Amphetamine (CHEM002138)
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| Version | 1.0 | ||||||||
| Creation Date | 2009-07-21 20:26:14 UTC | ||||||||
| Update Date | 2026-05-14 16:24:31 UTC | ||||||||
| Accession Number | CHEM002138 | ||||||||
| Identification | |||||||||
| Common Name | Amphetamine | ||||||||
| Class | Small Molecule | ||||||||
| Description | 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. | ||||||||
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| Chemical Structure |  | ||||||||
| Synonyms | Not Available | ||||||||
| Chemical Formula | C9H13N | ||||||||
| Average Molecular Mass | 135.206 g/mol | ||||||||
| Monoisotopic Mass | 135.105 g/mol | ||||||||
| CAS Registry Number | 300-62-9 | ||||||||
| IUPAC Name | 1-phenylpropan-2-amine | ||||||||
| Traditional Name | Not Available | ||||||||
| SMILES | CC(N)CC1=CC=CC=C1 | ||||||||
| InChI Identifier | InChI=1/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3 | ||||||||
| InChI Key | InChIKey=KWTSXDURSIMDCE-UHFFFAOYNA-N | ||||||||
| Chemical Taxonomy | |||||||||
| Classification | Not classified | ||||||||
| Biological Properties | |||||||||
| Status | Detected and Not Quantified | ||||||||
| Origin | Exogenous | ||||||||
| Cellular Locations |
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| Biofluid Locations | Not Available | ||||||||
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| Pathways | Not Available | ||||||||
| Applications | |||||||||
| Biological Roles | |||||||||
| Chemical Roles | Not Available | ||||||||
| Physical Properties | |||||||||
| State | Solid | ||||||||
| Appearance | White powder. | ||||||||
| Experimental Properties |
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| Predicted Properties | Not Available | ||||||||
| Spectra | |||||||||
| Spectra |
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| Toxicity Profile | |||||||||
| Route of Exposure | Oral. Amphetamine forms easily absorbed molecules that are highly lipid soluble. | ||||||||
| Mechanism of Toxicity | Amphetamines stimulate the release of norepinephrine from central adrenergic receptors. At higher dosages, they cause release of dopamine from the mesocorticolimbic system and the nigrostriatal dopamine systems. Amphetamine may also act as a direct agonist on central 5-HT receptors and may inhibit monoamine oxidase (MAO). In the periphery, amphetamines are believed to cause the release of noradrenaline by acting on the adrenergic nerve terminals and alpha- and beta-receptors. Modulation of serotonergic pathways may contribute to the calming affect. The drug interacts with VMAT enzymes to enhance release of DA and 5-HT from vesicles. It may also directly cause the reversal of DAT and SERT. | ||||||||
| Metabolism | Hepatic Half Life: 10 hours | ||||||||
| Toxicity Values | LD50: 180 mg/kg (Subcutaneous, Rat) (1) | ||||||||
| Lethal Dose | Not Available | ||||||||
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). | ||||||||
| Uses/Sources | For treatment of Attention Deficit Disorder with Hyperactivity (ADDH) and narcolepsy in children. | ||||||||
| Minimum Risk Level | Not Available | ||||||||
| Health Effects | Prolonged use may cause hallucinations and intense paranoia. Amphetamines are psychologically addictive. Users who stop using them report that they experience various mood problems such as aggression and anxiety and intense cravings for the drugs. Using large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion. | ||||||||
| Symptoms | The most common presenting symptoms seen are agitation, hallucinations, suicidal behaviour, and chest pain. | ||||||||
| Treatment | Management of acute amphetamine intoxication is largely symptomatic and includes gastric lavage, administration of activated charcoal, administration of a cathartic and sedation. (8) | ||||||||
| Concentrations | |||||||||
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| External Links | |||||||||
| Identifiers | Not Available | ||||||||
| References | |||||||||
| Synthesis Reference | Guohong Wang, “Composition and methods for synthesis of novel tracers for detecting amphetamine and methamphetamine in samples.” U.S. Patent US20020090661, issued July 11, 2002. | ||||||||
| MSDS | Not Available | ||||||||
| General References | Not Available | ||||||||
