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Chemistry

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Also known as: Paramorphine, 115-37-7, Thebain, 3-o-methyl-oripavin, 4,5alpha-epoxy-3,6-dimethoxy-17-methyl-6,8-morphinadien, 2p9mkg8gx7

Molecular Formula

C₁₉H₂₁NO₃

Molecular Weight

311.4 g/mol

InChI Key

FQXXSQDCDRQNQE-VMDGZTHMSA-N

FDA UNII

2P9MKG8GX7

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)

1 2D Structure

Thebaine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4R,7aR,12bS)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline

2.1.2 InChI

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

2.1.3 InChI Key

FQXXSQDCDRQNQE-VMDGZTHMSA-N

2.1.4 Canonical SMILES

CN1CCC23C4C(=CC=C2C1CC5=C3C(=C(C=C5)OC)O4)OC

2.1.5 Isomeric SMILES

CN1CC[C@]23[C@@H]4C(=CC=C2[C@H]1CC5=C3C(=C(C=C5)OC)O4)OC

2.2 Other Identifiers

2.2.1 UNII

2P9MKG8GX7

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. Paramorphine

2. 115-37-7

3. Thebain

4. 3-o-methyl-oripavin

5. 4,5alpha-epoxy-3,6-dimethoxy-17-methyl-6,8-morphinadien

6. 2p9mkg8gx7

7. (5r,9r,13s)-4,5-epoxy-3,6-dimethoxy-9alpha-methyl-6,8-morphinadien

8. Chebi:9519

9. (4r,7ar,12bs)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline

10. Ncgc00160239-01

11. Dsstox_cid_26099

12. Dsstox_rid_81337

13. Dsstox_gsid_46099

14. (5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan

15. 3,6-dimethoxy-17-methyl-6,7,8,14-tetradehydro-4,5alpha-epoxymorphinan

16. Cas-115-37-7

17. Einecs 204-084-1

18. Unii-2p9mkg8gx7

19. Tebaine

20. Thenaine

21. Kodein

22. Dea No. 9333

23. Thebaine, Powder

24. Ncgc00247709-01

25. Thebaine [mi]

26. Thebaine [who-dd]

27. Schembl37580

28. Chembl403893

29. Ids-nt-002

30. Dtxsid7046099

31. Schembl19880976

32. Thebaine 0.1 Mg/ml In Methanol

33. Bdbm224032

34. Tox21_111751

35. Tox21_112863

36. Zinc53199482

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

38. C06173

39. Codeine Monohydrate Impurity G [ep Impurity]

40. Q63392872

41. Oxycodone Hydrochloride Impurity F [ep Impurity]

42. Thebaine, European Pharmacopoeia (ep) Reference Standard

43. Codeine Hydrochloride Dihydrate Impurity G [ep Impurity]

44. Codeine Phosphate Hemihydrate Impurity G [ep Impurity]

45. Codeine Phosphate Sesquihydrate Impurity G [ep Impurity]

46. 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan

47. Hydrocodone Hydrogen Tartrate 2.5-hydrate Impurity I [ep Impurity]

48. (5.alpha.)-6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan

49. Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-,(5.alpha.)-

50. Thebaine Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

51. D4r

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₉H₂₁NO₃
Molecular Weight	311.4 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	2
Exact Mass	311.15214353 g/mol
Monoisotopic Mass	311.15214353 g/mol
Topological Polar Surface Area	30.9 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	585
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Narcotics

Agents that induce NARCOSIS. Narcotics include agents that cause somnolence or induced sleep (STUPOR); natural or synthetic derivatives of OPIUM or MORPHINE or any substance that has such effects. They are potent inducers of ANALGESIA and OPIOID-RELATED DISORDERS. (See all compounds classified as Narcotics.)

Convulsants

Substances that act in the brain stem or spinal cord to produce tonic or clonic convulsions, often by removing normal inhibitory tone. They were formerly used to stimulate respiration or as antidotes to barbiturate overdose. They are now most commonly used as experimental tools. (See all compounds classified as Convulsants.)

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