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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
- All
- Classifications
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- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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Other Resources (Internet Locators)
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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/s1InChIKey
KWTSXDURSIMDCE-QMMMGPOBSA-NSmiles
C[C@H](N)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.