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Substance Name: Thebaine
RN: 115-37-7
UNII: 2P9MKG8GX7
InChIKey: FQXXSQDCDRQNQE-VMDGZTHMSA-N

Note

  • A drug that is derived from opium, which contains from 0.3-1.5% thebaine depending on its origin. It produces strychnine-like convulsions rather than narcosis. It may be habit-forming and is a controlled substance (opiate) listed in the U.S. Code of Federal Regulations, Title 21 Part 1308.12 (1985). (From Merck Index, 11th ed)

Molecular Formula

  • C19-H21-N-O3

Molecular Weight

  • 311.3789
 

Classification Codes

Classification Codes

  • Analgesics
  • Central Nervous System Agents
  • Central Nervous System Depressants
  • Central Nervous System Stimulants
  • Convulsants
  • Drug / Therapeutic Agent
  • Narcotics
  • Peripheral Nervous System Agents
  • Sensory System Agents

Superlist Classification Code

  • DEA Schedule II
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Names and Synonyms

Name of Substance

  • Thebaine

MeSH Heading

  • Thebaine

Synonyms

  • (5R,9R,13S)-4,5-Epoxy-3,6-dimethoxy-9alpha-methyl-6,8-morphinadien
  • 3-O-Methyl-oripavin
  • 4,5alpha-Epoxy-3,6-dimethoxy-17-methyl-6,8-morphinadien
  • EINECS 204-084-1
  • Paramorphine
  • Thebain
  • Thebaine
  • UNII-2P9MKG8GX7

Systematic Names

  • Morphinan, 6,7,8,14-tetradehydro-4,5-alpha-epoxy-3,6-dimethoxy-17-methyl-
  • Thebaine

Superlist Names

  • DEA No. 9333
  • Thebaine

Registry Numbers

CAS Registry Number

  • 115-37-7

FDA UNII

  • 2P9MKG8GX7

System Generated Number

  • 0000115377

Structure Descriptors

InChI

1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18+,19+/m1/s1

InChIKey

FQXXSQDCDRQNQE-VMDGZTHMSA-N

Smiles

COC1=CC=C2[C@H]3Cc4ccc(OC)c5O[C@@H]1[C@]2(CCN3C)c45

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 20mg/kg (20mg/kg)   Agents and Actions, A Swiss Journal of Pharmacology. Vol. 6, Pg. 755, 1976.
mouse LD50 oral 54mg/kg (54mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 20, 1995.
mouse LD50 subcutaneous 31mg/kg (31mg/kg)   "Public Health Reports, Supplement." Vol. 138, Pg. 31, 1938.
rat LD50 oral 114mg/kg (114mg/kg)   Toksikologicheskii Vestnik. Vol. (4), Pg. 20, 1995.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 193 deg C   EXP
pKa Dissociation Constant 6.05 (none)   EXP
log P (octanol-water) 2.020 (none)   EST
Water Solubility 680 mg/L 15 EXP
Vapor Pressure 3.88E-07 mm Hg 25 EST
Henry's Law Constant 1.63E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 5.07E-10 cm3/molecule-sec 25 EST

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