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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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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 3
Topological polar surface area 12.03
Molecular weight 149.12
XLogP 2.15
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 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
InChI Key MYWUZJCMWCOHBA-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. US FDA (1943)
IUPAC Name Click here for help
N-methyl-1-phenylpropan-2-amine
International Nonproprietary Names Click here for help
INN number INN
1879 metamfetamine
Synonyms Click here for help
deoxyephedrine | Desoxyn® | DL-methamphetamine | methamphetamine hydrochloride
Database Links Click here for help
GtoPdb PubChem SID 178101505
PubChem CID 1206
Search Google for chemical match using the InChIKey MYWUZJCMWCOHBA-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MYWUZJCMWCOHBA
Search PubMed clinical trials metamfetamine
Search PubMed titles metamfetamine
Search PubMed titles/abstracts metamfetamine
UniChem Compound Search for chemical match using the InChIKey MYWUZJCMWCOHBA-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MYWUZJCMWCOHBA-UHFFFAOYSA-N
Wikipedia Methamphetamine