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537-46-2 molecular structure
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methyl[(2S)-1-phenylpropan-2-yl]amine

ChemBase ID: 1357
Molecular Formular: C10H15N
Molecular Mass: 149.2328
Monoisotopic Mass: 149.12044949
SMILES and InChIs

SMILES:
N([C@H](Cc1ccccc1)C)C
Canonical SMILES:
CN[C@H](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/t9-/m0/s1
InChIKey:
MYWUZJCMWCOHBA-VIFPVBQESA-N

Cite this record

CBID:1357 http://www.chembase.cn/molecule-1357.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
methyl[(2S)-1-phenylpropan-2-yl]amine
IUPAC Traditional name
methamphetamine
Brand Name
Desoxyn
Desyphed
Desyphed hydrochloride
Metamfetamine
Metamfetamine-m
Norodin
Speed
Stimulex
Synonyms
(+ )-methylamphetamine
(+)-(s)-deoxyephedrine
(+)-(s)-n-alpha-dimethylphenethylamine
(+)-2-(N-Methylamino)-1-phenylpropane
(+)-methamphetamine
(+)-methylamphetamine
(+)-n,alpha-dimethyl-beta-phenylethylamine
(+)-n,alpha-dimethylphenethylamine
(+)-n-methylamphetamine
(2S)-N-methyl-1-phenylpropan-2-amine
(s)-(+)-deoxyephedrine
(s)-(+)-methamphetamine
(s)-(+)-n,alpha,dimethylphenethylamine
(s)-methamphetamine
(s)-methylamphetamine
(s)-n,alpha-dimethylbenzeneethanamine
(s)-n,alpha-dimethylbenzeneethanoamine
1-Phenyl-2-methylamino-propan [German]
1-Phenyl-2-methylaminopropane
2S-(+)-Methamphetamine
D-(s)-methamphetamine
D-1-Phenyl-2-methylaminopropane
d-1-Phenyl-2-methylaminopropan [German]
D-deoxyephedrine
D-methylamphetamine
D-methamphetamine
D-desoxyephedrine
D-n,alpha-dimethylphenethylamine
D-n-methylamphetamine
D-phenylisopropylmethylamine
Desoxyephedrine hydrochloride
L-methamphetamine
Metamfetamina [inn-spanish]
Metamfetaminum [inn-latin]
Metamphetamine
Metanfetamina [inn-spanish]
Methamphetaminum [inn-latin]
Methyl-beta-phenylisopropylamine
Methylamphetamine
N-Methyl-1-phenyl-2-propanamine
N-methyl-beta-phenylisopropylamin [german]
N-methyl-beta-phenylisopropylamine
N-methylamphetamine
S-(+)-methamphetamine
Ice
Meth
Methamphetamine
CAS Number
537-46-2
PubChem SID
160964817
46508541
PubChem CID
10836

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB01577 external link
PubChem 10836 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -0.9906569  LogD (pH = 7.4) -0.43709657 
Log P 2.236831  Molar Refractivity 48.4798 cm3
Polarizability 19.21153 Å3 Polar Surface Area 12.03 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.23  LOG S -2.21 
Solubility (Water) 9.28e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
2.07 [HANSCH,C ET AL. (1995)] expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01577 external link
Item Information
Drug Groups illicit; approved
Description Methamphetamine is a psychostimulant and sympathomimetic drug. It is a member of the amphetamine group of sympathomimetic amines. Methamphetamine can induce effects such as euphoria, increased alertness and energy, and enhanced self-esteem. It is a scheduled drug in most countries due to its high potential for addiction and abuse.
Indication For the treatment of Attention Deficit Disorder with Hyperactivity (ADHD) and exogenous obesity.
Pharmacology Methamphetamine is a potent central nervous system stimulant which affects neurochemical mechanisms responsible for regulating heart rate, body temperature, blood pressure, appetite, attention, mood and responses associated with alertness or alarm conditions. The acute effects of the drug closely resemble the physiological and psychological effects of an epinephrine-provoked fight-or-flight response, including increased heart rate and blood pressure, vasoconstriction (constriction of the arterial walls), bronchodilation, and hyperglycemia (increased blood sugar). Users experience an increase in focus, increased mental alertness, and the elimination of fatigue, as well as a decrease in appetite.
Toxicity Manifestations of acute overdosage with methamphetamine include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, panic states, hyperpyrexia, and rhabdomyolysis. Fatigue and depression usually follow the central stimulation. Cardiovascular effects include arrhythmias, hypertension or hypotension, and circulatory collapse. Gastrointestinal symptoms include nausea, vomiting, diarrhea, and abdominal cramps. Fatal poisoning usually terminates in convulsions and coma.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. The primary site of metabolism is in the liver by aromatic hydroxylation, N-dealkylation and deamination. At least seven metabolites have been identified in the urine, with the main metabolites being amphetamine (active) and 4-hydroxymethamphetamine. Other minor metabolites include 4-hydroxyamphetamine, norephedrine, and 4-hydroxynorephedrine.
Absorption Methamphetamine is rapidly absorbed from the gastrointestinal tract with peak methamphetamine concentrations occurring in 3.13 to 6.3 hours post ingestion. Methamphetamine is also well absorbed following inhalation and following intranasal administration. It is distributed to most parts of the body. Because methamphetamine has a high lipophilicity it is distributed across the blood brain barrier and crosses the placenta.
Half Life The biological half-life has been reported in the range of 4 to 5 hours.
Elimination Excretion occurs primarily in the urine, the rate of which is dependent on urine pH. Between 30-54% of an oral dose is excreted in urine as unchanged methamphetamine and 10-23% as unchanged amphetamine. Following an intravenous dose, 45% is excreted as unchanged parent drug and 7% amphetamine.
References
Schepers RJ, Oyler JM, Joseph RE Jr, Cone EJ, Moolchan ET, Huestis MA: Methamphetamine and amphetamine pharmacokinetics in oral fluid and plasma after controlled oral methamphetamine administration to human volunteers. Clin Chem. 2003 Jan;49(1):121-32. [Pubmed]
McGregor C, Srisurapanont M, Jittiwutikarn J, Laobhripatr S, Wongtan T, White JM: The nature, time course and severity of methamphetamine withdrawal. Addiction. 2005 Sep;100(9):1320-9. [Pubmed]
Bennett BA, Hollingsworth CK, Martin RS, Harp JJ: Methamphetamine-induced alterations in dopamine transporter function. Brain Res. 1998 Jan 26;782(1-2):219-27. [Pubmed]
Hasan AA, Ciancio S: Relationship between amphetamine ingestion and gingival enlargement. Pediatr Dent. 2004 Sep-Oct;26(5):396-400. [Pubmed]
Shaner JW: Caries associated with methamphetamine abuse. J Mich Dent Assoc. 2002 Sep;84(9):42-7. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Schepers RJ, Oyler JM, Joseph RE Jr, Cone EJ, Moolchan ET, Huestis MA: Methamphetamine and amphetamine pharmacokinetics in oral fluid and plasma after controlled oral methamphetamine administration to human volunteers. Clin Chem. 2003 Jan;49(1):121-32. Pubmed
  • • McGregor C, Srisurapanont M, Jittiwutikarn J, Laobhripatr S, Wongtan T, White JM: The nature, time course and severity of methamphetamine withdrawal. Addiction. 2005 Sep;100(9):1320-9. Pubmed
  • • Bennett BA, Hollingsworth CK, Martin RS, Harp JJ: Methamphetamine-induced alterations in dopamine transporter function. Brain Res. 1998 Jan 26;782(1-2):219-27. Pubmed
  • • Hasan AA, Ciancio S: Relationship between amphetamine ingestion and gingival enlargement. Pediatr Dent. 2004 Sep-Oct;26(5):396-400. Pubmed
  • • Shaner JW: Caries associated with methamphetamine abuse. J Mich Dent Assoc. 2002 Sep;84(9):42-7. Pubmed
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