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51-64-9 molecular structure
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(2S)-1-phenylpropan-2-amine

ChemBase ID: 67
Molecular Formular: C9H13N
Molecular Mass: 135.20622
Monoisotopic Mass: 135.10479942
SMILES and InChIs

SMILES:
N[C@H](Cc1ccccc1)C
Canonical SMILES:
C[C@@H](Cc1ccccc1)N
InChI:
InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m0/s1
InChIKey:
KWTSXDURSIMDCE-QMMMGPOBSA-N

Cite this record

CBID:67 http://www.chembase.cn/molecule-67.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-1-phenylpropan-2-amine
IUPAC Systematic name
(2S)-1-phenylpropan-2-amine
IUPAC Traditional name
amphetamine
dextroamphetamine
Brand Name
Actedron
Adipan
Allodene
Anorexide
Anorexine
Benzebar
Benzedrine
Benzolone
Desoxyn
Dexampex
Dexedrine
Dextrostat
Elastonon
Fenamin
Ferndex
Finam
Isoamycin
Isoamyne
Isomyn
Amsustain
Dephadren
Dexacaps
Mecodrin
Methampex
Norephedrane
Novydrine
Oktedrin
Ortedrine
Dexadrine
Dexedrine Spansule
Dexidrine
Paredrine
Percomon
Phenamine
Phenedrine
Profamina
Propisamine
Psychedrine
Raphetamine
Rhinalator
Simpatedrin
Simpatina
Sympamin
Sympamine
Sympatedrine
Weckamine
Synonyms
S(+)-amphetamine
Dextroamphetamine
Dexanfetamina [inn-spanish]
Dexamphetaminum [inn-latin]
Dexamfetaminum [inn-latin]
(+/-)-beta-Phenylisopropylamine
Dexamfetamine
Dexamfetamina [inn-spanish]
(+/-)-Benzedrine
(+/-)-Desoxynorephedrine
1-Methyl-2-phenylethylamine
1-Phenyl-2-aminopropane
Desamfetamina
D-amphetamine
D-am
3-Methoxy-a-methylbenzeneethanamine
3-Methoxyamphetamine
3-Methoxyphenylisopropylamine
alpha-Methylbenzeneethaneamine
Amphetamine Sulfate
beta-Aminopropylbenzene
dl-1-Phenyl-2-aminopropane
DL-alpha-Methylphenethylamine
dl-Amphetamine
dl-Benzedrine
Fenylo-izopropylaminyl
m-Methoxy-a-methylphenethylamine
m-Methoxyamphetamine
D-alpha-methylphenethylamine
D-2-Amino-1-phenylpropane
Methamphetamine HCL
[1-(3-Methoxyphenyl)-2-propyl]amine
D-1-Phenyl-2-aminopropane
d-1-Phenyl-2-aminopropan [German]
D-1-Phenyl-2-aminopropan
D-(s)-amphetamine
Phenylisopropylamine
Amfetamine
beta-phenyl-isopropylamine
D-(+)-amphetamine
(s)-amphetamine
(s)-alpha-phenylethylamine
(s)-alpha-methylphenethylamine
(s)-alpha-methylbenzeneethanamine
(S)-1-phenyl-2-propylamine
(S)-1-Phenyl-2-propanamine
(S)-1-phenyl-2-aminopropane
(s)-(+)-beta-phenylisopropylamine
(s)-(+)-amphetamine
(2S)-1-phenylpropan-2-amine
(2S)-(+)-Amphetamine
(+)-phenaminum
(+)-amphetamine
(+)-alpha-methylphenylethylamine
(+)-alpha-methylphenethylamine
(+)-(s)-amphetamine
Dexamphetamine
Dextroamphetamine sulfate
Dextroamphetamine
Amphetamine
CAS Number
51-64-9
300-62-9
EC Number
200-112-1
Beilstein Number
2205872
PubChem SID
160963530
46506252
PubChem CID
5826
CHEBI ID
4469
ATC CODE
N06BA02
CHEMBL
612
Chemspider ID
5621
DrugBank ID
DB01576
Gmelin ID
1125854
KEGG ID
D03740
MeSH Name
Dextroamphetamine
Unique Ingredient Identifier
TZ47U051FI
Wikipedia Title
Dextroamphetamine

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -1.2147744  LogD (pH = 7.4) -0.67093694 
Log P 1.8042505  Molar Refractivity 43.7052 cm3
Polarizability 17.364613 Å3 Polar Surface Area 26.02 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 1.85  LOG S -1.89 
Solubility (Water) 1.74e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Bioassay(PubChem)
Solubility
Slightly expand Show data source
Partition Coefficient
1.789 expand Show data source
Hydrophobicity(logP)
1.76 [SANGSTER (1994); similar isomer] expand Show data source
1.8 expand Show data source
Admin Routes
Oral, insufflation, rectal, sublingual expand Show data source
Bioavailability
~75% (oral) expand Show data source
Excretion
~45% (renal) expand Show data source
Half Life
~10-12 hrs expand Show data source
Metabolism
Hepatic expand Show data source
Legal Status
Class B (UK) expand Show data source
S8 (Australia) expand Show data source
Schedule I (Canada) expand Show data source
Schedule II (US) expand Show data source
Pregnancy Category
B3 (Australia) expand Show data source
C (US) expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00182 external link
Item Information
Drug Groups illicit; approved
Description Amphetamine is a chiral compound. The racemic mixture can be divided into its optical antipodes: levo- and dextro-amphetamine. Amphetamine is the parent compound of its own structural class, comprising a broad range of psychoactive derivatives, e.g., MDMA (Ecstasy) and the N-methylated form, methamphetamine. Amphetamine is a homologue of phenethylamine.
Indication For treatment of Attention Deficit Disorder with Hyperactivity (ADDH) and narcolepsy in children.
Pharmacology Amphetamine and dextroamphetamine, non-catechloamine sypathomimetic agents, are used in combination to treat attention-deficit hyperactivity disorder (ADHD) or narcolepsy. Adderall consists of equivalent amounts of amphetamine aspartate, amphetamine sulfate, dextroamphetamine saccharate, and dextroamphetamine sulfate.
Toxicity LD50=180 mg/kg(subcutaneous injection in rat). The most common presenting symptoms seen are agitation, hallucinations, suicidal behaviour, and chest pain.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Amphetamine forms easily absorbed molecules that are highly lipid soluble
Half Life 10 hours
Protein Binding 15-40%
References
Leith NJ, Kuczenski R: Chronic amphetamine: tolerance and reverse tolerance reflect different behavioral actions of the drug. Pharmacol Biochem Behav. 1981 Sep;15(3):399-404. [Pubmed]
Chaudhry IA, Turkanis SA, Karler R: Characteristics of "reverse tolerance" to amphetamine-induced locomotor stimulation in mice. Neuropharmacology. 1988 Aug;27(8):777-81. [Pubmed]
Sax KW, Strakowski SM: Behavioral sensitization in humans. J Addict Dis. 2001;20(3):55-65. [Pubmed]
Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
DrugBank - DB01576 external link
Item Information
Drug Groups illicit; approved
Description Dextroamphetamine is the dextrorotary stereoisomer of the amphetamine molecule, which can take two different forms. It is a slightly polar, weak base and is lipophilic.
Indication Used to treat attention deficit hyperactivity disorder (ADHD).
Pharmacology Amphetamines such as dextroamphetamine are noncatecholamine, sympathomimetic amines with CNS stimulant activity. Peripheral actions include elevations of systolic and diastolic blood pressures and weak bronchodilator and respiratory stimulant action. There is neither specific evidence that clearly establishes the mechanism whereby amphetamines produce mental and behavioral effects in children, nor conclusive evidence regarding how these effects relate to the condition of the central nervous system.
Toxicity In rats, the oral LD50 of dextroamphetamine sulfate is 96.8 mg/kg. Manifestations of acute overdosage with amphetamines include restlessness, tremor, hyperreflexia, rhabdomyolysis, rapid respiration, hyperpyrexia, confusion, assaultiveness, hallucinations, panic states. 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 is usually preceded by convulsions and coma.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption Oral bioavailability is over 75%.
Half Life 10-28 hours (average is approximately 12 hours)
References
Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H: Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems. Xenobiotica. 1984 Nov;14(11):861-6. [Pubmed]
Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. [Pubmed]
Wagner GJ, Rabkin R: Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry. 2000 Jun;61(6):436-40. [Pubmed]
Martinsson L, Yang X, Beck O, Wahlgren NG, Eksborg S: Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol. 2003 Sep-Oct;26(5):270-6. [Pubmed]
Butefisch CM, Davis BC, Sawaki L, Waldvogel D, Classen J, Kopylev L, Cohen LG: Modulation of use-dependent plasticity by d-amphetamine. Ann Neurol. 2002 Jan;51(1):59-68. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. Pubmed
  • • Yamada H, Baba T, Hirata Y, Oguri K, Yoshimura H: Studies on N-demethylation of methamphetamine by liver microsomes of guinea-pigs and rats: the role of flavin-containing mono-oxygenase and cytochrome P-450 systems. Xenobiotica. 1984 Nov;14(11):861-6. Pubmed
  • • Wagner GJ, Rabkin R: Effects of dextroamphetamine on depression and fatigue in men with HIV: a double-blind, placebo-controlled trial. J Clin Psychiatry. 2000 Jun;61(6):436-40. Pubmed
  • • Martinsson L, Yang X, Beck O, Wahlgren NG, Eksborg S: Pharmacokinetics of dexamphetamine in acute stroke. Clin Neuropharmacol. 2003 Sep-Oct;26(5):270-6. Pubmed
  • • Butefisch CM, Davis BC, Sawaki L, Waldvogel D, Classen J, Kopylev L, Cohen LG: Modulation of use-dependent plasticity by d-amphetamine. Ann Neurol. 2002 Jan;51(1):59-68. Pubmed
  • • Sax KW, Strakowski SM: Behavioral sensitization in humans. J Addict Dis. 2001;20(3):55-65. Pubmed
  • • Leith NJ, Kuczenski R: Chronic amphetamine: tolerance and reverse tolerance reflect different behavioral actions of the drug. Pharmacol Biochem Behav. 1981 Sep;15(3):399-404. Pubmed
  • • Chaudhry IA, Turkanis SA, Karler R: Characteristics of "reverse tolerance" to amphetamine-induced locomotor stimulation in mice. Neuropharmacology. 1988 Aug;27(8):777-81. Pubmed
  • • Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. Pubmed
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PATENTS

PATENTS

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