(1S,5R,13R)-10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,14,16-pentaene

• ChemBase ID: 129841
• Molecular Formular: C19H21NO3
• Molecular Mass: 311.37494
• Monoisotopic Mass: 311.15214354
• SMILES: O(c1ccc2c3c1O[C@H]1C(=CC=C4[C@H](N(CC[C@]314)C)C2)OC)C
• Canonical SMILES: COC1=CC=C2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC
• 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
• InChIKey: FQXXSQDCDRQNQE-VMDGZTHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R)-10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,14,16-pentaene; (1S,5R,13R)-10,14-dimethoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18),14,16-pentaene
• IUPAC Traditional name: thebaine
• Synonyms: Thebaine; Paramorphine; Thebaine

Database IDs

• CAS Number: 115-37-7
• EC Number: 204-084-1
• MDL Number: MFCD00027409
• PubChem SID: 24900006; 162224127
• PubChem CID: 5324289
• CHEBI ID: 9519
• CHEMBL: 403893
• Chemspider ID: 4481822
• KEGG ID: C06173
• MeSH Name: Thebaine
• Unique Ingredient Identifier: 2P9MKG8GX7
• Wikipedia Title: Thebaine

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.2559863
• LogD (pH = 7.4): 0.5094419
• Log P: 1.5322096
• Molar Refractivity: 90.6597 cm^3
• Polarizability: 34.35827 Å^3
• Polar Surface Area: 30.93 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• RTECS: QD2975000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28
• Safety Statements: 22-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H310-H330
• GHS Precautionary statements: P260-P280-P284-P301 + P310-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2
• Drug Control: USDEA Schedule II; Home Office Schedule 2; stupéfiant; kontrollierte Droge in Deutschland; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Dependency Liability: Low
• Metabolism: O-demethylation
• Legal Status: Class A (UK); Schedule II (US)

DETAILS

Sigma Aldrich - T2019

Biochem/physiol Actions
The (-)-isomer of thebaine is the naturally-occurring constituent of opium that is a precursor of morphine. It has poor antinociceptive activity and induces convulsions. It binds to μ and δ opioid receptors in vitro.
Physical form
Alkaloid powder