoroamphetamine • 4-Fluoromethamphetamine • 4-Fluoromethcathinone • 4-Methylmethcathinone • 4-MTA • Aletamine • Amfepentorex • Amphechloral • Amphetamine (Dextroamphetamine, Adderall) • Amphetaminil • Benzphetamine • Bupropion • Cathinone • Chlorphentermine • Clenbuterol • Clobenzorex • Clortermine • Diethylpropion • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone • Ephedrine • Epinephrine • Ethcathinone • Ethylamphetamine • Fenethylline • Fenfluramine • Fenproporex • Fludorex • Furfenorex • Levomethamphetamine • Lisdexamfetamine • MDMA • Mefenorex • Methamphetamine • Methcathinone • Methoxyphedrine • Methylone • Octopamine • Ortetamine • Parahydroxyamphetamine • PCA • PIA • PMA • PMEA • PMMA • PPAP • Phendimetrazine • Phenmetrazine • Phentermine • Phenylephrine • Phenylpropanolamine • Propylamphetamine • Pseudoephedrine • Selegiline • Synephrine • Xylopropamine Phenylaminooxazoles 4-Methyl-aminorex • Aminorex • Clominorex • Fenozolone • Fluminorex • Pemoline • Thozalinone Piperazines 2C-B-BZP • BZP • GBR-12783 • GBR-12935 • GBR-13069 • GBR-13098 • GBR-13119 • MeOPP • MBZP • Vanoxerine Piperidines 2-Benzylpiperidine • Desoxypipradrol • Diphemethoxidine • Ethylphenidate • HDMP-28 • (-)-Methyl-1-methyl-4β-(2-naphthyl)piperidine-3β-carboxylate • Methylphenidate (Dexmethylphenidate) • Nocaine • Phacetoperane • Pipradrol Tropanes 3α-Bis-(4-fluorophenyl)methoxytropane • 3α-((4-Chlorophenyl)phenylmethoxy)tropane • 3-Pseudotropyl-4-fluorobenzoate • Altropane • Brasofensine • CFT (WIN 35,428) • β-CIT (RTI-55) • Cocaethylene • Cocaine • β-CPPIT • Dichloropane (RTI-111) • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • PIT • PTT • RTI-31 • RTI-32 • RTI-51 • RTI-112 • RTI-113 • RTI-121 (IPCIT) • RTI-126 • RTI-150 • RTI-171 • RTI-177 • RTI-336 • Tesofensine • Troparil (β-CPT, WIN 35,065-2) • WF-23 • WF-33 • WF-60 Xanthines Aminophylline • Caffeine • Dimethazan • Paraxanthine • Theobromine • Theophylline Others Amineptine • Bemegride • Benzydamine • BPAP • BTQ • Clofenciclan • Cypenamine • Cyprodenate • Diclofensine • Dimethocaine • Diphenyl prolinol • Ethamivan • Fencamfamine • Feprosidnine • Gilutensin • GYKI-52895 • Hexacyclonate • Indanorex • Indatraline • LR-5182 • Mazindol • Mesocarb • Naphthylisopropylamine • Nikethamide • Nomifensine • Phthalimidopropiophenone • Prolintane • Sibutramine • Yohimbine • Zylofuramine See also Sympathomimetic amines

v • d • e Phenethylamines 2C-B • 2C-C • 2C-D • 2C-E • 2C-I • 2C-N • 2C-T-2 • 2C-T-21 • 2C-T-4 • 2C-T-7 • 2C-T-8 • 3C-E • 4-FMP • Bupropion • Cathine • Cathinone • Clenbuterol • DESOXY • Dextroamphetamine • Methamphetamine • Diethylcathinone • Dimethylcathinone • DOC • DOB • DOI • DOM • bk-MBDB • Dopamine • Br-DFLY • Ephedrine • Epinephrine • Escaline • Etafedrine • Fenfluramine • Levosalbutamol • Levmetamfetamine • MBDB • MDA • MDMA • MDMC • MDEA • MDPV • Mescaline • Methcathinone • Norepinephrine • Phentermine • Salbutamol • Tyramine • Venlafaxine

Template:ChemicalSources

v • d • e The 20 Common Amino Acids ("dp" = data page) Branched-chain amino acids Isoleucine (dp) | Leucine (dp) | Valine (dp) Other Alanine (dp) | Arginine (dp) | Asparagine (dp) | Aspartic acid (dp) | Cysteine (dp) | Glutamic acid (dp) | Glutamine (dp) | Glycine (dp) | Histidine (dp) | Lysine (dp) | Methionine (dp) | Phenylalanine (dp) | Proline (dp) | Serine (dp) | Threonine (dp) | Tryptophan (dp) | Tyrosine (dp) Major families of biochemicals Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides