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Substance Name: Amphetamine
RN: 300-62-9
UNII: CK833KGX7E
InChIKey: KWTSXDURSIMDCE-UHFFFAOYSA-N

Note

  • A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.

Molecular Formula

  • C9-H13-N

Molecular Weight

  • 135.2087
 

Classification Codes

Classification Codes

  • Adrenergic Agents
  • Adrenergic Uptake Inhibitors
  • Autonomic Agents
  • Central Nervous System Agents
  • Central Nervous System Stimulants
  • Dopamine Agents
  • Dopamine Uptake Inhibitors
  • Drug / Therapeutic Agent
  • Human Data
  • Membrane Transport Modulators
  • Mutation Data
  • Neurotransmitter Agents
  • Neurotransmitter Uptake Inhibitors
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sympathomimetics

Superlist Classification Codes

  • DEA Schedule II
  • Threshold Planning Quantity (TPQ) = 1000 lb

Names and Synonyms

Results Name

  • Amphetamine

Name of Substance

  • Amfetamine [INN:BAN]
  • Amphetamine

MeSH Heading

  • Amphetamine

Synonyms

  • (+-)-alpha-Methylbenzeneethanamine
  • (+-)-alpha-Methylphenethylamine
  • (+-)-alpha-Methylphenylethylamine
  • (+-)-Benzedrine
  • (Phenylisopropyl)amine
  • 1-Methyl-2-phenylethylamine
  • 1-Phenyl-2-amino-propan
  • 1-Phenyl-2-amino-propan [German]
  • 1-Phenyl-2-aminopropane
  • 1-Phenyl-2-aminopropane (VAN)
  • 1-Phenyl-2-propanamine
  • 1-Phenyl-2-propylamine
  • 2-Amino-1-phenylpropane
  • 3-Amino-1-propylbenzene
  • 3-Phenyl-2-propylamine
  • Actedron
  • Adderall
  • Adderall XR
  • Adipan
  • Adzenys ER
  • AI3-02438
  • Allodene
  • alpha-Methylbenzeneethaneamine
  • alpha-Methylphenethylamine
  • Amfetamina
  • Amfetamina [INN-Spanish]
  • Amfetamina [Italian]
  • Amfetamine
  • Amfetaminum
  • Amfetaminum [INN-Latin]
  • Amphetamine
  • Amphetamine mixture with Dextroamphetamine
  • Amphetamine salts
  • Anfetamina
  • Anfetamina [Spanish]
  • Anorexide
  • Anorexine
  • Benzebar
  • Benzedrine
  • Benzeneethanamine, alpha-methyl-, (+-)-
  • Benzolone
  • beta-Aminopropylbenzene
  • beta-Aminopropylbenzene (VAN)
  • beta-Phenylisopropylamin
  • beta-Phenylisopropylamin [German]
  • Delcobese
  • Desoxynorephedrine
  • dl-alpha-Methylphenethylamine
  • Dyanavel XR
  • EINECS 200-458-3
  • EINECS 206-096-2
  • Elastonon
  • Fenopromin
  • Fenylo-izopropylaminyl
  • Fenylo-izopropylaminyl [Polish]
  • Finam
  • HSDB 3287
  • Isoamyne
  • Isomyn
  • Mecodrin
  • Mydrial
  • Norephedrane
  • Novydrine
  • NSC 27159
  • NT-0201
  • Obesin
  • Obesine
  • Oktedrin
  • Ortedrine
  • Percomon
  • Phenamine
  • Phenedrine
  • Phenethylamine, alpha-methyl-, (+-)-
  • Profamina
  • Propisamine
  • Protioamphetamine
  • Psychedrine
  • racemic-Desoxynor-ephedrine
  • Raphetamine
  • Rhinalator
  • Simpatedrin
  • Simpatina
  • Sympamine
  • Sympatedrine
  • UNII-CK833KGX7E
  • Weckamine

Systematic Names

  • alpha-Methylphenethylamine
  • Amphetamine
  • Benzeneethanamine, alpha-methyl-
  • Benzeneethanamine, alpha-methyl-, (+-)-
  • Phenethylamine, alpha-methyl-

Superlist Names

  • Amphetamine
  • Amphetamine, its salts, optical isomers, and salts of its optical isomers
  • DEA No. 1100

Registry Numbers

CAS Registry Number

  • 300-62-9

FDA UNII

  • CK833KGX7E

Other Registry Numbers

  • 17108-96-2
  • 60-15-1
  • 96332-84-2

Related Registry Number

  • 60-13-9 (sulfate (2:1))

System Generated Number

  • 0000300629

Structure Descriptors

InChI

InChI=1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3

InChIKey

KWTSXDURSIMDCE-UHFFFAOYSA-N

Smiles

CC(N)Cc1ccccc1

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo subcutaneous 20mg/kg (20mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 149, 1948.
guinea pig LDLo oral 200mg/kg (200mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR		 Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 128, Pg. 680, 1938.
guinea pig LDLo parenteral 20mg/kg (20mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR		 Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 128, Pg. 680, 1938.
guinea pig LDLo subcutaneous 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: TREMOR		 Comptes Rendus des Seances de la Societe de Biologie et de Ses Filiales. Vol. 128, Pg. 680, 1938.
mammal (species unspecified) LD50 intraperitoneal 65mg/kg (65mg/kg)   Biochimie. Vol. 63, Pg. 495, 1981.
mammal (species unspecified) LD50 oral 135mg/kg (135mg/kg)   Biochimie. Vol. 63, Pg. 495, 1981.
man LDLo unreported 2206ug/kg (2.206mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
monkey LDLo subcutaneous 20mg/kg (20mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 149, 1948.
mouse LD50 intraperitoneal 5500ug/kg (5.5mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 161, Pg. 206, 1966.
mouse LD50 intravenous 15mg/kg (15mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 146, Pg. 392, 1963.
mouse LD50 oral 21mg/kg (21mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 810, 1973.
mouse LD50 subcutaneous 15mg/kg (15mg/kg)   Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 4, Pg. 139, 1945.
mouse LD50 unreported 8800ug/kg (8.8mg/kg)   Acta Physiologica Academiae Scientiarum Hungaricae. Vol. 32, Pg. 377, 1967.
rabbit LDLo intravenous 25mg/kg (25mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 149, 1948.
rabbit LDLo subcutaneous 20mg/kg (20mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 149, 1948.
rat LD50 oral 30mg/kg (30mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 810, 1973.
rat LD50 subcutaneous 180mg/kg (180mg/kg) BEHAVIORAL: EXCITEMENT Journal of Pharmacology and Experimental Therapeutics. Vol. 85, Pg. 119, 1945.
rat LDLo intraperitoneal 23mg/kg (23mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 195, Pg. 647, 1940.
rat LDLo intravenous 20mg/kg (20mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 101, 1948.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Boiling Point 203 deg C   EXP
pKa Dissociation Constant 10.13 (none) 20 EXP
log P (octanol-water) 1.76 (none)   EXP
Water Solubility 2.80E+04 mg/L 25 EST
Vapor Pressure 0.24 mm Hg 20 EXP
Henry's Law Constant 1.08E-06 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.94E-11 cm3/molecule-sec 25 EST

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