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Encyclopedia > Dextromethamphetamine
Dextromethamphetamine
Systematic (IUPAC) name
N-methyl-1-phenyl-propan-2-amine
Identifiers
CAS number 537-46-2
ATC code N06BA03
PubChem 1206
Chemical data
Formula C10H15N 
Mol. mass 149.233 g/mol
SMILES search in eMolecules, PubChem
Synonyms dextromethylamphetamine
Pharmacokinetic data
Bioavailability  ?
Metabolism Hepatic
Half life 9-15 hours[1]
Excretion Renal
Therapeutic considerations
Pregnancy cat.

C(US) Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Atomic mass 12. ... This article is about the chemistry of hydrogen. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Atomic mass 14. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Look up Synonym in Wiktionary, the free dictionary. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The liver is an organ in vertebrates including humans. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Legal status

Schedule I(CA) Schedule II(US) Class A(NZ)
Schedule 5(SA)
Injectable:Class A, Oral: A(UK) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Controlled Drugs and Substances Act is Canadas federal drug control statute. ... Motto: (Latin for From Sea to Sea) Anthem: O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  - Monarch Queen Elizabeth II  - Governor General Michaëlle Jean  - Prime Minister Stephen Harper Establishment    - British North America Act... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from... This article is about the country on the southern tip of the African continent. ...

Routes Oral

Dextromethamphetamine (dextro-N-α-dimethyl-phenethylamine is an N-methylated analog of dextroamphetamine. It is a psychostimulant drug acting as a dopamine and adrenergic reuptake inhibitor and as a sympathomimetic that, after rapidly entering the brain, triggers a cascading release of dopamine, norepinephrine and to a lesser extent, serotonin. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Dextrorotation is the property of rotating plane polarized light clockwise. ... Methylation is a term used in the chemical sciences to denote the attachment or substitution of a methyl group on various substrates. ... The Alpha carbon refers to the first carbon after the carbon that attaches to the functional group. ... In chemistry a methyl-group is a hydrophobic Alkyl functional group which is derived from methane (CH4). ... Phenethylamine, or β-Phenylethylamine, is an alkaloid and monoamine. ... An analog is in chemistry a chemical closely related to another usually sharing the same nucleus. ... Dextroamphetamine (also known as dextroamphetamine sulfate, dexamphetamine sulphate, d-amphetamine, dexamphetamine, Dexedrine, Dextrostat, Dexampex, Ferndex, Oxydess II, Robese, Spancap #1, and, informally, Dex), a stereoisomer of amphetamine, is a potent central nervous system stimulant that induces the release of the neurotransmitters dopamine and norepinephrine into nerve synapses in certain areas... Stimulants are drugs that increase alertness and wakefulness. ... A psychoactive drug or psychotropic substance is a chemical substance that acts primarily upon the central nervous system where it alters brain function, resulting in temporary changes in perception, mood, consciousness and behavior. ... This does not cite its references or sources. ... The adrenergic receptors (or adrenoceptors) are a class of G-protein coupled receptors that is the target of catecholamines. ... Reuptake is the reabsorption of a neurotransmitter by the molecular transporter of a pre-synaptic neuron after it has performed its function of transmitting a neural impulse. ... Sympathomimetic drugs are substances that mimic the effects of the hormones adrenaline and noradrenaline. ... For more specific information about the human brain, see its main article at human brain A sketch of the human brain by artist Priyan Weerappuli, imposed upon his sketch of the profile of Michaelangelos David In animals, the brain, or encephalon (Greek for in the head), is the control... Technical advancements in recent years have allowed progress toward the understanding of the brain and how drugs can be made to affect it. ... This article or section is in need of attention from an expert on the subject. ... Norepinephrine (INN) or noradrenaline (BAN) is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ... Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract. ...


Other common names for dextromethamphetamine include d-methamphetamine, dexmethamphetamine, (S)-(+)-methamphetamine. Dextromethamphetamine is prescribed for narcolepsy, attention-deficit hyperactivity disorder, and extreme obesity under the brand name Desoxyn, manufactured by Ovation Pharma. Narcolepsy is a neurological condition most characterized by Excessive Daytime Sleepiness (EDS) you will most likely experience insomnia, episodes of sleep and disorder of REM or rapid eye movement sleep. ... Attention-Deficit/Hyperactivity Disorder (ADHD) (sometimes referred to as ADD for those without hyperactivity) is thought to be a neurological disorder, always present from childhood, which manifests itself with symptoms such as hyperactivity, forgetfulness, poor impulse control, and distractibility. ... Bulk pharmaceutical bottle of Desoxyn Desoxyn® CII is a brand pharmaceutical form of dextromethamphetamine hydrochloride (also known as desoxyephedrine, hence the name Desoxyn), indicated for treatment of Attention Deficit Disorder/Attention Deficit/Hyperactivity Disorder (ADD/ADHD), narcolepsy, and exogenous obesity. ... Ovation Pharma is a manufacturer of pharmaceuticals products including Desoxyn. ...

Contents

Pharmacology

Dextromethamphetamine 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 dextroamphetamine, rendering the substance more lipid soluble and easing transport across the blood brain barrier. A diagram showing the CNS: 1. ... Stimulants are drugs that increase alertness and wakefulness. ... Dextroamphetamine (also known as dextroamphetamine sulfate, dexamphetamine sulphate, d-amphetamine, dexamphetamine, Dexedrine, Dextrostat, Dexampex, Ferndex, Oxydess II, Robese, Spancap #1, and, informally, Dex), a stereoisomer of amphetamine, is a potent central nervous system stimulant that induces the release of the neurotransmitters dopamine and norepinephrine into nerve synapses in certain areas...


Dextromethamphetamine causes the dopamine and norepinephrine 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. Dextromethamphetamine 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).[2] At high doses it is a potent neurotoxin, shown to cause dopaminergic degeneration.[3][4] This article or section is in need of attention from an expert on the subject. ... Norepinephrine (INN) or noradrenaline (BAN) is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ... Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract. ... Norepinephrine (INN) or noradrenaline (BAN) is a catecholamine and a phenethylamine with chemical formula C8H11NO3. ... This article or section is in need of attention from an expert on the subject. ... Serotonin (5-hydroxytryptamine, or 5-HT) is a monoamine neurotransmitter synthesized in serotonergic neurons in the central nervous system (CNS) and enterochromaffin cells in the gastrointestinal tract. ...


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. Adrenaline redirects here. ... The fight-or-flight response, also called the acute stress response, was first described by Walter Cannon in 1929. ... A bronchodilator is a medication intended to improve bronchial airflow. ... Hyperglycemia or High Blood Sugar is a condition in which an excessive amount of glucose circulates in the blood plasma. ...


Tolerance

As with other amphetamines, tolerance to dextromethamphetamine 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 dextromethamphetamine for years without escalating doses or any apparent loss of effect. Narcolepsy is a neurological condition most characterized by Excessive Daytime Sleepiness (EDS) you will most likely experience insomnia, episodes of sleep and disorder of REM or rapid eye movement sleep. ...


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 dextromethamphetamine may eventually cause the receptors to downregulate in order to compensate for increased levels of dopamine within the synaptic cleft.[5] Tachyphylaxis is a medical term describing a rapidly decreasing response to a drug following administration of the initial doses. ... Downregulation is the process by which a cell decreases the number of receptors to a given hormone or neurotransmitter to reduce its sensitivity to this molecule. ...


Legality

South Africa

In South Africa, dextromethamphetamine is classified as a Schedule 5 drug, and is listed as Undesirable Dependence-Producing Substances in Part III of Schedule 2 of the Drugs and Drug Trafficking Act, 1992 (Act No 140 of 1992).[6]


United States

Dextromethamphetamine is classified as a Schedule II substance by the Drug Enforcement Administration under the Convention on Psychotropic Substances.[7] The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Since 1973, the DEA has enforced the drug laws in the United States. ... Opened for signature February 21, 1971 in Vienna Entered into force August 16, 1976 Conditions for entry into force 40 ratifications Parties 175 The Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics. ...


Footnotes

  1. ^ Methamphetamine and amphetamine pharmacokinetics in oral fluid and plasma after controlled oral methamphetamine administration to human volunteers.
  2. ^ R.B. Rothman, M.H. Baumann (2002): Pharmacology and Therapeutics 95, 73-85 (page 76)
  3. ^ Itzhak Y, Martin J, Ali S (2002). "Methamphetamine-induced dopaminergic neurotoxicity in mice: long-lasting sensitization to the locomotor stimulation and desensitization to the rewarding effects of methamphetamine.". Prog Neuropsychopharmacol Biol Psychiatry 26 (6): 1177-83. PMID 12452543. 
  4. ^ C. Davidson, A. J. Gow, T. H. Lee, E. H. Ellinwood (2001). "Methamphetamine neurotoxicity: necrotic and apoptotic mechanisms and relevance to human abuse and treatment". Brain Research Reviews 36 (1): 1-22. DOI:10.1016/S0165-0173(01)00054-6. 
  5. ^ Bennett B, Hollingsworth C, Martin R, Harp J (1998). "Methamphetamine-induced alterations in dopamine transporter function.". Brain Res 782 (1-2): 219-27. PMID 9519266. 
  6. ^ http://www.saps.gov.za/drugs/ats.htm
  7. ^ http://www.incb.org/pdf/e/list/green.pdf
Amphetamines (N06BA) - edit

{01-Amphetamine/dl-Amphetamine} {02-Dextroamphetamine} {03-Dextromethamphetamine} Amphetamine is a synthetic drug originally developed (and still used) as an appetite suppressant. ... A section of the Anatomical Therapeutic Chemical Classification System. ... Amphetamine (alpha-methyl-phenethylamine), is a stimulant that is now primarily used to treat narcolepsy and attention-deficit hyperactivity disorder. ... Benzedrine is the trade name of the racemic variant of amphetamine (dl-amphetamine). ... Dextroamphetamine (also known as dextroamphetamine sulfate, dexamphetamine sulphate, d-amphetamine, dexamphetamine, Dexedrine, Dextrostat, Dexampex, Ferndex, Oxydess II, Robese, Spancap #1, and, informally, Dex), a stereoisomer of amphetamine, is a potent central nervous system stimulant that induces the release of the neurotransmitters dopamine and norepinephrine into nerve synapses in certain areas...


no ATC code: {4-FMP} {4-MTA} {Benzphetamine} {MDMA} {MDA} {MDEA} {Paramethoxyamphetamine} The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... 4-FMP molecular structure 4-FMP 4-FMP, also known by its full chemical name 4-fluoroamphetamine, or 4-Fluoro-alpha-Methyl-Phenethylamine, is a central nervous system stimulant. ... 4MT structure 4-methylthioamphetamine is a drug known as 4MT, 4-MTA, Flatliners, 1-(4-methylthiophenyl)-2-aminopropane. ... USA by Pharmacia. ... MDMA (3,4-methylenedioxymethamphetamine), most commonly known by the street names ecstasy or XTC (for more names see the full list), is a synthetic entactogen of the phenethylamine family, whose primary effect is believed to be the stimulation of secretion as well as inhibition of re-uptake of large amounts... 3,4-Methylenedioxyamphetamine, or MDA, is a psychedelic hallucinogenic drug and empathogen/entactogen of the phenethylamine family. ... MDEA MDEA can also be Methyl Diethanol Amine, a chemical compound used in gas treating MDEA (also MDE), which stands for 3,4-methylenedioxy-N-ethylamphetamine, is a psychedelic hallucinogenic drug and Empathogen-Entactogen of the phenethylamine family. ... PMA (p-methoxyamphetamine) is a dangerous synthetic drug, psycho stimulant and hallucinogen. ...



 
 

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