METHAMPHETAMINE
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Basic Info
| Common Name | METHAMPHETAMINE(F00170) |
| 2D Structure | |
| FRCD ID | F00170 |
| CAS Number | |
| PubChem CID | 10836 |
| Formula | C10H15N |
| IUPAC Name | (2S)-N-methyl-1-phenylpropan-2-amine |
| InChI Key | MYWUZJCMWCOHBA-VIFPVBQESA-N |
| InChI | InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m0/s1 |
| Canonical SMILES | CC(CC1=CC=CC=C1)NC |
| Isomeric SMILES | C[C@@H](CC1=CC=CC=C1)NC |
| Synonyms |
Metamfetamine
Methylamphetamine
METHAMPHETAMINE
d-Deoxyephedrine
d-Desoxyephedrine
d-Methamphetamine
d-N-Methylamphetamine
Metamphetamine
L-Methamphetamine
d-Methylamphetamine
|
| Classifies |
Predicted: Illegal Additives
|
| Update Date | Nov 13, 2018 16:48 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Phenethylamines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Amphetamines and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Amphetamine or derivatives - Phenylpropane - Aralkylamine - Secondary amine - Secondary aliphatic amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Organonitrogen compound - Amine - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 149.237 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 3 |
| Complexity | 95 |
| Monoisotopic Mass | 149.12 |
| Exact Mass | 149.12 |
| XLogP | 2.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9695 |
| Human Intestinal Absorption | HIA+ | 0.9930 |
| Caco-2 Permeability | Caco2+ | 0.8675 |
| P-glycoprotein Substrate | Non-substrate | 0.6682 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9338 |
| Non-inhibitor | 0.9816 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.7360 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.8644 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7898 |
| CYP450 2D6 Substrate | Substrate | 0.8919 |
| CYP450 3A4 Substrate | Non-substrate | 0.7000 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6771 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9570 |
| CYP450 2D6 Inhibitor | Inhibitor | 0.8695 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7754 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9536 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9095 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9443 |
| Non-inhibitor | 0.9118 | |
| AMES Toxicity | Non AMES toxic | 0.9306 |
| Carcinogens | Non-carcinogens | 0.8161 |
| Fish Toxicity | High FHMT | 0.8914 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9569 |
| Honey Bee Toxicity | Low HBT | 0.5191 |
| Biodegradation | Not ready biodegradable | 0.7508 |
| Acute Oral Toxicity | II | 0.7678 |
| Carcinogenicity (Three-class) | Non-required | 0.7799 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.2176 | LogS |
| Caco-2 Permeability | 1.7532 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 3.1862 | LD50, mol/kg |
| Fish Toxicity | 1.0832 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.5067 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Exposure to Far Infrared Ray Protects Methamphetamine-Induced BehavioralSensitization in Glutathione Peroxidase-1 Knockout Mice via AttenuatingMitochondrial Burdens and Dopamine D1 Receptor Activation. | Neurochem Res | 2018 May | 29687308 |
| Protein Kinase Cδ Gene Depletion Protects Against Methamphetamine-InducedImpairments in Recognition Memory and ERK1/2 Signaling via Upregulation ofGlutathione Peroxidase-1 Gene. | Mol Neurobiol | 2018 May | 28597397 |
| Role of Mitochondria in Methamphetamine-Induced Dopaminergic Neurotoxicity:Involvement in Oxidative Stress, Neuroinflammation, and Pro-apoptosis-A Review. | Neurochem Res | 2018 Jan | 28589520 |
| Brain Renin-Angiotensin System Blockade Attenuates Methamphetamine-InducedHyperlocomotion and Neurotoxicity. | Neurotherapeutics | 2018 Apr | 29464572 |
| Methamphetamine Induces Anhedonic-Like Behavior and Impairs Frontal CorticalEnergetics in Mice. | CNS Neurosci Ther | 2017 Feb | 27762079 |
| The behavioral effects of chronic sugar and/or caffeine consumption in adult and adolescent rats. | Behav Neurosci | 2017 Aug | 28714720 |
| Adenosine 2A receptors modulate reward behaviours for methamphetamine. | Addict Biol | 2016 Mar | 25612195 |
| Zerovalent iron and iron(VI): Effective means for the removal of psychoactivepharmaceuticals and illicit drugs from wastewaters. | Sci Total Environ | 2016 Jan 1 | 26376114 |
| Serum Zinc, Copper, Iron, and Magnesium Levels in Iranian Drug Users: A CaseControl Study. | J Addict Med | 2015 Jul-Aug | 26125147 |
| Effects of the trace amine associated receptor 1 agonist RO5263397 onabuse-related behavioral indices of methamphetamine in rats. | Int J Neuropsychopharmacol | 2014 Oct 31 | 25522401 |
| Expression of HIV gp120 protein increases sensitivity to the rewarding propertiesof methamphetamine in mice. | Addict Biol | 2014 Jul | 23252824 |
| Attenuation of reinstatement of methamphetamine-, sucrose-, and food-seekingbehavior in rats by fenobam, a metabotropic glutamate receptor 5 negativeallosteric modulator. | Psychopharmacology (Berl) | 2013 Jan | 22820868 |
| Treatment of methamphetamine abuse: an antibody-based immunotherapy approach. | J Food Drug Anal | 2013 Dec | 26334109 |
| Differential phosphoproteome of the striatum from pleiotrophin knockout andmidkine knockout mice treated with amphetamine: correlations withamphetamine-induced neurotoxicity. | Toxicology | 2013 Apr 5 | 23459167 |
| Antipsychotic-like activity of noni (Morinda citrifolia Linn.) in mice. | BMC Complement Altern Med | 2012 Oct 19 | 23082808 |
| Complex role of zinc in methamphetamine toxicity in vitro. | Neuroscience | 2010 Nov 24 | 20801194 |
| Three paths to better tyrosine kinase inhibition behind the blood-brain barrierin treating chronic myelogenous leukemia and glioblastoma with imatinib. | Transl Oncol | 2010 Feb | 20165690 |
| The novel pyrrolidine nor-lobelane analog UKCP-110[cis-2,5-di-(2-phenethyl)-pyrrolidine hydrochloride] inhibits VMAT2 function,methamphetamine-evoked dopamine release, and methamphetamine self-administration in rats. | J Pharmacol Exp Ther | 2010 Dec | 20805303 |
| Drugs of abuse that mediate advanced glycation end product formation: a chemical link to disease pathology. | Acc Chem Res | 2009 May 19 | 19275211 |
| Evaluation of different RT enzyme standards for quantitation of retrovirusesusing the single-tube fluorescent product-enhanced reverse transcriptase assay. | J Virol Methods | 2009 May | 19186191 |