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Substance Name: Dextroamphetamine [USAN]
RN: 51-64-9
UNII: TZ47U051FI
InChIKey: KWTSXDURSIMDCE-QMMMGPOBSA-N

Note

  • The d-form of AMPHETAMINE. It is a central nervous system stimulant and a sympathomimetic. It has also been used in the treatment of narcolepsy and of attention deficit disorders and hyperactivity in children. Dextroamphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulating release of monamines, and inhibiting monoamine oxidase. It is also a drug of abuse and a psychotomimetic.

Molecular Formula

  • C9-H13-N

Molecular Weight

  • 135.209
 

Classification Codes

Classification Codes

  • Central Nervous System Agents
  • Central Nervous System Stimulants
  • Dopamine Agents
  • Dopamine Uptake Inhibitors
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Reproductive Effect
  • Stimulant (Central)

Superlist Classification Code

  • DEA Schedule II

Names and Synonyms

Name of Substance

  • Dexamfetamine [INN]
  • Dextroamphetamine
  • Dextroamphetamine [USAN]

MeSH Heading

  • Dextroamphetamine

Synonyms

  • (+)-(S)-Amphetamine
  • (+)-alpha-Methylphenethylamine
  • (+)-alpha-Methylphenylethylamine
  • (+)-Amphetamine
  • (+)-Phenaminum
  • (2S)-(+)-Amphetamine
  • (S)-(+)-Amphetamine
  • (S)-(+)-beta-Phenylisopropylamine
  • (S)-1-Phenyl-2-aminopropane
  • (S)-1-Phenyl-2-propylamine
  • (S)-alpha-Methylphenethylamine
  • (S)-alpha-Phenylethylamine
  • (S)-Amphetamine
  • 4-12-00-02587 (Beilstein Handbook Reference)
  • alpha-Methylphenethylamine, d-form
  • Amsustain
  • BRN 2205872
  • D-(S)-Amphetamine
  • d-1-Phenyl-2-aminopropan
  • d-1-Phenyl-2-aminopropan [German]
  • d-1-Phenyl-2-aminopropane
  • d-2-Amino-1-phenylpropane
  • d-alpha-Methylphenethylamine
  • D-AM
  • D-Amphetamine
  • Dephadren
  • Desamfetamina
  • Desamfetamina [DCIT]
  • Desoxyn
  • Dexadrine
  • Dexamfetamina
  • Dexamfetamina [INN-Spanish]
  • Dexamfetamine
  • Dexamfetaminum
  • Dexamfetaminum [INN-Latin]
  • Dexamphetamine
  • Dexamphetaminum
  • Dexamphetaminum [INN-Latin]
  • Dexanfetamina
  • Dexanfetamina [INN-Spanish]
  • Dexidrine
  • Dextroamphetamine
  • EINECS 200-112-1
  • HSDB 3055
  • NSC 73713
  • Phenethylamine, alpha-methyl-, (+)-
  • Phenethylamine, alpha-methyl-, d-
  • Sympamin
  • UNII-TZ47U051FI

Systematic Names

  • Benzeneethanamine, alpha-methyl-, (alphaS)-
  • Benzeneethanamine, alpha-methyl-, (S)-
  • Dexamphetamine
  • Phenethylamine, alpha-methyl-, (+)-

Superlist Names

  • Amphetamine [DEA]
  • DEA No. 1100
  • Dexedrine

Registry Numbers

CAS Registry Number

  • 51-64-9

FDA UNII

  • TZ47U051FI

System Generated Number

  • 0000051649

Structure Descriptors

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

Smiles

C[C@H](N)Cc1ccccc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 3600ug/kg/10D (3.6mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) American Journal of Psychiatry. Vol. 143, Pg. 1176, 1985.
dog LDLo oral 6400ug/kg (6.4mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 84, 1973.
gerbil LD50 intraperitoneal 17600ug/kg (17.6mg/kg)   Gerontology Vol. 23, Pg. 165, 1977.
gerbil LD50 intraperitoneal 17600ug/kg (17.6mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Gerontology Vol. 23, Pg. 165, 1977.
mammal (species unspecified) LD50 oral 375mg/kg (375mg/kg) BEHAVIORAL: FOOD INTAKE (ANIMAL)

KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

BEHAVIORAL: ANTICONVULSANT		 Journal of Medicinal Chemistry. Vol. 8, Pg. 836, 1965.
man TDLo oral 42mg/kg/25W-I (42mg/kg) BEHAVIORAL: TOXIC PSYCHOSIS Biological Psychiatry. Vol. 20, Pg. 1332, 1985.
monkey LDLo oral 32mg/kg (32mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 84, 1973.
mouse LD50 intraperitoneal 4400ug/kg (4.4mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 161, Pg. 206, 1966.
mouse LD50 intravenous 25mg/kg (25mg/kg)   Journal of Medicinal Chemistry. Vol. 15, Pg. 410, 1972.
mouse LD50 oral 40mg/kg (40mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA		 Toxicology and Applied Pharmacology. Vol. 41, Pg. 329, 1977.
mouse LD50 subcutaneous 20mg/kg (20mg/kg) BEHAVIORAL: EXCITEMENT Archives Internationales de Pharmacodynamie et de Therapie. Vol. 146, Pg. 392, 1963.
rat LD50 oral 38mg/kg (38mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 subcutaneous 200mg/kg (200mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 84, 1973.
rat LDLo intraperitoneal 20mg/kg (20mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 195, Pg. 647, 1940.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point < 25 deg C   EXP
Boiling Point 203 deg C   EXP
pKa Dissociation Constant 9.9 (none)   EXP
log P (octanol-water) 1.76 (none)   EXP
Atmospheric OH Rate Constant 4.94E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.