methamphetamine   Click here for help

GtoPdb Ligand ID: 4803

Synonyms: deoxyephedrine | Desoxyn® | DL-methamphetamine | methamphetamine hydrochloride
Approved drug
methamphetamine is an approved drug (FDA (1943))
Compound class: Synthetic organic
Comment: Methamphetamine refers to the racemic free base mixture of the dextromethamphetamine (PubChem CID 10836) and levomethamphetamine (PubChem CID 36604) stereo-isomers. We show the structure without specified stereochemistry to represent the mixture. Methamphetamine use as a sympathomimetic has been largely replaced by safer substitutes with comparable clinical efficacy, but reduced propensity for serious side-effects and illicit recreational use. The production, distribution, sale, and possession of methamphetamine is restricted or illegal in many jurisdictions.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 12.03
Molecular weight 149.12
XLogP 2.15
No. Lipinski's rules broken 0
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Canonical SMILES CNC(Cc1ccccc1)C
Isomeric SMILES CNC(Cc1ccccc1)C
InChI InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of ADHD and exogenous obesity.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
After entering the brain, methamphetamine causes a cascading release of noradrenaline, dopamine and serotonin. Also acts as a monoamine oxidase inhibitor and a dopaminergic and adrenergic reuptake inhibitor.