amphetamine   Click here for help

GtoPdb Ligand ID: 4804

Synonyms: (±)-amphetamine | Amphetamine Sulfate® | DL-amphetamine
Approved drug
amphetamine is an approved drug (FDA (no history prior to 1976))
Compound class: Synthetic organic
Comment: Amphetamine is a central nervous system stimulant and an appetite suppressant.
Amphetamine can activate carbonic anhydrases, and is most potent at the CA5A and CA7 isoforms (KA values 810 and 910 nM respectively) [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 26.02
Molecular weight 135.1
XLogP 1.76
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(Cc1ccccc1)N
Isomeric SMILES CC(Cc1ccccc1)N
InChI InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
InChI Key KWTSXDURSIMDCE-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (no history prior to 1976))
IUPAC Name Click here for help
1-phenylpropan-2-amine
International Nonproprietary Names Click here for help
INN number INN
377 amfetamine
Synonyms Click here for help
(±)-amphetamine | Amphetamine Sulfate® | DL-amphetamine
Database Links Click here for help
CAS Registry No. 300-62-9 (source: Scifinder)
ChEMBL Ligand CHEMBL405
DrugBank Ligand DB00182
DrugCentral Ligand 195
GtoPdb PubChem SID 178101506
PubChem CID 3007
Search Google for chemical match using the InChIKey KWTSXDURSIMDCE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone KWTSXDURSIMDCE
Search PubMed clinical trials amfetamine
Search PubMed titles amfetamine
Search PubMed titles/abstracts amfetamine
UniChem Compound Search for chemical match using the InChIKey KWTSXDURSIMDCE-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey KWTSXDURSIMDCE-UHFFFAOYSA-N
Wikipedia Amphetamine