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51-64-9 分子结构
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(2S)-1-phenylpropan-2-amine

ChemBase编号:67
分子式:C9H13N
平均质量:135.20622
单一同位素质量:135.10479942
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-1-phenylpropan-2-amine
IUPAC系统名
(2S)-1-phenylpropan-2-amine
IUPAC传统名
amphetamine
dextroamphetamine
商标名
Actedron
Adipan
Allodene
Anorexide
Anorexine
Benzebar
Benzedrine
Benzolone
Desoxyn
Dexampex
Dexedrine
Dextrostat
Elastonon
Fenamin
Ferndex
Finam
Isoamycin
Isoamyne
Isomyn
Mecodrin
Methampex
Norephedrane
Novydrine
Oktedrin
Ortedrine
Paredrine
Percomon
Phenamine
Phenedrine
Profamina
Propisamine
Psychedrine
Raphetamine
Rhinalator
Simpatedrin
Simpatina
Sympamin
Sympamine
Sympatedrine
Weckamine
Amsustain
Dephadren
Dexacaps
Dexadrine
Dexedrine Spansule
Dexidrine
别名
(+/-)-beta-Phenylisopropylamine
(+/-)-Benzedrine
(+/-)-Desoxynorephedrine
1-Methyl-2-phenylethylamine
1-Phenyl-2-aminopropane
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
Methamphetamine HCL
[1-(3-Methoxyphenyl)-2-propyl]amine
Phenylisopropylamine
Amfetamine
beta-phenyl-isopropylamine
Amphetamine
S(+)-amphetamine
Dextroamphetamine
Dexanfetamina [inn-spanish]
Dexamphetaminum [inn-latin]
Dexamfetaminum [inn-latin]
Dexamfetamine
Dexamfetamina [inn-spanish]
Desamfetamina
D-amphetamine
D-am
D-alpha-methylphenethylamine
D-2-Amino-1-phenylpropane
D-1-Phenyl-2-aminopropane
d-1-Phenyl-2-aminopropan [German]
D-1-Phenyl-2-aminopropan
D-(s)-amphetamine
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
CAS号
51-64-9
300-62-9
EC号
200-112-1
Beilstein号
2205872
PubChem SID
160963530
46506252
PubChem CID
5826
CHEBI ID
4469
ATC码
N06BA02
CHEMBL
612
Chemspider ID
5621
DrugBank ID
DB01576
Gmelin ID
1125854
KEGG ID
D03740
医学主题词(MeSH)
Dextroamphetamine
美国药典/FDA物质标识码
TZ47U051FI
维基百科标题
Dextroamphetamine

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) -1.2147744  LogD (pH = 7.4) -0.67093694 
Log P 1.8042505  摩尔折射率 43.7052 cm3
极化性 17.364613 Å3 极化表面积 26.02 Å2
可自由旋转的化学键 里宾斯基五规则 true 
Log P 1.85  LOG S -1.89 
溶解度 1.74e+00 g/l 

分子性质

分子性质

理化性质 药理学性质 生物活性(PubChem)
溶解度
Slightly expand 查看数据来源
分配系数
1.789 expand 查看数据来源
疏水性(logP)
1.76 [SANGSTER (1994); similar isomer] expand 查看数据来源
1.8 expand 查看数据来源
给药途径
Oral, insufflation, rectal, sublingual expand 查看数据来源
生物利用度
~75% (oral) expand 查看数据来源
排泄
~45% (renal) expand 查看数据来源
半衰期
~10-12 hrs expand 查看数据来源
代谢
Hepatic expand 查看数据来源
法定药品分级
Class B (UK) expand 查看数据来源
S8 (Australia) expand 查看数据来源
Schedule I (Canada) expand 查看数据来源
Schedule II (US) expand 查看数据来源
妊娠期药物分类
B3 (Australia) expand 查看数据来源
C (US) expand 查看数据来源

详细说明

详细说明

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

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • 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
  • 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
  • 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
  • Warneke L: Psychostimulants in psychiatry. Can J Psychiatry. 1990 Feb;35(1):3-10. Pubmed
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专利

专利

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