AmphetamineBall-and-stick models of amphetamine enantiomersClinical dataPronunciationTrade namesEvekeo, Adderall, othersOther namesα-methylphenethylamine, β-phenylisopropylamine, thyramineAHFS/Drugs.comMonographMedlinePlusa616004License dataUSDailyMed: AmphetamineDependenceliabilityPhysical: NonePsychological: ModerateAddictionliabilityModerateRoutes ofadministrationMedical: OralRecreational: Oral, insufflation, rectal, intramuscular, intravenousDrug classStimulant; anorectic; norepinephrine-dopamine releasing agentATC codeN06BA01 (WHO) N06BA02 (WHO) N06BA12 (WHO)Physiological dataReceptorsTAAR1, VMAT2, 5HT1AMetabolismCYP2D6, DBH, FMO3Legal statusLegal statusAU:S8 (Controlled drug)BR:Class A3 (Psychoactive drugs)CA: Schedule IDE: Anlage III (Special prescription form required)NZ: Class BUK:Class BUS:Schedule IIUN:Psychotropic Schedule IISE: Förteckning II (in some forms, like Dextroamphetamine and Lisdexamfetamine)Pharmacokinetic dataBioavailabilityOral: ~90%Protein binding16-20%MetabolismCYP2D6, DBH, FMO3Metabolites4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, N-hydroxyamphetamine, benzoic acid, hippuric acid, norephedrine, phenylacetoneOnset of actionIR dosing: 30-45 minutesXR dosing: 1.5–2 hoursElimination half-lifeD-amph: 9–11 hoursL-amph: 11–14 hourspH-dependent: 7–34 hoursDuration of actionIR dosing: 3–6 hoursXR dosing: 8–12 hoursExcretionPrimarily renal;pH-dependent range: 1–75%IdentifiersIUPAC name(RS)-1-phenylpropan-2-amineCAS Number300-62-9PubChemCID3007IUPHAR/BPS4804DrugBankDB00182ChemSpider13852819UNIICK833KGX7EKEGGD07445ChEBICHEBI:2679ChEMBLChEMBL405NIAID ChemDB018564CompTox Dashboard(EPA)DTXSID4022600ECHA InfoCard100.005.543Chemical and physical dataFormulaC9H13NMolar mass135.210 g·mol3D model (JSmol)Interactive imageChiralityRacemic mixtureDensity.936 g/cm at 25 °CMelting point11.3 °C (52.3 °F) Boiling point203 °C (397 °F) at 760 mmHgSMILESNC(C)Cc1ccccc1InChIInChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3Key:KWTSXDURSIMDCE-UHFFFAOYSA-N(verify)Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD) and narcolepsy; it is also used to treat binge eating disorder in the form of lisdexamfetamine.
MethamphetamineCentral nervous system stimulantPharmaceutical compoundBall-and-stick models of methamphetamine enantiomersClinical dataPronunciation(), (), () Trade namesDesoxyn, othersOther namesN-methylamphetamine, N,α-dimethylphenethylamine, desoxyephedrineAHFS/Drugs.comMonographPregnancycategoryAU: X (High risk)The system is developed for medicine that can be prescribed, but the equivalent is category X.DependenceliabilityPhysical: NonePsychological: Very highAddictionliabilityVery highRoutes ofadministrationBy mouth, intravenous, intramuscular, subcutaneous, inhalation, insufflation, rectal, vaginalDrug classStimulant;Serotonin–norepinephrine–dopamine releasing agentATC codeN06BA03 (WHO) Legal statusLegal statusAU: S8 (Controlled drug)BR: Class F2 (Prohibited psychotropics)CA: Schedule IDE: Anlage II (Authorized trade only, not prescriptible)NZ: Class AUK: Class AUS: Schedule IIUN: Psychotropic Schedule IIEU: Rx-onlySE: Förteckning IPharmacokinetic dataBioavailabilityOral: 67%Intranasal: 79%Inhalation: 67–90%Intravenous: 100%Protein bindingVaries widelyMetabolismCYP2D6 and FMO3Metabolites• Amphetamine • Pholedrine • N-Hydroxymethamphetamine • NorephedrineOnset of actionOral: 3 hours (peak)Intranasal: <15 minutesInhalation: <18 minutesIntravenous: <15 minutesElimination half-life9–12 hours (range 5–30 hours); irrespective of routeDuration of action8–12 hoursExcretionPrimarily kidneyIdentifiersIUPAC name(RS)-N-methyl-1-phenylpropan-2-amineCAS Number537-46-2(dl)-Methamphetamine hydrochloride: 300-42-5PubChemCID1206IUPHAR/BPS4803DrugBankDB01577ChemSpider1169UNII44RAL3456C(dl)-Methamphetamine hydrochloride: 24GNZ56D62KEGGD08187ChEBICHEBI:6809ChEMBLChEMBL1201201PDB ligandB40 (PDBe, RCSB PDB)CompTox Dashboard(EPA)DTXSID3043861ECHA InfoCard100.028.690 100.023.121, 100.028.690Chemical and physical dataFormulaC10H15NMolar mass149.237 g·mol3D model (JSmol)Interactive imageChiralityRacemic mixtureMelting point170 °C (338 °F) Boiling point212 °C (414 °F) at 760 mmHgSMILESCNC(C)Cc1ccccc1InChIInChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3Key:MYWUZJCMWCOHBA-UHFFFAOYSA-N (verify)Methamphetamine is a central nervous system (CNS) stimulant that is primarily used as a recreational or performance-enhancing drug and less commonly as a second-line treatment for attention deficit hyperactivity disorder (ADHD).
StimulantStimulants (also called a central nervous system stimulant, psychostimulant, or colloquially an upper) are a class of psychoactive drugs that increase alertness. They are used for various purposes, such as enhancing attention, motivation, cognition, mood, and physical activity. Some stimulants occur in nature while others are synthetic. Common stimulants include caffeine, nicotine, cocaine, amphetamine, methamphetamine, methylphenidate, and modafinil.
EntactogenClass of psychoactive drugs that produce empathic experiencesEntactogens, also known as empathogens or connectogens, are a class of psychoactive drugs that induce experiences of emotional communion, oneness, connectedness, emotional openness—that is, empathy—as particularly observed and reported for experiences with MDMA (ecstasy).
Derivative (chemistry)In chemistry, a derivative is a compound that is from a similar compound by a chemical reaction, or that can be imagined to arise from another compound, if one atom or group of atoms is replaced with another atom or group of atoms. The exact definition of "derivative" depends on the specific context. The related term structural analogue is common in organic chemistry.
CathinoneChemical compoundPharmaceutical compoundCathinone (; also known as β-ketoamphetamine) is a monoaminealkaloid found in the shrubCatha edulis (khat) and is chemically similar to ephedrine, cathine, methcathinone and other amphetamines. It is probably the main contributor to the stimulant effect of khat. Cathinone differs from many other amphetamines in that it has a ketonefunctional group.
EphedrineEphedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin.SubstituentIn organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. The suffix -yl is used when naming organic compounds that contain a single bond replacing one hydrogen; -ylidene and -ylidyne are used with double bonds and triple bonds, respectively.
Hydrogen atomA hydrogen atom is an atom of the chemical elementhydrogen. The electrically neutral hydrogen atom contains a single positively charged proton in the nucleus, and a single negatively charged electron bound to the nucleus by the Coulomb force. Atomic hydrogen constitutes about 74% of the baryonic mass of the universe. In everyday life on Earth, isolated hydrogen atoms (called "atomic hydrogen") are extremely rare.
Chemical compoundA chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element is therefore not a compound. A compound can be transformed into a different substance by a chemical reaction, which may involve interactions with other substances.
Substitution reactionA substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a compound is replaced by another functional group. Substitution reactions are of prime importance in organic chemistry.
HallucinogenClass of drugsHallucinogens, also known as psychedelics, entheogens, or historically as psychotomimetics, are a broad and diverse class of psychoactive drugs that can induce altered states of consciousness characterized by marked changes in perception, mood, cognition, and self-experience, along with a range of other psychological alterations.*As an Amazon Associate I earn from qualifying purchases.