Thebaine

HCID 5324289CAS 115-37-7

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Basic information

Standard SMILES: COC1=CC=C2[C@H]3Cc4ccc(OC)c5c4[C@@]2(CCN3C)[C@H]1O5
InChIKey: FQXXSQDCDRQNQE-VMDGZTHMSA-N
Molecular formula: C19H21NO3
Average molar mass: 311.4 g/mol
Monoisotopic mass: 311.15214353

Overview

Thebaine is a morphinane alkaloid and an organic heteropentacyclic compound. It is functionally related to an oripavine. It is a conjugate base of a thebaine(1+).

Names & identifiers

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

Names & synonyms

THEBAINEParamorphine115-37-7Thebain3-O-Methyl-oripavinDTXSID70460992P9MKG8GX74,5alpha-Epoxy-3,6-dimethoxy-17-methyl-6,8-morphinadien(5R,9R,13S)-4,5-Epoxy-3,6-dimethoxy-9alpha-methyl-6,8-morphinadienCHEBI:9519IDS-NT-002DTXCID5026099

Show more names

(4R,7aR,12bS)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline3,6-dimethoxy-17-methyl-6,7,8,14-tetradehydro-4,5alpha-epoxymorphinan(5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan(4R,7aR,12bS)-7,9-dimethoxy-3-methyl-2,4,7a,13-tetrahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolineRefChem:389309204-084-1NCGC00160239-01Thebaine (1.0mg/ml in Acetonitrile)

Database identifiers

CAS: 115-37-7
PubChem CID: 5324289
DTXSID: DTXSID7046099
ChEMBL: CHEMBL403893
ChEBI: CHEBI:9519
UNII: 2P9MKG8GX7
EC Number: 204-084-1
Nikkaji: J5.266C

Properties

Computed structural properties

XLogP: 2.2
Topological polar surface area: 30.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 23
Formal charge: 0
Complexity: 585

Experimental & physicochemical properties

Drugs · 3 items

DEA NFLIS-Drug Category -> Narcotic Analgesics

DEA Schedule II Controlled Substance

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

SpringerMaterials PropertiesCrystal structure

Human DrugsPharmaceuticals

Collision Cross Section172.2 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated]

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H300 (20%): Fatal if swallowed [Danger Acute toxicity, oral]

P233, P260, P261, P262, P264, P270, P271, P272, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P333+P317, P342+P316, P361+P364, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 220 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

DEA schedule II controlled substance

Status: Active Update: 20-03-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/19283

Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-, (5.alpha.)-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-, (5.alpha.)-: Environment tier I assessment

Hazard Classes and CategoriesAcute Tox. 2 (20%)

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

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.

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.