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Substance Name: Methadone [INN:BAN]
RN: 76-99-3
UNII: UC6VBE7V1Z
InChIKey: USSIQXCVUWKGNF-UHFFFAOYSA-N

Note

  • A synthetic opioid that is used as the hydrochloride. It is an opioid analgesic that is primarily a mu-opioid agonist. It has actions and uses similar to those of MORPHINE. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1082-3)

Molecular Formula

  • C21-H27-N-O

Molecular Weight

  • 309.4503
 

Classification Codes

Classification Codes

  • Analgesics
  • Analgesics, Opioid
  • Antitussive Agents
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Narcotics
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Respiratory System Agents
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule II

Names and Synonyms

Name of Substance

  • Methadone
  • Methadone [INN:BAN]

MeSH Heading

  • Methadone

Synonyms

  • (+-)-Methadone
  • 3-14-00-00279 (Beilstein Handbook Reference)
  • 6-Dimethylamino-4,4-diphenyl-3-heptanone
  • A 4624
  • Adanon
  • Algovetin
  • Amidon
  • Amidone
  • AN 148
  • BRN 3213669
  • Diaminon
  • dl-Methadone
  • Dolophin
  • Dolophine
  • EINECS 200-996-9
  • Eptadone
  • Heptadone
  • Heptanon
  • Heptanon (pharmaceutical)
  • Hoechst 10820
  • HSDB 3119
  • K 174
  • Ketalgin
  • Metadona
  • Metadona [INN-Spanish]
  • Metadona [Spanish]
  • Metadone
  • Metadone [DCIT]
  • Methadon
  • Methadona
  • Methadona [Spanish]
  • Methadone
  • Methadonum
  • Methadonum [INN-Latin]
  • Methadonum [Latin]
  • Phenadone
  • Physeptone
  • Polamivet
  • Racemic methadone
  • Sedo-Rapide
  • UNII-UC6VBE7V1Z

Systematic Names

  • 3-Heptanone, 6-(dimethylamino)-4,4-diphenyl-
  • Methadone

Superlist Names

  • DEA No. 9250
  • Methadone

Registry Numbers

CAS Registry Number

  • 76-99-3

FDA UNII

  • UC6VBE7V1Z

Other Registry Number

  • 297-88-1

Related Registry Number

  • 1095-90-5 (hydrochloride)

System Generated Number

  • 0000076993

Structure Descriptors

InChI

1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3

InChIKey

USSIQXCVUWKGNF-UHFFFAOYSA-N

Smiles

CCC(=O)C(CC(C)N(C)C)(c1ccccc1)c2ccccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 1538ug/kg (1.538mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Clinical Toxicology. Vol. 6, Pg. 175, 1973.
dog LDLo intravenous 26mg/kg (26mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 157, 1973.
human TDLo oral 1560ug/kg (1.56mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: COMA
Clinical Toxicology. Vol. 6, Pg. 175, 1973.
infant LDLo oral 1313ug/kg (1.313mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
American Journal of Emergency Medicine. Vol. 6, Pg. 511, 1988.
infant TDLo oral 2mg/kg (2mg/kg) BEHAVIORAL: COMA Clinical Toxicology. Vol. 6, Pg. 175, 1973.
man TDLo intravenous 571ug/kg/5H-I (0.571mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

GASTROINTESTINAL: NAUSEA OR VOMITING
Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 11, Pg. 346, 1952.
mouse LD50 intraperitoneal 35mg/kg (35mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
mouse LD50 intravenous 20mg/kg (20mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: STIFFNESS
Journal of Pharmacology and Experimental Therapeutics. Vol. 99, Pg. 163, 1950.
mouse LD50 oral 70mg/kg (70mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
mouse LD50 subcutaneous 35mg/kg (35mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 376, 1962.
rat LD50 intraperitoneal 18mg/kg (18mg/kg)   Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 47, Pg. 323, 1958.
rat LD50 intravenous 11mg/kg (11mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 25, Pg. 929, 1973.
rat LD50 oral 86mg/kg (86mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 180, Pg. 155, 1969.
rat LD50 subcutaneous 30mg/kg (30mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 3, Pg. 238, 1953.
rat LD50 unreported 28mg/kg (28mg/kg) BEHAVIORAL: ANALGESIA Pharmacological Research Communications. Vol. 5, Pg. 175, 1973.
rat LDLo intraspinal 2mg/kg (2mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ANALGESIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Acta Pharmacologica et Toxicologica. Vol. 56, Pg. 50, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
pKa Dissociation Constant 8.94 (none) 25 EXP
log P (octanol-water) 3.93 (none)   EXP
Water Solubility 48.5 mg/L 25 EST
Vapor Pressure 1.12E-06 mm Hg 25 EST
Henry's Law Constant 4.97E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.05E-10 cm3/molecule-sec 25 EST

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