CAS No.60-15-1 alpha-methylphenethylamine


Name alpha-methylphenethylamine
CAS Registry Number 60-15-1
Synonyms 3-Phenyl-2-propylamine;1-Phenyl-2-propanamine;2-Aminopropylbenzene;3-Phenyl-2-propanamine
Molecular Structure alpha-methylphenethylamine   60-15-1
Molecular Formula C9H13N
Molecular Weight

CAS 60-15-1 Wiki / 60-15-1 MSDS

INN: Amfetamine
An image of the amphetamine compound
A 3d image of the D-amphetamine compound
Clinical data
Pronunciation /æmˈfɛtəmn/
Trade names Adderall, Adzenys XR-ODT, Dyanavel XR, Evekeo, others
AHFS/ amphetamine
License data
  • US FDA: Amphetamine
  • US: C (Risk not ruled out)
Physical: none[1]
Psychological: moderate[2]
Routes of
Medical: oral, intravenous[3]
Recreational: oral, insufflation, rectal, intravenous, intramuscular
Drug class CNS stimulant
ATC code
  • N06BA01 (WHO)
Legal status
Legal status
  • AU: S8 (Controlled)
  • BR: Class A3 (Psychoactive drugs)
  • CA: Schedule I
  • DE: Anlage III (Special prescription form required)
  • NZ: Class B
  • UK: Class B
  • US: Schedule II
  • UN: Psychotropic Schedule II
Pharmacokinetic data
Bioavailability Oral 75–100%[9]
Protein binding 15–40%[10]
Metabolism CYP2D6,[4] DBH,[5][6] FMO3[5][7][8]
Metabolites 4-hydroxyamphetamine, 4-hydroxynorephedrine, 4-hydroxyphenylacetone, benzoic acid, hippuric acid, norephedrine, phenylacetone[4][11][12]
Onset of action IR dosing: 30–60 minutes[13]
XR dosing: 1.5–2 hours[14][15]
Biological half-life D-amph: 9–11 hours[4][16]
L-amph: 11–14 hours[4][16]
pH-dependent: 8–31 hours[17]
Duration of action IR dosing: 3–6 hours[2][14][18]
XR dosing: 8–12 hours[2][14][18]
Excretion Primarily renal;
pH-dependent range: 1–75%[4]
Synonyms α-methylphenethylamine
CAS Number
  • 300-62-9 YesY
PubChem CID
  • 3007
  • 4804
  • DB00182 YesY
  • 13852819 YesY
  • CK833KGX7E
  • D07445 YesY
  • CHEBI:2679 YesY
  • CHEMBL405 YesY
  • 018564
PDB ligand
ECHA InfoCard 100.005.543
Chemical and physical data
Formula C9H13N
Molar mass 135.20622 g/mol[19]
3D model (JSmol)
  • Interactive image
Chirality Racemic mixture[20]
Density .936 g/cm3 at 25 °C[21]
Melting point 11.3 °C (52.3 °F) (predicted)[22]
Boiling point 203 °C (397 °F) at 760 mmHg[23]

Amphetamine[note 1] (contracted from alpha‑methylphenethylamine) is a potent central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered in 1887 and exists as two enantiomers:[note 2] levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers, levoamphetamine and dextroamphetamine, in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.[sources 1]

The first amphetamine pharmaceutical was Benzedrine, a brand which was used to treat a variety of conditions. Currently, pharmaceutical amphetamine is prescribed as racemic amphetamine, Adderall,[note 3] dextroamphetamine, or the inactive prodrug lisdexamfetamine. Amphetamine, through activation of a trace amine receptor, increases monoamine and excitatory neurotransmitter activity in the brain, with its most pronounced effects targeting the catecholamine neurotransmitters norepinephrine and dopamine.[sources 2]

At therapeutic doses, amphetamine causes emotional and cognitive effects such as euphoria, change in desire for sex, increased wakefulness, and improved cognitive control. It induces physical effects such as decreased reaction time, fatigue resistance, and increased muscle strength. Larger doses of amphetamine may impair cognitive function and induce rapid muscle breakdown. Drug addiction is a serious risk with large recreational doses but is unlikely to arise from typical long-term medical use at therapeutic doses. Very high doses can result in psychosis (e.g., delusions and paranoia) which rarely occurs at therapeutic doses even during long-term use. Recreational doses are generally much larger than prescribed therapeutic doses and carry a far greater risk of serious side effects.[sources 3]

Amphetamine belongs to the phenethylamine class. It is also the parent compound of its own structural class, the substituted amphetamines,[note 4] which includes prominent substances such as bupropion, cathinone, MDMA, and methamphetamine. As a member of the phenethylamine class, amphetamine is also chemically related to the naturally occurring trace amine neuromodulators, specifically phenethylamine and N-methylphenethylamine, both of which are produced within the human body. Phenethylamine is the parent compound of amphetamine, while N-methylphenethylamine is a positional isomer of amphetamine that differs only in the placement of the methyl group.[sources 4]