(2S)-1-phenylpropan-2-amine

• ChemBase ID: 67
• Molecular Formular: C9H13N
• Molecular Mass: 135.20622
• Monoisotopic Mass: 135.10479942
• 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

NAMES AND DATABASE IDS

Names

• 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; 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
• Synonyms: (+/-)-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

Database IDs

• 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

CALCULATED PROPERTIES

JChem

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -1.2147744
• LogD (pH = 7.4): -0.67093694
• Log P: 1.8042505
• Molar Refractivity: 43.7052 cm^3
• Polarizability: 17.364613 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.85
• LOG S: -1.89
• Solubility (Water): 1.74e+00 g/l

PROPERTIES

Physical Property

• Solubility: Slightly
• Partition Coefficient: 1.789
• Hydrophobicity(logP): 1.76 [SANGSTER (1994); similar isomer]; 1.8

Pharmacology Properties

• Admin Routes: Oral, insufflation, rectal, sublingual
• Bioavailability: ~75% (oral)
• Excretion: ~45% (renal)
• Half Life: ~10-12 hrs
• Metabolism: Hepatic
• Legal Status: Class B (UK); S8 (Australia); Schedule I (Canada); Schedule II (US)
• Pregnancy Category: B3 (Australia); C (US)

DETAILS

DrugBank - DB00182

• 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

• 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

• 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